ChemWiki - User contributions [en]

It07:Testosterone

2007-11-09T14:15:37Z

Arw06: /* Spectroscopic Data */

{| style="float: right; clear: right; margin: 0 0 0.5em 1em; background: #ffffff;" class="toccolours" border="0" cellpadding="1" align="right" width="300"
! colspan="2" align="center" bgcolor="#dddddd"| Testosterone 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Testosterone structure.png]] 
|-
! colspan="2" align="center" bgcolor="#dddddd"|IUPAC Systematic name
|-
| colspan="2" align="center"| {{{|IUPAC_name = (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,1
6,17-dodecahydrocyclopenta[a]phenanthren-3-one
}}}
|-
! colspan="2" align="center" bgcolor="#dddddd"|Indentifiers
|-
! align="left" bgcolor="#ddeeff" width="120"|[http://en.wikipedia.org/wiki/ATC_code ATC Code]
| align="center"| G03BA03
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/CAS_number CAS number]
| align="center"|58-22-0
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/PubChem PubChem (CID)]
| align="center"|[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6013 6013]
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| align="center"|[http://www.emolecules.com/cgi-bin/search?t=ss&q=CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C
CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C]
|-
! colspan="2" align="center" bgcolor="#dddddd"| Chemical Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| align="center"|C19H28O2
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Molecular_weight Molar mass]
| align="center"|288.43g/mol
|-
! colspan="2" align="center" bgcolor="#dddddd"| Pharmacokinetic Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Bioavailability Bioavailability]
| align="center"|low (due to extensive first pass metabolism)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Metabolism Metabolism]
| align="center"|Liver, Testis and Prostate
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Elimination_half-life Half life]
| align="center"|2-4 hours
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Excretion Excretion]
| align="center"|Urine (90%), feces (6%)
|-
! colspan="2" align="center" bgcolor="#dddddd"| Therapeutic considerations
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Pregnancy_category Pregnancy cat.]
| align="center"|X (USA), Teratogenic effects

|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Regulation_of_therapeutic_goods Legal status]
| align="center"|Schedule III (USA)
Schedule IV (Canada)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Route_of_administration Routes]
| align="center"|Intramuscular injection, transdermal (cream, gel, or patch), sub-'Q' pellet
|-

|}

==Introduction==
The human body produces testosterone, which is the most important male sex hormone. Testosterone is an essential steroid hormone, which is from the androgen hormone group. Testosterone is primarily secreted in the testes of males, which is where the hormone is produced, and the ovaries of females. Minute amounts are secreted by the adrenal glands, which can be found on top of the kidneys. It is the main male sex hormone and it is an anabolic steroid. Testosterone is responsible for development of male characteristics like body and facial hair, muscle growth, strength, and a deep voice. Testosterone at the normal levels in the body influences the production of sperm, which ties in with the promotion of sexual function and in the promotion of sex drive.

[[Image:Test.jpg]]

==Functionality==

The hormone, testosterone, effects humans and other vertebrates by either of the two main hormonal mechanisms; first of these mechanisms is by activation of the androgen receptor (either directly or as DHT) or second is by the conversion to estradiol and the activation of certain estrogen receptors.

''Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5-alpha reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T.[citation needed] The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects. It is important to note that if there is a 5-alpha reductase deficiency, the body (of a human) will continue growing into a female with testicles.''<ref>http://en.wikipedia.org/wiki/Testosterone</ref>

The testerone androgen receptors occur in a large number of different vertebrate body system tissues. Both sexes respond quite similarly to levels of testerone. There is a large difference in the amount of testosterone found in each sex at prenatally, at puberty, and throughout life and this accounts for the share of characteristic biological differences between the sexes.

The brain and the skeletal system are two important tissues in humans, where the principle effect of testosterone is to carry out aromatization of the estradiol. In the bones, estradiol speeds up the maturation of the cartilage into bone and thus leads to the closure of the epiphyses and signals the completion of bone growth.

In the CNS (central nervous system), testosterone is aromatized to estradiol. Not testosterone but estradiol that serves as the most important hormonal feedback signal to the hypothalamus (plays a major role in LH release/production). In a number of mammals, prenatal or perinatal "masculinisation" of the sexually dimorphic sections of the brain by estradiol. This will lead to male sexual behaviour in later life of the mammal.

==Production==
[[Image:Steroidogenesis.gif|thumb|Description]]

==The 3D Molecular Structure==

<jmol>
<jmolApplet>
<title>Hyoscine</title><color>black</color>
<size>350</size>
<script>zoom 120; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Testosterone.pdb</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>dots on</script>
<text>Turn dots on</text>
</jmolButton>
<jmolButton>
<script>dots off</script>
<text>Turn dots off</text>
</jmolButton>
</jmol>

==Spectroscopic Data==

==='''IR Spectrum: Testosterone'''===

[[Image:Testosterone_ir.JPG]]

==='''Mass Spectrum: Testosterone'''===

[[Image:Testosterone_mass.JPG]]

==='''H-NMR Spectrum: Testosterone'''===

[[Image:Testosterone_nmr.JPG]]

==== '''Assignments''' ====

[[Image:Testosterone_nmr_structure.JPG]]

Assign. Shift(ppm)
A 5.731
B 3.655
C 2.424
D 2.391
E 2.347
F 2.278
G 1.6
J 2.084
K 2.034
L 1.862
M 1.848
N 1.702
O 1.628
P 1.603
Q 1.579
R 1.466
S 1.436
T 1.313
U 1.198
V 1.093
W 1.007
X 0.978
Y 0.932
Z 0.795

ASSIGNED BY 600MHZ,C-H COSY,H-H COSY,NOESY AND LAOCN CALCULATION.
K.HAYAMIZU ET AL,MAGN.RESON.CHEM.,28,(1990). <ref>http://riodb01.ibase.aist.go.jp/sdbs/cgi-bin/direct_frame_top.cgi</ref>

== References ==

<references/>

It07:Methylenedioxymethamphetamine

2007-11-09T14:11:08Z

Arw06:

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Methylenedioxymethamphetamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Methylenedioxymethamphetamine.jpg]]

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3,4-methylenedioxy-N-methylamphetamine

|-
| Other names
| N-methyl 1-1-(3,4-methylenedioxyphenyl)-2-propanamine, MDMA, Ecstacy
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C11H15NO2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN[C@@H](C)CC1=CC(OCO2)=C2C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 193.24g/mol
|-
| Appearance
| White crystalline solid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 69610-10-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| -144.4F 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 148 F
|-
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| Neurotoxic 

|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
|-
| Related compounds

| Amphetamine, MDEA, Methylenedioxymethcathinone, Paramethoxyamphetamine.
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-

== Methylenedioxymethamphetamine ==

Often known as MDMA or Ecstacy, 3,4-methylenedioxy-N-methylamphetamine is a semisynthetic empathogen-entactogen, an illegal drug that acts as a stimulant producing an psychedelic energizing effect, as well as distortions in time, perception and enhanced enjoyment of tactile experiences. MDMA exerts its primary effects on neurons in the brain that use the chemical serotonin to communicate with other neurons. Aside from recreational purposes, it is used as a tool to supplement various practices including meditation, psychonautics, and illicit psychedelic psychotherapy.
Research in animals indicates that MDMA is neurotoxic; whether or not this is also true in humans is currently an area of intense investigation. MDMA can also be dangerous to health and, on rare occasions, lethal.

[[Image:Ecstacy-02.jpg]]
<ref>http://www.usdoj.gov/dea/photos/mdma/ecstacy-02.jpg</ref>

== History ==

MDMA was first synthesized in 1912, soon after it was patented in Germany by the Merck Company. At that time it was not the subject of human research, but Merck stumbled across MDMA when they tried to synthesize Hydrastinin, a vasoconstrictive and styptic medicine. MDMA was an unplanned by-product of this synthesis. In the 1950s it was briefly researched by the U.S. Government as part of the CIA's and the Army's chemical warfare investigations into MDMA as a truth serum, which proved to be unsuitable. The first reported recreational use was in the 1960s, where it became known as the love drug. In the mid-70s, the psychedelic therapy community rediscovered it and psychiatrists and therapists began to use it to supplement psychotherapy. In the early 1980s, the drug began to be used recreationally, most notably in Dallas, under the name the street name 'Ecstasy'. The non-medical and therapeutic use of MDMA was made illegal in the USA in 1985. Soon afterwards its use rapidly spread outside the United States, where it was widely used in the UK and other parts of Europe, becoming an integral part of the rave subculture and other psychedelic and dancefloor influenced music scenes.<ref>http://www.a1b2c3.com/drugs/x_01.htm</ref>

== Synthesis ==

Reaction Overview:
The 'ketone' approach is one of many synthesis schemes for the production of MDMA. This basic scheme is the oxidation of the plant oil 'safrole' (1-allyl-3,4-methylenedioxybenzene) into a ketone (3,4-methylenedioxyphenyl-2-propanone), which is then condensed with methylamine and reduced to the final MDMA product.

[[Image:Mdma_synthesis.JPG]]

Step 1: Peroxyacid oxidation (requires isomerization of safrole).

Step 2: Reversible imine formation, which reacts spontaneously when the ketone is added to a solution of methylamine.

Step 3: Reduction, permanently converts the imine to MDMA.
<ref>http://thedea.org/synthesis.html</ref>

== Effects on the Human Body ==

The most common use of MDMA is for recreational purposes. Classed as a stimulant, the effects produced on the human body include euphoria, increased awareness of the senses, feelings of openness, empathy, heightened self-awareness and feeling of mental clarity. Tactile sensations are enhanced for some users resulting in physical contact with others more intense. ‘Alexander Shulgin stated that the single best use of MDMA was to facilitate more direct communication between people involved in significant emotional relationships.’ Physical effects on the body include sweaty palms, heavy sweating, increased heart rate, increased body temperature, and heightened touch sensations.

Naturally there are many health risks involved in taking a stimulant such as MDMA. Physically these risks include hypertension, dehydration and hyperthermia. This is mostly due to the drug's stimulatory effects masking the body's normal sense of exhaustion and thirst.
MDMA is also neurotoxic which means it interferes with brain chemistry, sometimes permanently. The metabolism of MDMA leads to the lipid peroxidation of serotonergic neurons, thus interfering with the brain's ability to effectively use serotonin.
Psychologically, MDMA use often results in a rebound period of poor mood, often known as a ‘comedown’. Obviously this varies in length between different users but can often lead to lasting depression and anxiety in vulnerable users. The longer the time MDMA is active in the brain, the greater the neurotoxic damage to the brain and the greater the risk of short-term emotional problems. The more times MDMA is taken, the greater the risk of any long-term problems.

===Short Term Effects===
In significantly high doses, MDMA can interfere with the body’s ability to regulate temperature, thus effecting homeostasis. On the very rare, but unpredictable occasions, this can possibly lead to a quick sharp increase in body's core temperature (leads to hyperthermia), resulting in failure in the following major organs; liver, kidney, and in cardiovascular system and the worst case scenario is death.

MDMA is a drug that can unfortunately interfere with the body's metabolism of the drug and this can lead to potentially harmful levels, especially if the drug is repeatedly used in a short space of time.

Users of MDMA can face many of the same risks/side effects as casual and frequent users of other stimulants; like cocaine and amphetamines. These typically include increases in heart rate and blood pressure, which is has significantly higher risk for people with either circulatory problems or heart disease, and other symptoms include muscle tension, involuntary teeth clenching, nausea, blurred vision, faintness, and chills or sweating.

Almost two thirds of people who use MDMA report withdrawal symptoms, including fatigue, loss of appetite, depressed feelings, and trouble concentrating.

===Long Term Effects===

MDMA exposure can lead to long-term damage to the neurons in the brain that are involved in the following; mood, thinking, and judgment. There has been a study in nonhuman primates that has been found to show that exposure to MDMA for only 4 days had caused severe damage to serotonin nerve terminals that became apparent 6 to 7 years later. However,similar neurotoxicity in humans has not been definitively shown, but the wealth of all the animal research indicating MDMA’s damaging properties strongly suggests that MDMA an unsafe drug for human consumption.<ref>http://www.usdoj.gov/dea/concern/mdma.html</ref>

== Commonly used names==

MDMA, Ecstasy, XTC, E, X, Beans, Adams, Hug Drug, Disco Biscuit. <ref>http://www.usdoj.gov/dea/concern/mdma.html
</ref>

== Legal Status ==

MDMA is Class A in the UK, making it illegal to sell, buy, or possess without a license. This is typical of almost all countries around the world, but there are however a few countries including Canada and Belgium where possession is legal with a prescription or licence.<ref>http://www.erowid.org/chemicals/mdma/</ref>

== Spectroscopic Data ==

'''NMR Spectrum: 3,4-methylenedioxy-N-methylamphetamine'''

[[Image:Mdma_nmr.JPG]]
<ref>http://www.rsc.org/delivery/_ArticleLinking/DisplayArticleForFree.cfm?doi=b201496n</ref>

== References ==

<references/>

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

It07:Testosterone

2007-11-09T12:28:25Z

Arw06: /* Spectroscopic Data */

{| style="float: right; clear: right; margin: 0 0 0.5em 1em; background: #ffffff;" class="toccolours" border="0" cellpadding="1" align="right" width="300"
! colspan="2" align="center" bgcolor="#dddddd"| Testosterone 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Testosterone structure.png]] 
|-
! colspan="2" align="center" bgcolor="#dddddd"|IUPAC Systematic name
|-
| colspan="2" align="center"| {{{|IUPAC_name = (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,1
6,17-dodecahydrocyclopenta[a]phenanthren-3-one
}}}
|-
! colspan="2" align="center" bgcolor="#dddddd"|Indentifiers
|-
! align="left" bgcolor="#ddeeff" width="120"|[http://en.wikipedia.org/wiki/ATC_code ATC Code]
| align="center"| G03BA03
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/CAS_number CAS number]
| align="center"|58-22-0
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/PubChem PubChem (CID)]
| align="center"|[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6013 6013]
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| align="center"|[http://www.emolecules.com/cgi-bin/search?t=ss&q=CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C
CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C]
|-
! colspan="2" align="center" bgcolor="#dddddd"| Chemical Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| align="center"|C19H28O2
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Molecular_weight Molar mass]
| align="center"|288.43g/mol
|-
! colspan="2" align="center" bgcolor="#dddddd"| Pharmacokinetic Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Bioavailability Bioavailability]
| align="center"|low (due to extensive first pass metabolism)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Metabolism Metabolism]
| align="center"|Liver, Testis and Prostate
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Elimination_half-life Half life]
| align="center"|2-4 hours
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Excretion Excretion]
| align="center"|Urine (90%), feces (6%)
|-
! colspan="2" align="center" bgcolor="#dddddd"| Therapeutic considerations
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Pregnancy_category Pregnancy cat.]
| align="center"|X (USA), Teratogenic effects

|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Regulation_of_therapeutic_goods Legal status]
| align="center"|Schedule III (USA)
Schedule IV (Canada)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Route_of_administration Routes]
| align="center"|Intramuscular injection, transdermal (cream, gel, or patch), sub-'Q' pellet
|-

|}

==Introduction==
The human body produces testosterone, which is the most important male sex hormone. Testosterone is an essential steroid hormone, which is from the androgen hormone group. Testosterone is primarily secreted in the testes of males, which is where the hormone is produced, and the ovaries of females. Minute amounts are secreted by the adrenal glands, which can be found on top of the kidneys. It is the main male sex hormone and it is an anabolic steroid. Testosterone is responsible for development of male characteristics like body and facial hair, muscle growth, strength, and a deep voice. Testosterone at the normal levels in the body influences the production of sperm, which ties in with the promotion of sexual function and in the promotion of sex drive.

[[Image:Test.jpg]]

==How it works==

The hormone, testosterone, effects humans and other vertebrates by either of the two main hormonal mechanisms; first of these mechanisms is by activation of the androgen receptor (either directly or as DHT) or second is by the conversion to estradiol and the activation of certain estrogen receptors.

''Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5-alpha reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T.[citation needed] The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects. It is important to note that if there is a 5-alpha reductase deficiency, the body (of a human) will continue growing into a female with testicles.''<ref>http://en.wikipedia.org/wiki/Testosterone</ref>

The testerone androgen receptors occur in a large number of different vertebrate body system tissues. Both sexes respond quite similarly to levels of testerone. There is a large difference in the amount of testosterone found in each sex at prenatally, at puberty, and throughout life and this accounts for the share of characteristic biological differences between the sexes.

The brain and the skeletal system are two important tissues in humans, where the principle effect of testosterone is to carry out aromatization of the estradiol. In the bones, estradiol speeds up the maturation of the cartilage into bone and thus leads to the closure of the epiphyses and signals the completion of bone growth.

In the CNS (central nervous system), testosterone is aromatized to estradiol. Not testosterone but estradiol that serves as the most important hormonal feedback signal to the hypothalamus (plays a major role in LH release/production). In a number of mammals, prenatal or perinatal "masculinisation" of the sexually dimorphic sections of the brain by estradiol. This will lead to male sexual behaviour in later life of the mammal.

==Production==
[[Image:Steroidogenesis.gif|thumb|Description]]

==The 3D Molecular Structure==

<jmol>
<jmolApplet>
<title>Hyoscine</title><color>black</color>
<size>350</size>
<script>zoom 120; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Testosterone.pdb</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>dots on</script>
<text>Turn dots on</text>
</jmolButton>
<jmolButton>
<script>dots off</script>
<text>Turn dots off</text>
</jmolButton>
</jmol>

==Spectroscopic Data==

==='''IR Spectrum: Testosterone'''===

[[Image:Testosterone_ir.JPG]]

==='''Mass Spectrum: Testosterone'''===

[[Image:Testosterone_mass.JPG]]

==='''NMR Spectrum: Testosterone'''===

[[Image:Testosterone_nmr.JPG]]

==== '''Assignments''' ====

[[Image:Testosterone_nmr_structure.JPG]]

Assign. Shift(ppm)
A 5.731
B 3.655
C 2.424
D 2.391
E 2.347
F 2.278
G 1.6
J 2.084
K 2.034
L 1.862
M 1.848
N 1.702
O 1.628
P 1.603
Q 1.579
R 1.466
S 1.436
T 1.313
U 1.198
V 1.093
W 1.007
X 0.978
Y 0.932
Z 0.795

ASSIGNED BY 600MHZ,C-H COSY,H-H COSY,NOESY AND LAOCN CALCULATION.
K.HAYAMIZU ET AL,MAGN.RESON.CHEM.,28,(1990). <ref>http://riodb01.ibase.aist.go.jp/sdbs/cgi-bin/direct_frame_top.cgi</ref>

== References ==

<references/>

It07:Testosterone

2007-11-09T12:25:33Z

Arw06:

{| style="float: right; clear: right; margin: 0 0 0.5em 1em; background: #ffffff;" class="toccolours" border="0" cellpadding="1" align="right" width="300"
! colspan="2" align="center" bgcolor="#dddddd"| Testosterone 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Testosterone structure.png]] 
|-
! colspan="2" align="center" bgcolor="#dddddd"|IUPAC Systematic name
|-
| colspan="2" align="center"| {{{|IUPAC_name = (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,1
6,17-dodecahydrocyclopenta[a]phenanthren-3-one
}}}
|-
! colspan="2" align="center" bgcolor="#dddddd"|Indentifiers
|-
! align="left" bgcolor="#ddeeff" width="120"|[http://en.wikipedia.org/wiki/ATC_code ATC Code]
| align="center"| G03BA03
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/CAS_number CAS number]
| align="center"|58-22-0
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/PubChem PubChem (CID)]
| align="center"|[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6013 6013]
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| align="center"|[http://www.emolecules.com/cgi-bin/search?t=ss&q=CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C
CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C]
|-
! colspan="2" align="center" bgcolor="#dddddd"| Chemical Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| align="center"|C19H28O2
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Molecular_weight Molar mass]
| align="center"|288.43g/mol
|-
! colspan="2" align="center" bgcolor="#dddddd"| Pharmacokinetic Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Bioavailability Bioavailability]
| align="center"|low (due to extensive first pass metabolism)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Metabolism Metabolism]
| align="center"|Liver, Testis and Prostate
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Elimination_half-life Half life]
| align="center"|2-4 hours
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Excretion Excretion]
| align="center"|Urine (90%), feces (6%)
|-
! colspan="2" align="center" bgcolor="#dddddd"| Therapeutic considerations
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Pregnancy_category Pregnancy cat.]
| align="center"|X (USA), Teratogenic effects

|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Regulation_of_therapeutic_goods Legal status]
| align="center"|Schedule III (USA)
Schedule IV (Canada)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Route_of_administration Routes]
| align="center"|Intramuscular injection, transdermal (cream, gel, or patch), sub-'Q' pellet
|-

|}

==Introduction==
The human body produces testosterone, which is the most important male sex hormone. Testosterone is an essential steroid hormone, which is from the androgen hormone group. Testosterone is primarily secreted in the testes of males, which is where the hormone is produced, and the ovaries of females. Minute amounts are secreted by the adrenal glands, which can be found on top of the kidneys. It is the main male sex hormone and it is an anabolic steroid. Testosterone is responsible for development of male characteristics like body and facial hair, muscle growth, strength, and a deep voice. Testosterone at the normal levels in the body influences the production of sperm, which ties in with the promotion of sexual function and in the promotion of sex drive.

[[Image:Test.jpg]]

==How it works==

The hormone, testosterone, effects humans and other vertebrates by either of the two main hormonal mechanisms; first of these mechanisms is by activation of the androgen receptor (either directly or as DHT) or second is by the conversion to estradiol and the activation of certain estrogen receptors.

''Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5-alpha reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T.[citation needed] The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects. It is important to note that if there is a 5-alpha reductase deficiency, the body (of a human) will continue growing into a female with testicles.''<ref>http://en.wikipedia.org/wiki/Testosterone</ref>

The testerone androgen receptors occur in a large number of different vertebrate body system tissues. Both sexes respond quite similarly to levels of testerone. There is a large difference in the amount of testosterone found in each sex at prenatally, at puberty, and throughout life and this accounts for the share of characteristic biological differences between the sexes.

The brain and the skeletal system are two important tissues in humans, where the principle effect of testosterone is to carry out aromatization of the estradiol. In the bones, estradiol speeds up the maturation of the cartilage into bone and thus leads to the closure of the epiphyses and signals the completion of bone growth.

In the CNS (central nervous system), testosterone is aromatized to estradiol. Not testosterone but estradiol that serves as the most important hormonal feedback signal to the hypothalamus (plays a major role in LH release/production). In a number of mammals, prenatal or perinatal "masculinisation" of the sexually dimorphic sections of the brain by estradiol. This will lead to male sexual behaviour in later life of the mammal.

==Production==
[[Image:Steroidogenesis.gif|thumb|Description]]

==The 3D Molecular Structure==

<jmol>
<jmolApplet>
<title>Hyoscine</title><color>black</color>
<size>350</size>
<script>zoom 120; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Testosterone.pdb</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>dots on</script>
<text>Turn dots on</text>
</jmolButton>
<jmolButton>
<script>dots off</script>
<text>Turn dots off</text>
</jmolButton>
</jmol>

==Spectroscopic Data==

==='''IR Spectrum: Testosterone'''===

[[Image:Testosterone_ir.JPG]]

==='''Mass Spectrum: Testosterone'''===

[[Image:Testosterone_mass.JPG]]

==='''NMR Spectrum: Testosterone'''===

[[Image:Testosterone_nmr.JPG]]

==== '''Assignments''' ====

[[Image:Testosterone_nmr_structure.JPG]]

Assign. Shift(ppm)
A 5.731
B 3.655
C 2.424
D 2.391
E 2.347
F 2.278
G 1.6
J 2.084
K 2.034
L 1.862
M 1.848
N 1.702
O 1.628
P 1.603
Q 1.579
R 1.466
S 1.436
T 1.313
U 1.198
V 1.093
W 1.007
X 0.978
Y 0.932
Z 0.795

ASSIGNED BY 600MHZ,C-H COSY,H-H COSY,NOESY AND LAOCN CALCULATION.
K.HAYAMIZU ET AL,MAGN.RESON.CHEM.,28,(1990).

== References ==

<references/>

It07:Testosterone

2007-11-09T12:24:33Z

Arw06: /* '''NMR Spectrum: Testosterone''' */

{| style="float: right; clear: right; margin: 0 0 0.5em 1em; background: #ffffff;" class="toccolours" border="0" cellpadding="1" align="right" width="300"
! colspan="2" align="center" bgcolor="#dddddd"| Testosterone 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Testosterone structure.png]] 
|-
! colspan="2" align="center" bgcolor="#dddddd"|IUPAC Systematic name
|-
| colspan="2" align="center"| {{{|IUPAC_name = (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,1
6,17-dodecahydrocyclopenta[a]phenanthren-3-one
}}}
|-
! colspan="2" align="center" bgcolor="#dddddd"|Indentifiers
|-
! align="left" bgcolor="#ddeeff" width="120"|[http://en.wikipedia.org/wiki/ATC_code ATC Code]
| align="center"| G03BA03
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/CAS_number CAS number]
| align="center"|58-22-0
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/PubChem PubChem (CID)]
| align="center"|[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6013 6013]
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| align="center"|[http://www.emolecules.com/cgi-bin/search?t=ss&q=CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C
CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C]
|-
! colspan="2" align="center" bgcolor="#dddddd"| Chemical Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| align="center"|C19H28O2
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Molecular_weight Molar mass]
| align="center"|288.43g/mol
|-
! colspan="2" align="center" bgcolor="#dddddd"| Pharmacokinetic Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Bioavailability Bioavailability]
| align="center"|low (due to extensive first pass metabolism)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Metabolism Metabolism]
| align="center"|Liver, Testis and Prostate
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Elimination_half-life Half life]
| align="center"|2-4 hours
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Excretion Excretion]
| align="center"|Urine (90%), feces (6%)
|-
! colspan="2" align="center" bgcolor="#dddddd"| Therapeutic considerations
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Pregnancy_category Pregnancy cat.]
| align="center"|X (USA), Teratogenic effects

|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Regulation_of_therapeutic_goods Legal status]
| align="center"|Schedule III (USA)
Schedule IV (Canada)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Route_of_administration Routes]
| align="center"|Intramuscular injection, transdermal (cream, gel, or patch), sub-'Q' pellet
|-

|}

==Introduction==
The human body produces testosterone, which is the most important male sex hormone. Testosterone is an essential steroid hormone, which is from the androgen hormone group. Testosterone is primarily secreted in the testes of males, which is where the hormone is produced, and the ovaries of females. Minute amounts are secreted by the adrenal glands, which can be found on top of the kidneys. It is the main male sex hormone and it is an anabolic steroid. Testosterone is responsible for development of male characteristics like body and facial hair, muscle growth, strength, and a deep voice. Testosterone at the normal levels in the body influences the production of sperm, which ties in with the promotion of sexual function and in the promotion of sex drive.

[[Image:Test.jpg]]

==How it works==

The hormone, testosterone, effects humans and other vertebrates by either of the two main hormonal mechanisms; first of these mechanisms is by activation of the androgen receptor (either directly or as DHT) or second is by the conversion to estradiol and the activation of certain estrogen receptors.

''Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5-alpha reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T.[citation needed] The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects. It is important to note that if there is a 5-alpha reductase deficiency, the body (of a human) will continue growing into a female with testicles.''<ref>http://en.wikipedia.org/wiki/Testosterone</ref>

The testerone androgen receptors occur in a large number of different vertebrate body system tissues. Both sexes respond quite similarly to levels of testerone. There is a large difference in the amount of testosterone found in each sex at prenatally, at puberty, and throughout life and this accounts for the share of characteristic biological differences between the sexes.

The brain and the skeletal system are two important tissues in humans, where the principle effect of testosterone is to carry out aromatization of the estradiol. In the bones, estradiol speeds up the maturation of the cartilage into bone and thus leads to the closure of the epiphyses and signals the completion of bone growth.

In the CNS (central nervous system), testosterone is aromatized to estradiol. Not testosterone but estradiol that serves as the most important hormonal feedback signal to the hypothalamus (plays a major role in LH release/production). In a number of mammals, prenatal or perinatal "masculinisation" of the sexually dimorphic sections of the brain by estradiol. This will lead to male sexual behaviour in later life of the mammal.

==Production==
[[Image:Steroidogenesis.gif|thumb|Description]]

==The 3D Molecular Structure==

<jmol>
<jmolApplet>
<title>Hyoscine</title><color>black</color>
<size>350</size>
<script>zoom 120; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Testosterone.pdb</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>dots on</script>
<text>Turn dots on</text>
</jmolButton>
<jmolButton>
<script>dots off</script>
<text>Turn dots off</text>
</jmolButton>
</jmol>

==Spectroscopic Data==

==='''IR Spectrum: Testosterone'''===

[[Image:Testosterone_ir.JPG]]

==='''Mass Spectrum: Testosterone'''===

[[Image:Testosterone_mass.JPG]]

==='''NMR Spectrum: Testosterone'''===

[[Image:Testosterone_nmr.JPG]]

==== '''Assignments''' ====

[[Image:Testosterone_nmr_structure.JPG]]

Assign. Shift(ppm)
A 5.731
B 3.655
C 2.424
D 2.391
E 2.347
F 2.278
G 1.6
J 2.084
K 2.034
L 1.862
M 1.848
N 1.702
O 1.628
P 1.603
Q 1.579
R 1.466
S 1.436
T 1.313
U 1.198
V 1.093
W 1.007
X 0.978
Y 0.932
Z 0.795

ASSIGNED BY 600MHZ,C-H COSY,H-H COSY,NOESY AND LAOCN CALCULATION.
K.HAYAMIZU ET AL,MAGN.RESON.CHEM.,28,(1990).

It07:Testosterone

2007-11-09T12:24:02Z

Arw06: /* '''NMR Spectrum: Testosterone''' */

{| style="float: right; clear: right; margin: 0 0 0.5em 1em; background: #ffffff;" class="toccolours" border="0" cellpadding="1" align="right" width="300"
! colspan="2" align="center" bgcolor="#dddddd"| Testosterone 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Testosterone structure.png]] 
|-
! colspan="2" align="center" bgcolor="#dddddd"|IUPAC Systematic name
|-
| colspan="2" align="center"| {{{|IUPAC_name = (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,1
6,17-dodecahydrocyclopenta[a]phenanthren-3-one
}}}
|-
! colspan="2" align="center" bgcolor="#dddddd"|Indentifiers
|-
! align="left" bgcolor="#ddeeff" width="120"|[http://en.wikipedia.org/wiki/ATC_code ATC Code]
| align="center"| G03BA03
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/CAS_number CAS number]
| align="center"|58-22-0
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/PubChem PubChem (CID)]
| align="center"|[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6013 6013]
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| align="center"|[http://www.emolecules.com/cgi-bin/search?t=ss&q=CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C
CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C]
|-
! colspan="2" align="center" bgcolor="#dddddd"| Chemical Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| align="center"|C19H28O2
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Molecular_weight Molar mass]
| align="center"|288.43g/mol
|-
! colspan="2" align="center" bgcolor="#dddddd"| Pharmacokinetic Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Bioavailability Bioavailability]
| align="center"|low (due to extensive first pass metabolism)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Metabolism Metabolism]
| align="center"|Liver, Testis and Prostate
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Elimination_half-life Half life]
| align="center"|2-4 hours
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Excretion Excretion]
| align="center"|Urine (90%), feces (6%)
|-
! colspan="2" align="center" bgcolor="#dddddd"| Therapeutic considerations
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Pregnancy_category Pregnancy cat.]
| align="center"|X (USA), Teratogenic effects

|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Regulation_of_therapeutic_goods Legal status]
| align="center"|Schedule III (USA)
Schedule IV (Canada)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Route_of_administration Routes]
| align="center"|Intramuscular injection, transdermal (cream, gel, or patch), sub-'Q' pellet
|-

|}

==Introduction==
The human body produces testosterone, which is the most important male sex hormone. Testosterone is an essential steroid hormone, which is from the androgen hormone group. Testosterone is primarily secreted in the testes of males, which is where the hormone is produced, and the ovaries of females. Minute amounts are secreted by the adrenal glands, which can be found on top of the kidneys. It is the main male sex hormone and it is an anabolic steroid. Testosterone is responsible for development of male characteristics like body and facial hair, muscle growth, strength, and a deep voice. Testosterone at the normal levels in the body influences the production of sperm, which ties in with the promotion of sexual function and in the promotion of sex drive.

[[Image:Test.jpg]]

==How it works==

The hormone, testosterone, effects humans and other vertebrates by either of the two main hormonal mechanisms; first of these mechanisms is by activation of the androgen receptor (either directly or as DHT) or second is by the conversion to estradiol and the activation of certain estrogen receptors.

''Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5-alpha reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T.[citation needed] The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects. It is important to note that if there is a 5-alpha reductase deficiency, the body (of a human) will continue growing into a female with testicles.''<ref>http://en.wikipedia.org/wiki/Testosterone</ref>

The testerone androgen receptors occur in a large number of different vertebrate body system tissues. Both sexes respond quite similarly to levels of testerone. There is a large difference in the amount of testosterone found in each sex at prenatally, at puberty, and throughout life and this accounts for the share of characteristic biological differences between the sexes.

The brain and the skeletal system are two important tissues in humans, where the principle effect of testosterone is to carry out aromatization of the estradiol. In the bones, estradiol speeds up the maturation of the cartilage into bone and thus leads to the closure of the epiphyses and signals the completion of bone growth.

In the CNS (central nervous system), testosterone is aromatized to estradiol. Not testosterone but estradiol that serves as the most important hormonal feedback signal to the hypothalamus (plays a major role in LH release/production). In a number of mammals, prenatal or perinatal "masculinisation" of the sexually dimorphic sections of the brain by estradiol. This will lead to male sexual behaviour in later life of the mammal.

==Production==
[[Image:Steroidogenesis.gif|thumb|Description]]

==The 3D Molecular Structure==

<jmol>
<jmolApplet>
<title>Hyoscine</title><color>black</color>
<size>350</size>
<script>zoom 120; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Testosterone.pdb</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>dots on</script>
<text>Turn dots on</text>
</jmolButton>
<jmolButton>
<script>dots off</script>
<text>Turn dots off</text>
</jmolButton>
</jmol>

==Spectroscopic Data==

==='''IR Spectrum: Testosterone'''===

[[Image:Testosterone_ir.JPG]]

==='''Mass Spectrum: Testosterone'''===

[[Image:Testosterone_mass.JPG]]

==='''NMR Spectrum: Testosterone'''===

[[Image:Testosterone_nmr.JPG]]

==== '''Assignments''' ====

[[Image:Testosterone_nmr_structure.JPG]]

Assign. Shift(ppm)
A 5.731
B 3.655
C 2.424
D 2.391
E 2.347
F 2.278
G 1.6
J 2.084
K 2.034
L 1.862
M 1.848
N 1.702
O 1.628
P 1.603
Q 1.579
R 1.466
S 1.436
T 1.313
U 1.198
V 1.093
W 1.007
X 0.978
Y 0.932
Z 0.795

ASSIGNED BY 600MHZ,C-H COSY,H-H COSY,NOESY AND LAOCN CALCULATION.
K.HAYAMIZU ET AL,MAGN.RESON.CHEM.,28,(1990).

It07:Testosterone

2007-11-09T12:23:19Z

Arw06: /* Spectroscopic Data */

{| style="float: right; clear: right; margin: 0 0 0.5em 1em; background: #ffffff;" class="toccolours" border="0" cellpadding="1" align="right" width="300"
! colspan="2" align="center" bgcolor="#dddddd"| Testosterone 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Testosterone structure.png]] 
|-
! colspan="2" align="center" bgcolor="#dddddd"|IUPAC Systematic name
|-
| colspan="2" align="center"| {{{|IUPAC_name = (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,1
6,17-dodecahydrocyclopenta[a]phenanthren-3-one
}}}
|-
! colspan="2" align="center" bgcolor="#dddddd"|Indentifiers
|-
! align="left" bgcolor="#ddeeff" width="120"|[http://en.wikipedia.org/wiki/ATC_code ATC Code]
| align="center"| G03BA03
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/CAS_number CAS number]
| align="center"|58-22-0
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/PubChem PubChem (CID)]
| align="center"|[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6013 6013]
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| align="center"|[http://www.emolecules.com/cgi-bin/search?t=ss&q=CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C
CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C]
|-
! colspan="2" align="center" bgcolor="#dddddd"| Chemical Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| align="center"|C19H28O2
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Molecular_weight Molar mass]
| align="center"|288.43g/mol
|-
! colspan="2" align="center" bgcolor="#dddddd"| Pharmacokinetic Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Bioavailability Bioavailability]
| align="center"|low (due to extensive first pass metabolism)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Metabolism Metabolism]
| align="center"|Liver, Testis and Prostate
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Elimination_half-life Half life]
| align="center"|2-4 hours
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Excretion Excretion]
| align="center"|Urine (90%), feces (6%)
|-
! colspan="2" align="center" bgcolor="#dddddd"| Therapeutic considerations
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Pregnancy_category Pregnancy cat.]
| align="center"|X (USA), Teratogenic effects

|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Regulation_of_therapeutic_goods Legal status]
| align="center"|Schedule III (USA)
Schedule IV (Canada)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Route_of_administration Routes]
| align="center"|Intramuscular injection, transdermal (cream, gel, or patch), sub-'Q' pellet
|-

|}

==Introduction==
The human body produces testosterone, which is the most important male sex hormone. Testosterone is an essential steroid hormone, which is from the androgen hormone group. Testosterone is primarily secreted in the testes of males, which is where the hormone is produced, and the ovaries of females. Minute amounts are secreted by the adrenal glands, which can be found on top of the kidneys. It is the main male sex hormone and it is an anabolic steroid. Testosterone is responsible for development of male characteristics like body and facial hair, muscle growth, strength, and a deep voice. Testosterone at the normal levels in the body influences the production of sperm, which ties in with the promotion of sexual function and in the promotion of sex drive.

[[Image:Test.jpg]]

==How it works==

The hormone, testosterone, effects humans and other vertebrates by either of the two main hormonal mechanisms; first of these mechanisms is by activation of the androgen receptor (either directly or as DHT) or second is by the conversion to estradiol and the activation of certain estrogen receptors.

''Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5-alpha reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T.[citation needed] The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects. It is important to note that if there is a 5-alpha reductase deficiency, the body (of a human) will continue growing into a female with testicles.''<ref>http://en.wikipedia.org/wiki/Testosterone</ref>

The testerone androgen receptors occur in a large number of different vertebrate body system tissues. Both sexes respond quite similarly to levels of testerone. There is a large difference in the amount of testosterone found in each sex at prenatally, at puberty, and throughout life and this accounts for the share of characteristic biological differences between the sexes.

The brain and the skeletal system are two important tissues in humans, where the principle effect of testosterone is to carry out aromatization of the estradiol. In the bones, estradiol speeds up the maturation of the cartilage into bone and thus leads to the closure of the epiphyses and signals the completion of bone growth.

In the CNS (central nervous system), testosterone is aromatized to estradiol. Not testosterone but estradiol that serves as the most important hormonal feedback signal to the hypothalamus (plays a major role in LH release/production). In a number of mammals, prenatal or perinatal "masculinisation" of the sexually dimorphic sections of the brain by estradiol. This will lead to male sexual behaviour in later life of the mammal.

==Production==
[[Image:Steroidogenesis.gif|thumb|Description]]

==The 3D Molecular Structure==

<jmol>
<jmolApplet>
<title>Hyoscine</title><color>black</color>
<size>350</size>
<script>zoom 120; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Testosterone.pdb</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>dots on</script>
<text>Turn dots on</text>
</jmolButton>
<jmolButton>
<script>dots off</script>
<text>Turn dots off</text>
</jmolButton>
</jmol>

==Spectroscopic Data==

==='''IR Spectrum: Testosterone'''===

[[Image:Testosterone_ir.JPG]]

==='''Mass Spectrum: Testosterone'''===

[[Image:Testosterone_mass.JPG]]

==='''NMR Spectrum: Testosterone'''===

[[Image:Testosterone_nmr.JPG]]

[[Image:Testosterone_nmr_structure.JPG]]

Assign. Shift(ppm)
A 5.731
B 3.655
C 2.424
D 2.391
E 2.347
F 2.278
G 1.6
J 2.084
K 2.034
L 1.862
M 1.848
N 1.702
O 1.628
P 1.603
Q 1.579
R 1.466
S 1.436
T 1.313
U 1.198
V 1.093
W 1.007
X 0.978
Y 0.932
Z 0.795

ASSIGNED BY 600MHZ,C-H COSY,H-H COSY,NOESY AND LAOCN CALCULATION.
K.HAYAMIZU ET AL,MAGN.RESON.CHEM.,28,(1990).

It07:Testosterone

2007-11-09T12:19:01Z

Arw06: /* Spectroscopic Data */

{| style="float: right; clear: right; margin: 0 0 0.5em 1em; background: #ffffff;" class="toccolours" border="0" cellpadding="1" align="right" width="300"
! colspan="2" align="center" bgcolor="#dddddd"| Testosterone 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Testosterone structure.png]] 
|-
! colspan="2" align="center" bgcolor="#dddddd"|IUPAC Systematic name
|-
| colspan="2" align="center"| {{{|IUPAC_name = (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,1
6,17-dodecahydrocyclopenta[a]phenanthren-3-one
}}}
|-
! colspan="2" align="center" bgcolor="#dddddd"|Indentifiers
|-
! align="left" bgcolor="#ddeeff" width="120"|[http://en.wikipedia.org/wiki/ATC_code ATC Code]
| align="center"| G03BA03
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/CAS_number CAS number]
| align="center"|58-22-0
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/PubChem PubChem (CID)]
| align="center"|[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6013 6013]
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| align="center"|[http://www.emolecules.com/cgi-bin/search?t=ss&q=CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C
CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C]
|-
! colspan="2" align="center" bgcolor="#dddddd"| Chemical Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| align="center"|C19H28O2
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Molecular_weight Molar mass]
| align="center"|288.43g/mol
|-
! colspan="2" align="center" bgcolor="#dddddd"| Pharmacokinetic Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Bioavailability Bioavailability]
| align="center"|low (due to extensive first pass metabolism)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Metabolism Metabolism]
| align="center"|Liver, Testis and Prostate
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Elimination_half-life Half life]
| align="center"|2-4 hours
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Excretion Excretion]
| align="center"|Urine (90%), feces (6%)
|-
! colspan="2" align="center" bgcolor="#dddddd"| Therapeutic considerations
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Pregnancy_category Pregnancy cat.]
| align="center"|X (USA), Teratogenic effects

|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Regulation_of_therapeutic_goods Legal status]
| align="center"|Schedule III (USA)
Schedule IV (Canada)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Route_of_administration Routes]
| align="center"|Intramuscular injection, transdermal (cream, gel, or patch), sub-'Q' pellet
|-

|}

==Introduction==
The human body produces testosterone, which is the most important male sex hormone. Testosterone is an essential steroid hormone, which is from the androgen hormone group. Testosterone is primarily secreted in the testes of males, which is where the hormone is produced, and the ovaries of females. Minute amounts are secreted by the adrenal glands, which can be found on top of the kidneys. It is the main male sex hormone and it is an anabolic steroid. Testosterone is responsible for development of male characteristics like body and facial hair, muscle growth, strength, and a deep voice. Testosterone at the normal levels in the body influences the production of sperm, which ties in with the promotion of sexual function and in the promotion of sex drive.

==How it works==

The hormone, testosterone, effects humans and other vertebrates by either of the two main hormonal mechanisms; first of these mechanisms is by activation of the androgen receptor (either directly or as DHT) or second is by the conversion to estradiol and the activation of certain estrogen receptors.

''Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5-alpha reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T.[citation needed] The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects. It is important to note that if there is a 5-alpha reductase deficiency, the body (of a human) will continue growing into a female with testicles.''<ref>http://en.wikipedia.org/wiki/Testosterone</ref>

The testerone androgen receptors occur in a large number of different vertebrate body system tissues. Both sexes respond quite similarly to levels of testerone. There is a large difference in the amount of testosterone found in each sex at prenatally, at puberty, and throughout life and this accounts for the share of characteristic biological differences between the sexes.

==Production==
[[Image:Steroidogenesis.gif|thumb|Description]]

[[Image:Test.jpg]]

===The 3D Molecular Structure===

<jmol>
<jmolApplet>
<title>Hyoscine</title><color>black</color>
<size>350</size>
<script>zoom 120; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Testosterone.pdb</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>dots on</script>
<text>Turn dots on</text>
</jmolButton>
<jmolButton>
<script>dots off</script>
<text>Turn dots off</text>
</jmolButton>
</jmol>

==Spectroscopic Data==

==='''IR Spectrum: Testosterone'''===

[[Image:Testosterone_ir.JPG]]

==='''Mass Spectrum: Testosterone'''===

[[Image:Testosterone_mass.JPG]]

==='''NMR Spectrum: Testosterone'''===

[[Image:Testosterone_nmr.JPG]]

[[Image:Testosterone_nmr_structure.JPG]]

It07:Testosterone

2007-11-09T12:17:49Z

Arw06: /* Spectroscopic Data */

{| style="float: right; clear: right; margin: 0 0 0.5em 1em; background: #ffffff;" class="toccolours" border="0" cellpadding="1" align="right" width="300"
! colspan="2" align="center" bgcolor="#dddddd"| Testosterone 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Testosterone structure.png]] 
|-
! colspan="2" align="center" bgcolor="#dddddd"|IUPAC Systematic name
|-
| colspan="2" align="center"| {{{|IUPAC_name = (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,1
6,17-dodecahydrocyclopenta[a]phenanthren-3-one
}}}
|-
! colspan="2" align="center" bgcolor="#dddddd"|Indentifiers
|-
! align="left" bgcolor="#ddeeff" width="120"|[http://en.wikipedia.org/wiki/ATC_code ATC Code]
| align="center"| G03BA03
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/CAS_number CAS number]
| align="center"|58-22-0
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/PubChem PubChem (CID)]
| align="center"|[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6013 6013]
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| align="center"|[http://www.emolecules.com/cgi-bin/search?t=ss&q=CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C
CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C]
|-
! colspan="2" align="center" bgcolor="#dddddd"| Chemical Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| align="center"|C19H28O2
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Molecular_weight Molar mass]
| align="center"|288.43g/mol
|-
! colspan="2" align="center" bgcolor="#dddddd"| Pharmacokinetic Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Bioavailability Bioavailability]
| align="center"|low (due to extensive first pass metabolism)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Metabolism Metabolism]
| align="center"|Liver, Testis and Prostate
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Elimination_half-life Half life]
| align="center"|2-4 hours
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Excretion Excretion]
| align="center"|Urine (90%), feces (6%)
|-
! colspan="2" align="center" bgcolor="#dddddd"| Therapeutic considerations
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Pregnancy_category Pregnancy cat.]
| align="center"|X (USA), Teratogenic effects

|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Regulation_of_therapeutic_goods Legal status]
| align="center"|Schedule III (USA)
Schedule IV (Canada)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Route_of_administration Routes]
| align="center"|Intramuscular injection, transdermal (cream, gel, or patch), sub-'Q' pellet
|-

|}

==Introduction==
The human body produces testosterone, which is the most important male sex hormone. Testosterone is an essential steroid hormone, which is from the androgen hormone group. Testosterone is primarily secreted in the testes of males, which is where the hormone is produced, and the ovaries of females. Minute amounts are secreted by the adrenal glands, which can be found on top of the kidneys. It is the main male sex hormone and it is an anabolic steroid. Testosterone is responsible for development of male characteristics like body and facial hair, muscle growth, strength, and a deep voice. Testosterone at the normal levels in the body influences the production of sperm, which ties in with the promotion of sexual function and in the promotion of sex drive.

==How it works==

The hormone, testosterone, effects humans and other vertebrates by either of the two main hormonal mechanisms; first of these mechanisms is by activation of the androgen receptor (either directly or as DHT) or second is by the conversion to estradiol and the activation of certain estrogen receptors.

''Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5-alpha reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T.[citation needed] The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects. It is important to note that if there is a 5-alpha reductase deficiency, the body (of a human) will continue growing into a female with testicles.''<ref>http://en.wikipedia.org/wiki/Testosterone</ref>

The testerone androgen receptors occur in a large number of different vertebrate body system tissues. Both sexes respond quite similarly to levels of testerone. There is a large difference in the amount of testosterone found in each sex at prenatally, at puberty, and throughout life and this accounts for the share of characteristic biological differences between the sexes.

==Production==
[[Image:Steroidogenesis.gif|thumb|Description]]

[[Image:Test.jpg]]

===The 3D Molecular Structure===

<jmol>
<jmolApplet>
<title>Hyoscine</title><color>black</color>
<size>350</size>
<script>zoom 120; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Testosterone.pdb</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>dots on</script>
<text>Turn dots on</text>
</jmolButton>
<jmolButton>
<script>dots off</script>
<text>Turn dots off</text>
</jmolButton>
</jmol>

==Spectroscopic Data==

==='''IR Spectrum: Testosterone'''===

[[Image:Testosterone_ir.JPG]]

==='''Mass Spectrum: Testosterone'''===

[[Image:Testosterone_mass.JPG]]

==='''NMR Spectrum: Testosterone'''===

[[Image:Testosterone_nmr.JPG]]

It07:Testosterone

2007-11-09T12:17:07Z

Arw06: /* Spectroscopic Data */

{| style="float: right; clear: right; margin: 0 0 0.5em 1em; background: #ffffff;" class="toccolours" border="0" cellpadding="1" align="right" width="300"
! colspan="2" align="center" bgcolor="#dddddd"| Testosterone 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Testosterone structure.png]] 
|-
! colspan="2" align="center" bgcolor="#dddddd"|IUPAC Systematic name
|-
| colspan="2" align="center"| {{{|IUPAC_name = (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,1
6,17-dodecahydrocyclopenta[a]phenanthren-3-one
}}}
|-
! colspan="2" align="center" bgcolor="#dddddd"|Indentifiers
|-
! align="left" bgcolor="#ddeeff" width="120"|[http://en.wikipedia.org/wiki/ATC_code ATC Code]
| align="center"| G03BA03
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/CAS_number CAS number]
| align="center"|58-22-0
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/PubChem PubChem (CID)]
| align="center"|[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6013 6013]
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| align="center"|[http://www.emolecules.com/cgi-bin/search?t=ss&q=CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C
CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C]
|-
! colspan="2" align="center" bgcolor="#dddddd"| Chemical Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| align="center"|C19H28O2
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Molecular_weight Molar mass]
| align="center"|288.43g/mol
|-
! colspan="2" align="center" bgcolor="#dddddd"| Pharmacokinetic Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Bioavailability Bioavailability]
| align="center"|low (due to extensive first pass metabolism)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Metabolism Metabolism]
| align="center"|Liver, Testis and Prostate
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Elimination_half-life Half life]
| align="center"|2-4 hours
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Excretion Excretion]
| align="center"|Urine (90%), feces (6%)
|-
! colspan="2" align="center" bgcolor="#dddddd"| Therapeutic considerations
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Pregnancy_category Pregnancy cat.]
| align="center"|X (USA), Teratogenic effects

|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Regulation_of_therapeutic_goods Legal status]
| align="center"|Schedule III (USA)
Schedule IV (Canada)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Route_of_administration Routes]
| align="center"|Intramuscular injection, transdermal (cream, gel, or patch), sub-'Q' pellet
|-

|}

==Introduction==
The human body produces testosterone, which is the most important male sex hormone. Testosterone is an essential steroid hormone, which is from the androgen hormone group. Testosterone is primarily secreted in the testes of males, which is where the hormone is produced, and the ovaries of females. Minute amounts are secreted by the adrenal glands, which can be found on top of the kidneys. It is the main male sex hormone and it is an anabolic steroid. Testosterone is responsible for development of male characteristics like body and facial hair, muscle growth, strength, and a deep voice. Testosterone at the normal levels in the body influences the production of sperm, which ties in with the promotion of sexual function and in the promotion of sex drive.

==How it works==

The hormone, testosterone, effects humans and other vertebrates by either of the two main hormonal mechanisms; first of these mechanisms is by activation of the androgen receptor (either directly or as DHT) or second is by the conversion to estradiol and the activation of certain estrogen receptors.

''Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5-alpha reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T.[citation needed] The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects. It is important to note that if there is a 5-alpha reductase deficiency, the body (of a human) will continue growing into a female with testicles.''<ref>http://en.wikipedia.org/wiki/Testosterone</ref>

The testerone androgen receptors occur in a large number of different vertebrate body system tissues. Both sexes respond quite similarly to levels of testerone. There is a large difference in the amount of testosterone found in each sex at prenatally, at puberty, and throughout life and this accounts for the share of characteristic biological differences between the sexes.

==Production==
[[Image:Steroidogenesis.gif|thumb|Description]]

[[Image:Test.jpg]]

===The 3D Molecular Structure===

<jmol>
<jmolApplet>
<title>Hyoscine</title><color>black</color>
<size>350</size>
<script>zoom 120; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Testosterone.pdb</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>dots on</script>
<text>Turn dots on</text>
</jmolButton>
<jmolButton>
<script>dots off</script>
<text>Turn dots off</text>
</jmolButton>
</jmol>

==Spectroscopic Data==

==='''IR Spectrum: Testosterone'''===

[[Image:Testosterone_ir.JPG]]

==='''Mass Spectrum: Testosterone'''===

[[Image:Testosterone_mass.JPG]]

==='''NMR Spectrum: Testosterone'''===

[[Image:Testosterone_nmr.JPG]]

It07:Testosterone

2007-11-09T12:16:26Z

Arw06: /* Spectroscopic Data */

{| style="float: right; clear: right; margin: 0 0 0.5em 1em; background: #ffffff;" class="toccolours" border="0" cellpadding="1" align="right" width="300"
! colspan="2" align="center" bgcolor="#dddddd"| Testosterone 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Testosterone structure.png]] 
|-
! colspan="2" align="center" bgcolor="#dddddd"|IUPAC Systematic name
|-
| colspan="2" align="center"| {{{|IUPAC_name = (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,1
6,17-dodecahydrocyclopenta[a]phenanthren-3-one
}}}
|-
! colspan="2" align="center" bgcolor="#dddddd"|Indentifiers
|-
! align="left" bgcolor="#ddeeff" width="120"|[http://en.wikipedia.org/wiki/ATC_code ATC Code]
| align="center"| G03BA03
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/CAS_number CAS number]
| align="center"|58-22-0
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/PubChem PubChem (CID)]
| align="center"|[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6013 6013]
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| align="center"|[http://www.emolecules.com/cgi-bin/search?t=ss&q=CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C
CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C]
|-
! colspan="2" align="center" bgcolor="#dddddd"| Chemical Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| align="center"|C19H28O2
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Molecular_weight Molar mass]
| align="center"|288.43g/mol
|-
! colspan="2" align="center" bgcolor="#dddddd"| Pharmacokinetic Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Bioavailability Bioavailability]
| align="center"|low (due to extensive first pass metabolism)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Metabolism Metabolism]
| align="center"|Liver, Testis and Prostate
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Elimination_half-life Half life]
| align="center"|2-4 hours
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Excretion Excretion]
| align="center"|Urine (90%), feces (6%)
|-
! colspan="2" align="center" bgcolor="#dddddd"| Therapeutic considerations
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Pregnancy_category Pregnancy cat.]
| align="center"|X (USA), Teratogenic effects

|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Regulation_of_therapeutic_goods Legal status]
| align="center"|Schedule III (USA)
Schedule IV (Canada)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Route_of_administration Routes]
| align="center"|Intramuscular injection, transdermal (cream, gel, or patch), sub-'Q' pellet
|-

|}

==Introduction==
The human body produces testosterone, which is the most important male sex hormone. Testosterone is an essential steroid hormone, which is from the androgen hormone group. Testosterone is primarily secreted in the testes of males, which is where the hormone is produced, and the ovaries of females. Minute amounts are secreted by the adrenal glands, which can be found on top of the kidneys. It is the main male sex hormone and it is an anabolic steroid. Testosterone is responsible for development of male characteristics like body and facial hair, muscle growth, strength, and a deep voice. Testosterone at the normal levels in the body influences the production of sperm, which ties in with the promotion of sexual function and in the promotion of sex drive.

==How it works==

The hormone, testosterone, effects humans and other vertebrates by either of the two main hormonal mechanisms; first of these mechanisms is by activation of the androgen receptor (either directly or as DHT) or second is by the conversion to estradiol and the activation of certain estrogen receptors.

''Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5-alpha reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T.[citation needed] The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects. It is important to note that if there is a 5-alpha reductase deficiency, the body (of a human) will continue growing into a female with testicles.''<ref>http://en.wikipedia.org/wiki/Testosterone</ref>

The testerone androgen receptors occur in a large number of different vertebrate body system tissues. Both sexes respond quite similarly to levels of testerone. There is a large difference in the amount of testosterone found in each sex at prenatally, at puberty, and throughout life and this accounts for the share of characteristic biological differences between the sexes.

==Production==
[[Image:Steroidogenesis.gif|thumb|Description]]

[[Image:Test.jpg]]

===The 3D Molecular Structure===

<jmol>
<jmolApplet>
<title>Hyoscine</title><color>black</color>
<size>350</size>
<script>zoom 120; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Testosterone.pdb</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>dots on</script>
<text>Turn dots on</text>
</jmolButton>
<jmolButton>
<script>dots off</script>
<text>Turn dots off</text>
</jmolButton>
</jmol>

==Spectroscopic Data==

'''IR Spectrum: Testosterone'''

[[Image:Testosterone_ir.JPG]]

'''Mass Spectrum: Testosterone'''

[[Image:Testosterone_mass.JPG]]

'''NMR Spectrum: Testosterone'''

[[Image:Testosterone_nmr.JPG]]

It07:Testosterone

2007-11-09T12:13:46Z

Arw06: /* Spectroscopic Data */

{| style="float: right; clear: right; margin: 0 0 0.5em 1em; background: #ffffff;" class="toccolours" border="0" cellpadding="1" align="right" width="300"
! colspan="2" align="center" bgcolor="#dddddd"| Testosterone 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Testosterone structure.png]] 
|-
! colspan="2" align="center" bgcolor="#dddddd"|IUPAC Systematic name
|-
| colspan="2" align="center"| {{{|IUPAC_name = (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,1
6,17-dodecahydrocyclopenta[a]phenanthren-3-one
}}}
|-
! colspan="2" align="center" bgcolor="#dddddd"|Indentifiers
|-
! align="left" bgcolor="#ddeeff" width="120"|[http://en.wikipedia.org/wiki/ATC_code ATC Code]
| align="center"| G03BA03
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/CAS_number CAS number]
| align="center"|58-22-0
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/PubChem PubChem (CID)]
| align="center"|[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6013 6013]
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| align="center"|[http://www.emolecules.com/cgi-bin/search?t=ss&q=CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C
CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C]
|-
! colspan="2" align="center" bgcolor="#dddddd"| Chemical Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| align="center"|C19H28O2
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Molecular_weight Molar mass]
| align="center"|288.43g/mol
|-
! colspan="2" align="center" bgcolor="#dddddd"| Pharmacokinetic Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Bioavailability Bioavailability]
| align="center"|low (due to extensive first pass metabolism)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Metabolism Metabolism]
| align="center"|Liver, Testis and Prostate
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Elimination_half-life Half life]
| align="center"|2-4 hours
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Excretion Excretion]
| align="center"|Urine (90%), feces (6%)
|-
! colspan="2" align="center" bgcolor="#dddddd"| Therapeutic considerations
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Pregnancy_category Pregnancy cat.]
| align="center"|X (USA), Teratogenic effects

|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Regulation_of_therapeutic_goods Legal status]
| align="center"|Schedule III (USA)
Schedule IV (Canada)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Route_of_administration Routes]
| align="center"|Intramuscular injection, transdermal (cream, gel, or patch), sub-'Q' pellet
|-

|}

==Introduction==
The human body produces testosterone, which is the most important male sex hormone. Testosterone is an essential steroid hormone, which is from the androgen hormone group. Testosterone is primarily secreted in the testes of males, which is where the hormone is produced, and the ovaries of females. Minute amounts are secreted by the adrenal glands, which can be found on top of the kidneys. It is the main male sex hormone and it is an anabolic steroid. Testosterone is responsible for development of male characteristics like body and facial hair, muscle growth, strength, and a deep voice. Testosterone at the normal levels in the body influences the production of sperm, which ties in with the promotion of sexual function and in the promotion of sex drive.

==How it works==

The hormone, testosterone, effects humans and other vertebrates by either of the two main hormonal mechanisms; first of these mechanisms is by activation of the androgen receptor (either directly or as DHT) or second is by the conversion to estradiol and the activation of certain estrogen receptors.

''Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5-alpha reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T.[citation needed] The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects. It is important to note that if there is a 5-alpha reductase deficiency, the body (of a human) will continue growing into a female with testicles.''<ref>http://en.wikipedia.org/wiki/Testosterone</ref>

The testerone androgen receptors occur in a large number of different vertebrate body system tissues. Both sexes respond quite similarly to levels of testerone. There is a large difference in the amount of testosterone found in each sex at prenatally, at puberty, and throughout life and this accounts for the share of characteristic biological differences between the sexes.

==Production==
[[Image:Steroidogenesis.gif|thumb|Description]]

[[Image:Test.jpg]]

===The 3D Molecular Structure===

<jmol>
<jmolApplet>
<title>Hyoscine</title><color>black</color>
<size>350</size>
<script>zoom 120; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Testosterone.pdb</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>dots on</script>
<text>Turn dots on</text>
</jmolButton>
<jmolButton>
<script>dots off</script>
<text>Turn dots off</text>
</jmolButton>
</jmol>

==Spectroscopic Data==

'''IR Spectrum: Testosterone'''
[[Image:Testosterone_ir.JPG]]

'''Mass Spectrum: Testosterone'''
[[Image:Testosterone_mass.JPG]]

'''NMR Spectrum: Testosterone'''
[[Image:Testosterone_nmr.JPG]]

It07:Testosterone

2007-11-09T12:13:15Z

Arw06: /* Spectroscopic Data */

{| style="float: right; clear: right; margin: 0 0 0.5em 1em; background: #ffffff;" class="toccolours" border="0" cellpadding="1" align="right" width="300"
! colspan="2" align="center" bgcolor="#dddddd"| Testosterone 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Testosterone structure.png]] 
|-
! colspan="2" align="center" bgcolor="#dddddd"|IUPAC Systematic name
|-
| colspan="2" align="center"| {{{|IUPAC_name = (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,1
6,17-dodecahydrocyclopenta[a]phenanthren-3-one
}}}
|-
! colspan="2" align="center" bgcolor="#dddddd"|Indentifiers
|-
! align="left" bgcolor="#ddeeff" width="120"|[http://en.wikipedia.org/wiki/ATC_code ATC Code]
| align="center"| G03BA03
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/CAS_number CAS number]
| align="center"|58-22-0
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/PubChem PubChem (CID)]
| align="center"|[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6013 6013]
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| align="center"|[http://www.emolecules.com/cgi-bin/search?t=ss&q=CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C
CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C]
|-
! colspan="2" align="center" bgcolor="#dddddd"| Chemical Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| align="center"|C19H28O2
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Molecular_weight Molar mass]
| align="center"|288.43g/mol
|-
! colspan="2" align="center" bgcolor="#dddddd"| Pharmacokinetic Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Bioavailability Bioavailability]
| align="center"|low (due to extensive first pass metabolism)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Metabolism Metabolism]
| align="center"|Liver, Testis and Prostate
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Elimination_half-life Half life]
| align="center"|2-4 hours
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Excretion Excretion]
| align="center"|Urine (90%), feces (6%)
|-
! colspan="2" align="center" bgcolor="#dddddd"| Therapeutic considerations
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Pregnancy_category Pregnancy cat.]
| align="center"|X (USA), Teratogenic effects

|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Regulation_of_therapeutic_goods Legal status]
| align="center"|Schedule III (USA)
Schedule IV (Canada)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Route_of_administration Routes]
| align="center"|Intramuscular injection, transdermal (cream, gel, or patch), sub-'Q' pellet
|-

|}

==Introduction==
The human body produces testosterone, which is the most important male sex hormone. Testosterone is an essential steroid hormone, which is from the androgen hormone group. Testosterone is primarily secreted in the testes of males, which is where the hormone is produced, and the ovaries of females. Minute amounts are secreted by the adrenal glands, which can be found on top of the kidneys. It is the main male sex hormone and it is an anabolic steroid. Testosterone is responsible for development of male characteristics like body and facial hair, muscle growth, strength, and a deep voice. Testosterone at the normal levels in the body influences the production of sperm, which ties in with the promotion of sexual function and in the promotion of sex drive.

==How it works==

The hormone, testosterone, effects humans and other vertebrates by either of the two main hormonal mechanisms; first of these mechanisms is by activation of the androgen receptor (either directly or as DHT) or second is by the conversion to estradiol and the activation of certain estrogen receptors.

''Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5-alpha reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T.[citation needed] The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects. It is important to note that if there is a 5-alpha reductase deficiency, the body (of a human) will continue growing into a female with testicles.''<ref>http://en.wikipedia.org/wiki/Testosterone</ref>

The testerone androgen receptors occur in a large number of different vertebrate body system tissues. Both sexes respond quite similarly to levels of testerone. There is a large difference in the amount of testosterone found in each sex at prenatally, at puberty, and throughout life and this accounts for the share of characteristic biological differences between the sexes.

==Production==
[[Image:Steroidogenesis.gif|thumb|Description]]

[[Image:Test.jpg]]

===The 3D Molecular Structure===

<jmol>
<jmolApplet>
<title>Hyoscine</title><color>black</color>
<size>350</size>
<script>zoom 120; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Testosterone.pdb</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>dots on</script>
<text>Turn dots on</text>
</jmolButton>
<jmolButton>
<script>dots off</script>
<text>Turn dots off</text>
</jmolButton>
</jmol>

==Spectroscopic Data==

'''IR Spectrum: Testosterone'''
[[Image:Testosterone_ir.JPG]]

'''Mass Spectrum: Testosterone'''
[[Image:Testosterone_mass.JPG]]

'''NMR Spectrum: Testosterone'''
[[Image:Testosterone_nmr.JPG]]
[[Image:Testosterone_nmr_structure.JPG]]

File:Testosterone nmr structure.JPG

2007-11-09T12:12:15Z

Arw06:

It07:Testosterone

2007-11-09T12:11:31Z

Arw06: /* Spectras */

{| style="float: right; clear: right; margin: 0 0 0.5em 1em; background: #ffffff;" class="toccolours" border="0" cellpadding="1" align="right" width="300"
! colspan="2" align="center" bgcolor="#dddddd"| Testosterone 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Testosterone structure.png]] 
|-
! colspan="2" align="center" bgcolor="#dddddd"|IUPAC Systematic name
|-
| colspan="2" align="center"| {{{|IUPAC_name = (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,1
6,17-dodecahydrocyclopenta[a]phenanthren-3-one
}}}
|-
! colspan="2" align="center" bgcolor="#dddddd"|Indentifiers
|-
! align="left" bgcolor="#ddeeff" width="120"|[http://en.wikipedia.org/wiki/ATC_code ATC Code]
| align="center"| G03BA03
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/CAS_number CAS number]
| align="center"|58-22-0
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/PubChem PubChem (CID)]
| align="center"|[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6013 6013]
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| align="center"|[http://www.emolecules.com/cgi-bin/search?t=ss&q=CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C
CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C]
|-
! colspan="2" align="center" bgcolor="#dddddd"| Chemical Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| align="center"|C19H28O2
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Molecular_weight Molar mass]
| align="center"|288.43g/mol
|-
! colspan="2" align="center" bgcolor="#dddddd"| Pharmacokinetic Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Bioavailability Bioavailability]
| align="center"|low (due to extensive first pass metabolism)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Metabolism Metabolism]
| align="center"|Liver, Testis and Prostate
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Elimination_half-life Half life]
| align="center"|2-4 hours
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Excretion Excretion]
| align="center"|Urine (90%), feces (6%)
|-
! colspan="2" align="center" bgcolor="#dddddd"| Therapeutic considerations
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Pregnancy_category Pregnancy cat.]
| align="center"|X (USA), Teratogenic effects

|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Regulation_of_therapeutic_goods Legal status]
| align="center"|Schedule III (USA)
Schedule IV (Canada)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Route_of_administration Routes]
| align="center"|Intramuscular injection, transdermal (cream, gel, or patch), sub-'Q' pellet
|-

|}

==Introduction==
The human body produces testosterone, which is the most important male sex hormone. Testosterone is an essential steroid hormone, which is from the androgen hormone group. Testosterone is primarily secreted in the testes of males, which is where the hormone is produced, and the ovaries of females. Minute amounts are secreted by the adrenal glands, which can be found on top of the kidneys. It is the main male sex hormone and it is an anabolic steroid. Testosterone is responsible for development of male characteristics like body and facial hair, muscle growth, strength, and a deep voice. Testosterone at the normal levels in the body influences the production of sperm, which ties in with the promotion of sexual function and in the promotion of sex drive.

==How it works==

The hormone, testosterone, effects humans and other vertebrates by either of the two main hormonal mechanisms; first of these mechanisms is by activation of the androgen receptor (either directly or as DHT) or second is by the conversion to estradiol and the activation of certain estrogen receptors.

''Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5-alpha reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T.[citation needed] The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects. It is important to note that if there is a 5-alpha reductase deficiency, the body (of a human) will continue growing into a female with testicles.''<ref>http://en.wikipedia.org/wiki/Testosterone</ref>

The testerone androgen receptors occur in a large number of different vertebrate body system tissues. Both sexes respond quite similarly to levels of testerone. There is a large difference in the amount of testosterone found in each sex at prenatally, at puberty, and throughout life and this accounts for the share of characteristic biological differences between the sexes.

==Production==
[[Image:Steroidogenesis.gif|thumb|Description]]

[[Image:Test.jpg]]

===The 3D Molecular Structure===

<jmol>
<jmolApplet>
<title>Hyoscine</title><color>black</color>
<size>350</size>
<script>zoom 120; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Testosterone.pdb</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>dots on</script>
<text>Turn dots on</text>
</jmolButton>
<jmolButton>
<script>dots off</script>
<text>Turn dots off</text>
</jmolButton>
</jmol>

==Spectroscopic Data==

'''IR Spectrum: Testosterone'''
[[Image:Testosterone_ir.JPG]]

'''Mass Spectrum: Testosterone'''
[[Image:Testosterone_mass.JPG]]

'''NMR Spectrum: Testosterone'''
[[Image:Testosterone_nmr.JPG]]

It07:Testosterone

2007-11-09T12:11:09Z

Arw06: /* Spectras */

{| style="float: right; clear: right; margin: 0 0 0.5em 1em; background: #ffffff;" class="toccolours" border="0" cellpadding="1" align="right" width="300"
! colspan="2" align="center" bgcolor="#dddddd"| Testosterone 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Testosterone structure.png]] 
|-
! colspan="2" align="center" bgcolor="#dddddd"|IUPAC Systematic name
|-
| colspan="2" align="center"| {{{|IUPAC_name = (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,1
6,17-dodecahydrocyclopenta[a]phenanthren-3-one
}}}
|-
! colspan="2" align="center" bgcolor="#dddddd"|Indentifiers
|-
! align="left" bgcolor="#ddeeff" width="120"|[http://en.wikipedia.org/wiki/ATC_code ATC Code]
| align="center"| G03BA03
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/CAS_number CAS number]
| align="center"|58-22-0
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/PubChem PubChem (CID)]
| align="center"|[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6013 6013]
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| align="center"|[http://www.emolecules.com/cgi-bin/search?t=ss&q=CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C
CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C]
|-
! colspan="2" align="center" bgcolor="#dddddd"| Chemical Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| align="center"|C19H28O2
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Molecular_weight Molar mass]
| align="center"|288.43g/mol
|-
! colspan="2" align="center" bgcolor="#dddddd"| Pharmacokinetic Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Bioavailability Bioavailability]
| align="center"|low (due to extensive first pass metabolism)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Metabolism Metabolism]
| align="center"|Liver, Testis and Prostate
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Elimination_half-life Half life]
| align="center"|2-4 hours
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Excretion Excretion]
| align="center"|Urine (90%), feces (6%)
|-
! colspan="2" align="center" bgcolor="#dddddd"| Therapeutic considerations
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Pregnancy_category Pregnancy cat.]
| align="center"|X (USA), Teratogenic effects

|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Regulation_of_therapeutic_goods Legal status]
| align="center"|Schedule III (USA)
Schedule IV (Canada)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Route_of_administration Routes]
| align="center"|Intramuscular injection, transdermal (cream, gel, or patch), sub-'Q' pellet
|-

|}

==Introduction==
The human body produces testosterone, which is the most important male sex hormone. Testosterone is an essential steroid hormone, which is from the androgen hormone group. Testosterone is primarily secreted in the testes of males, which is where the hormone is produced, and the ovaries of females. Minute amounts are secreted by the adrenal glands, which can be found on top of the kidneys. It is the main male sex hormone and it is an anabolic steroid. Testosterone is responsible for development of male characteristics like body and facial hair, muscle growth, strength, and a deep voice. Testosterone at the normal levels in the body influences the production of sperm, which ties in with the promotion of sexual function and in the promotion of sex drive.

==How it works==

The hormone, testosterone, effects humans and other vertebrates by either of the two main hormonal mechanisms; first of these mechanisms is by activation of the androgen receptor (either directly or as DHT) or second is by the conversion to estradiol and the activation of certain estrogen receptors.

''Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5-alpha reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T.[citation needed] The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects. It is important to note that if there is a 5-alpha reductase deficiency, the body (of a human) will continue growing into a female with testicles.''<ref>http://en.wikipedia.org/wiki/Testosterone</ref>

The testerone androgen receptors occur in a large number of different vertebrate body system tissues. Both sexes respond quite similarly to levels of testerone. There is a large difference in the amount of testosterone found in each sex at prenatally, at puberty, and throughout life and this accounts for the share of characteristic biological differences between the sexes.

==Production==
[[Image:Steroidogenesis.gif|thumb|Description]]

[[Image:Test.jpg]]

===The 3D Molecular Structure===

<jmol>
<jmolApplet>
<title>Hyoscine</title><color>black</color>
<size>350</size>
<script>zoom 120; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Testosterone.pdb</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>dots on</script>
<text>Turn dots on</text>
</jmolButton>
<jmolButton>
<script>dots off</script>
<text>Turn dots off</text>
</jmolButton>
</jmol>

==Spectras==

'''IR Spectrum: Testosterone'''
[[Image:Testosterone_ir.JPG]]

'''Mass Spectrum: Testosterone'''
[[Image:Testosterone_mass.JPG]]

'''NMR Spectrum: Testosterone'''
[[Image:Testosterone_nmr.JPG]]

It07:Testosterone

2007-11-09T12:10:37Z

Arw06: /* Spectras */

{| style="float: right; clear: right; margin: 0 0 0.5em 1em; background: #ffffff;" class="toccolours" border="0" cellpadding="1" align="right" width="300"
! colspan="2" align="center" bgcolor="#dddddd"| Testosterone 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Testosterone structure.png]] 
|-
! colspan="2" align="center" bgcolor="#dddddd"|IUPAC Systematic name
|-
| colspan="2" align="center"| {{{|IUPAC_name = (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,1
6,17-dodecahydrocyclopenta[a]phenanthren-3-one
}}}
|-
! colspan="2" align="center" bgcolor="#dddddd"|Indentifiers
|-
! align="left" bgcolor="#ddeeff" width="120"|[http://en.wikipedia.org/wiki/ATC_code ATC Code]
| align="center"| G03BA03
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/CAS_number CAS number]
| align="center"|58-22-0
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/PubChem PubChem (CID)]
| align="center"|[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6013 6013]
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| align="center"|[http://www.emolecules.com/cgi-bin/search?t=ss&q=CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C
CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C]
|-
! colspan="2" align="center" bgcolor="#dddddd"| Chemical Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| align="center"|C19H28O2
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Molecular_weight Molar mass]
| align="center"|288.43g/mol
|-
! colspan="2" align="center" bgcolor="#dddddd"| Pharmacokinetic Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Bioavailability Bioavailability]
| align="center"|low (due to extensive first pass metabolism)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Metabolism Metabolism]
| align="center"|Liver, Testis and Prostate
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Elimination_half-life Half life]
| align="center"|2-4 hours
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Excretion Excretion]
| align="center"|Urine (90%), feces (6%)
|-
! colspan="2" align="center" bgcolor="#dddddd"| Therapeutic considerations
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Pregnancy_category Pregnancy cat.]
| align="center"|X (USA), Teratogenic effects

|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Regulation_of_therapeutic_goods Legal status]
| align="center"|Schedule III (USA)
Schedule IV (Canada)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Route_of_administration Routes]
| align="center"|Intramuscular injection, transdermal (cream, gel, or patch), sub-'Q' pellet
|-

|}

==Introduction==
The human body produces testosterone, which is the most important male sex hormone. Testosterone is an essential steroid hormone, which is from the androgen hormone group. Testosterone is primarily secreted in the testes of males, which is where the hormone is produced, and the ovaries of females. Minute amounts are secreted by the adrenal glands, which can be found on top of the kidneys. It is the main male sex hormone and it is an anabolic steroid. Testosterone is responsible for development of male characteristics like body and facial hair, muscle growth, strength, and a deep voice. Testosterone at the normal levels in the body influences the production of sperm, which ties in with the promotion of sexual function and in the promotion of sex drive.

==How it works==

The hormone, testosterone, effects humans and other vertebrates by either of the two main hormonal mechanisms; first of these mechanisms is by activation of the androgen receptor (either directly or as DHT) or second is by the conversion to estradiol and the activation of certain estrogen receptors.

''Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5-alpha reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T.[citation needed] The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects. It is important to note that if there is a 5-alpha reductase deficiency, the body (of a human) will continue growing into a female with testicles.''<ref>http://en.wikipedia.org/wiki/Testosterone</ref>

The testerone androgen receptors occur in a large number of different vertebrate body system tissues. Both sexes respond quite similarly to levels of testerone. There is a large difference in the amount of testosterone found in each sex at prenatally, at puberty, and throughout life and this accounts for the share of characteristic biological differences between the sexes.

==Production==
[[Image:Steroidogenesis.gif|thumb|Description]]

[[Image:Test.jpg]]

===The 3D Molecular Structure===

<jmol>
<jmolApplet>
<title>Hyoscine</title><color>black</color>
<size>350</size>
<script>zoom 120; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Testosterone.pdb</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>dots on</script>
<text>Turn dots on</text>
</jmolButton>
<jmolButton>
<script>dots off</script>
<text>Turn dots off</text>
</jmolButton>
</jmol>

==Spectras==

IR Spectrum: Testosterone
[[Image:Testosterone_ir.JPG]]

Mass Spectrum: Testosterone
[[Image:Testosterone_mass.JPG]]

NMR Spectrum: Testosterone
[[Image:Testosterone_nmr.JPG]]

It07:Testosterone

2007-11-09T12:07:38Z

Arw06: /* Spectras */

{| style="float: right; clear: right; margin: 0 0 0.5em 1em; background: #ffffff;" class="toccolours" border="0" cellpadding="1" align="right" width="300"
! colspan="2" align="center" bgcolor="#dddddd"| Testosterone 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Testosterone structure.png]] 
|-
! colspan="2" align="center" bgcolor="#dddddd"|IUPAC Systematic name
|-
| colspan="2" align="center"| {{{|IUPAC_name = (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,1
6,17-dodecahydrocyclopenta[a]phenanthren-3-one
}}}
|-
! colspan="2" align="center" bgcolor="#dddddd"|Indentifiers
|-
! align="left" bgcolor="#ddeeff" width="120"|[http://en.wikipedia.org/wiki/ATC_code ATC Code]
| align="center"| G03BA03
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/CAS_number CAS number]
| align="center"|58-22-0
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/PubChem PubChem (CID)]
| align="center"|[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6013 6013]
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| align="center"|[http://www.emolecules.com/cgi-bin/search?t=ss&q=CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C
CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C]
|-
! colspan="2" align="center" bgcolor="#dddddd"| Chemical Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| align="center"|C19H28O2
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Molecular_weight Molar mass]
| align="center"|288.43g/mol
|-
! colspan="2" align="center" bgcolor="#dddddd"| Pharmacokinetic Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Bioavailability Bioavailability]
| align="center"|low (due to extensive first pass metabolism)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Metabolism Metabolism]
| align="center"|Liver, Testis and Prostate
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Elimination_half-life Half life]
| align="center"|2-4 hours
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Excretion Excretion]
| align="center"|Urine (90%), feces (6%)
|-
! colspan="2" align="center" bgcolor="#dddddd"| Therapeutic considerations
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Pregnancy_category Pregnancy cat.]
| align="center"|X (USA), Teratogenic effects

|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Regulation_of_therapeutic_goods Legal status]
| align="center"|Schedule III (USA)
Schedule IV (Canada)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Route_of_administration Routes]
| align="center"|Intramuscular injection, transdermal (cream, gel, or patch), sub-'Q' pellet
|-

|}

==Introduction==
The human body produces testosterone, which is the most important male sex hormone. Testosterone is an essential steroid hormone, which is from the androgen hormone group. Testosterone is primarily secreted in the testes of males, which is where the hormone is produced, and the ovaries of females. Minute amounts are secreted by the adrenal glands, which can be found on top of the kidneys. It is the main male sex hormone and it is an anabolic steroid. Testosterone is responsible for development of male characteristics like body and facial hair, muscle growth, strength, and a deep voice. Testosterone at the normal levels in the body influences the production of sperm, which ties in with the promotion of sexual function and in the promotion of sex drive.

==How it works==

The hormone, testosterone, effects humans and other vertebrates by either of the two main hormonal mechanisms; first of these mechanisms is by activation of the androgen receptor (either directly or as DHT) or second is by the conversion to estradiol and the activation of certain estrogen receptors.

''Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5-alpha reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T.[citation needed] The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects. It is important to note that if there is a 5-alpha reductase deficiency, the body (of a human) will continue growing into a female with testicles.''<ref>http://en.wikipedia.org/wiki/Testosterone</ref>

The testerone androgen receptors occur in a large number of different vertebrate body system tissues. Both sexes respond quite similarly to levels of testerone. There is a large difference in the amount of testosterone found in each sex at prenatally, at puberty, and throughout life and this accounts for the share of characteristic biological differences between the sexes.

==Production==
[[Image:Steroidogenesis.gif|thumb|Description]]

[[Image:Test.jpg]]

===The 3D Molecular Structure===

<jmol>
<jmolApplet>
<title>Hyoscine</title><color>black</color>
<size>350</size>
<script>zoom 120; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Testosterone.pdb</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>dots on</script>
<text>Turn dots on</text>
</jmolButton>
<jmolButton>
<script>dots off</script>
<text>Turn dots off</text>
</jmolButton>
</jmol>

==Spectras==
[[Image:Testosterone_ir.JPG]]
[[Image:Testosterone_mass.JPG]]
[[Image:Testosterone_nmr.JPG]]

It07:Testosterone

2007-11-09T12:06:56Z

Arw06: /* Spectras */

{| style="float: right; clear: right; margin: 0 0 0.5em 1em; background: #ffffff;" class="toccolours" border="0" cellpadding="1" align="right" width="300"
! colspan="2" align="center" bgcolor="#dddddd"| Testosterone 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Testosterone structure.png]] 
|-
! colspan="2" align="center" bgcolor="#dddddd"|IUPAC Systematic name
|-
| colspan="2" align="center"| {{{|IUPAC_name = (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,1
6,17-dodecahydrocyclopenta[a]phenanthren-3-one
}}}
|-
! colspan="2" align="center" bgcolor="#dddddd"|Indentifiers
|-
! align="left" bgcolor="#ddeeff" width="120"|[http://en.wikipedia.org/wiki/ATC_code ATC Code]
| align="center"| G03BA03
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/CAS_number CAS number]
| align="center"|58-22-0
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/PubChem PubChem (CID)]
| align="center"|[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6013 6013]
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| align="center"|[http://www.emolecules.com/cgi-bin/search?t=ss&q=CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C
CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C]
|-
! colspan="2" align="center" bgcolor="#dddddd"| Chemical Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| align="center"|C19H28O2
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Molecular_weight Molar mass]
| align="center"|288.43g/mol
|-
! colspan="2" align="center" bgcolor="#dddddd"| Pharmacokinetic Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Bioavailability Bioavailability]
| align="center"|low (due to extensive first pass metabolism)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Metabolism Metabolism]
| align="center"|Liver, Testis and Prostate
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Elimination_half-life Half life]
| align="center"|2-4 hours
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Excretion Excretion]
| align="center"|Urine (90%), feces (6%)
|-
! colspan="2" align="center" bgcolor="#dddddd"| Therapeutic considerations
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Pregnancy_category Pregnancy cat.]
| align="center"|X (USA), Teratogenic effects

|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Regulation_of_therapeutic_goods Legal status]
| align="center"|Schedule III (USA)
Schedule IV (Canada)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Route_of_administration Routes]
| align="center"|Intramuscular injection, transdermal (cream, gel, or patch), sub-'Q' pellet
|-

|}

==Introduction==
The human body produces testosterone, which is the most important male sex hormone. Testosterone is an essential steroid hormone, which is from the androgen hormone group. Testosterone is primarily secreted in the testes of males, which is where the hormone is produced, and the ovaries of females. Minute amounts are secreted by the adrenal glands, which can be found on top of the kidneys. It is the main male sex hormone and it is an anabolic steroid. Testosterone is responsible for development of male characteristics like body and facial hair, muscle growth, strength, and a deep voice. Testosterone at the normal levels in the body influences the production of sperm, which ties in with the promotion of sexual function and in the promotion of sex drive.

==How it works==

The hormone, testosterone, effects humans and other vertebrates by either of the two main hormonal mechanisms; first of these mechanisms is by activation of the androgen receptor (either directly or as DHT) or second is by the conversion to estradiol and the activation of certain estrogen receptors.

''Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5-alpha reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T.[citation needed] The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects. It is important to note that if there is a 5-alpha reductase deficiency, the body (of a human) will continue growing into a female with testicles.''<ref>http://en.wikipedia.org/wiki/Testosterone</ref>

The testerone androgen receptors occur in a large number of different vertebrate body system tissues. Both sexes respond quite similarly to levels of testerone. There is a large difference in the amount of testosterone found in each sex at prenatally, at puberty, and throughout life and this accounts for the share of characteristic biological differences between the sexes.

==Production==
[[Image:Steroidogenesis.gif|thumb|Description]]

[[Image:Test.jpg]]

===The 3D Molecular Structure===

<jmol>
<jmolApplet>
<title>Hyoscine</title><color>black</color>
<size>350</size>
<script>zoom 120; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Testosterone.pdb</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>dots on</script>
<text>Turn dots on</text>
</jmolButton>
<jmolButton>
<script>dots off</script>
<text>Turn dots off</text>
</jmolButton>
</jmol>

==Spectras==
[[Image:Testosterone_ir.JPG]]
[[Image:Testosterone_mass.JPG]]

It07:Testosterone

2007-11-09T12:06:00Z

Arw06: /* Spectras */

{| style="float: right; clear: right; margin: 0 0 0.5em 1em; background: #ffffff;" class="toccolours" border="0" cellpadding="1" align="right" width="300"
! colspan="2" align="center" bgcolor="#dddddd"| Testosterone 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Testosterone structure.png]] 
|-
! colspan="2" align="center" bgcolor="#dddddd"|IUPAC Systematic name
|-
| colspan="2" align="center"| {{{|IUPAC_name = (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,1
6,17-dodecahydrocyclopenta[a]phenanthren-3-one
}}}
|-
! colspan="2" align="center" bgcolor="#dddddd"|Indentifiers
|-
! align="left" bgcolor="#ddeeff" width="120"|[http://en.wikipedia.org/wiki/ATC_code ATC Code]
| align="center"| G03BA03
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/CAS_number CAS number]
| align="center"|58-22-0
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/PubChem PubChem (CID)]
| align="center"|[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6013 6013]
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| align="center"|[http://www.emolecules.com/cgi-bin/search?t=ss&q=CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C
CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C]
|-
! colspan="2" align="center" bgcolor="#dddddd"| Chemical Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| align="center"|C19H28O2
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Molecular_weight Molar mass]
| align="center"|288.43g/mol
|-
! colspan="2" align="center" bgcolor="#dddddd"| Pharmacokinetic Data
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Bioavailability Bioavailability]
| align="center"|low (due to extensive first pass metabolism)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Metabolism Metabolism]
| align="center"|Liver, Testis and Prostate
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Elimination_half-life Half life]
| align="center"|2-4 hours
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Excretion Excretion]
| align="center"|Urine (90%), feces (6%)
|-
! colspan="2" align="center" bgcolor="#dddddd"| Therapeutic considerations
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Pregnancy_category Pregnancy cat.]
| align="center"|X (USA), Teratogenic effects

|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Regulation_of_therapeutic_goods Legal status]
| align="center"|Schedule III (USA)
Schedule IV (Canada)
|-
! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Route_of_administration Routes]
| align="center"|Intramuscular injection, transdermal (cream, gel, or patch), sub-'Q' pellet
|-

|}

==Introduction==
The human body produces testosterone, which is the most important male sex hormone. Testosterone is an essential steroid hormone, which is from the androgen hormone group. Testosterone is primarily secreted in the testes of males, which is where the hormone is produced, and the ovaries of females. Minute amounts are secreted by the adrenal glands, which can be found on top of the kidneys. It is the main male sex hormone and it is an anabolic steroid. Testosterone is responsible for development of male characteristics like body and facial hair, muscle growth, strength, and a deep voice. Testosterone at the normal levels in the body influences the production of sperm, which ties in with the promotion of sexual function and in the promotion of sex drive.

==How it works==

The hormone, testosterone, effects humans and other vertebrates by either of the two main hormonal mechanisms; first of these mechanisms is by activation of the androgen receptor (either directly or as DHT) or second is by the conversion to estradiol and the activation of certain estrogen receptors.

''Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5-alpha reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T.[citation needed] The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects. It is important to note that if there is a 5-alpha reductase deficiency, the body (of a human) will continue growing into a female with testicles.''<ref>http://en.wikipedia.org/wiki/Testosterone</ref>

The testerone androgen receptors occur in a large number of different vertebrate body system tissues. Both sexes respond quite similarly to levels of testerone. There is a large difference in the amount of testosterone found in each sex at prenatally, at puberty, and throughout life and this accounts for the share of characteristic biological differences between the sexes.

==Production==
[[Image:Steroidogenesis.gif|thumb|Description]]

[[Image:Test.jpg]]

===The 3D Molecular Structure===

<jmol>
<jmolApplet>
<title>Hyoscine</title><color>black</color>
<size>350</size>
<script>zoom 120; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Testosterone.pdb</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>dots on</script>
<text>Turn dots on</text>
</jmolButton>
<jmolButton>
<script>dots off</script>
<text>Turn dots off</text>
</jmolButton>
</jmol>

==Spectras==
[[Image:Testosterone_ir.JPG]]

File:Testosterone nmr.JPG

2007-11-09T12:04:33Z

Arw06:

File:Testosterone mass.JPG

2007-11-09T12:04:07Z

Arw06:

File:Testosterone ir.JPG

2007-11-09T12:02:40Z

Arw06:

It07:Methylenedioxymethamphetamine

2007-11-08T16:02:05Z

Arw06: /* Spectroscopic Data */

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Methylenedioxymethamphetamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Methylenedioxymethamphetamine.jpg]]

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3,4-methylenedioxy-N-methylamphetamine

|-
| Other names
| N-methyl 1-1-(3,4-methylenedioxyphenyl)-2-propanamine, MDMA, Ecstacy
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C11H15NO2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN[C@@H](C)CC1=CC(OCO2)=C2C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 193.24g/mol
|-
| Appearance
| White crystalline solid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 69610-10-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| -144.4F 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 148 F
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| Neurotoxic 

|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
|-
| Related compounds

| Amphetamine, MDEA, Methylenedioxymethcathinone, Paramethoxyamphetamine.
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-

== Methylenedioxymethamphetamine ==

Often known as MDMA or Ecstacy, 3,4-methylenedioxy-N-methylamphetamine is a semisynthetic empathogen-entactogen, an illegal drug that acts as a stimulant producing an psychedelic energizing effect, as well as distortions in time, perception and enhanced enjoyment of tactile experiences. MDMA exerts its primary effects on neurons in the brain that use the chemical serotonin to communicate with other neurons. Aside from recreational purposes, it is used as a tool to supplement various practices including meditation, psychonautics, and illicit psychedelic psychotherapy.
Research in animals indicates that MDMA is neurotoxic; whether or not this is also true in humans is currently an area of intense investigation. MDMA can also be dangerous to health and, on rare occasions, lethal.

[[Image:Ecstacy-02.jpg]]
<ref>http://www.usdoj.gov/dea/photos/mdma/ecstacy-02.jpg</ref>

== History ==

MDMA was first synthesized in 1912, soon after it was patented in Germany by the Merck Company. At that time it was not the subject of human research, but Merck stumbled across MDMA when they tried to synthesize Hydrastinin, a vasoconstrictive and styptic medicine. MDMA was an unplanned by-product of this synthesis. In the 1950s it was briefly researched by the U.S. Government as part of the CIA's and the Army's chemical warfare investigations into MDMA as a truth serum, which proved to be unsuitable. The first reported recreational use was in the 1960s, where it became known as the love drug. In the mid-70s, the psychedelic therapy community rediscovered it and psychiatrists and therapists began to use it to supplement psychotherapy. In the early 1980s, the drug began to be used recreationally, most notably in Dallas, under the name the street name 'Ecstasy'. The non-medical and therapeutic use of MDMA was made illegal in the USA in 1985. Soon afterwards its use rapidly spread outside the United States, where it was widely used in the UK and other parts of Europe, becoming an integral part of the rave subculture and other psychedelic and dancefloor influenced music scenes.<ref>http://www.a1b2c3.com/drugs/x_01.htm</ref>

== Synthesis ==

Reaction Overview:
The 'ketone' approach is one of many synthesis schemes for the production of MDMA. This basic scheme is the oxidation of the plant oil 'safrole' (1-allyl-3,4-methylenedioxybenzene) into a ketone (3,4-methylenedioxyphenyl-2-propanone), which is then condensed with methylamine and reduced to the final MDMA product.

[[Image:Mdma_synthesis.JPG]]

Step 1: Peroxyacid oxidation (requires isomerization of safrole).

Step 2: Reversible imine formation, which reacts spontaneously when the ketone is added to a solution of methylamine.

Step 3: Reduction, permanently converts the imine to MDMA.
<ref>http://thedea.org/synthesis.html</ref>

== Effects on the Human Body ==

The most common use of MDMA is for recreational purposes. Classed as a stimulant, the effects produced on the human body include euphoria, increased awareness of the senses, feelings of openness, empathy, heightened self-awareness and feeling of mental clarity. Tactile sensations are enhanced for some users resulting in physical contact with others more intense. ‘Alexander Shulgin stated that the single best use of MDMA was to facilitate more direct communication between people involved in significant emotional relationships.’ Physical effects on the body include sweaty palms, heavy sweating, increased heart rate, increased body temperature, and heightened touch sensations.

Naturally there are many health risks involved in taking a stimulant such as MDMA. Physically these risks include hypertension, dehydration and hyperthermia. This is mostly due to the drug's stimulatory effects masking the body's normal sense of exhaustion and thirst.
MDMA is also neurotoxic which means it interferes with brain chemistry, sometimes permanently. The metabolism of MDMA leads to the lipid peroxidation of serotonergic neurons, thus interfering with the brain's ability to effectively use serotonin.
Psychologically, MDMA use often results in a rebound period of poor mood, often known as a ‘comedown’. Obviously this varies in length between different users but can often lead to lasting depression and anxiety in vulnerable users. The longer the time MDMA is active in the brain, the greater the neurotoxic damage to the brain and the greater the risk of short-term emotional problems. The more times MDMA is taken, the greater the risk of any long-term problems.

===Short Term Effects===
In significantly high doses, MDMA can interfere with the body’s ability to regulate temperature, thus effecting homeostasis. On the very rare, but unpredictable occasions, this can possibly lead to a quick sharp increase in body's core temperature (leads to hyperthermia), resulting in failure in the following major organs; liver, kidney, and in cardiovascular system and the worst case scenario is death.

MDMA is a drug that can unfortunately interfere with the body's metabolism of the drug and this can lead to potentially harmful levels, especially if the drug is repeatedly used in a short space of time.

Users of MDMA can face many of the same risks/side effects as casual and frequent users of other stimulants; like cocaine and amphetamines. These typically include increases in heart rate and blood pressure, which is has significantly higher risk for people with either circulatory problems or heart disease, and other symptoms include muscle tension, involuntary teeth clenching, nausea, blurred vision, faintness, and chills or sweating.

Almost two thirds of people who use MDMA report withdrawal symptoms, including fatigue, loss of appetite, depressed feelings, and trouble concentrating.

===Long Term Effects===

MDMA exposure can lead to long-term damage to the neurons in the brain that are involved in the following; mood, thinking, and judgment. There has been a study in nonhuman primates that has been found to show that exposure to MDMA for only 4 days had caused severe damage to serotonin nerve terminals that became apparent 6 to 7 years later. However,similar neurotoxicity in humans has not been definitively shown, but the wealth of all the animal research indicating MDMA’s damaging properties strongly suggests that MDMA an unsafe drug for human consumption.<ref>http://www.usdoj.gov/dea/concern/mdma.html</ref>

== Commonly used names==

MDMA, Ecstasy, XTC, E, X, Beans, Adams, Hug Drug, Disco Biscuit. <ref>http://www.usdoj.gov/dea/concern/mdma.html
</ref>

== Legal Status ==

MDMA is Class A in the UK, making it illegal to sell, buy, or possess without a license. This is typical of almost all countries around the world, but there are however a few countries including Canada and Belgium where possession is legal with a prescription or licence.<ref>http://www.erowid.org/chemicals/mdma/</ref>

== Spectroscopic Data ==

'''NMR Spectrum: 3,4-methylenedioxy-N-methylamphetamine'''

[[Image:Mdma_nmr.JPG]]
<ref>http://www.rsc.org/delivery/_ArticleLinking/DisplayArticleForFree.cfm?doi=b201496n</ref>

== References ==

<references/>

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

It07:Methylenedioxymethamphetamine

2007-11-08T15:57:59Z

Arw06: /* References */

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Methylenedioxymethamphetamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Methylenedioxymethamphetamine.jpg]]

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3,4-methylenedioxy-N-methylamphetamine

|-
| Other names
| N-methyl 1-1-(3,4-methylenedioxyphenyl)-2-propanamine, MDMA, Ecstacy
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C11H15NO2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN[C@@H](C)CC1=CC(OCO2)=C2C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 193.24g/mol
|-
| Appearance
| White crystalline solid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 69610-10-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| -144.4F 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 148 F
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| Neurotoxic 

|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
|-
| Related compounds

| Amphetamine, MDEA, Methylenedioxymethcathinone, Paramethoxyamphetamine.
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-

== Methylenedioxymethamphetamine ==

Often known as MDMA or Ecstacy, 3,4-methylenedioxy-N-methylamphetamine is a semisynthetic empathogen-entactogen, an illegal drug that acts as a stimulant producing an psychedelic energizing effect, as well as distortions in time, perception and enhanced enjoyment of tactile experiences. MDMA exerts its primary effects on neurons in the brain that use the chemical serotonin to communicate with other neurons. Aside from recreational purposes, it is used as a tool to supplement various practices including meditation, psychonautics, and illicit psychedelic psychotherapy.
Research in animals indicates that MDMA is neurotoxic; whether or not this is also true in humans is currently an area of intense investigation. MDMA can also be dangerous to health and, on rare occasions, lethal.

[[Image:Ecstacy-02.jpg]]
<ref>http://www.usdoj.gov/dea/photos/mdma/ecstacy-02.jpg</ref>

== History ==

MDMA was first synthesized in 1912, soon after it was patented in Germany by the Merck Company. At that time it was not the subject of human research, but Merck stumbled across MDMA when they tried to synthesize Hydrastinin, a vasoconstrictive and styptic medicine. MDMA was an unplanned by-product of this synthesis. In the 1950s it was briefly researched by the U.S. Government as part of the CIA's and the Army's chemical warfare investigations into MDMA as a truth serum, which proved to be unsuitable. The first reported recreational use was in the 1960s, where it became known as the love drug. In the mid-70s, the psychedelic therapy community rediscovered it and psychiatrists and therapists began to use it to supplement psychotherapy. In the early 1980s, the drug began to be used recreationally, most notably in Dallas, under the name the street name 'Ecstasy'. The non-medical and therapeutic use of MDMA was made illegal in the USA in 1985. Soon afterwards its use rapidly spread outside the United States, where it was widely used in the UK and other parts of Europe, becoming an integral part of the rave subculture and other psychedelic and dancefloor influenced music scenes.<ref>http://www.a1b2c3.com/drugs/x_01.htm</ref>

== Synthesis ==

Reaction Overview:
The 'ketone' approach is one of many synthesis schemes for the production of MDMA. This basic scheme is the oxidation of the plant oil 'safrole' (1-allyl-3,4-methylenedioxybenzene) into a ketone (3,4-methylenedioxyphenyl-2-propanone), which is then condensed with methylamine and reduced to the final MDMA product.

[[Image:Mdma_synthesis.JPG]]

Step 1: Peroxyacid oxidation (requires isomerization of safrole).

Step 2: Reversible imine formation, which reacts spontaneously when the ketone is added to a solution of methylamine.

Step 3: Reduction, permanently converts the imine to MDMA.
<ref>http://thedea.org/synthesis.html</ref>

== Effects on the Human Body ==

The most common use of MDMA is for recreational purposes. Classed as a stimulant, the effects produced on the human body include euphoria, increased awareness of the senses, feelings of openness, empathy, heightened self-awareness and feeling of mental clarity. Tactile sensations are enhanced for some users resulting in physical contact with others more intense. ‘Alexander Shulgin stated that the single best use of MDMA was to facilitate more direct communication between people involved in significant emotional relationships.’ Physical effects on the body include sweaty palms, heavy sweating, increased heart rate, increased body temperature, and heightened touch sensations.

Naturally there are many health risks involved in taking a stimulant such as MDMA. Physically these risks include hypertension, dehydration and hyperthermia. This is mostly due to the drug's stimulatory effects masking the body's normal sense of exhaustion and thirst.
MDMA is also neurotoxic which means it interferes with brain chemistry, sometimes permanently. The metabolism of MDMA leads to the lipid peroxidation of serotonergic neurons, thus interfering with the brain's ability to effectively use serotonin.
Psychologically, MDMA use often results in a rebound period of poor mood, often known as a ‘comedown’. Obviously this varies in length between different users but can often lead to lasting depression and anxiety in vulnerable users. The longer the time MDMA is active in the brain, the greater the neurotoxic damage to the brain and the greater the risk of short-term emotional problems. The more times MDMA is taken, the greater the risk of any long-term problems.

===Short Term Effects===
In significantly high doses, MDMA can interfere with the body’s ability to regulate temperature, thus effecting homeostasis. On the very rare, but unpredictable occasions, this can possibly lead to a quick sharp increase in body's core temperature (leads to hyperthermia), resulting in failure in the following major organs; liver, kidney, and in cardiovascular system and the worst case scenario is death.

MDMA is a drug that can unfortunately interfere with the body's metabolism of the drug and this can lead to potentially harmful levels, especially if the drug is repeatedly used in a short space of time.

Users of MDMA can face many of the same risks/side effects as casual and frequent users of other stimulants; like cocaine and amphetamines. These typically include increases in heart rate and blood pressure, which is has significantly higher risk for people with either circulatory problems or heart disease, and other symptoms include muscle tension, involuntary teeth clenching, nausea, blurred vision, faintness, and chills or sweating.

Almost two thirds of people who use MDMA report withdrawal symptoms, including fatigue, loss of appetite, depressed feelings, and trouble concentrating.

===Long Term Effects===

MDMA exposure can lead to long-term damage to the neurons in the brain that are involved in the following; mood, thinking, and judgment. There has been a study in nonhuman primates that has been found to show that exposure to MDMA for only 4 days had caused severe damage to serotonin nerve terminals that became apparent 6 to 7 years later. However,similar neurotoxicity in humans has not been definitively shown, but the wealth of all the animal research indicating MDMA’s damaging properties strongly suggests that MDMA an unsafe drug for human consumption.<ref>http://www.usdoj.gov/dea/concern/mdma.html</ref>

== Commonly used names==

MDMA, Ecstasy, XTC, E, X, Beans, Adams, Hug Drug, Disco Biscuit. <ref>http://www.usdoj.gov/dea/concern/mdma.html
</ref>

== Legal Status ==

MDMA is Class A in the UK, making it illegal to sell, buy, or possess without a license. This is typical of almost all countries around the world, but there are however a few countries including Canada and Belgium where possession is legal with a prescription or licence.<ref>http://www.erowid.org/chemicals/mdma/</ref>

== Spectroscopic Data ==

'''NMR Spectrum: 3,4-methylenedioxy-N-methylamphetamine'''

[[Image:Mdma_nmr.JPG]]

== References ==

<references/>

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

It07:Methylenedioxymethamphetamine

2007-11-08T15:57:29Z

Arw06: /* Legal Status */

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Methylenedioxymethamphetamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Methylenedioxymethamphetamine.jpg]]

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3,4-methylenedioxy-N-methylamphetamine

|-
| Other names
| N-methyl 1-1-(3,4-methylenedioxyphenyl)-2-propanamine, MDMA, Ecstacy
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C11H15NO2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN[C@@H](C)CC1=CC(OCO2)=C2C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 193.24g/mol
|-
| Appearance
| White crystalline solid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 69610-10-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| -144.4F 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 148 F
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| Neurotoxic 

|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
|-
| Related compounds

| Amphetamine, MDEA, Methylenedioxymethcathinone, Paramethoxyamphetamine.
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-

== Methylenedioxymethamphetamine ==

Often known as MDMA or Ecstacy, 3,4-methylenedioxy-N-methylamphetamine is a semisynthetic empathogen-entactogen, an illegal drug that acts as a stimulant producing an psychedelic energizing effect, as well as distortions in time, perception and enhanced enjoyment of tactile experiences. MDMA exerts its primary effects on neurons in the brain that use the chemical serotonin to communicate with other neurons. Aside from recreational purposes, it is used as a tool to supplement various practices including meditation, psychonautics, and illicit psychedelic psychotherapy.
Research in animals indicates that MDMA is neurotoxic; whether or not this is also true in humans is currently an area of intense investigation. MDMA can also be dangerous to health and, on rare occasions, lethal.

[[Image:Ecstacy-02.jpg]]
<ref>http://www.usdoj.gov/dea/photos/mdma/ecstacy-02.jpg</ref>

== History ==

MDMA was first synthesized in 1912, soon after it was patented in Germany by the Merck Company. At that time it was not the subject of human research, but Merck stumbled across MDMA when they tried to synthesize Hydrastinin, a vasoconstrictive and styptic medicine. MDMA was an unplanned by-product of this synthesis. In the 1950s it was briefly researched by the U.S. Government as part of the CIA's and the Army's chemical warfare investigations into MDMA as a truth serum, which proved to be unsuitable. The first reported recreational use was in the 1960s, where it became known as the love drug. In the mid-70s, the psychedelic therapy community rediscovered it and psychiatrists and therapists began to use it to supplement psychotherapy. In the early 1980s, the drug began to be used recreationally, most notably in Dallas, under the name the street name 'Ecstasy'. The non-medical and therapeutic use of MDMA was made illegal in the USA in 1985. Soon afterwards its use rapidly spread outside the United States, where it was widely used in the UK and other parts of Europe, becoming an integral part of the rave subculture and other psychedelic and dancefloor influenced music scenes.<ref>http://www.a1b2c3.com/drugs/x_01.htm</ref>

== Synthesis ==

Reaction Overview:
The 'ketone' approach is one of many synthesis schemes for the production of MDMA. This basic scheme is the oxidation of the plant oil 'safrole' (1-allyl-3,4-methylenedioxybenzene) into a ketone (3,4-methylenedioxyphenyl-2-propanone), which is then condensed with methylamine and reduced to the final MDMA product.

[[Image:Mdma_synthesis.JPG]]

Step 1: Peroxyacid oxidation (requires isomerization of safrole).

Step 2: Reversible imine formation, which reacts spontaneously when the ketone is added to a solution of methylamine.

Step 3: Reduction, permanently converts the imine to MDMA.
<ref>http://thedea.org/synthesis.html</ref>

== Effects on the Human Body ==

The most common use of MDMA is for recreational purposes. Classed as a stimulant, the effects produced on the human body include euphoria, increased awareness of the senses, feelings of openness, empathy, heightened self-awareness and feeling of mental clarity. Tactile sensations are enhanced for some users resulting in physical contact with others more intense. ‘Alexander Shulgin stated that the single best use of MDMA was to facilitate more direct communication between people involved in significant emotional relationships.’ Physical effects on the body include sweaty palms, heavy sweating, increased heart rate, increased body temperature, and heightened touch sensations.

Naturally there are many health risks involved in taking a stimulant such as MDMA. Physically these risks include hypertension, dehydration and hyperthermia. This is mostly due to the drug's stimulatory effects masking the body's normal sense of exhaustion and thirst.
MDMA is also neurotoxic which means it interferes with brain chemistry, sometimes permanently. The metabolism of MDMA leads to the lipid peroxidation of serotonergic neurons, thus interfering with the brain's ability to effectively use serotonin.
Psychologically, MDMA use often results in a rebound period of poor mood, often known as a ‘comedown’. Obviously this varies in length between different users but can often lead to lasting depression and anxiety in vulnerable users. The longer the time MDMA is active in the brain, the greater the neurotoxic damage to the brain and the greater the risk of short-term emotional problems. The more times MDMA is taken, the greater the risk of any long-term problems.

===Short Term Effects===
In significantly high doses, MDMA can interfere with the body’s ability to regulate temperature, thus effecting homeostasis. On the very rare, but unpredictable occasions, this can possibly lead to a quick sharp increase in body's core temperature (leads to hyperthermia), resulting in failure in the following major organs; liver, kidney, and in cardiovascular system and the worst case scenario is death.

MDMA is a drug that can unfortunately interfere with the body's metabolism of the drug and this can lead to potentially harmful levels, especially if the drug is repeatedly used in a short space of time.

Users of MDMA can face many of the same risks/side effects as casual and frequent users of other stimulants; like cocaine and amphetamines. These typically include increases in heart rate and blood pressure, which is has significantly higher risk for people with either circulatory problems or heart disease, and other symptoms include muscle tension, involuntary teeth clenching, nausea, blurred vision, faintness, and chills or sweating.

Almost two thirds of people who use MDMA report withdrawal symptoms, including fatigue, loss of appetite, depressed feelings, and trouble concentrating.

===Long Term Effects===

MDMA exposure can lead to long-term damage to the neurons in the brain that are involved in the following; mood, thinking, and judgment. There has been a study in nonhuman primates that has been found to show that exposure to MDMA for only 4 days had caused severe damage to serotonin nerve terminals that became apparent 6 to 7 years later. However,similar neurotoxicity in humans has not been definitively shown, but the wealth of all the animal research indicating MDMA’s damaging properties strongly suggests that MDMA an unsafe drug for human consumption.<ref>http://www.usdoj.gov/dea/concern/mdma.html</ref>

== Commonly used names==

MDMA, Ecstasy, XTC, E, X, Beans, Adams, Hug Drug, Disco Biscuit. <ref>http://www.usdoj.gov/dea/concern/mdma.html
</ref>

== Legal Status ==

MDMA is Class A in the UK, making it illegal to sell, buy, or possess without a license. This is typical of almost all countries around the world, but there are however a few countries including Canada and Belgium where possession is legal with a prescription or licence.<ref>http://www.erowid.org/chemicals/mdma/</ref>

== Spectroscopic Data ==

'''NMR Spectrum: 3,4-methylenedioxy-N-methylamphetamine'''

[[Image:Mdma_nmr.JPG]]

== References ==

<references/>
http://www.erowid.org/chemicals/mdma/
http://thedea.org/synthesis.html
http://www.a1b2c3.com/drugs/x_01.htm

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

It07:Methylenedioxymethamphetamine

2007-11-08T15:55:00Z

Arw06: /* Short Term Effets */

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Methylenedioxymethamphetamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Methylenedioxymethamphetamine.jpg]]

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3,4-methylenedioxy-N-methylamphetamine

|-
| Other names
| N-methyl 1-1-(3,4-methylenedioxyphenyl)-2-propanamine, MDMA, Ecstacy
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C11H15NO2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN[C@@H](C)CC1=CC(OCO2)=C2C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 193.24g/mol
|-
| Appearance
| White crystalline solid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 69610-10-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| -144.4F 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 148 F
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| Neurotoxic 

|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
|-
| Related compounds

| Amphetamine, MDEA, Methylenedioxymethcathinone, Paramethoxyamphetamine.
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-

== Methylenedioxymethamphetamine ==

Often known as MDMA or Ecstacy, 3,4-methylenedioxy-N-methylamphetamine is a semisynthetic empathogen-entactogen, an illegal drug that acts as a stimulant producing an psychedelic energizing effect, as well as distortions in time, perception and enhanced enjoyment of tactile experiences. MDMA exerts its primary effects on neurons in the brain that use the chemical serotonin to communicate with other neurons. Aside from recreational purposes, it is used as a tool to supplement various practices including meditation, psychonautics, and illicit psychedelic psychotherapy.
Research in animals indicates that MDMA is neurotoxic; whether or not this is also true in humans is currently an area of intense investigation. MDMA can also be dangerous to health and, on rare occasions, lethal.

[[Image:Ecstacy-02.jpg]]
<ref>http://www.usdoj.gov/dea/photos/mdma/ecstacy-02.jpg</ref>

== History ==

MDMA was first synthesized in 1912, soon after it was patented in Germany by the Merck Company. At that time it was not the subject of human research, but Merck stumbled across MDMA when they tried to synthesize Hydrastinin, a vasoconstrictive and styptic medicine. MDMA was an unplanned by-product of this synthesis. In the 1950s it was briefly researched by the U.S. Government as part of the CIA's and the Army's chemical warfare investigations into MDMA as a truth serum, which proved to be unsuitable. The first reported recreational use was in the 1960s, where it became known as the love drug. In the mid-70s, the psychedelic therapy community rediscovered it and psychiatrists and therapists began to use it to supplement psychotherapy. In the early 1980s, the drug began to be used recreationally, most notably in Dallas, under the name the street name 'Ecstasy'. The non-medical and therapeutic use of MDMA was made illegal in the USA in 1985. Soon afterwards its use rapidly spread outside the United States, where it was widely used in the UK and other parts of Europe, becoming an integral part of the rave subculture and other psychedelic and dancefloor influenced music scenes.<ref>http://www.a1b2c3.com/drugs/x_01.htm</ref>

== Synthesis ==

Reaction Overview:
The 'ketone' approach is one of many synthesis schemes for the production of MDMA. This basic scheme is the oxidation of the plant oil 'safrole' (1-allyl-3,4-methylenedioxybenzene) into a ketone (3,4-methylenedioxyphenyl-2-propanone), which is then condensed with methylamine and reduced to the final MDMA product.

[[Image:Mdma_synthesis.JPG]]

Step 1: Peroxyacid oxidation (requires isomerization of safrole).

Step 2: Reversible imine formation, which reacts spontaneously when the ketone is added to a solution of methylamine.

Step 3: Reduction, permanently converts the imine to MDMA.
<ref>http://thedea.org/synthesis.html</ref>

== Effects on the Human Body ==

The most common use of MDMA is for recreational purposes. Classed as a stimulant, the effects produced on the human body include euphoria, increased awareness of the senses, feelings of openness, empathy, heightened self-awareness and feeling of mental clarity. Tactile sensations are enhanced for some users resulting in physical contact with others more intense. ‘Alexander Shulgin stated that the single best use of MDMA was to facilitate more direct communication between people involved in significant emotional relationships.’ Physical effects on the body include sweaty palms, heavy sweating, increased heart rate, increased body temperature, and heightened touch sensations.

Naturally there are many health risks involved in taking a stimulant such as MDMA. Physically these risks include hypertension, dehydration and hyperthermia. This is mostly due to the drug's stimulatory effects masking the body's normal sense of exhaustion and thirst.
MDMA is also neurotoxic which means it interferes with brain chemistry, sometimes permanently. The metabolism of MDMA leads to the lipid peroxidation of serotonergic neurons, thus interfering with the brain's ability to effectively use serotonin.
Psychologically, MDMA use often results in a rebound period of poor mood, often known as a ‘comedown’. Obviously this varies in length between different users but can often lead to lasting depression and anxiety in vulnerable users. The longer the time MDMA is active in the brain, the greater the neurotoxic damage to the brain and the greater the risk of short-term emotional problems. The more times MDMA is taken, the greater the risk of any long-term problems.

===Short Term Effects===
In significantly high doses, MDMA can interfere with the body’s ability to regulate temperature, thus effecting homeostasis. On the very rare, but unpredictable occasions, this can possibly lead to a quick sharp increase in body's core temperature (leads to hyperthermia), resulting in failure in the following major organs; liver, kidney, and in cardiovascular system and the worst case scenario is death.

MDMA is a drug that can unfortunately interfere with the body's metabolism of the drug and this can lead to potentially harmful levels, especially if the drug is repeatedly used in a short space of time.

Users of MDMA can face many of the same risks/side effects as casual and frequent users of other stimulants; like cocaine and amphetamines. These typically include increases in heart rate and blood pressure, which is has significantly higher risk for people with either circulatory problems or heart disease, and other symptoms include muscle tension, involuntary teeth clenching, nausea, blurred vision, faintness, and chills or sweating.

Almost two thirds of people who use MDMA report withdrawal symptoms, including fatigue, loss of appetite, depressed feelings, and trouble concentrating.

===Long Term Effects===

MDMA exposure can lead to long-term damage to the neurons in the brain that are involved in the following; mood, thinking, and judgment. There has been a study in nonhuman primates that has been found to show that exposure to MDMA for only 4 days had caused severe damage to serotonin nerve terminals that became apparent 6 to 7 years later. However,similar neurotoxicity in humans has not been definitively shown, but the wealth of all the animal research indicating MDMA’s damaging properties strongly suggests that MDMA an unsafe drug for human consumption.<ref>http://www.usdoj.gov/dea/concern/mdma.html</ref>

== Commonly used names==

MDMA, Ecstasy, XTC, E, X, Beans, Adams, Hug Drug, Disco Biscuit. <ref>http://www.usdoj.gov/dea/concern/mdma.html
</ref>

== Legal Status ==

MDMA is Class A in the UK, making it illegal to sell, buy, or possess without a license. This is typical of almost all countries around the world, but there are however a few countries including Canada and Belgium where possession is legal with a prescription or licence.

== Spectroscopic Data ==

'''NMR Spectrum: 3,4-methylenedioxy-N-methylamphetamine'''

[[Image:Mdma_nmr.JPG]]

== References ==

<references/>
http://www.erowid.org/chemicals/mdma/
http://thedea.org/synthesis.html
http://www.a1b2c3.com/drugs/x_01.htm

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

It07:Methylenedioxymethamphetamine

2007-11-08T15:53:33Z

Arw06: /* Synthesis */

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Methylenedioxymethamphetamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Methylenedioxymethamphetamine.jpg]]

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3,4-methylenedioxy-N-methylamphetamine

|-
| Other names
| N-methyl 1-1-(3,4-methylenedioxyphenyl)-2-propanamine, MDMA, Ecstacy
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C11H15NO2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN[C@@H](C)CC1=CC(OCO2)=C2C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 193.24g/mol
|-
| Appearance
| White crystalline solid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 69610-10-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| -144.4F 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 148 F
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| Neurotoxic 

|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
|-
| Related compounds

| Amphetamine, MDEA, Methylenedioxymethcathinone, Paramethoxyamphetamine.
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-

== Methylenedioxymethamphetamine ==

Often known as MDMA or Ecstacy, 3,4-methylenedioxy-N-methylamphetamine is a semisynthetic empathogen-entactogen, an illegal drug that acts as a stimulant producing an psychedelic energizing effect, as well as distortions in time, perception and enhanced enjoyment of tactile experiences. MDMA exerts its primary effects on neurons in the brain that use the chemical serotonin to communicate with other neurons. Aside from recreational purposes, it is used as a tool to supplement various practices including meditation, psychonautics, and illicit psychedelic psychotherapy.
Research in animals indicates that MDMA is neurotoxic; whether or not this is also true in humans is currently an area of intense investigation. MDMA can also be dangerous to health and, on rare occasions, lethal.

[[Image:Ecstacy-02.jpg]]
<ref>http://www.usdoj.gov/dea/photos/mdma/ecstacy-02.jpg</ref>

== History ==

MDMA was first synthesized in 1912, soon after it was patented in Germany by the Merck Company. At that time it was not the subject of human research, but Merck stumbled across MDMA when they tried to synthesize Hydrastinin, a vasoconstrictive and styptic medicine. MDMA was an unplanned by-product of this synthesis. In the 1950s it was briefly researched by the U.S. Government as part of the CIA's and the Army's chemical warfare investigations into MDMA as a truth serum, which proved to be unsuitable. The first reported recreational use was in the 1960s, where it became known as the love drug. In the mid-70s, the psychedelic therapy community rediscovered it and psychiatrists and therapists began to use it to supplement psychotherapy. In the early 1980s, the drug began to be used recreationally, most notably in Dallas, under the name the street name 'Ecstasy'. The non-medical and therapeutic use of MDMA was made illegal in the USA in 1985. Soon afterwards its use rapidly spread outside the United States, where it was widely used in the UK and other parts of Europe, becoming an integral part of the rave subculture and other psychedelic and dancefloor influenced music scenes.<ref>http://www.a1b2c3.com/drugs/x_01.htm</ref>

== Synthesis ==

Reaction Overview:
The 'ketone' approach is one of many synthesis schemes for the production of MDMA. This basic scheme is the oxidation of the plant oil 'safrole' (1-allyl-3,4-methylenedioxybenzene) into a ketone (3,4-methylenedioxyphenyl-2-propanone), which is then condensed with methylamine and reduced to the final MDMA product.

[[Image:Mdma_synthesis.JPG]]

Step 1: Peroxyacid oxidation (requires isomerization of safrole).

Step 2: Reversible imine formation, which reacts spontaneously when the ketone is added to a solution of methylamine.

Step 3: Reduction, permanently converts the imine to MDMA.
<ref>http://thedea.org/synthesis.html</ref>

== Effects on the Human Body ==

The most common use of MDMA is for recreational purposes. Classed as a stimulant, the effects produced on the human body include euphoria, increased awareness of the senses, feelings of openness, empathy, heightened self-awareness and feeling of mental clarity. Tactile sensations are enhanced for some users resulting in physical contact with others more intense. ‘Alexander Shulgin stated that the single best use of MDMA was to facilitate more direct communication between people involved in significant emotional relationships.’ Physical effects on the body include sweaty palms, heavy sweating, increased heart rate, increased body temperature, and heightened touch sensations.

Naturally there are many health risks involved in taking a stimulant such as MDMA. Physically these risks include hypertension, dehydration and hyperthermia. This is mostly due to the drug's stimulatory effects masking the body's normal sense of exhaustion and thirst.
MDMA is also neurotoxic which means it interferes with brain chemistry, sometimes permanently. The metabolism of MDMA leads to the lipid peroxidation of serotonergic neurons, thus interfering with the brain's ability to effectively use serotonin.
Psychologically, MDMA use often results in a rebound period of poor mood, often known as a ‘comedown’. Obviously this varies in length between different users but can often lead to lasting depression and anxiety in vulnerable users. The longer the time MDMA is active in the brain, the greater the neurotoxic damage to the brain and the greater the risk of short-term emotional problems. The more times MDMA is taken, the greater the risk of any long-term problems.

===Short Term Effets===
In significantly high doses, MDMA can interfere with the body’s ability to regulate temperature, thus effecting homeostasis. On the very rare, but unpredictable occasions, this can possibly lead to a quick sharp increase in body's core temperature (leads to hyperthermia), resulting in failure in the following major organs; liver, kidney, and in cardiovascular system and the worst case scenario is death.

MDMA is a drug that can unfortunately interfere with the body's metabolism of the drug and this can lead to potentially harmful levels, especially if the drug is repeatedly used in a short space of time.

Users of MDMA can face many of the same risks/side effects as casual and frequent users of other stimulants; like cocaine and amphetamines. These typically include increases in heart rate and blood pressure, which is has significantly higher risk for people with either circulatory problems or heart disease, and other symptoms include muscle tension, involuntary teeth clenching, nausea, blurred vision, faintness, and chills or sweating.

Almost two thirds of people who use MDMA report withdrawal symptoms, including fatigue, loss of appetite, depressed feelings, and trouble concentrating.

===Long Term Effects===

MDMA exposure can lead to long-term damage to the neurons in the brain that are involved in the following; mood, thinking, and judgment. There has been a study in nonhuman primates that has been found to show that exposure to MDMA for only 4 days had caused severe damage to serotonin nerve terminals that became apparent 6 to 7 years later. However,similar neurotoxicity in humans has not been definitively shown, but the wealth of all the animal research indicating MDMA’s damaging properties strongly suggests that MDMA an unsafe drug for human consumption.<ref>http://www.usdoj.gov/dea/concern/mdma.html</ref>

== Commonly used names==

MDMA, Ecstasy, XTC, E, X, Beans, Adams, Hug Drug, Disco Biscuit. <ref>http://www.usdoj.gov/dea/concern/mdma.html
</ref>

== Legal Status ==

MDMA is Class A in the UK, making it illegal to sell, buy, or possess without a license. This is typical of almost all countries around the world, but there are however a few countries including Canada and Belgium where possession is legal with a prescription or licence.

== Spectroscopic Data ==

'''NMR Spectrum: 3,4-methylenedioxy-N-methylamphetamine'''

[[Image:Mdma_nmr.JPG]]

== References ==

<references/>
http://www.erowid.org/chemicals/mdma/
http://thedea.org/synthesis.html
http://www.a1b2c3.com/drugs/x_01.htm

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

It07:Methylenedioxymethamphetamine

2007-11-08T15:52:44Z

Arw06:

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Methylenedioxymethamphetamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Methylenedioxymethamphetamine.jpg]]

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3,4-methylenedioxy-N-methylamphetamine

|-
| Other names
| N-methyl 1-1-(3,4-methylenedioxyphenyl)-2-propanamine, MDMA, Ecstacy
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C11H15NO2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN[C@@H](C)CC1=CC(OCO2)=C2C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 193.24g/mol
|-
| Appearance
| White crystalline solid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 69610-10-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| -144.4F 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 148 F
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| Neurotoxic 

|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
|-
| Related compounds

| Amphetamine, MDEA, Methylenedioxymethcathinone, Paramethoxyamphetamine.
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-

== Methylenedioxymethamphetamine ==

Often known as MDMA or Ecstacy, 3,4-methylenedioxy-N-methylamphetamine is a semisynthetic empathogen-entactogen, an illegal drug that acts as a stimulant producing an psychedelic energizing effect, as well as distortions in time, perception and enhanced enjoyment of tactile experiences. MDMA exerts its primary effects on neurons in the brain that use the chemical serotonin to communicate with other neurons. Aside from recreational purposes, it is used as a tool to supplement various practices including meditation, psychonautics, and illicit psychedelic psychotherapy.
Research in animals indicates that MDMA is neurotoxic; whether or not this is also true in humans is currently an area of intense investigation. MDMA can also be dangerous to health and, on rare occasions, lethal.

[[Image:Ecstacy-02.jpg]]
<ref>http://www.usdoj.gov/dea/photos/mdma/ecstacy-02.jpg</ref>

== History ==

MDMA was first synthesized in 1912, soon after it was patented in Germany by the Merck Company. At that time it was not the subject of human research, but Merck stumbled across MDMA when they tried to synthesize Hydrastinin, a vasoconstrictive and styptic medicine. MDMA was an unplanned by-product of this synthesis. In the 1950s it was briefly researched by the U.S. Government as part of the CIA's and the Army's chemical warfare investigations into MDMA as a truth serum, which proved to be unsuitable. The first reported recreational use was in the 1960s, where it became known as the love drug. In the mid-70s, the psychedelic therapy community rediscovered it and psychiatrists and therapists began to use it to supplement psychotherapy. In the early 1980s, the drug began to be used recreationally, most notably in Dallas, under the name the street name 'Ecstasy'. The non-medical and therapeutic use of MDMA was made illegal in the USA in 1985. Soon afterwards its use rapidly spread outside the United States, where it was widely used in the UK and other parts of Europe, becoming an integral part of the rave subculture and other psychedelic and dancefloor influenced music scenes.<ref>http://www.a1b2c3.com/drugs/x_01.htm</ref>

== Synthesis ==

Reaction Overview:
The 'ketone' approach is one of many synthesis schemes for the production of MDMA. This basic scheme is the oxidation of the plant oil 'safrole' (1-allyl-3,4-methylenedioxybenzene) into a ketone (3,4-methylenedioxyphenyl-2-propanone), which is then condensed with methylamine and reduced to the final MDMA product.

[[Image:Mdma_synthesis.JPG]]

Step 1: Peroxyacid oxidation (requires isomerization of safrole).

Step 2: Reversible imine formation, which reacts spontaneously when the ketone is added to a solution of methylamine.

Step 3: Reduction, permanently converts the imine to MDMA.
''http://thedea.org/synthesis.html''

== Effects on the Human Body ==

The most common use of MDMA is for recreational purposes. Classed as a stimulant, the effects produced on the human body include euphoria, increased awareness of the senses, feelings of openness, empathy, heightened self-awareness and feeling of mental clarity. Tactile sensations are enhanced for some users resulting in physical contact with others more intense. ‘Alexander Shulgin stated that the single best use of MDMA was to facilitate more direct communication between people involved in significant emotional relationships.’ Physical effects on the body include sweaty palms, heavy sweating, increased heart rate, increased body temperature, and heightened touch sensations.

Naturally there are many health risks involved in taking a stimulant such as MDMA. Physically these risks include hypertension, dehydration and hyperthermia. This is mostly due to the drug's stimulatory effects masking the body's normal sense of exhaustion and thirst.
MDMA is also neurotoxic which means it interferes with brain chemistry, sometimes permanently. The metabolism of MDMA leads to the lipid peroxidation of serotonergic neurons, thus interfering with the brain's ability to effectively use serotonin.
Psychologically, MDMA use often results in a rebound period of poor mood, often known as a ‘comedown’. Obviously this varies in length between different users but can often lead to lasting depression and anxiety in vulnerable users. The longer the time MDMA is active in the brain, the greater the neurotoxic damage to the brain and the greater the risk of short-term emotional problems. The more times MDMA is taken, the greater the risk of any long-term problems.

===Short Term Effets===
In significantly high doses, MDMA can interfere with the body’s ability to regulate temperature, thus effecting homeostasis. On the very rare, but unpredictable occasions, this can possibly lead to a quick sharp increase in body's core temperature (leads to hyperthermia), resulting in failure in the following major organs; liver, kidney, and in cardiovascular system and the worst case scenario is death.

MDMA is a drug that can unfortunately interfere with the body's metabolism of the drug and this can lead to potentially harmful levels, especially if the drug is repeatedly used in a short space of time.

Users of MDMA can face many of the same risks/side effects as casual and frequent users of other stimulants; like cocaine and amphetamines. These typically include increases in heart rate and blood pressure, which is has significantly higher risk for people with either circulatory problems or heart disease, and other symptoms include muscle tension, involuntary teeth clenching, nausea, blurred vision, faintness, and chills or sweating.

Almost two thirds of people who use MDMA report withdrawal symptoms, including fatigue, loss of appetite, depressed feelings, and trouble concentrating.

===Long Term Effects===

MDMA exposure can lead to long-term damage to the neurons in the brain that are involved in the following; mood, thinking, and judgment. There has been a study in nonhuman primates that has been found to show that exposure to MDMA for only 4 days had caused severe damage to serotonin nerve terminals that became apparent 6 to 7 years later. However,similar neurotoxicity in humans has not been definitively shown, but the wealth of all the animal research indicating MDMA’s damaging properties strongly suggests that MDMA an unsafe drug for human consumption.<ref>http://www.usdoj.gov/dea/concern/mdma.html</ref>

== Commonly used names==

MDMA, Ecstasy, XTC, E, X, Beans, Adams, Hug Drug, Disco Biscuit. <ref>http://www.usdoj.gov/dea/concern/mdma.html
</ref>

== Legal Status ==

MDMA is Class A in the UK, making it illegal to sell, buy, or possess without a license. This is typical of almost all countries around the world, but there are however a few countries including Canada and Belgium where possession is legal with a prescription or licence.

== Spectroscopic Data ==

'''NMR Spectrum: 3,4-methylenedioxy-N-methylamphetamine'''

[[Image:Mdma_nmr.JPG]]

== References ==

<references/>
http://www.erowid.org/chemicals/mdma/
http://thedea.org/synthesis.html
http://www.a1b2c3.com/drugs/x_01.htm

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

It07:Methylenedioxymethamphetamine

2007-11-08T15:49:27Z

Arw06: /* References */

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Methylenedioxymethamphetamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Methylenedioxymethamphetamine.jpg]]

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3,4-methylenedioxy-N-methylamphetamine

|-
| Other names
| N-methyl 1-1-(3,4-methylenedioxyphenyl)-2-propanamine, MDMA, Ecstacy
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C11H15NO2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN[C@@H](C)CC1=CC(OCO2)=C2C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 193.24g/mol
|-
| Appearance
| White crystalline solid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 69610-10-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| -144.4F 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 148 F
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| Neurotoxic 

|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
|-
| Related compounds

| Amphetamine, MDEA, Methylenedioxymethcathinone, Paramethoxyamphetamine.
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-

== Methylenedioxymethamphetamine ==

Often known as MDMA or Ecstacy, 3,4-methylenedioxy-N-methylamphetamine is a semisynthetic empathogen-entactogen, an illegal drug that acts as a stimulant producing an psychedelic energizing effect, as well as distortions in time, perception and enhanced enjoyment of tactile experiences. MDMA exerts its primary effects on neurons in the brain that use the chemical serotonin to communicate with other neurons. Aside from recreational purposes, it is used as a tool to supplement various practices including meditation, psychonautics, and illicit psychedelic psychotherapy.
Research in animals indicates that MDMA is neurotoxic; whether or not this is also true in humans is currently an area of intense investigation. MDMA can also be dangerous to health and, on rare occasions, lethal.

[[Image:Ecstacy-02.jpg]]
<ref>http://www.usdoj.gov/dea/photos/mdma/ecstacy-02.jpg</ref>

== History ==

MDMA was first synthesized in 1912, soon after it was patented in Germany by the Merck Company. At that time it was not the subject of human research, but Merck stumbled across MDMA when they tried to synthesize Hydrastinin, a vasoconstrictive and styptic medicine. MDMA was an unplanned by-product of this synthesis. In the 1950s it was briefly researched by the U.S. Government as part of the CIA's and the Army's chemical warfare investigations into MDMA as a truth serum, which proved to be unsuitable. The first reported recreational use was in the 1960s, where it became known as the love drug. In the mid-70s, the psychedelic therapy community rediscovered it and psychiatrists and therapists began to use it to supplement psychotherapy. In the early 1980s, the drug began to be used recreationally, most notably in Dallas, under the name the street name 'Ecstasy'. The non-medical and therapeutic use of MDMA was made illegal in the USA in 1985. Soon afterwards its use rapidly spread outside the United States, where it was widely used in the UK and other parts of Europe, becoming an integral part of the rave subculture and other psychedelic and dancefloor influenced music scenes.

== Synthesis ==

Reaction Overview:
The 'ketone' approach is one of many synthesis schemes for the production of MDMA. This basic scheme is the oxidation of the plant oil 'safrole' (1-allyl-3,4-methylenedioxybenzene) into a ketone (3,4-methylenedioxyphenyl-2-propanone), which is then condensed with methylamine and reduced to the final MDMA product.

[[Image:Mdma_synthesis.JPG]]

Step 1: Peroxyacid oxidation (requires isomerization of safrole).

Step 2: Reversible imine formation, which reacts spontaneously when the ketone is added to a solution of methylamine.

Step 3: Reduction, permanently converts the imine to MDMA.
''http://thedea.org/synthesis.html''

== Effects on the Human Body ==

The most common use of MDMA is for recreational purposes. Classed as a stimulant, the effects produced on the human body include euphoria, increased awareness of the senses, feelings of openness, empathy, heightened self-awareness and feeling of mental clarity. Tactile sensations are enhanced for some users resulting in physical contact with others more intense. ‘Alexander Shulgin stated that the single best use of MDMA was to facilitate more direct communication between people involved in significant emotional relationships.’ Physical effects on the body include sweaty palms, heavy sweating, increased heart rate, increased body temperature, and heightened touch sensations.

Naturally there are many health risks involved in taking a stimulant such as MDMA. Physically these risks include hypertension, dehydration and hyperthermia. This is mostly due to the drug's stimulatory effects masking the body's normal sense of exhaustion and thirst.
MDMA is also neurotoxic which means it interferes with brain chemistry, sometimes permanently. The metabolism of MDMA leads to the lipid peroxidation of serotonergic neurons, thus interfering with the brain's ability to effectively use serotonin.
Psychologically, MDMA use often results in a rebound period of poor mood, often known as a ‘comedown’. Obviously this varies in length between different users but can often lead to lasting depression and anxiety in vulnerable users. The longer the time MDMA is active in the brain, the greater the neurotoxic damage to the brain and the greater the risk of short-term emotional problems. The more times MDMA is taken, the greater the risk of any long-term problems.

===Short Term Effets===
In significantly high doses, MDMA can interfere with the body’s ability to regulate temperature, thus effecting homeostasis. On the very rare, but unpredictable occasions, this can possibly lead to a quick sharp increase in body's core temperature (leads to hyperthermia), resulting in failure in the following major organs; liver, kidney, and in cardiovascular system and the worst case scenario is death.

MDMA is a drug that can unfortunately interfere with the body's metabolism of the drug and this can lead to potentially harmful levels, especially if the drug is repeatedly used in a short space of time.

Users of MDMA can face many of the same risks/side effects as casual and frequent users of other stimulants; like cocaine and amphetamines. These typically include increases in heart rate and blood pressure, which is has significantly higher risk for people with either circulatory problems or heart disease, and other symptoms include muscle tension, involuntary teeth clenching, nausea, blurred vision, faintness, and chills or sweating.

Almost two thirds of people who use MDMA report withdrawal symptoms, including fatigue, loss of appetite, depressed feelings, and trouble concentrating.

===Long Term Effects===

MDMA exposure can lead to long-term damage to the neurons in the brain that are involved in the following; mood, thinking, and judgment. There has been a study in nonhuman primates that has been found to show that exposure to MDMA for only 4 days had caused severe damage to serotonin nerve terminals that became apparent 6 to 7 years later. However,similar neurotoxicity in humans has not been definitively shown, but the wealth of all the animal research indicating MDMA’s damaging properties strongly suggests that MDMA an unsafe drug for human consumption.<ref>http://www.usdoj.gov/dea/concern/mdma.html</ref>

== Commonly used names==

MDMA, Ecstasy, XTC, E, X, Beans, Adams, Hug Drug, Disco Biscuit. <ref>http://www.usdoj.gov/dea/concern/mdma.html
</ref>

== Legal Status ==

MDMA is Class A in the UK, making it illegal to sell, buy, or possess without a license. This is typical of almost all countries around the world, but there are however a few countries including Canada and Belgium where possession is legal with a prescription or licence.

== Spectroscopic Data ==

'''NMR Spectrum: 3,4-methylenedioxy-N-methylamphetamine'''

[[Image:Mdma_nmr.JPG]]

== References ==

<references/>
http://www.erowid.org/chemicals/mdma/
http://thedea.org/synthesis.html

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

It07:Methylenedioxymethamphetamine

2007-11-08T15:49:02Z

Arw06:

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Methylenedioxymethamphetamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Methylenedioxymethamphetamine.jpg]]

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3,4-methylenedioxy-N-methylamphetamine

|-
| Other names
| N-methyl 1-1-(3,4-methylenedioxyphenyl)-2-propanamine, MDMA, Ecstacy
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C11H15NO2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN[C@@H](C)CC1=CC(OCO2)=C2C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 193.24g/mol
|-
| Appearance
| White crystalline solid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 69610-10-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| -144.4F 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 148 F
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| Neurotoxic 

|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
|-
| Related compounds

| Amphetamine, MDEA, Methylenedioxymethcathinone, Paramethoxyamphetamine.
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-

== Methylenedioxymethamphetamine ==

Often known as MDMA or Ecstacy, 3,4-methylenedioxy-N-methylamphetamine is a semisynthetic empathogen-entactogen, an illegal drug that acts as a stimulant producing an psychedelic energizing effect, as well as distortions in time, perception and enhanced enjoyment of tactile experiences. MDMA exerts its primary effects on neurons in the brain that use the chemical serotonin to communicate with other neurons. Aside from recreational purposes, it is used as a tool to supplement various practices including meditation, psychonautics, and illicit psychedelic psychotherapy.
Research in animals indicates that MDMA is neurotoxic; whether or not this is also true in humans is currently an area of intense investigation. MDMA can also be dangerous to health and, on rare occasions, lethal.

[[Image:Ecstacy-02.jpg]]
<ref>http://www.usdoj.gov/dea/photos/mdma/ecstacy-02.jpg</ref>

== History ==

MDMA was first synthesized in 1912, soon after it was patented in Germany by the Merck Company. At that time it was not the subject of human research, but Merck stumbled across MDMA when they tried to synthesize Hydrastinin, a vasoconstrictive and styptic medicine. MDMA was an unplanned by-product of this synthesis. In the 1950s it was briefly researched by the U.S. Government as part of the CIA's and the Army's chemical warfare investigations into MDMA as a truth serum, which proved to be unsuitable. The first reported recreational use was in the 1960s, where it became known as the love drug. In the mid-70s, the psychedelic therapy community rediscovered it and psychiatrists and therapists began to use it to supplement psychotherapy. In the early 1980s, the drug began to be used recreationally, most notably in Dallas, under the name the street name 'Ecstasy'. The non-medical and therapeutic use of MDMA was made illegal in the USA in 1985. Soon afterwards its use rapidly spread outside the United States, where it was widely used in the UK and other parts of Europe, becoming an integral part of the rave subculture and other psychedelic and dancefloor influenced music scenes.

== Synthesis ==

Reaction Overview:
The 'ketone' approach is one of many synthesis schemes for the production of MDMA. This basic scheme is the oxidation of the plant oil 'safrole' (1-allyl-3,4-methylenedioxybenzene) into a ketone (3,4-methylenedioxyphenyl-2-propanone), which is then condensed with methylamine and reduced to the final MDMA product.

[[Image:Mdma_synthesis.JPG]]

Step 1: Peroxyacid oxidation (requires isomerization of safrole).

Step 2: Reversible imine formation, which reacts spontaneously when the ketone is added to a solution of methylamine.

Step 3: Reduction, permanently converts the imine to MDMA.
''http://thedea.org/synthesis.html''

== Effects on the Human Body ==

The most common use of MDMA is for recreational purposes. Classed as a stimulant, the effects produced on the human body include euphoria, increased awareness of the senses, feelings of openness, empathy, heightened self-awareness and feeling of mental clarity. Tactile sensations are enhanced for some users resulting in physical contact with others more intense. ‘Alexander Shulgin stated that the single best use of MDMA was to facilitate more direct communication between people involved in significant emotional relationships.’ Physical effects on the body include sweaty palms, heavy sweating, increased heart rate, increased body temperature, and heightened touch sensations.

Naturally there are many health risks involved in taking a stimulant such as MDMA. Physically these risks include hypertension, dehydration and hyperthermia. This is mostly due to the drug's stimulatory effects masking the body's normal sense of exhaustion and thirst.
MDMA is also neurotoxic which means it interferes with brain chemistry, sometimes permanently. The metabolism of MDMA leads to the lipid peroxidation of serotonergic neurons, thus interfering with the brain's ability to effectively use serotonin.
Psychologically, MDMA use often results in a rebound period of poor mood, often known as a ‘comedown’. Obviously this varies in length between different users but can often lead to lasting depression and anxiety in vulnerable users. The longer the time MDMA is active in the brain, the greater the neurotoxic damage to the brain and the greater the risk of short-term emotional problems. The more times MDMA is taken, the greater the risk of any long-term problems.

===Short Term Effets===
In significantly high doses, MDMA can interfere with the body’s ability to regulate temperature, thus effecting homeostasis. On the very rare, but unpredictable occasions, this can possibly lead to a quick sharp increase in body's core temperature (leads to hyperthermia), resulting in failure in the following major organs; liver, kidney, and in cardiovascular system and the worst case scenario is death.

MDMA is a drug that can unfortunately interfere with the body's metabolism of the drug and this can lead to potentially harmful levels, especially if the drug is repeatedly used in a short space of time.

Users of MDMA can face many of the same risks/side effects as casual and frequent users of other stimulants; like cocaine and amphetamines. These typically include increases in heart rate and blood pressure, which is has significantly higher risk for people with either circulatory problems or heart disease, and other symptoms include muscle tension, involuntary teeth clenching, nausea, blurred vision, faintness, and chills or sweating.

Almost two thirds of people who use MDMA report withdrawal symptoms, including fatigue, loss of appetite, depressed feelings, and trouble concentrating.

===Long Term Effects===

MDMA exposure can lead to long-term damage to the neurons in the brain that are involved in the following; mood, thinking, and judgment. There has been a study in nonhuman primates that has been found to show that exposure to MDMA for only 4 days had caused severe damage to serotonin nerve terminals that became apparent 6 to 7 years later. However,similar neurotoxicity in humans has not been definitively shown, but the wealth of all the animal research indicating MDMA’s damaging properties strongly suggests that MDMA an unsafe drug for human consumption.<ref>http://www.usdoj.gov/dea/concern/mdma.html</ref>

== Commonly used names==

MDMA, Ecstasy, XTC, E, X, Beans, Adams, Hug Drug, Disco Biscuit. <ref>http://www.usdoj.gov/dea/concern/mdma.html
</ref>

== Legal Status ==

MDMA is Class A in the UK, making it illegal to sell, buy, or possess without a license. This is typical of almost all countries around the world, but there are however a few countries including Canada and Belgium where possession is legal with a prescription or licence.

== Spectroscopic Data ==

'''NMR Spectrum: 3,4-methylenedioxy-N-methylamphetamine'''

[[Image:Mdma_nmr.JPG]]

== References ==

<references/>
http://www.erowid.org/chemicals/mdma/

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

It07:Methylenedioxymethamphetamine

2007-11-08T15:46:29Z

Arw06: /* References */

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Methylenedioxymethamphetamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Methylenedioxymethamphetamine.jpg]]

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3,4-methylenedioxy-N-methylamphetamine

|-
| Other names
| N-methyl 1-1-(3,4-methylenedioxyphenyl)-2-propanamine, MDMA, Ecstacy
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C11H15NO2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN[C@@H](C)CC1=CC(OCO2)=C2C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 193.24g/mol
|-
| Appearance
| White crystalline solid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 69610-10-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| -144.4F 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 148 F
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| Neurotoxic 

|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
|-
| Related compounds

| Amphetamine, MDEA, Methylenedioxymethcathinone, Paramethoxyamphetamine.
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-

== Methylenedioxymethamphetamine ==

Often known as MDMA or Ecstacy, 3,4-methylenedioxy-N-methylamphetamine is a semisynthetic empathogen-entactogen, an illegal drug that acts as a stimulant producing an psychedelic energizing effect, as well as distortions in time, perception and enhanced enjoyment of tactile experiences. MDMA exerts its primary effects on neurons in the brain that use the chemical serotonin to communicate with other neurons. Aside from recreational purposes, it is used as a tool to supplement various practices including meditation, psychonautics, and illicit psychedelic psychotherapy.
Research in animals indicates that MDMA is neurotoxic; whether or not this is also true in humans is currently an area of intense investigation. MDMA can also be dangerous to health and, on rare occasions, lethal.

[[Image:Ecstacy-02.jpg]]
<ref>http://www.usdoj.gov/dea/photos/mdma/ecstacy-02.jpg</ref>

== History ==

MDMA was first synthesized in 1912, soon after it was patented in Germany by the Merck Company. At that time it was not the subject of human research, but Merck stumbled across MDMA when they tried to synthesize Hydrastinin, a vasoconstrictive and styptic medicine. MDMA was an unplanned by-product of this synthesis. In the 1950s it was briefly researched by the U.S. Government as part of the CIA's and the Army's chemical warfare investigations into MDMA as a truth serum, which proved to be unsuitable. The first reported recreational use was in the 1960s, where it became known as the love drug. In the mid-70s, the psychedelic therapy community rediscovered it and psychiatrists and therapists began to use it to supplement psychotherapy. In the early 1980s, the drug began to be used recreationally, most notably in Dallas, under the name the street name 'Ecstasy'. The non-medical and therapeutic use of MDMA was made illegal in the USA in 1985. Soon afterwards its use rapidly spread outside the United States, where it was widely used in the UK and other parts of Europe, becoming an integral part of the rave subculture and other psychedelic and dancefloor influenced music scenes.

== Synthesis ==

Reaction Overview:
The 'ketone' approach is one of many synthesis schemes for the production of MDMA. This basic scheme is the oxidation of the plant oil 'safrole' (1-allyl-3,4-methylenedioxybenzene) into a ketone (3,4-methylenedioxyphenyl-2-propanone), which is then condensed with methylamine and reduced to the final MDMA product.

[[Image:Mdma_synthesis.JPG]]

Step 1: Peroxyacid oxidation (requires isomerization of safrole).

Step 2: Reversible imine formation, which reacts spontaneously when the ketone is added to a solution of methylamine.

Step 3: Reduction, permanently converts the imine to MDMA.

== Effects on the Human Body ==

The most common use of MDMA is for recreational purposes. Classed as a stimulant, the effects produced on the human body include euphoria, increased awareness of the senses, feelings of openness, empathy, heightened self-awareness and feeling of mental clarity. Tactile sensations are enhanced for some users resulting in physical contact with others more intense. ‘Alexander Shulgin stated that the single best use of MDMA was to facilitate more direct communication between people involved in significant emotional relationships.’ Physical effects on the body include sweaty palms, heavy sweating, increased heart rate, increased body temperature, and heightened touch sensations.

Naturally there are many health risks involved in taking a stimulant such as MDMA. Physically these risks include hypertension, dehydration and hyperthermia. This is mostly due to the drug's stimulatory effects masking the body's normal sense of exhaustion and thirst.
MDMA is also neurotoxic which means it interferes with brain chemistry, sometimes permanently. The metabolism of MDMA leads to the lipid peroxidation of serotonergic neurons, thus interfering with the brain's ability to effectively use serotonin.
Psychologically, MDMA use often results in a rebound period of poor mood, often known as a ‘comedown’. Obviously this varies in length between different users but can often lead to lasting depression and anxiety in vulnerable users. The longer the time MDMA is active in the brain, the greater the neurotoxic damage to the brain and the greater the risk of short-term emotional problems. The more times MDMA is taken, the greater the risk of any long-term problems.

===Short Term Effets===
In significantly high doses, MDMA can interfere with the body’s ability to regulate temperature, thus effecting homeostasis. On the very rare, but unpredictable occasions, this can possibly lead to a quick sharp increase in body's core temperature (leads to hyperthermia), resulting in failure in the following major organs; liver, kidney, and in cardiovascular system and the worst case scenario is death.

MDMA is a drug that can unfortunately interfere with the body's metabolism of the drug and this can lead to potentially harmful levels, especially if the drug is repeatedly used in a short space of time.

Users of MDMA can face many of the same risks/side effects as casual and frequent users of other stimulants; like cocaine and amphetamines. These typically include increases in heart rate and blood pressure, which is has significantly higher risk for people with either circulatory problems or heart disease, and other symptoms include muscle tension, involuntary teeth clenching, nausea, blurred vision, faintness, and chills or sweating.

Almost two thirds of people who use MDMA report withdrawal symptoms, including fatigue, loss of appetite, depressed feelings, and trouble concentrating.

===Long Term Effects===

MDMA exposure can lead to long-term damage to the neurons in the brain that are involved in the following; mood, thinking, and judgment. There has been a study in nonhuman primates that has been found to show that exposure to MDMA for only 4 days had caused severe damage to serotonin nerve terminals that became apparent 6 to 7 years later. However,similar neurotoxicity in humans has not been definitively shown, but the wealth of all the animal research indicating MDMA’s damaging properties strongly suggests that MDMA an unsafe drug for human consumption.<ref>http://www.usdoj.gov/dea/concern/mdma.html</ref>

== Commonly used names==

MDMA, Ecstasy, XTC, E, X, Beans, Adams, Hug Drug, Disco Biscuit. <ref>http://www.usdoj.gov/dea/concern/mdma.html
</ref>

== Legal Status ==

MDMA is Class A in the UK, making it illegal to sell, buy, or possess without a license. This is typical of almost all countries around the world, but there are however a few countries including Canada and Belgium where possession is legal with a prescription or licence.

== Spectroscopic Data ==

'''NMR Spectrum: 3,4-methylenedioxy-N-methylamphetamine'''

[[Image:Mdma_nmr.JPG]]

== References ==

<references/>
http://www.erowid.org/chemicals/mdma/

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

It07:Methylenedioxymethamphetamine

2007-11-08T15:39:58Z

Arw06:

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Methylenedioxymethamphetamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Methylenedioxymethamphetamine.jpg]]

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3,4-methylenedioxy-N-methylamphetamine

|-
| Other names
| N-methyl 1-1-(3,4-methylenedioxyphenyl)-2-propanamine, MDMA, Ecstacy
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C11H15NO2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN[C@@H](C)CC1=CC(OCO2)=C2C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 193.24g/mol
|-
| Appearance
| White crystalline solid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 69610-10-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| -144.4F 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 148 F
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| Neurotoxic 

|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
|-
| Related compounds

| Amphetamine, MDEA, Methylenedioxymethcathinone, Paramethoxyamphetamine.
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-

== Methylenedioxymethamphetamine ==

Often known as MDMA or Ecstacy, 3,4-methylenedioxy-N-methylamphetamine is a semisynthetic empathogen-entactogen, an illegal drug that acts as a stimulant producing an psychedelic energizing effect, as well as distortions in time, perception and enhanced enjoyment of tactile experiences. MDMA exerts its primary effects on neurons in the brain that use the chemical serotonin to communicate with other neurons. Aside from recreational purposes, it is used as a tool to supplement various practices including meditation, psychonautics, and illicit psychedelic psychotherapy.
Research in animals indicates that MDMA is neurotoxic; whether or not this is also true in humans is currently an area of intense investigation. MDMA can also be dangerous to health and, on rare occasions, lethal.

[[Image:Ecstacy-02.jpg]]
<ref>http://www.usdoj.gov/dea/photos/mdma/ecstacy-02.jpg</ref>

== History ==

MDMA was first synthesized in 1912, soon after it was patented in Germany by the Merck Company. At that time it was not the subject of human research, but Merck stumbled across MDMA when they tried to synthesize Hydrastinin, a vasoconstrictive and styptic medicine. MDMA was an unplanned by-product of this synthesis. In the 1950s it was briefly researched by the U.S. Government as part of the CIA's and the Army's chemical warfare investigations into MDMA as a truth serum, which proved to be unsuitable. The first reported recreational use was in the 1960s, where it became known as the love drug. In the mid-70s, the psychedelic therapy community rediscovered it and psychiatrists and therapists began to use it to supplement psychotherapy. In the early 1980s, the drug began to be used recreationally, most notably in Dallas, under the name the street name 'Ecstasy'. The non-medical and therapeutic use of MDMA was made illegal in the USA in 1985. Soon afterwards its use rapidly spread outside the United States, where it was widely used in the UK and other parts of Europe, becoming an integral part of the rave subculture and other psychedelic and dancefloor influenced music scenes.

== Synthesis ==

Reaction Overview:
The 'ketone' approach is one of many synthesis schemes for the production of MDMA. This basic scheme is the oxidation of the plant oil 'safrole' (1-allyl-3,4-methylenedioxybenzene) into a ketone (3,4-methylenedioxyphenyl-2-propanone), which is then condensed with methylamine and reduced to the final MDMA product.

[[Image:Mdma_synthesis.JPG]]

Step 1: Peroxyacid oxidation (requires isomerization of safrole).

Step 2: Reversible imine formation, which reacts spontaneously when the ketone is added to a solution of methylamine.

Step 3: Reduction, permanently converts the imine to MDMA.

== Effects on the Human Body ==

The most common use of MDMA is for recreational purposes. Classed as a stimulant, the effects produced on the human body include euphoria, increased awareness of the senses, feelings of openness, empathy, heightened self-awareness and feeling of mental clarity. Tactile sensations are enhanced for some users resulting in physical contact with others more intense. ‘Alexander Shulgin stated that the single best use of MDMA was to facilitate more direct communication between people involved in significant emotional relationships.’ Physical effects on the body include sweaty palms, heavy sweating, increased heart rate, increased body temperature, and heightened touch sensations.

Naturally there are many health risks involved in taking a stimulant such as MDMA. Physically these risks include hypertension, dehydration and hyperthermia. This is mostly due to the drug's stimulatory effects masking the body's normal sense of exhaustion and thirst.
MDMA is also neurotoxic which means it interferes with brain chemistry, sometimes permanently. The metabolism of MDMA leads to the lipid peroxidation of serotonergic neurons, thus interfering with the brain's ability to effectively use serotonin.
Psychologically, MDMA use often results in a rebound period of poor mood, often known as a ‘comedown’. Obviously this varies in length between different users but can often lead to lasting depression and anxiety in vulnerable users. The longer the time MDMA is active in the brain, the greater the neurotoxic damage to the brain and the greater the risk of short-term emotional problems. The more times MDMA is taken, the greater the risk of any long-term problems.

===Short Term Effets===
In significantly high doses, MDMA can interfere with the body’s ability to regulate temperature, thus effecting homeostasis. On the very rare, but unpredictable occasions, this can possibly lead to a quick sharp increase in body's core temperature (leads to hyperthermia), resulting in failure in the following major organs; liver, kidney, and in cardiovascular system and the worst case scenario is death.

MDMA is a drug that can unfortunately interfere with the body's metabolism of the drug and this can lead to potentially harmful levels, especially if the drug is repeatedly used in a short space of time.

Users of MDMA can face many of the same risks/side effects as casual and frequent users of other stimulants; like cocaine and amphetamines. These typically include increases in heart rate and blood pressure, which is has significantly higher risk for people with either circulatory problems or heart disease, and other symptoms include muscle tension, involuntary teeth clenching, nausea, blurred vision, faintness, and chills or sweating.

Almost two thirds of people who use MDMA report withdrawal symptoms, including fatigue, loss of appetite, depressed feelings, and trouble concentrating.

===Long Term Effects===

MDMA exposure can lead to long-term damage to the neurons in the brain that are involved in the following; mood, thinking, and judgment. There has been a study in nonhuman primates that has been found to show that exposure to MDMA for only 4 days had caused severe damage to serotonin nerve terminals that became apparent 6 to 7 years later. However,similar neurotoxicity in humans has not been definitively shown, but the wealth of all the animal research indicating MDMA’s damaging properties strongly suggests that MDMA an unsafe drug for human consumption.<ref>http://www.usdoj.gov/dea/concern/mdma.html</ref>

== Commonly used names==

MDMA, Ecstasy, XTC, E, X, Beans, Adams, Hug Drug, Disco Biscuit. <ref>http://www.usdoj.gov/dea/concern/mdma.html
</ref>

== Legal Status ==

MDMA is Class A in the UK, making it illegal to sell, buy, or possess without a license. This is typical of almost all countries around the world, but there are however a few countries including Canada and Belgium where possession is legal with a prescription or licence.

== Spectroscopic Data ==

'''NMR Spectrum: 3,4-methylenedioxy-N-methylamphetamine'''

[[Image:Mdma_nmr.JPG]]

== References ==

<references/>

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

It07:Methylenedioxymethamphetamine

2007-11-08T15:39:10Z

Arw06:

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Methylenedioxymethamphetamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Methylenedioxymethamphetamine.jpg]]

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3,4-methylenedioxy-N-methylamphetamine

|-
| Other names
| N-methyl 1-1-(3,4-methylenedioxyphenyl)-2-propanamine, MDMA, Ecstacy
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C11H15NO2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN[C@@H](C)CC1=CC(OCO2)=C2C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 193.24g/mol
|-
| Appearance
| White crystalline solid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 69610-10-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| -144.4F 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 148 F
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| Neurotoxic 

|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
|-
| Related compounds

| Amphetamine, MDEA, Methylenedioxymethcathinone, Paramethoxyamphetamine.
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-

== Methylenedioxymethamphetamine ==

Often known as MDMA or Ecstacy, 3,4-methylenedioxy-N-methylamphetamine is a semisynthetic empathogen-entactogen, an illegal drug that acts as a stimulant producing an psychedelic energizing effect, as well as distortions in time, perception and enhanced enjoyment of tactile experiences. MDMA exerts its primary effects on neurons in the brain that use the chemical serotonin to communicate with other neurons. Aside from recreational purposes, it is used as a tool to supplement various practices including meditation, psychonautics, and illicit psychedelic psychotherapy.
Research in animals indicates that MDMA is neurotoxic; whether or not this is also true in humans is currently an area of intense investigation. MDMA can also be dangerous to health and, on rare occasions, lethal.

[[Image:Ecstacy-02.jpg]]
<ref>http://www.usdoj.gov/dea/photos/mdma/ecstacy-02.jpg</ref>

== History ==

MDMA was first synthesized in 1912, soon after it was patented in Germany by the Merck Company. At that time it was not the subject of human research, but Merck stumbled across MDMA when they tried to synthesize Hydrastinin, a vasoconstrictive and styptic medicine. MDMA was an unplanned by-product of this synthesis. In the 1950s it was briefly researched by the U.S. Government as part of the CIA's and the Army's chemical warfare investigations into MDMA as a truth serum, which proved to be unsuitable. The first reported recreational use was in the 1960s, where it became known as the love drug. In the mid-70s, the psychedelic therapy community rediscovered it and psychiatrists and therapists began to use it to supplement psychotherapy. In the early 1980s, the drug began to be used recreationally, most notably in Dallas, under the name the street name 'Ecstasy'. The non-medical and therapeutic use of MDMA was made illegal in the USA in 1985. Soon afterwards its use rapidly spread outside the United States, where it was widely used in the UK and other parts of Europe, becoming an integral part of the rave subculture and other psychedelic and dancefloor influenced music scenes.

== Synthesis ==

Reaction Overview:
The 'ketone' approach is one of many synthesis schemes for the production of MDMA. This basic scheme is the oxidation of the plant oil 'safrole' (1-allyl-3,4-methylenedioxybenzene) into a ketone (3,4-methylenedioxyphenyl-2-propanone), which is then condensed with methylamine and reduced to the final MDMA product.

[[Image:Mdma_synthesis.JPG]]

Step 1: Peroxyacid oxidation (requires isomerization of safrole).

Step 2: Reversible imine formation, which reacts spontaneously when the ketone is added to a solution of methylamine.

Step 3: Reduction, permanently converts the imine to MDMA.

== Effects on the Human Body ==

The most common use of MDMA is for recreational purposes. Classed as a stimulant, the effects produced on the human body include euphoria, increased awareness of the senses, feelings of openness, empathy, heightened self-awareness and feeling of mental clarity. Tactile sensations are enhanced for some users resulting in physical contact with others more intense. ‘Alexander Shulgin stated that the single best use of MDMA was to facilitate more direct communication between people involved in significant emotional relationships.’ Physical effects on the body include sweaty palms, heavy sweating, increased heart rate, increased body temperature, and heightened touch sensations.

Naturally there are many health risks involved in taking a stimulant such as MDMA. Physically these risks include hypertension, dehydration and hyperthermia. This is mostly due to the drug's stimulatory effects masking the body's normal sense of exhaustion and thirst.
MDMA is also neurotoxic which means it interferes with brain chemistry, sometimes permanently. The metabolism of MDMA leads to the lipid peroxidation of serotonergic neurons, thus interfering with the brain's ability to effectively use serotonin.
Psychologically, MDMA use often results in a rebound period of poor mood, often known as a ‘comedown’. Obviously this varies in length between different users but can often lead to lasting depression and anxiety in vulnerable users. The longer the time MDMA is active in the brain, the greater the neurotoxic damage to the brain and the greater the risk of short-term emotional problems. The more times MDMA is taken, the greater the risk of any long-term problems.

===Short Term Effets===
In significantly high doses, MDMA can interfere with the body’s ability to regulate temperature, thus effecting homeostasis. On the very rare, but unpredictable occasions, this can possibly lead to a quick sharp increase in body's core temperature (leads to hyperthermia), resulting in failure in the following major organs; liver, kidney, and in cardiovascular system and the worst case scenario is death.

MDMA is a drug that can unfortunately interfere with the body's metabolism of the drug and this can lead to potentially harmful levels, especially if the drug is repeatedly used in a short space of time.

Users of MDMA can face many of the same risks/side effects as casual and frequent users of other stimulants; like cocaine and amphetamines. These typically include increases in heart rate and blood pressure, which is has significantly higher risk for people with either circulatory problems or heart disease, and other symptoms include muscle tension, involuntary teeth clenching, nausea, blurred vision, faintness, and chills or sweating.

Almost two thirds of people who use MDMA report withdrawal symptoms, including fatigue, loss of appetite, depressed feelings, and trouble concentrating.

===Long Term Effects===

MDMA exposure can lead to long-term damage to the neurons in the brain that are involved in the following; mood, thinking, and judgment. There has been a study in nonhuman primates that has been found to show that exposure to MDMA for only 4 days had caused severe damage to serotonin nerve terminals that became apparent 6 to 7 years later. However,similar neurotoxicity in humans has not been definitively shown, but the wealth of all the animal research indicating MDMA’s damaging properties strongly suggests that MDMA an unsafe drug for human consumption.<ref>http://www.usdoj.gov/dea/concern/mdma.html</ref>

== Commonly used names==

MDMA, Ecstasy, XTC, E, X, Beans, Adams, Hug Drug, Disco Biscuit. <ref>http://www.usdoj.gov/dea/concern/mdma.html
</ref>

== Legal Status ==

MDMA is Class A in the UK, making it illegal to sell, buy, or possess without a license. This is typical of almost all countries around the world, but there are however a few countries including Canada and Belgium where possession is legal with a prescription or licence.

== Spectroscopic Data ==

'''NMR Spectrum: 3,4-methylenedioxy-N-methylamphetamine'''

[[Image:Mdma_nmr.JPG]]

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

== References ==

<references/>

It07:Methylenedioxymethamphetamine

2007-11-08T15:35:33Z

Arw06:

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Methylenedioxymethamphetamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Methylenedioxymethamphetamine.jpg]]

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3,4-methylenedioxy-N-methylamphetamine

|-
| Other names
| N-methyl 1-1-(3,4-methylenedioxyphenyl)-2-propanamine, MDMA, Ecstacy
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C11H15NO2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN[C@@H](C)CC1=CC(OCO2)=C2C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 193.24g/mol
|-
| Appearance
| White crystalline solid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 69610-10-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| -144.4F 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 148 F
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
|-
| Related compounds

| Amphetamine, MDEA, Methylenedioxymethcathinone, Paramethoxyamphetamine.
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-

== Methylenedioxymethamphetamine ==

Often known as MDMA or Ecstacy, 3,4-methylenedioxy-N-methylamphetamine is a semisynthetic empathogen-entactogen, an illegal drug that acts as a stimulant producing an psychedelic energizing effect, as well as distortions in time, perception and enhanced enjoyment of tactile experiences. MDMA exerts its primary effects on neurons in the brain that use the chemical serotonin to communicate with other neurons. Aside from recreational purposes, it is used as a tool to supplement various practices including meditation, psychonautics, and illicit psychedelic psychotherapy.
Research in animals indicates that MDMA is neurotoxic; whether or not this is also true in humans is currently an area of intense investigation. MDMA can also be dangerous to health and, on rare occasions, lethal.

[[Image:Ecstacy-02.jpg]]
<ref>http://www.usdoj.gov/dea/photos/mdma/ecstacy-02.jpg</ref>

== History ==

MDMA was first synthesized in 1912, soon after it was patented in Germany by the Merck Company. At that time it was not the subject of human research, but Merck stumbled across MDMA when they tried to synthesize Hydrastinin, a vasoconstrictive and styptic medicine. MDMA was an unplanned by-product of this synthesis. In the 1950s it was briefly researched by the U.S. Government as part of the CIA's and the Army's chemical warfare investigations into MDMA as a truth serum, which proved to be unsuitable. The first reported recreational use was in the 1960s, where it became known as the love drug. In the mid-70s, the psychedelic therapy community rediscovered it and psychiatrists and therapists began to use it to supplement psychotherapy. In the early 1980s, the drug began to be used recreationally, most notably in Dallas, under the name the street name 'Ecstasy'. The non-medical and therapeutic use of MDMA was made illegal in the USA in 1985. Soon afterwards its use rapidly spread outside the United States, where it was widely used in the UK and other parts of Europe, becoming an integral part of the rave subculture and other psychedelic and dancefloor influenced music scenes.

== Synthesis ==

Reaction Overview:
The 'ketone' approach is one of many synthesis schemes for the production of MDMA. This basic scheme is the oxidation of the plant oil 'safrole' (1-allyl-3,4-methylenedioxybenzene) into a ketone (3,4-methylenedioxyphenyl-2-propanone), which is then condensed with methylamine and reduced to the final MDMA product.

[[Image:Mdma_synthesis.JPG]]

Step 1: Peroxyacid oxidation (requires isomerization of safrole).

Step 2: Reversible imine formation, which reacts spontaneously when the ketone is added to a solution of methylamine.

Step 3: Reduction, permanently converts the imine to MDMA.

== Effects on the Human Body ==

The most common use of MDMA is for recreational purposes. Classed as a stimulant, the effects produced on the human body include euphoria, increased awareness of the senses, feelings of openness, empathy, heightened self-awareness and feeling of mental clarity. Tactile sensations are enhanced for some users resulting in physical contact with others more intense. ‘Alexander Shulgin stated that the single best use of MDMA was to facilitate more direct communication between people involved in significant emotional relationships.’ Physical effects on the body include sweaty palms, heavy sweating, increased heart rate, increased body temperature, and heightened touch sensations.

Naturally there are many health risks involved in taking a stimulant such as MDMA. Physically these risks include hypertension, dehydration and hyperthermia. This is mostly due to the drug's stimulatory effects masking the body's normal sense of exhaustion and thirst.
MDMA is also neurotoxic which means it interferes with brain chemistry, sometimes permanently. The metabolism of MDMA leads to the lipid peroxidation of serotonergic neurons, thus interfering with the brain's ability to effectively use serotonin.
Psychologically, MDMA use often results in a rebound period of poor mood, often known as a ‘comedown’. Obviously this varies in length between different users but can often lead to lasting depression and anxiety in vulnerable users. The longer the time MDMA is active in the brain, the greater the neurotoxic damage to the brain and the greater the risk of short-term emotional problems. The more times MDMA is taken, the greater the risk of any long-term problems.

===Short Term Effets===
In significantly high doses, MDMA can interfere with the body’s ability to regulate temperature, thus effecting homeostasis. On the very rare, but unpredictable occasions, this can possibly lead to a quick sharp increase in body's core temperature (leads to hyperthermia), resulting in failure in the following major organs; liver, kidney, and in cardiovascular system and the worst case scenario is death.

MDMA is a drug that can unfortunately interfere with the body's metabolism of the drug and this can lead to potentially harmful levels, especially if the drug is repeatedly used in a short space of time.

Users of MDMA can face many of the same risks/side effects as casual and frequent users of other stimulants; like cocaine and amphetamines. These typically include increases in heart rate and blood pressure, which is has significantly higher risk for people with either circulatory problems or heart disease, and other symptoms include muscle tension, involuntary teeth clenching, nausea, blurred vision, faintness, and chills or sweating.

Almost two thirds of people who use MDMA report withdrawal symptoms, including fatigue, loss of appetite, depressed feelings, and trouble concentrating.

===Long Term Effects===

MDMA exposure can lead to long-term damage to the neurons in the brain that are involved in the following; mood, thinking, and judgment. There has been a study in nonhuman primates that has been found to show that exposure to MDMA for only 4 days had caused severe damage to serotonin nerve terminals that became apparent 6 to 7 years later. However,similar neurotoxicity in humans has not been definitively shown, but the wealth of all the animal research indicating MDMA’s damaging properties strongly suggests that MDMA an unsafe drug for human consumption.<ref>http://www.usdoj.gov/dea/concern/mdma.html</ref>

== Commonly used names==

MDMA, Ecstasy, XTC, E, X, Beans, Adams, Hug Drug, Disco Biscuit. <ref>http://www.usdoj.gov/dea/concern/mdma.html
</ref>

== Legal Status ==

MDMA is Class A in the UK, making it illegal to sell, buy, or possess without a license. This is typical of almost all countries around the world, but there are however a few countries including Canada and Belgium where possession is legal with a prescription or licence.

== Spectroscopic Data ==

'''NMR Spectrum: 3,4-methylenedioxy-N-methylamphetamine'''

[[Image:Mdma_nmr.JPG]]

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

== References ==

<references/>

It07:Methylenedioxymethamphetamine

2007-11-08T15:33:57Z

Arw06: /* Effects on the Human Body */

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Methylenedioxymethamphetamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Methylenedioxymethamphetamine.jpg]]

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3,4-methylenedioxy-N-methylamphetamine

|-
| Other names
| N-methyl 1-1-(3,4-methylenedioxyphenyl)-2-propanamine, MDMA, Ecstacy
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C11H15NO2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN[C@@H](C)CC1=CC(OCO2)=C2C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 193.24g/mol
|-
| Appearance
| White crystalline solid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 69610-10-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| -144.4F 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 148 F
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
|-
| Related compounds

| Amphetamine, MDEA, Methylenedioxymethcathinone, Paramethoxyamphetamine.
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-

== Methylenedioxymethamphetamine ==

Often known as MDMA or Ecstacy, 3,4-methylenedioxy-N-methylamphetamine is a semisynthetic empathogen-entactogen, an illegal drug that acts as a stimulant producing an psychedelic energizing effect, as well as distortions in time, perception and enhanced enjoyment of tactile experiences. MDMA exerts its primary effects on neurons in the brain that use the chemical serotonin to communicate with other neurons. Aside from recreational purposes, it is used as a tool to supplement various practices including meditation, psychonautics, and illicit psychedelic psychotherapy.
Research in animals indicates that MDMA is neurotoxic; whether or not this is also true in humans is currently an area of intense investigation. MDMA can also be dangerous to health and, on rare occasions, lethal.

[[Image:Ecstacy-02.jpg]]
<ref>http://www.usdoj.gov/dea/photos/mdma/ecstacy-02.jpg</ref>

== History ==

MDMA was first synthesized in 1912, soon after it was patented in Germany by the Merck Company. At that time it was not the subject of human research, but Merck stumbled across MDMA when they tried to synthesize Hydrastinin, a vasoconstrictive and styptic medicine. MDMA was an unplanned by-product of this synthesis. In the 1950s it was briefly researched by the U.S. Government as part of the CIA's and the Army's chemical warfare investigations into MDMA as a truth serum, which proved to be unsuitable. The first reported recreational use was in the 1960s, where it became known as the love drug. In the mid-70s, the psychedelic therapy community rediscovered it and psychiatrists and therapists began to use it to supplement psychotherapy. In the early 1980s, the drug began to be used recreationally, most notably in Dallas, under the name the street name 'Ecstasy'. The non-medical and therapeutic use of MDMA was made illegal in the USA in 1985. Soon afterwards its use rapidly spread outside the United States, where it was widely used in the UK and other parts of Europe, becoming an integral part of the rave subculture and other psychedelic and dancefloor influenced music scenes.

== Synthesis ==

Reaction Overview:
The 'ketone' approach is one of many synthesis schemes for the production of MDMA. This basic scheme is the oxidation of the plant oil 'safrole' (1-allyl-3,4-methylenedioxybenzene) into a ketone (3,4-methylenedioxyphenyl-2-propanone), which is then condensed with methylamine and reduced to the final MDMA product.

[[Image:Mdma_synthesis.JPG]]

Step 1: Peroxyacid oxidation (requires isomerization of safrole).

Step 2: Reversible imine formation, which reacts spontaneously when the ketone is added to a solution of methylamine.

Step 3: Reduction, permanently converts the imine to MDMA.

== Effects on the Human Body ==

The most common use of MDMA is for recreational purposes. Classed as a stimulant, the effects produced on the human body include euphoria, increased awareness of the senses, feelings of openness, empathy, heightened self-awareness and feeling of mental clarity. Tactile sensations are enhanced for some users resulting in physical contact with others more intense. ‘Alexander Shulgin stated that the single best use of MDMA was to facilitate more direct communication between people involved in significant emotional relationships.’ Physical effects on the body include sweaty palms, heavy sweating, increased heart rate, increased body temperature, and heightened touch sensations.

Naturally there are many health risks involved in taking a stimulant such as MDMA. Physically these risks include hypertension, dehydration and hyperthermia. This is mostly due to the drug's stimulatory effects masking the body's normal sense of exhaustion and thirst.
MDMA is also neurotoxic which means it interferes with brain chemistry, sometimes permanently. The metabolism of MDMA leads to the lipid peroxidation of serotonergic neurons, thus interfering with the brain's ability to effectively use serotonin.
Psychologically, MDMA use often results in a rebound period of poor mood, often known as a ‘comedown’. Obviously this varies in length between different users but can often lead to lasting depression and anxiety in vulnerable users. The longer the time MDMA is active in the brain, the greater the neurotoxic damage to the brain and the greater the risk of short-term emotional problems. The more times MDMA is taken, the greater the risk of any long-term problems.

===Short Term Effets===
In significantly high doses, MDMA can interfere with the body’s ability to regulate temperature, thus effecting homeostasis. On the very rare, but unpredictable occasions, this can possibly lead to a quick sharp increase in body's core temperature (leads to hyperthermia), resulting in failure in the following major organs; liver, kidney, and in cardiovascular system and the worst case scenario is death.

MDMA is a drug that can unfortunately interfere with the body's metabolism of the drug and this can lead to potentially harmful levels, especially if the drug is repeatedly used in a short space of time.

Users of MDMA can face many of the same risks/side effects as casual and frequent users of other stimulants; like cocaine and amphetamines. These typically include increases in heart rate and blood pressure, which is has significantly higher risk for people with either circulatory problems or heart disease, and other symptoms include muscle tension, involuntary teeth clenching, nausea, blurred vision, faintness, and chills or sweating.

Almost two thirds of people who use MDMA report withdrawal symptoms, including fatigue, loss of appetite, depressed feelings, and trouble concentrating.

===Long Term Effects===

MDMA exposure can lead to long-term damage to the neurons in the brain that are involved in the following; mood, thinking, and judgment. There has been a study in nonhuman primates that has been found to show that exposure to MDMA for only 4 days had caused severe damage to serotonin nerve terminals that became apparent 6 to 7 years later. However,similar neurotoxicity in humans has not been definitively shown, but the wealth of all the animal research indicating MDMA’s damaging properties strongly suggests that MDMA an unsafe drug for human consumption. Go<ref>http://www.usdoj.gov/dea/concern/mdma.html</ref>

== Commonly used names==

MDMA, Ecstasy, XTC, E, X, Beans, Adams, Hug Drug, Disco Biscuit, Go<ref>http://www.usdoj.gov/dea/concern/mdma.html
</ref>

== Legal Status ==

MDMA is Class A in the UK, making it illegal to sell, buy, or possess without a license. This is typical of almost all countries around the world, but there are however a few countries including Canada and Belgium where possession is legal with a prescription or licence.

== Spectroscopic Data ==

'''NMR Spectrum: 3,4-methylenedioxy-N-methylamphetamine'''

[[Image:Mdma_nmr.JPG]]

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

== References ==

<references/>

It07:Methylenedioxymethamphetamine

2007-11-08T15:30:38Z

Arw06:

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Methylenedioxymethamphetamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Methylenedioxymethamphetamine.jpg]]

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3,4-methylenedioxy-N-methylamphetamine

|-
| Other names
| N-methyl 1-1-(3,4-methylenedioxyphenyl)-2-propanamine, MDMA, Ecstacy
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C11H15NO2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN[C@@H](C)CC1=CC(OCO2)=C2C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 193.24g/mol
|-
| Appearance
| White crystalline solid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 69610-10-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| -144.4F 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 148 F
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
|-
| Related compounds

| Amphetamine, MDEA, Methylenedioxymethcathinone, Paramethoxyamphetamine.
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-

== Methylenedioxymethamphetamine ==

Often known as MDMA or Ecstacy, 3,4-methylenedioxy-N-methylamphetamine is a semisynthetic empathogen-entactogen, an illegal drug that acts as a stimulant producing an psychedelic energizing effect, as well as distortions in time, perception and enhanced enjoyment of tactile experiences. MDMA exerts its primary effects on neurons in the brain that use the chemical serotonin to communicate with other neurons. Aside from recreational purposes, it is used as a tool to supplement various practices including meditation, psychonautics, and illicit psychedelic psychotherapy.
Research in animals indicates that MDMA is neurotoxic; whether or not this is also true in humans is currently an area of intense investigation. MDMA can also be dangerous to health and, on rare occasions, lethal.

[[Image:Ecstacy-02.jpg]]
<ref>http://www.usdoj.gov/dea/photos/mdma/ecstacy-02.jpg</ref>

== History ==

MDMA was first synthesized in 1912, soon after it was patented in Germany by the Merck Company. At that time it was not the subject of human research, but Merck stumbled across MDMA when they tried to synthesize Hydrastinin, a vasoconstrictive and styptic medicine. MDMA was an unplanned by-product of this synthesis. In the 1950s it was briefly researched by the U.S. Government as part of the CIA's and the Army's chemical warfare investigations into MDMA as a truth serum, which proved to be unsuitable. The first reported recreational use was in the 1960s, where it became known as the love drug. In the mid-70s, the psychedelic therapy community rediscovered it and psychiatrists and therapists began to use it to supplement psychotherapy. In the early 1980s, the drug began to be used recreationally, most notably in Dallas, under the name the street name 'Ecstasy'. The non-medical and therapeutic use of MDMA was made illegal in the USA in 1985. Soon afterwards its use rapidly spread outside the United States, where it was widely used in the UK and other parts of Europe, becoming an integral part of the rave subculture and other psychedelic and dancefloor influenced music scenes.

== Synthesis ==

Reaction Overview:
The 'ketone' approach is one of many synthesis schemes for the production of MDMA. This basic scheme is the oxidation of the plant oil 'safrole' (1-allyl-3,4-methylenedioxybenzene) into a ketone (3,4-methylenedioxyphenyl-2-propanone), which is then condensed with methylamine and reduced to the final MDMA product.

[[Image:Mdma_synthesis.JPG]]

Step 1: Peroxyacid oxidation (requires isomerization of safrole).

Step 2: Reversible imine formation, which reacts spontaneously when the ketone is added to a solution of methylamine.

Step 3: Reduction, permanently converts the imine to MDMA.

== Effects on the Human Body ==

The most common use of MDMA is for recreational purposes. Classed as a stimulant, the effects produced on the human body include euphoria, increased awareness of the senses, feelings of openness, empathy, heightened self-awareness and feeling of mental clarity. Tactile sensations are enhanced for some users resulting in physical contact with others more intense. ‘Alexander Shulgin stated that the single best use of MDMA was to facilitate more direct communication between people involved in significant emotional relationships.’ Physical effects on the body include sweaty palms, heavy sweating, increased heart rate, increased body temperature, and heightened touch sensations.

Naturally there are many health risks involved in taking a stimulant such as MDMA. Physically these risks include hypertension, dehydration and hyperthermia. This is mostly due to the drug's stimulatory effects masking the body's normal sense of exhaustion and thirst.
MDMA is also neurotoxic which means it interferes with brain chemistry, sometimes permanently. The metabolism of MDMA leads to the lipid peroxidation of serotonergic neurons, thus interfering with the brain's ability to effectively use serotonin.
Psychologically, MDMA use often results in a rebound period of poor mood, often known as a ‘comedown’. Obviously this varies in length between different users but can often lead to lasting depression and anxiety in vulnerable users. The longer the time MDMA is active in the brain, the greater the neurotoxic damage to the brain and the greater the risk of short-term emotional problems. The more times MDMA is taken, the greater the risk of any long-term problems.

===Short Term Effets===
In significantly high doses, MDMA can interfere with the body’s ability to regulate temperature, thus effecting homeostasis. On the very rare,but unpredictable occasions, this can possibly lead to a quick sharp increase in body's core temperature (leads to hyperthermia), resulting in failure in the following major organs; liver, kidney, and in cardiovascular system and the worst case scenario is death.

MDMA is a drug that can unfortunately interfere with the body's metabolism of the drug and this can lead to potentially harmful levels, especially if the drug is repeatedly used in a short space of time.

Users of MDMA can face many of the same risks/side effects as casual and frequent users of other stimulants; like cocaine and amphetamines. These typically include increases in heart rate and blood pressure, which is has significantly higher risk for people with either circulatory problems or heart disease, and other symptoms include muscle tension, involuntary teeth clenching, nausea, blurred vision, faintness, and chills or sweating.

Almost two thirds of people who use MDMA report withdrawal symptoms, including fatigue, loss of appetite, depressed feelings, and trouble concentrating.Go<ref>http://www.usdoj.gov/dea/concern/mdma.html</ref>

===Long Term Effects===

MDMA exposure can lead to long-term damage to the neurons in the brain that are involved in the following; mood, thinking, and judgment. There has been a study in nonhuman primates that has been found to show that exposure to MDMA for only 4 days had caused severe damage to serotonin nerve terminals that became apparent 6 to 7 years later. However,similar neurotoxicity in humans has not been definitively shown, but the wealth of all the animal research indicating MDMA’s damaging properties strongly suggests that MDMA an unsafe drug for human consumption. Go<ref>http://www.usdoj.gov/dea/concern/mdma.html</ref>

== Commonly used names==

MDMA, Ecstasy, XTC, E, X, Beans, Adams, Hug Drug, Disco Biscuit, Go<ref>http://www.usdoj.gov/dea/concern/mdma.html
</ref>

== Legal Status ==

MDMA is Class A in the UK, making it illegal to sell, buy, or possess without a license. This is typical of almost all countries around the world, but there are however a few countries including Canada and Belgium where possession is legal with a prescription or licence.

== Spectroscopic Data ==

'''NMR Spectrum: 3,4-methylenedioxy-N-methylamphetamine'''

[[Image:Mdma_nmr.JPG]]

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

== References ==

<references/>

It07:Methylenedioxymethamphetamine

2007-11-08T15:18:48Z

Arw06: /* Methylenedioxymethamphetamine */

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Methylenedioxymethamphetamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Methylenedioxymethamphetamine.jpg]]

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3,4-methylenedioxy-N-methylamphetamine

|-
| Other names
| N-methyl 1-1-(3,4-methylenedioxyphenyl)-2-propanamine, MDMA, Ecstacy
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C11H15NO2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN[C@@H](C)CC1=CC(OCO2)=C2C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 193.24g/mol
|-
| Appearance
| White crystalline solid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 69610-10-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| -144.4F 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 148 F
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
|-
| Related compounds

| Amphetamine, MDEA, Methylenedioxymethcathinone, Paramethoxyamphetamine.
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-

== Methylenedioxymethamphetamine ==

Often known as MDMA or Ecstacy, 3,4-methylenedioxy-N-methylamphetamine is a semisynthetic empathogen-entactogen, an illegal drug that acts as a stimulant producing an psychedelic energizing effect, as well as distortions in time, perception and enhanced enjoyment of tactile experiences. MDMA exerts its primary effects on neurons in the brain that use the chemical serotonin to communicate with other neurons. Aside from recreational purposes, it is used as a tool to supplement various practices including meditation, psychonautics, and illicit psychedelic psychotherapy.
Research in animals indicates that MDMA is neurotoxic; whether or not this is also true in humans is currently an area of intense investigation. MDMA can also be dangerous to health and, on rare occasions, lethal.

[[Image:Ecstacy-02.jpg]]
<ref>http://www.usdoj.gov/dea/photos/mdma/ecstacy-02.jpg</ref>

== History ==

MDMA was first synthesized in 1912, soon after it was patented in Germany by the Merck Company. At that time it was not the subject of human research, but Merck stumbled across MDMA when they tried to synthesize Hydrastinin, a vasoconstrictive and styptic medicine. MDMA was an unplanned by-product of this synthesis. In the 1950s it was briefly researched by the U.S. Government as part of the CIA's and the Army's chemical warfare investigations into MDMA as a truth serum, which proved to be unsuitable. The first reported recreational use was in the 1960s, where it became known as the love drug. In the mid-70s, the psychedelic therapy community rediscovered it and psychiatrists and therapists began to use it to supplement psychotherapy. In the early 1980s, the drug began to be used recreationally, most notably in Dallas, under the name the street name 'Ecstasy'. The non-medical and therapeutic use of MDMA was made illegal in the USA in 1985. Soon afterwards its use rapidly spread outside the United States, where it was widely used in the UK and other parts of Europe, becoming an integral part of the rave subculture and other psychedelic and dancefloor influenced music scenes.

== Synthesis ==

Reaction Overview:
The 'ketone' approach is one of many synthesis schemes for the production of MDMA. This basic scheme is the oxidation of the plant oil 'safrole' (1-allyl-3,4-methylenedioxybenzene) into a ketone (3,4-methylenedioxyphenyl-2-propanone), which is then condensed with methylamine and reduced to the final MDMA product.

[[Image:Mdma_synthesis.JPG]]

Step 1: Peroxyacid oxidation (requires isomerization of safrole).

Step 2: Reversible imine formation, which reacts spontaneously when the ketone is added to a solution of methylamine.

Step 3: Reduction, permanently converts the imine to MDMA.

== Effects on the Human Body ==

The most common use of MDMA is for recreational purposes. Classed as a stimulant, the effects produced on the human body include euphoria, increased awareness of the senses, feelings of openness, empathy, heightened self-awareness and feeling of mental clarity. Tactile sensations are enhanced for some users resulting in physical contact with others more intense. ‘Alexander Shulgin stated that the single best use of MDMA was to facilitate more direct communication between people involved in significant emotional relationships.’ Physical effects on the body include sweaty palms, heavy sweating, increased heart rate, increased body temperature, and heightened touch sensations.

Naturally there are many health risks involved in taking a stimulant such as MDMA. Physically these risks include hypertension, dehydration and hyperthermia. This is mostly due to the drug's stimulatory effects masking the body's normal sense of exhaustion and thirst.
MDMA is also neurotoxic which means it interferes with brain chemistry, sometimes permanently. The metabolism of MDMA leads to the lipid peroxidation of serotonergic neurons, thus interfering with the brain's ability to effectively use serotonin.
Psychologically, MDMA use often results in a rebound period of poor mood, often known as a ‘comedown’. Obviously this varies in length between different users but can often lead to lasting depression and anxiety in vulnerable users. The longer the time MDMA is active in the brain, the greater the neurotoxic damage to the brain and the greater the risk of short-term emotional problems. The more times MDMA is taken, the greater the risk of any long-term problems.

===Short Term Effets===
In significantly high doses, MDMA can interfere with the body’s ability to regulate temperature, thus effecting homeostasis. On the very rare,but unpredictable occasions, this can possibly lead to a quick sharp increase in body's core temperature (leads to hyperthermia), resulting in failure in the following major organs; liver, kidney, and in cardiovascular system and the worst case scenario is death.

MDMA is a drug that can unfortunately interfere with the body's metabolism of the drug and this can lead to potentially harmful levels, especially if the drug is repeatedly used in a short space of time.

Users of MDMA can face many of the same risks/side effects as casual and frequent users of other stimulants; like cocaine and amphetamines. These typically include increases in heart rate and blood pressure, which is has significantly higher risk for people with either circulatory problems or heart disease, and other symptoms include muscle tension, involuntary teeth clenching, nausea, blurred vision, faintness, and chills or sweating.

Almost two thirds of people who use MDMA report withdrawal symptoms, including fatigue, loss of appetite, depressed feelings, and trouble concentrating.Go<ref>http://www.usdoj.gov/dea/concern/mdma.html</ref>

===Long Term Effects===

MDMA exposure can lead to long-term damage to the neurons in the brain that are involved in the following; mood, thinking, and judgment. There has been a study in nonhuman primates that has been found to show that exposure to MDMA for only 4 days had caused severe damage to serotonin nerve terminals that became apparent 6 to 7 years later. However,similar neurotoxicity in humans has not been definitively shown, but the wealth of all the animal research indicating MDMA’s damaging properties strongly suggests that MDMA an unsafe drug for human consumption. Go<ref>http://www.usdoj.gov/dea/concern/mdma.html</ref>

== Commonly used names==

MDMA, Ecstasy, XTC, E, X, Beans, Adams, Hug Drug, Disco Biscuit, Go<ref>http://www.usdoj.gov/dea/concern/mdma.html
</ref>

== Spectroscopic Data ==

'''NMR Spectrum: 3,4-methylenedioxy-N-methylamphetamine'''

[[Image:Mdma_nmr.JPG]]

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

== References ==

<references/>

It07:Methylenedioxymethamphetamine

2007-11-01T12:12:56Z

Arw06:

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Methylenedioxymethamphetamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Methylenedioxymethamphetamine.jpg]]

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3,4-methylenedioxy-N-methylamphetamine

|-
| Other names
| N-methyl 1-1-(3,4-methylenedioxyphenyl)-2-propanamine, MDMA, Ecstacy
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C11H15NO2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN[C@@H](C)CC1=CC(OCO2)=C2C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 193.24g/mol
|-
| Appearance
| White crystalline solid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 69610-10-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| -144.4F 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 148 F
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
|-
| Related compounds

| Amphetamine, MDEA, Methylenedioxymethcathinone, Paramethoxyamphetamine.
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-

== Methylenedioxymethamphetamine ==

Often known as MDMA or Ecstacy, 3,4-methylenedioxy-N-methylamphetamine is a semisynthetic empathogen-entactogen, an illegal drug that acts as a stimulant producing an psychedelic energizing effect, as well as distortions in time, perception and enhanced enjoyment of tactile experiences. MDMA exerts its primary effects on neurons in the brain that use the chemical serotonin to communicate with other neurons. Aside from recreational purposes, it is used as a tool to supplement various practices including meditation, psychonautics, and illicit psychedelic psychotherapy.
Research in animals indicates that MDMA is neurotoxic; whether or not this is also true in humans is currently an area of intense investigation. MDMA can also be dangerous to health and, on rare occasions, lethal.

== History ==

MDMA was first synthesized in 1912, soon after it was patented in Germany by the Merck Company. At that time it was not the subject of human research, but Merck stumbled across MDMA when they tried to synthesize Hydrastinin, a vasoconstrictive and styptic medicine. MDMA was an unplanned by-product of this synthesis. In the 1950s it was briefly researched by the U.S. Government as part of the CIA's and the Army's chemical warfare investigations into MDMA as a truth serum, which proved to be unsuitable. The first reported recreational use was in the 1960s, where it became known as the love drug. In the mid-70s, the psychedelic therapy community rediscovered it and psychiatrists and therapists began to use it to supplement psychotherapy. In the early 1980s, the drug began to be used recreationally, most notably in Dallas, under the name the street name 'Ecstasy'. The non-medical and therapeutic use of MDMA was made illegal in the USA in 1985. Soon afterwards its use rapidly spread outside the United States, where it was widely used in the UK and other parts of Europe, becoming an integral part of the rave subculture and other psychedelic and dancefloor influenced music scenes.

== Synthesis ==

Reaction Overview:
The 'ketone' approach is one of many synthesis schemes for the production of MDMA. This basic scheme is the oxidation of the plant oil 'safrole' (1-allyl-3,4-methylenedioxybenzene) into a ketone (3,4-methylenedioxyphenyl-2-propanone), which is then condensed with methylamine and reduced to the final MDMA product.

[[Image:Mdma_synthesis.JPG]]

Step 1: Peroxyacid oxidation (requires isomerization of safrole).

Step 2: Reversible imine formation, which reacts spontaneously when the ketone is added to a solution of methylamine.

Step 3: Reduction, permanently converts the imine to MDMA.

== Effects on the Human Body ==

The most common use of MDMA is for recreational purposes. Classed as a stimulant, the effects produced on the human body include euphoria, increased awareness of the senses, feelings of openness, empathy, heightened self-awareness and feeling of mental clarity. Tactile sensations are enhanced for some users resulting in physical contact with others more intense. ‘Alexander Shulgin stated that the single best use of MDMA was to facilitate more direct communication between people involved in significant emotional relationships.’ Physical effects on the body include sweaty palms, heavy sweating, increased heart rate, increased body temperature, and heightened touch sensations.

Naturally there are many health risks involved in taking a stimulant such as MDMA. Physically these risks include hypertension, dehydration and hyperthermia. This is mostly due to the drug's stimulatory effects masking the body's normal sense of exhaustion and thirst.
MDMA is also neurotoxic which means it interferes with brain chemistry, sometimes permanently. The metabolism of MDMA leads to the lipid peroxidation of serotonergic neurons, thus interfering with the brain's ability to effectively use serotonin.
Psychologically, MDMA use often results in a rebound period of poor mood, often known as a ‘comedown’. Obviously this varies in length between different users but can often lead to lasting depression and anxiety in vulnerable users. The longer the time MDMA is active in the brain, the greater the neurotoxic damage to the brain and the greater the risk of short-term emotional problems. The more times MDMA is taken, the greater the risk of any long-term problems.

== Spectroscopic Data ==

'''NMR Spectrum: 3,4-methylenedioxy-N-methylamphetamine'''

[[Image:Mdma_nmr.JPG]]

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

== References ==

It07:Methylenedioxymethamphetamine

2007-11-01T12:10:54Z

Arw06:

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Methylenedioxymethamphetamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Methylenedioxymethamphetamine.jpg]]

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3,4-methylenedioxy-N-methylamphetamine

|-
| Other names
| N-methyl 1-1-(3,4-methylenedioxyphenyl)-2-propanamine, MDMA, Ecstacy
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C11H15NO2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN[C@@H](C)CC1=CC(OCO2)=C2C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 193.24g/mol
|-
| Appearance
| White crystalline solid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 69610-10-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| {{{Density}}} g/cm³ 
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| -144.4F 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 148 F
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
|-
| Related compounds

| Amphetamine, MDEA, Methylenedioxymethcathinone, Paramethoxyamphetamine.
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-

== Methylenedioxymethamphetamine ==

Often known as MDMA or Ecstacy, 3,4-methylenedioxy-N-methylamphetamine is a semisynthetic empathogen-entactogen, an illegal drug that acts as a stimulant producing an psychedelic energizing effect, as well as distortions in time, perception and enhanced enjoyment of tactile experiences. MDMA exerts its primary effects on neurons in the brain that use the chemical serotonin to communicate with other neurons. Aside from recreational purposes, it is used as a tool to supplement various practices including meditation, psychonautics, and illicit psychedelic psychotherapy.
Research in animals indicates that MDMA is neurotoxic; whether or not this is also true in humans is currently an area of intense investigation. MDMA can also be dangerous to health and, on rare occasions, lethal.

== History ==

MDMA was first synthesized in 1912, soon after it was patented in Germany by the Merck Company. At that time it was not the subject of human research, but Merck stumbled across MDMA when they tried to synthesize Hydrastinin, a vasoconstrictive and styptic medicine. MDMA was an unplanned by-product of this synthesis. In the 1950s it was briefly researched by the U.S. Government as part of the CIA's and the Army's chemical warfare investigations into MDMA as a truth serum, which proved to be unsuitable. The first reported recreational use was in the 1960s, where it became known as the love drug. In the mid-70s, the psychedelic therapy community rediscovered it and psychiatrists and therapists began to use it to supplement psychotherapy. In the early 1980s, the drug began to be used recreationally, most notably in Dallas, under the name the street name 'Ecstasy'. The non-medical and therapeutic use of MDMA was made illegal in the USA in 1985. Soon afterwards its use rapidly spread outside the United States, where it was widely used in the UK and other parts of Europe, becoming an integral part of the rave subculture and other psychedelic and dancefloor influenced music scenes.

== Synthesis ==

Reaction Overview:
The 'ketone' approach is one of many synthesis schemes for the production of MDMA. This basic scheme is the oxidation of the plant oil 'safrole' (1-allyl-3,4-methylenedioxybenzene) into a ketone (3,4-methylenedioxyphenyl-2-propanone), which is then condensed with methylamine and reduced to the final MDMA product.

[[Image:Mdma_synthesis.JPG]]

Step 1: Peroxyacid oxidation (requires isomerization of safrole).

Step 2: Reversible imine formation, which reacts spontaneously when the ketone is added to a solution of methylamine.

Step 3: Reduction, permanently converts the imine to MDMA.

== Effects on the Human Body ==

The most common use of MDMA is for recreational purposes. Classed as a stimulant, the effects produced on the human body include euphoria, increased awareness of the senses, feelings of openness, empathy, heightened self-awareness and feeling of mental clarity. Tactile sensations are enhanced for some users resulting in physical contact with others more intense. ‘Alexander Shulgin stated that the single best use of MDMA was to facilitate more direct communication between people involved in significant emotional relationships.’ Physical effects on the body include sweaty palms, heavy sweating, increased heart rate, increased body temperature, and heightened touch sensations.

Naturally there are many health risks involved in taking a stimulant such as MDMA. Physically these risks include hypertension, dehydration and hyperthermia. This is mostly due to the drug's stimulatory effects masking the body's normal sense of exhaustion and thirst.
MDMA is also neurotoxic which means it interferes with brain chemistry, sometimes permanently. The metabolism of MDMA leads to the lipid peroxidation of serotonergic neurons, thus interfering with the brain's ability to effectively use serotonin.
Psychologically, MDMA use often results in a rebound period of poor mood, often known as a ‘comedown’. Obviously this varies in length between different users but can often lead to lasting depression and anxiety in vulnerable users. The longer the time MDMA is active in the brain, the greater the neurotoxic damage to the brain and the greater the risk of short-term emotional problems. The more times MDMA is taken, the greater the risk of any long-term problems.

== Spectroscopic Data ==

'''NMR Spectrum: 3,4-methylenedioxy-N-methylamphetamine'''

[[Image:Mdma_nmr.JPG]]

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

== References ==

It07:Methylenedioxymethamphetamine

2007-11-01T12:10:23Z

Arw06:

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Methylenedioxymethamphetamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Methylenedioxymethamphetamine.jpg]]

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3,4-methylenedioxy-N-methylamphetamine

|-
| Other names
| N-methyl 1-1-(3,4-methylenedioxyphenyl)-2-propanamine, MDMA, Ecstacy
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C11H15NO2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN[C@@H](C)CC1=CC(OCO2)=C2C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 193.24g/mol
|-
| Appearance
| White crystalline solid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 69610-10-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| {{{Density}}} g/cm³ 
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| -144.4F 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 148 F
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| Amphetamine, MDEA, Methylenedioxymethcathinone, Paramethoxyamphetamine.
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-

== Methylenedioxymethamphetamine ==

Often known as MDMA or Ecstacy, 3,4-methylenedioxy-N-methylamphetamine is a semisynthetic empathogen-entactogen, an illegal drug that acts as a stimulant producing an psychedelic energizing effect, as well as distortions in time, perception and enhanced enjoyment of tactile experiences. MDMA exerts its primary effects on neurons in the brain that use the chemical serotonin to communicate with other neurons. Aside from recreational purposes, it is used as a tool to supplement various practices including meditation, psychonautics, and illicit psychedelic psychotherapy.
Research in animals indicates that MDMA is neurotoxic; whether or not this is also true in humans is currently an area of intense investigation. MDMA can also be dangerous to health and, on rare occasions, lethal.

== History ==

MDMA was first synthesized in 1912, soon after it was patented in Germany by the Merck Company. At that time it was not the subject of human research, but Merck stumbled across MDMA when they tried to synthesize Hydrastinin, a vasoconstrictive and styptic medicine. MDMA was an unplanned by-product of this synthesis. In the 1950s it was briefly researched by the U.S. Government as part of the CIA's and the Army's chemical warfare investigations into MDMA as a truth serum, which proved to be unsuitable. The first reported recreational use was in the 1960s, where it became known as the love drug. In the mid-70s, the psychedelic therapy community rediscovered it and psychiatrists and therapists began to use it to supplement psychotherapy. In the early 1980s, the drug began to be used recreationally, most notably in Dallas, under the name the street name 'Ecstasy'. The non-medical and therapeutic use of MDMA was made illegal in the USA in 1985. Soon afterwards its use rapidly spread outside the United States, where it was widely used in the UK and other parts of Europe, becoming an integral part of the rave subculture and other psychedelic and dancefloor influenced music scenes.

== Synthesis ==

Reaction Overview:
The 'ketone' approach is one of many synthesis schemes for the production of MDMA. This basic scheme is the oxidation of the plant oil 'safrole' (1-allyl-3,4-methylenedioxybenzene) into a ketone (3,4-methylenedioxyphenyl-2-propanone), which is then condensed with methylamine and reduced to the final MDMA product.

[[Image:Mdma_synthesis.JPG]]

Step 1: Peroxyacid oxidation (requires isomerization of safrole).

Step 2: Reversible imine formation, which reacts spontaneously when the ketone is added to a solution of methylamine.

Step 3: Reduction, permanently converts the imine to MDMA.

== Effects on the Human Body ==

The most common use of MDMA is for recreational purposes. Classed as a stimulant, the effects produced on the human body include euphoria, increased awareness of the senses, feelings of openness, empathy, heightened self-awareness and feeling of mental clarity. Tactile sensations are enhanced for some users resulting in physical contact with others more intense. ‘Alexander Shulgin stated that the single best use of MDMA was to facilitate more direct communication between people involved in significant emotional relationships.’ Physical effects on the body include sweaty palms, heavy sweating, increased heart rate, increased body temperature, and heightened touch sensations.

Naturally there are many health risks involved in taking a stimulant such as MDMA. Physically these risks include hypertension, dehydration and hyperthermia. This is mostly due to the drug's stimulatory effects masking the body's normal sense of exhaustion and thirst.
MDMA is also neurotoxic which means it interferes with brain chemistry, sometimes permanently. The metabolism of MDMA leads to the lipid peroxidation of serotonergic neurons, thus interfering with the brain's ability to effectively use serotonin.
Psychologically, MDMA use often results in a rebound period of poor mood, often known as a ‘comedown’. Obviously this varies in length between different users but can often lead to lasting depression and anxiety in vulnerable users. The longer the time MDMA is active in the brain, the greater the neurotoxic damage to the brain and the greater the risk of short-term emotional problems. The more times MDMA is taken, the greater the risk of any long-term problems.

== Spectroscopic Data ==

'''NMR Spectrum: 3,4-methylenedioxy-N-methylamphetamine'''

[[Image:Mdma_nmr.JPG]]

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

== References ==

It07:Methylenedioxymethamphetamine

2007-11-01T12:09:26Z

Arw06:

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Methylenedioxymethamphetamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Methylenedioxymethamphetamine.jpg]]

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3,4-methylenedioxy-N-methylamphetamine

|-
| Other names
| N-methyl 1-1-(3,4-methylenedioxyphenyl)-2-propanamine, MDMA, Ecstacy
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C11H15NO2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN[C@@H](C)CC1=CC(OCO2)=C2C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 193.24g/mol
|-
| Appearance
| White crystalline solid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 69610-10-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| {{{Density}}} g/cm³ 
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| -144.4F 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 148 F
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Amphetamine
MDEA
Methylenedioxymethcathinone
Paramethoxyamphet}}}
|-amine
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-

== Methylenedioxymethamphetamine ==

Often known as MDMA or Ecstacy, 3,4-methylenedioxy-N-methylamphetamine is a semisynthetic empathogen-entactogen, an illegal drug that acts as a stimulant producing an psychedelic energizing effect, as well as distortions in time, perception and enhanced enjoyment of tactile experiences. MDMA exerts its primary effects on neurons in the brain that use the chemical serotonin to communicate with other neurons. Aside from recreational purposes, it is used as a tool to supplement various practices including meditation, psychonautics, and illicit psychedelic psychotherapy.
Research in animals indicates that MDMA is neurotoxic; whether or not this is also true in humans is currently an area of intense investigation. MDMA can also be dangerous to health and, on rare occasions, lethal.

== History ==

MDMA was first synthesized in 1912, soon after it was patented in Germany by the Merck Company. At that time it was not the subject of human research, but Merck stumbled across MDMA when they tried to synthesize Hydrastinin, a vasoconstrictive and styptic medicine. MDMA was an unplanned by-product of this synthesis. In the 1950s it was briefly researched by the U.S. Government as part of the CIA's and the Army's chemical warfare investigations into MDMA as a truth serum, which proved to be unsuitable. The first reported recreational use was in the 1960s, where it became known as the love drug. In the mid-70s, the psychedelic therapy community rediscovered it and psychiatrists and therapists began to use it to supplement psychotherapy. In the early 1980s, the drug began to be used recreationally, most notably in Dallas, under the name the street name 'Ecstasy'. The non-medical and therapeutic use of MDMA was made illegal in the USA in 1985. Soon afterwards its use rapidly spread outside the United States, where it was widely used in the UK and other parts of Europe, becoming an integral part of the rave subculture and other psychedelic and dancefloor influenced music scenes.

== Synthesis ==

Reaction Overview:
The 'ketone' approach is one of many synthesis schemes for the production of MDMA. This basic scheme is the oxidation of the plant oil 'safrole' (1-allyl-3,4-methylenedioxybenzene) into a ketone (3,4-methylenedioxyphenyl-2-propanone), which is then condensed with methylamine and reduced to the final MDMA product.

[[Image:Mdma_synthesis.JPG]]

Step 1: Peroxyacid oxidation (requires isomerization of safrole).

Step 2: Reversible imine formation, which reacts spontaneously when the ketone is added to a solution of methylamine.

Step 3: Reduction, permanently converts the imine to MDMA.

== Effects on the Human Body ==

The most common use of MDMA is for recreational purposes. Classed as a stimulant, the effects produced on the human body include euphoria, increased awareness of the senses, feelings of openness, empathy, heightened self-awareness and feeling of mental clarity. Tactile sensations are enhanced for some users resulting in physical contact with others more intense. ‘Alexander Shulgin stated that the single best use of MDMA was to facilitate more direct communication between people involved in significant emotional relationships.’ Physical effects on the body include sweaty palms, heavy sweating, increased heart rate, increased body temperature, and heightened touch sensations.

Naturally there are many health risks involved in taking a stimulant such as MDMA. Physically these risks include hypertension, dehydration and hyperthermia. This is mostly due to the drug's stimulatory effects masking the body's normal sense of exhaustion and thirst.
MDMA is also neurotoxic which means it interferes with brain chemistry, sometimes permanently. The metabolism of MDMA leads to the lipid peroxidation of serotonergic neurons, thus interfering with the brain's ability to effectively use serotonin.
Psychologically, MDMA use often results in a rebound period of poor mood, often known as a ‘comedown’. Obviously this varies in length between different users but can often lead to lasting depression and anxiety in vulnerable users. The longer the time MDMA is active in the brain, the greater the neurotoxic damage to the brain and the greater the risk of short-term emotional problems. The more times MDMA is taken, the greater the risk of any long-term problems.

== Spectroscopic Data ==

'''NMR Spectrum: 3,4-methylenedioxy-N-methylamphetamine'''

[[Image:Mdma_nmr.JPG]]

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

== References ==

It07:Methylenedioxymethamphetamine

2007-11-01T12:08:45Z

Arw06:

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Methylenedioxymethamphetamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Methylenedioxymethamphetamine.jpg]]

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3,4-methylenedioxy-N-methylamphetamine

|-
| Other names
| N-methyl 1-1-(3,4-methylenedioxyphenyl)-2-propanamine, MDMA, Ecstacy
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C11H15NO2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN[C@@H](C)CC1=CC(OCO2)=C2C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 193.24g/mol
|-
| Appearance
| White crystalline solid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 69610-10-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| {{{Density}}} g/cm³ 
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| -144.4F 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 148 F
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-Amphetamine
MDEA
Methylenedioxymethcathinone
Paramethoxyamphetamine
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-

== Methylenedioxymethamphetamine ==

Often known as MDMA or Ecstacy, 3,4-methylenedioxy-N-methylamphetamine is a semisynthetic empathogen-entactogen, an illegal drug that acts as a stimulant producing an psychedelic energizing effect, as well as distortions in time, perception and enhanced enjoyment of tactile experiences. MDMA exerts its primary effects on neurons in the brain that use the chemical serotonin to communicate with other neurons. Aside from recreational purposes, it is used as a tool to supplement various practices including meditation, psychonautics, and illicit psychedelic psychotherapy.
Research in animals indicates that MDMA is neurotoxic; whether or not this is also true in humans is currently an area of intense investigation. MDMA can also be dangerous to health and, on rare occasions, lethal.

== History ==

MDMA was first synthesized in 1912, soon after it was patented in Germany by the Merck Company. At that time it was not the subject of human research, but Merck stumbled across MDMA when they tried to synthesize Hydrastinin, a vasoconstrictive and styptic medicine. MDMA was an unplanned by-product of this synthesis. In the 1950s it was briefly researched by the U.S. Government as part of the CIA's and the Army's chemical warfare investigations into MDMA as a truth serum, which proved to be unsuitable. The first reported recreational use was in the 1960s, where it became known as the love drug. In the mid-70s, the psychedelic therapy community rediscovered it and psychiatrists and therapists began to use it to supplement psychotherapy. In the early 1980s, the drug began to be used recreationally, most notably in Dallas, under the name the street name 'Ecstasy'. The non-medical and therapeutic use of MDMA was made illegal in the USA in 1985. Soon afterwards its use rapidly spread outside the United States, where it was widely used in the UK and other parts of Europe, becoming an integral part of the rave subculture and other psychedelic and dancefloor influenced music scenes.

== Synthesis ==

Reaction Overview:
The 'ketone' approach is one of many synthesis schemes for the production of MDMA. This basic scheme is the oxidation of the plant oil 'safrole' (1-allyl-3,4-methylenedioxybenzene) into a ketone (3,4-methylenedioxyphenyl-2-propanone), which is then condensed with methylamine and reduced to the final MDMA product.

[[Image:Mdma_synthesis.JPG]]

Step 1: Peroxyacid oxidation (requires isomerization of safrole).

Step 2: Reversible imine formation, which reacts spontaneously when the ketone is added to a solution of methylamine.

Step 3: Reduction, permanently converts the imine to MDMA.

== Effects on the Human Body ==

The most common use of MDMA is for recreational purposes. Classed as a stimulant, the effects produced on the human body include euphoria, increased awareness of the senses, feelings of openness, empathy, heightened self-awareness and feeling of mental clarity. Tactile sensations are enhanced for some users resulting in physical contact with others more intense. ‘Alexander Shulgin stated that the single best use of MDMA was to facilitate more direct communication between people involved in significant emotional relationships.’ Physical effects on the body include sweaty palms, heavy sweating, increased heart rate, increased body temperature, and heightened touch sensations.

Naturally there are many health risks involved in taking a stimulant such as MDMA. Physically these risks include hypertension, dehydration and hyperthermia. This is mostly due to the drug's stimulatory effects masking the body's normal sense of exhaustion and thirst.
MDMA is also neurotoxic which means it interferes with brain chemistry, sometimes permanently. The metabolism of MDMA leads to the lipid peroxidation of serotonergic neurons, thus interfering with the brain's ability to effectively use serotonin.
Psychologically, MDMA use often results in a rebound period of poor mood, often known as a ‘comedown’. Obviously this varies in length between different users but can often lead to lasting depression and anxiety in vulnerable users. The longer the time MDMA is active in the brain, the greater the neurotoxic damage to the brain and the greater the risk of short-term emotional problems. The more times MDMA is taken, the greater the risk of any long-term problems.

== Spectroscopic Data ==

'''NMR Spectrum: 3,4-methylenedioxy-N-methylamphetamine'''

[[Image:Mdma_nmr.JPG]]

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

== References ==

It07:Methylenedioxymethamphetamine

2007-11-01T12:06:30Z

Arw06:

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Methylenedioxymethamphetamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Methylenedioxymethamphetamine.jpg]]

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3,4-methylenedioxy-N-methylamphetamine

|-
| Other names
| N-methyl 1-1-(3,4-methylenedioxyphenyl)-2-propanamine, MDMA, Ecstacy
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C11H15NO2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN[C@@H](C)CC1=CC(OCO2)=C2C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 193.24g/mol
|-
| Appearance
| White crystalline solid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 69610-10-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| {{{Density}}} g/cm³ 
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| -144.4F 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 148 F
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-

== Methylenedioxymethamphetamine ==

Often known as MDMA or Ecstacy, 3,4-methylenedioxy-N-methylamphetamine is a semisynthetic empathogen-entactogen, an illegal drug that acts as a stimulant producing an psychedelic energizing effect, as well as distortions in time, perception and enhanced enjoyment of tactile experiences. MDMA exerts its primary effects on neurons in the brain that use the chemical serotonin to communicate with other neurons. Aside from recreational purposes, it is used as a tool to supplement various practices including meditation, psychonautics, and illicit psychedelic psychotherapy.
Research in animals indicates that MDMA is neurotoxic; whether or not this is also true in humans is currently an area of intense investigation. MDMA can also be dangerous to health and, on rare occasions, lethal.

== History ==

MDMA was first synthesized in 1912, soon after it was patented in Germany by the Merck Company. At that time it was not the subject of human research, but Merck stumbled across MDMA when they tried to synthesize Hydrastinin, a vasoconstrictive and styptic medicine. MDMA was an unplanned by-product of this synthesis. In the 1950s it was briefly researched by the U.S. Government as part of the CIA's and the Army's chemical warfare investigations into MDMA as a truth serum, which proved to be unsuitable. The first reported recreational use was in the 1960s, where it became known as the love drug. In the mid-70s, the psychedelic therapy community rediscovered it and psychiatrists and therapists began to use it to supplement psychotherapy. In the early 1980s, the drug began to be used recreationally, most notably in Dallas, under the name the street name 'Ecstasy'. The non-medical and therapeutic use of MDMA was made illegal in the USA in 1985. Soon afterwards its use rapidly spread outside the United States, where it was widely used in the UK and other parts of Europe, becoming an integral part of the rave subculture and other psychedelic and dancefloor influenced music scenes.

== Synthesis ==

Reaction Overview:
The 'ketone' approach is one of many synthesis schemes for the production of MDMA. This basic scheme is the oxidation of the plant oil 'safrole' (1-allyl-3,4-methylenedioxybenzene) into a ketone (3,4-methylenedioxyphenyl-2-propanone), which is then condensed with methylamine and reduced to the final MDMA product.

[[Image:Mdma_synthesis.JPG]]

Step 1: Peroxyacid oxidation (requires isomerization of safrole).

Step 2: Reversible imine formation, which reacts spontaneously when the ketone is added to a solution of methylamine.

Step 3: Reduction, permanently converts the imine to MDMA.

== Effects on the Human Body ==

The most common use of MDMA is for recreational purposes. Classed as a stimulant, the effects produced on the human body include euphoria, increased awareness of the senses, feelings of openness, empathy, heightened self-awareness and feeling of mental clarity. Tactile sensations are enhanced for some users resulting in physical contact with others more intense. ‘Alexander Shulgin stated that the single best use of MDMA was to facilitate more direct communication between people involved in significant emotional relationships.’ Physical effects on the body include sweaty palms, heavy sweating, increased heart rate, increased body temperature, and heightened touch sensations.

Naturally there are many health risks involved in taking a stimulant such as MDMA. Physically these risks include hypertension, dehydration and hyperthermia. This is mostly due to the drug's stimulatory effects masking the body's normal sense of exhaustion and thirst.
MDMA is also neurotoxic which means it interferes with brain chemistry, sometimes permanently. The metabolism of MDMA leads to the lipid peroxidation of serotonergic neurons, thus interfering with the brain's ability to effectively use serotonin.
Psychologically, MDMA use often results in a rebound period of poor mood, often known as a ‘comedown’. Obviously this varies in length between different users but can often lead to lasting depression and anxiety in vulnerable users. The longer the time MDMA is active in the brain, the greater the neurotoxic damage to the brain and the greater the risk of short-term emotional problems. The more times MDMA is taken, the greater the risk of any long-term problems.

== Spectroscopic Data ==

'''NMR Spectrum: 3,4-methylenedioxy-N-methylamphetamine'''

[[Image:Mdma_nmr.JPG]]

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

== References ==

It07:Methylenedioxymethamphetamine

2007-11-01T11:52:20Z

Arw06:

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Methylenedioxymethamphetamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Methylenedioxymethamphetamine.jpg]]

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3,4-methylenedioxy-N-methylamphetamine

|-
| Other names
| N-methyl 1-1-(3,4-methylenedioxyphenyl)-2-propanamine, MDMA, Ecstacy
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C11H15NO2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN[C@@H](C)CC1=CC(OCO2)=C2C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 193.24g/mol
|-
| Appearance
| White crystalline solid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 69610-10-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| {{{Density}}} g/cm³ 
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| -144.4F 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 148 F
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}
{{Chem-Data_Structure}}

== Methylenedioxymethamphetamine ==

Often known as MDMA or Ecstacy, 3,4-methylenedioxy-N-methylamphetamine is a semisynthetic empathogen-entactogen, an illegal drug that acts as a stimulant producing an psychedelic energizing effect, as well as distortions in time, perception and enhanced enjoyment of tactile experiences. MDMA exerts its primary effects on neurons in the brain that use the chemical serotonin to communicate with other neurons. Aside from recreational purposes, it is used as a tool to supplement various practices including meditation, psychonautics, and illicit psychedelic psychotherapy.
Research in animals indicates that MDMA is neurotoxic; whether or not this is also true in humans is currently an area of intense investigation. MDMA can also be dangerous to health and, on rare occasions, lethal.

== History ==

MDMA was first synthesized in 1912, soon after it was patented in Germany by the Merck Company. At that time it was not the subject of human research, but Merck stumbled across MDMA when they tried to synthesize Hydrastinin, a vasoconstrictive and styptic medicine. MDMA was an unplanned by-product of this synthesis. In the 1950s it was briefly researched by the U.S. Government as part of the CIA's and the Army's chemical warfare investigations into MDMA as a truth serum, which proved to be unsuitable. The first reported recreational use was in the 1960s, where it became known as the love drug. In the mid-70s, the psychedelic therapy community rediscovered it and psychiatrists and therapists began to use it to supplement psychotherapy. In the early 1980s, the drug began to be used recreationally, most notably in Dallas, under the name the street name 'Ecstasy'. The non-medical and therapeutic use of MDMA was made illegal in the USA in 1985. Soon afterwards its use rapidly spread outside the United States, where it was widely used in the UK and other parts of Europe, becoming an integral part of the rave subculture and other psychedelic and dancefloor influenced music scenes.

== Synthesis ==

Reaction Overview:
The 'ketone' approach is one of many synthesis schemes for the production of MDMA. This basic scheme is the oxidation of the plant oil 'safrole' (1-allyl-3,4-methylenedioxybenzene) into a ketone (3,4-methylenedioxyphenyl-2-propanone), which is then condensed with methylamine and reduced to the final MDMA product.

[[Image:Mdma_synthesis.JPG]]

Step 1: Peroxyacid oxidation (requires isomerization of safrole).

Step 2: Reversible imine formation, which reacts spontaneously when the ketone is added to a solution of methylamine.

Step 3: Reduction, permanently converts the imine to MDMA.

== Effects on the Human Body ==

The most common use of MDMA is for recreational purposes. Classed as a stimulant, the effects produced on the human body include euphoria, increased awareness of the senses, feelings of openness, empathy, heightened self-awareness and feeling of mental clarity. Tactile sensations are enhanced for some users resulting in physical contact with others more intense. ‘Alexander Shulgin stated that the single best use of MDMA was to facilitate more direct communication between people involved in significant emotional relationships.’ Physical effects on the body include sweaty palms, heavy sweating, increased heart rate, increased body temperature, and heightened touch sensations.

Naturally there are many health risks involved in taking a stimulant such as MDMA. Physically these risks include hypertension, dehydration and hyperthermia. This is mostly due to the drug's stimulatory effects masking the body's normal sense of exhaustion and thirst.
MDMA is also neurotoxic which means it interferes with brain chemistry, sometimes permanently. The metabolism of MDMA leads to the lipid peroxidation of serotonergic neurons, thus interfering with the brain's ability to effectively use serotonin.
Psychologically, MDMA use often results in a rebound period of poor mood, often known as a ‘comedown’. Obviously this varies in length between different users but can often lead to lasting depression and anxiety in vulnerable users. The longer the time MDMA is active in the brain, the greater the neurotoxic damage to the brain and the greater the risk of short-term emotional problems. The more times MDMA is taken, the greater the risk of any long-term problems.

== Spectroscopic Data ==

'''NMR Spectrum: 3,4-methylenedioxy-N-methylamphetamine'''

[[Image:Mdma_nmr.JPG]]

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

== References ==

It07:Methylenedioxymethamphetamine

2007-11-01T11:51:52Z

Arw06:

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Methylenedioxymethamphetamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Methylenedioxymethamphetamine.jpg]]

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3,4-methylenedioxy-N-methylamphetamine

|-
| Other names
| N-methyl 1-1-(3,4-methylenedioxyphenyl)-2-propanamine, MDMA, Ecstacy
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C11H15NO2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN[C@@H](C)CC1=CC(OCO2)=C2C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 193.24g/mol
|-
| Appearance
| White crystalline solid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 69610-10-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| {{{Density}}} g/cm³ 
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| -144.4F 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 148 F
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}
{{Chem-Data_Structure}}

== Methylenedioxymethamphetamine ==

Often known as MDMA or Ecstacy, 3,4-methylenedioxy-N-methylamphetamine is a semisynthetic empathogen-entactogen, an illegal drug that acts as a stimulant producing an psychedelic energizing effect, as well as distortions in time, perception and enhanced enjoyment of tactile experiences. MDMA exerts its primary effects on neurons in the brain that use the chemical serotonin to communicate with other neurons. Aside from recreational purposes, it is used as a tool to supplement various practices including meditation, psychonautics, and illicit psychedelic psychotherapy.
Research in animals indicates that MDMA is neurotoxic; whether or not this is also true in humans is currently an area of intense investigation. MDMA can also be dangerous to health and, on rare occasions, lethal.

== History ==

MDMA was first synthesized in 1912, soon after it was patented in Germany by the Merck Company. At that time it was not the subject of human research, but Merck stumbled across MDMA when they tried to synthesize Hydrastinin, a vasoconstrictive and styptic medicine. MDMA was an unplanned by-product of this synthesis. In the 1950s it was briefly researched by the U.S. Government as part of the CIA's and the Army's chemical warfare investigations into MDMA as a truth serum, which proved to be unsuitable. The first reported recreational use was in the 1960s, where it became known as the love drug. In the mid-70s, the psychedelic therapy community rediscovered it and psychiatrists and therapists began to use it to supplement psychotherapy. In the early 1980s, the drug began to be used recreationally, most notably in Dallas, under the name the street name 'Ecstasy'. The non-medical and therapeutic use of MDMA was made illegal in the USA in 1985. Soon afterwards its use rapidly spread outside the United States, where it was widely used in the UK and other parts of Europe, becoming an integral part of the rave subculture and other psychedelic and dancefloor influenced music scenes.

== Synthesis ==

Reaction Overview:
The 'ketone' approach is one of many synthesis schemes for the production of MDMA. This basic scheme is the oxidation of the plant oil 'safrole' (1-allyl-3,4-methylenedioxybenzene) into a ketone (3,4-methylenedioxyphenyl-2-propanone), which is then condensed with methylamine and reduced to the final MDMA product.

[[Image:Mdma_synthesis.JPG]]

Step 1: Peroxyacid oxidation (requires isomerization of safrole).

Step 2: Reversible imine formation, which reacts spontaneously when the ketone is added to a solution of methylamine.

Step 3: Reduction, permanently converts the imine to MDMA.

== Effects on the Human Body ==

The most common use of MDMA is for recreational purposes. Classed as a stimulant, the effects produced on the human body include euphoria, increased awareness of the senses, feelings of openness, empathy, heightened self-awareness and feeling of mental clarity. Tactile sensations are enhanced for some users resulting in physical contact with others more intense. ‘Alexander Shulgin stated that the single best use of MDMA was to facilitate more direct communication between people involved in significant emotional relationships.’ Physical effects on the body include sweaty palms, heavy sweating, increased heart rate, increased body temperature, and heightened touch sensations.

Naturally there are many health risks involved in taking a stimulant such as MDMA. Physically these risks include hypertension, dehydration and hyperthermia. This is mostly due to the drug's stimulatory effects masking the body's normal sense of exhaustion and thirst.
MDMA is also neurotoxic which means it interferes with brain chemistry, sometimes permanently. The metabolism of MDMA leads to the lipid peroxidation of serotonergic neurons, thus interfering with the brain's ability to effectively use serotonin.
Psychologically, MDMA use often results in a rebound period of poor mood, often known as a ‘comedown’. Obviously this varies in length between different users but can often lead to lasting depression and anxiety in vulnerable users. The longer the time MDMA is active in the brain, the greater the neurotoxic damage to the brain and the greater the risk of short-term emotional problems. The more times MDMA is taken, the greater the risk of any long-term problems.

== Spectroscopic Data ==

'''NMR Spectrum: 3,4-methylenedioxy-N-methylamphetamine'''

[[Image:Mdma_nmr.JPG]]

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

== References ==

It07:Methylenedioxymethamphetamine

2007-11-01T11:50:13Z

Arw06:

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Methylenedioxymethamphetamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Methylenedioxymethamphetamine.jpg]]

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3,4-methylenedioxy-N-methylamphetamine

|-
| Other names
| N-methyl 1-1-(3,4-methylenedioxyphenyl)-2-propanamine, MDMA, Ecstacy
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C11H15NO2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN[C@@H](C)CC1=CC(OCO2)=C2C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 193.24g/mol
|-
| Appearance
| White crystalline solid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 69610-10-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| {{{Density}}} g/cm³ 
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| -144.4F 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 148 F
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}
{{Chem-Data_Structure}}

== Methylenedioxymethamphetamine ==

Often known as MDMA or Ecstacy, 3,4-methylenedioxy-N-methylamphetamine is a semisynthetic empathogen-entactogen, an illegal drug that acts as a stimulant producing an psychedelic energizing effect, as well as distortions in time, perception and enhanced enjoyment of tactile experiences. MDMA exerts its primary effects on neurons in the brain that use the chemical serotonin to communicate with other neurons. Aside from recreational purposes, it is used as a tool to supplement various practices including meditation, psychonautics, and illicit psychedelic psychotherapy.
Research in animals indicates that MDMA is neurotoxic; whether or not this is also true in humans is currently an area of intense investigation. MDMA can also be dangerous to health and, on rare occasions, lethal.

== History ==

MDMA was first synthesized in 1912, soon after it was patented in Germany by the Merck Company. At that time it was not the subject of human research, but Merck stumbled across MDMA when they tried to synthesize Hydrastinin, a vasoconstrictive and styptic medicine. MDMA was an unplanned by-product of this synthesis. In the 1950s it was briefly researched by the U.S. Government as part of the CIA's and the Army's chemical warfare investigations into MDMA as a truth serum, which proved to be unsuitable. The first reported recreational use was in the 1960s, where it became known as the love drug. In the mid-70s, the psychedelic therapy community rediscovered it and psychiatrists and therapists began to use it to supplement psychotherapy. In the early 1980s, the drug began to be used recreationally, most notably in Dallas, under the name the street name 'Ecstasy'. The non-medical and therapeutic use of MDMA was made illegal in the USA in 1985. Soon afterwards its use rapidly spread outside the United States, where it was widely used in the UK and other parts of Europe, becoming an integral part of the rave subculture and other psychedelic and dancefloor influenced music scenes.

== Synthesis ==

Reaction Overview:
The 'ketone' approach is one of many synthesis schemes for the production of MDMA. This basic scheme is the oxidation of the plant oil 'safrole' (1-allyl-3,4-methylenedioxybenzene) into a ketone (3,4-methylenedioxyphenyl-2-propanone), which is then condensed with methylamine and reduced to the final MDMA product.

[[Image:Mdma_synthesis.JPG]]

Step 1: Peroxyacid oxidation (requires isomerization of safrole).

Step 2: Reversible imine formation, which reacts spontaneously when the ketone is added to a solution of methylamine.

Step 3: Reduction, permanently converts the imine to MDMA.

== Effects on the Human Body ==

The most common use of MDMA is for recreational purposes. Classed as a stimulant, the effects produced on the human body include euphoria, increased awareness of the senses, feelings of openness, empathy, heightened self-awareness and feeling of mental clarity. Tactile sensations are enhanced for some users resulting in physical contact with others more intense. ‘Alexander Shulgin stated that the single best use of MDMA was to facilitate more direct communication between people involved in significant emotional relationships.’ Physical effects on the body include sweaty palms, heavy sweating, increased heart rate, increased body temperature, and heightened touch sensations.

Naturally there are many health risks involved in taking a stimulant such as MDMA. Physically these risks include hypertension, dehydration and hyperthermia. This is mostly due to the drug's stimulatory effects masking the body's normal sense of exhaustion and thirst.
MDMA is also neurotoxic which means it interferes with brain chemistry, sometimes permanently. The metabolism of MDMA leads to the lipid peroxidation of serotonergic neurons, thus interfering with the brain's ability to effectively use serotonin.
Psychologically, MDMA use often results in a rebound period of poor mood, often known as a ‘comedown’. Obviously this varies in length between different users but can often lead to lasting depression and anxiety in vulnerable users. The longer the time MDMA is active in the brain, the greater the neurotoxic damage to the brain and the greater the risk of short-term emotional problems. The more times MDMA is taken, the greater the risk of any long-term problems.

== Spectroscopic Data ==

'''NMR Spectrum: 3,4-methylenedioxy-N-methylamphetamine'''

[[Image:Mdma_nmr.JPG]]

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

== References ==

It07:Methylenedioxymethamphetamine

2007-11-01T11:42:59Z

Arw06: /* Spectroscopic Data */

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Methylenedioxymethamphetamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Methylenedioxymethamphetamine.jpg]]

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3,4-methylenedioxy-N-methylamphetamine

|-
| Other names
| N-methyl 1-1-(3,4-methylenedioxyphenyl)-2-propanamine, MDMA, Ecstacy
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C11H15NO2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN[C@@H](C)CC1=CC(OCO2)=C2C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 193.24g/mol
|-
| Appearance
| White crystalline solid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 69610-10-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| {{{Density}}} g/cm³ 
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| -144.4F 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 148 F
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}
{{Chem-Data_Structure}}

== Methylenedioxymethamphetamine ==

Often known as MDMA or Ecstacy, 3,4-methylenedioxy-N-methylamphetamine is a semisynthetic empathogen-entactogen, an illegal drug that acts as a stimulant producing an psychedelic energizing effect, as well as distortions in time, perception and enhanced enjoyment of tactile experiences. MDMA exerts its primary effects on neurons in the brain that use the chemical serotonin to communicate with other neurons. Aside from recreational purposes, it is used as a tool to supplement various practices including meditation, psychonautics, and illicit psychedelic psychotherapy.
Research in animals indicates that MDMA is neurotoxic; whether or not this is also true in humans is currently an area of intense investigation. MDMA can also be dangerous to health and, on rare occasions, lethal.

== History ==

MDMA was first synthesized in 1912, soon after it was patented in Germany by the Merck Company. At that time it was not the subject of human research, but Merck stumbled across MDMA when they tried to synthesize Hydrastinin, a vasoconstrictive and styptic medicine. MDMA was an unplanned by-product of this synthesis. In the 1950s it was briefly researched by the U.S. Government as part of the CIA's and the Army's chemical warfare investigations into MDMA as a truth serum, which proved to be unsuitable. The first reported recreational use was in the 1960s, where it became known as the love drug. In the mid-70s, the psychedelic therapy community rediscovered it and psychiatrists and therapists began to use it to supplement psychotherapy. In the early 1980s, the drug began to be used recreationally, most notably in Dallas, under the name the street name 'Ecstasy'. The non-medical and therapeutic use of MDMA was made illegal in the USA in 1985. Soon afterwards its use rapidly spread outside the United States, where it was widely used in the UK and other parts of Europe, becoming an integral part of the rave subculture and other psychedelic and dancefloor influenced music scenes.

== Synthesis ==

Reaction Overview:
The 'ketone' approach is one of many synthesis schemes for the production of MDMA. This basic scheme is the oxidation of the plant oil 'safrole' (1-allyl-3,4-methylenedioxybenzene) into a ketone (3,4-methylenedioxyphenyl-2-propanone), which is then condensed with methylamine and reduced to the final MDMA product.

[[Image:Mdma_synthesis.JPG]]

Step 1: Peroxyacid oxidation (requires isomerization of safrole).

Step 2: Reversible imine formation, which reacts spontaneously when the ketone is added to a solution of methylamine.

Step 3: Reduction, permanently converts the imine to MDMA.

== Effects on the Human Body ==

The most common use of MDMA is for recreational purposes. Classed as a stimulant, the effects produced on the human body include euphoria, increased awareness of the senses, feelings of openness, empathy, heightened self-awareness and feeling of mental clarity. Tactile sensations are enhanced for some users resulting in physical contact with others more intense. ‘Alexander Shulgin stated that the single best use of MDMA was to facilitate more direct communication between people involved in significant emotional relationships.’ Physical effects on the body include sweaty palms, heavy sweating, increased heart rate, increased body temperature, and heightened touch sensations.

Naturally there are many health risks involved in taking a stimulant such as MDMA. Physically these risks include hypertension, dehydration and hyperthermia. This is mostly due to the drug's stimulatory effects masking the body's normal sense of exhaustion and thirst.
MDMA is also neurotoxic which means it interferes with brain chemistry, sometimes permanently. The metabolism of MDMA leads to the lipid peroxidation of serotonergic neurons, thus interfering with the brain's ability to effectively use serotonin.
Psychologically, MDMA use often results in a rebound period of poor mood, often known as a ‘comedown’. Obviously this varies in length between different users but can often lead to lasting depression and anxiety in vulnerable users. The longer the time MDMA is active in the brain, the greater the neurotoxic damage to the brain and the greater the risk of short-term emotional problems. The more times MDMA is taken, the greater the risk of any long-term problems.

== Spectroscopic Data ==

'''NMR Spectrum: 3,4-methylenedioxy-N-methylamphetamine'''

[[Image:Mdma_nmr.JPG]]

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

It07:Methylenedioxymethamphetamine

2007-11-01T11:41:38Z

Arw06:

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Methylenedioxymethamphetamine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Methylenedioxymethamphetamine.jpg]]

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3,4-methylenedioxy-N-methylamphetamine

|-
| Other names
| N-methyl 1-1-(3,4-methylenedioxyphenyl)-2-propanamine, MDMA, Ecstacy
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C11H15NO2
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CN[C@@H](C)CC1=CC(OCO2)=C2C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 193.24g/mol
|-
| Appearance
| White crystalline solid
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 69610-10-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| {{{Density}}} g/cm³ 
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| -144.4F 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| 148 F
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}
{{Chem-Data_Structure}}

== Methylenedioxymethamphetamine ==

Often known as MDMA or Ecstacy, 3,4-methylenedioxy-N-methylamphetamine is a semisynthetic empathogen-entactogen, an illegal drug that acts as a stimulant producing an psychedelic energizing effect, as well as distortions in time, perception and enhanced enjoyment of tactile experiences. MDMA exerts its primary effects on neurons in the brain that use the chemical serotonin to communicate with other neurons. Aside from recreational purposes, it is used as a tool to supplement various practices including meditation, psychonautics, and illicit psychedelic psychotherapy.
Research in animals indicates that MDMA is neurotoxic; whether or not this is also true in humans is currently an area of intense investigation. MDMA can also be dangerous to health and, on rare occasions, lethal.

== History ==

MDMA was first synthesized in 1912, soon after it was patented in Germany by the Merck Company. At that time it was not the subject of human research, but Merck stumbled across MDMA when they tried to synthesize Hydrastinin, a vasoconstrictive and styptic medicine. MDMA was an unplanned by-product of this synthesis. In the 1950s it was briefly researched by the U.S. Government as part of the CIA's and the Army's chemical warfare investigations into MDMA as a truth serum, which proved to be unsuitable. The first reported recreational use was in the 1960s, where it became known as the love drug. In the mid-70s, the psychedelic therapy community rediscovered it and psychiatrists and therapists began to use it to supplement psychotherapy. In the early 1980s, the drug began to be used recreationally, most notably in Dallas, under the name the street name 'Ecstasy'. The non-medical and therapeutic use of MDMA was made illegal in the USA in 1985. Soon afterwards its use rapidly spread outside the United States, where it was widely used in the UK and other parts of Europe, becoming an integral part of the rave subculture and other psychedelic and dancefloor influenced music scenes.

== Synthesis ==

Reaction Overview:
The 'ketone' approach is one of many synthesis schemes for the production of MDMA. This basic scheme is the oxidation of the plant oil 'safrole' (1-allyl-3,4-methylenedioxybenzene) into a ketone (3,4-methylenedioxyphenyl-2-propanone), which is then condensed with methylamine and reduced to the final MDMA product.

[[Image:Mdma_synthesis.JPG]]

Step 1: Peroxyacid oxidation (requires isomerization of safrole).

Step 2: Reversible imine formation, which reacts spontaneously when the ketone is added to a solution of methylamine.

Step 3: Reduction, permanently converts the imine to MDMA.

== Effects on the Human Body ==

The most common use of MDMA is for recreational purposes. Classed as a stimulant, the effects produced on the human body include euphoria, increased awareness of the senses, feelings of openness, empathy, heightened self-awareness and feeling of mental clarity. Tactile sensations are enhanced for some users resulting in physical contact with others more intense. ‘Alexander Shulgin stated that the single best use of MDMA was to facilitate more direct communication between people involved in significant emotional relationships.’ Physical effects on the body include sweaty palms, heavy sweating, increased heart rate, increased body temperature, and heightened touch sensations.

Naturally there are many health risks involved in taking a stimulant such as MDMA. Physically these risks include hypertension, dehydration and hyperthermia. This is mostly due to the drug's stimulatory effects masking the body's normal sense of exhaustion and thirst.
MDMA is also neurotoxic which means it interferes with brain chemistry, sometimes permanently. The metabolism of MDMA leads to the lipid peroxidation of serotonergic neurons, thus interfering with the brain's ability to effectively use serotonin.
Psychologically, MDMA use often results in a rebound period of poor mood, often known as a ‘comedown’. Obviously this varies in length between different users but can often lead to lasting depression and anxiety in vulnerable users. The longer the time MDMA is active in the brain, the greater the neurotoxic damage to the brain and the greater the risk of short-term emotional problems. The more times MDMA is taken, the greater the risk of any long-term problems.

== Spectroscopic Data ==

NMR Spectrum:

[[Image:Mdma_nmr.JPG]]

<jmol>
<jmolApplet>
<title>MDMA</title><color>white</color>
<size>300</size>
<script>zoom 100; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Mdma3D.PDB</uploadedFileContents>
</jmolApplet>

File:Mdma nmr.JPG

2007-11-01T11:40:15Z

Arw06: