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Safrole (data page)

2006-11-22T10:51:05Z

Bel05: Safrole (data page) moved to It:Safrole (data page)

#redirect [[It:Safrole (data page)]]

It:Safrole (data page)

2006-11-22T10:51:05Z

Bel05: Safrole (data page) moved to It:Safrole (data page)

This page provides supplementary chemical data on [[Safrole]]. 

== Material Safety Data Sheet == 

The handling of this chemical may incur notable safety precautions. It is highly recommend that you seek the Material Safety Datasheet ([http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]) for this chemical from a reliable source such as [http://www2.siri.org/msds/index.php SIRI], and follow its directions.

== Structure and properties == 

{| border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"
! {{chembox header}} | Structure and properties
|-
| [http://en.wikipedia.org/wiki/Index_of_refraction Index of refraction], ''n''D
| 1.5383 for 589.3nm, 20°C
|-
| [http://en.wikipedia.org/wiki/Abbe_number Abbe number]
|? 
|-
| [http://en.wikipedia.org/wiki/Dielectric_constant Dielectric constant], εr
| ? ε0 at ? °C 
|-
| [http://en.wikipedia.org/wiki/Bond_strength Bond strength]
| ? 
|-
| [http://en.wikipedia.org/wiki/Bond_length Bond length]
| ? 
|-
| [http://en.wikipedia.org/wiki/Bond_angle Bond angle]
| ? 
|-
| [http://en.wikipedia.org/wiki/Magnetic_susceptibility Magnetic susceptibility]
| ? 
|-
|}

== Thermodynamic properties == 

{| border="1" cellspacing="0" cellpadding="6" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"
! {{chembox header}} | Phase behavior
|-
| [http://en.wikipedia.org/wiki/Triple_point Triple point]
| ? K (? °C), ? Pa
|-
| [http://en.wikipedia.org/wiki/Critical_point_%28chemistry%29 Critical point]
| ? K (? °C), ? Pa
|-
| [http://en.wikipedia.org/wiki/Standard_enthalpy_change_of_fusion Std enthalpy change of fusion], Δfus''H''<s>o</s>
| ? kJ/mol
|-
| [http://en.wikipedia.org/wiki/Standard_entropy_change_of_fusion Std entropy change of fusion], Δfus''S''<s>o</s>
| ? J/(mol·K)
|-
| [http://en.wikipedia.org/wiki/Standard_enthalpy_change_of_vaporization Std enthalpy change of vaporization], Δvap''H''<s>o</s>
| ? kJ/mol
|-
| [http://en.wikipedia.org/wiki/Standard_entropy_change_of_vaporization Std entropy change of vaporization], Δvap''S''<s>o</s>
| ? J/(mol·K)
|-
! {{chembox header}} | Solid properties
|-
| [http://en.wikipedia.org/wiki/Standard_enthalpy_change_of_formation Std enthalpy change of formation], Δf''H''<s>o</s>solid
| ? kJ/mol
|-
| [http://en.wikipedia.org/wiki/Standard_molar_entropy Standard molar entropy], ''S''<s>o</s>solid
| ? J/(mol K)
|-
| [http://en.wikipedia.org/wiki/Heat_capacity Heat capacity], ''cp''
| ? J/(mol K)
|-
! {{chembox header}} | Liquid properties
|-
| [http://en.wikipedia.org/wiki/Standard_enthalpy_change_of_formation Std enthalpy change of formation], Δf''H''<s>o</s>liquid
| ? kJ/mol
|-
| [http://en.wikipedia.org/wiki/Standard_molar_entropy Standard molar entropy], ''S''<s>o</s>liquid
| ? J/(mol K)
|-
| [http://en.wikipedia.org/wiki/Heat_capacity Heat capacity], ''cp''
| ? J/(mol K)
|-
! {{chembox header}} | Gas properties
|-
| [http://en.wikipedia.org/wiki/Standard_enthalpy_change_of_formation Std enthalpy change of formation], Δf''H''<s>o</s>gas
| ? kJ/mol
|-
| [http://en.wikipedia.org/wiki/Standard_molar_entropy Standard molar entropy], ''S''<s>o</s>gas
| ? J/(mol K)
|-
| [http://en.wikipedia.org/wiki/Heat_capacity Heat capacity], ''cp''
| ? J/(mol K)
|-
|}

== Spectral data == 

{| border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"
! {{chembox header}} | [http://en.wikipedia.org/wiki/UV/VIS_spectroscopy UV-Vis]
|-
| [http://en.wikipedia.org/wiki/UV/VIS_spectroscopy λmax]
| ? [http://en.wikipedia.org/wiki/Nanometre nm]
|-
| [http://en.wikipedia.org/wiki/Extinction_coefficient Extinction coefficient], ε
| ?
|-
! {{chembox header}} | [http://en.wikipedia.org/wiki/Infrared_spectroscopy IR]
|-
| Major absorption bands
| ? [http://en.wikipedia.org/wiki/Centimetre cm]−1
|-
! {{chembox header}} | [http://en.wikipedia.org/wiki/NMR_Spectroscopy NMR]
|-
| [http://en.wikipedia.org/wiki/Proton_NMR Proton NMR] 
|  
|-
| [http://en.wikipedia.org/wiki/Carbon-13_NMR Carbon-13 NMR] 
|  
|-
| Other NMR data 
|  
|-
! {{chembox header}} | [http://en.wikipedia.org/wiki/Mass_Spectrometry MS]
|-
| Masses of main fragments
|   
|-
|}

== References ==


Except where noted otherwise, data relate to [http://en.wikipedia.org/wiki/Standard_ambient_temperature_and_pressure standard ambient temperature and pressure].

[http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Disclaimer] applies.

[[Category:Chemical data pages]]

It:Safrole

2006-11-22T10:50:34Z

Bel05:

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Safrole
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Safrole.gif|Safrole]]
|-
! {{chembox header}} colspan="3"|
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>365</size>
<color>white</color>
<script>zoom 120; wireframe on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Safrole.mol
title1
title2
22 23 0 0 0 0 0 0 0 0999 V2000
-4.1030 1.1330 0.6240 C 0 0 0 0 0 0 0 0 0 1
-3.3400 0.0700 0.5670 C 0 0 0 0 0 0 0 0 0 2
-2.6150 -0.2700 -0.7090 C 0 0 0 0 0 0 0 0 0 3
-1.1400 -0.4050 -0.4290 C 0 0 0 0 0 0 0 0 0 4
-0.6150 -1.6340 -0.0750 C 0 0 0 0 0 0 0 0 0 5
0.7370 -1.7630 0.1830 C 0 0 0 0 0 0 0 0 0 6
1.5690 -0.6600 0.0870 C 0 0 0 0 0 0 0 0 0 7
2.9130 -0.5190 0.2860 O 0 0 0 0 0 0 0 0 0 8
3.1320 0.8940 0.4470 C 0 0 0 0 0 0 0 0 0 9
2.0520 1.4940 -0.2930 O 0 0 0 0 0 0 0 0 0 10
1.0410 0.5790 -0.2690 C 0 0 0 0 0 0 0 0 0 11
-0.3150 0.6990 -0.5310 C 0 0 0 0 0 0 0 0 0 12
-4.5841 1.3583 1.4712 H 0 0 0 0 0 0 0 0 0 13
-4.2045 1.7193 -0.1797 H 0 0 0 0 0 0 0 0 0 14
-3.2387 -0.5162 1.3708 H 0 0 0 0 0 0 0 0 0 15
-2.9970 -1.2100 -1.1050 H 0 0 0 0 0 0 0 0 0 16
-2.7740 0.5240 -1.4400 H 0 0 0 0 0 0 0 0 0 17
-1.2145 -2.4313 -0.0054 H 0 0 0 0 0 0 0 0 0 18
1.1143 -2.6530 0.4390 H 0 0 0 0 0 0 0 0 0 19
3.0760 1.1730 1.4990 H 0 0 0 0 0 0 0 0 0 20
4.0940 1.1840 0.0230 H 0 0 0 0 0 0 0 0 0 21
-0.6965 1.5852 -0.7940 H 0 0 0 0 0 0 0 0 0 22
1 2 2 0 0 0
1 13 1 0 0 0
1 14 1 0 0 0
2 3 1 0 0 0
2 15 1 0 0 0
4 3 1 0 0 0
4 12 4 0 0 0
4 5 4 0 0 0
5 6 4 0 0 0
5 18 1 0 0 0
6 7 4 0 0 0
6 19 1 0 0 0
7 11 4 0 0 0
7 8 1 0 0 0
8 9 1 0 0 0
10 9 1 0 0 0
10 11 1 0 0 0
11 12 4 0 0 0
12 22 1 0 0 0
3 16 1 0 0 0
3 17 1 0 0 0
9 20 1 0 0 0
9 21 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"|5-(2-Propenyl)-1,3-benzodioxole
|-
| colspan="1" |Synonyms
| colspan="2" |Rhyuno oil
Allylcatechol methylene ether
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C10H10O2
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |C12=C(C=C(CC=C)C=C1)OCO2
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |162.188 g/mol
|-
| colspan="1" |Appearance
| colspan="2" |Colourless to slightly yellow liquid
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |94-59-7
|-
| colspan="1" |[http://en.wikipedia.org/wiki/EC-No EC number]
| colspan="2" |202-345-4
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Beilstein_database Beilstein Registry Number]
| colspan="2" |136380
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase]
| colspan="2" |1.095 g/cm3, liquid
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [http://en.wikipedia.org/wiki/Water_%28molecule%29 water]
| colspan="2" | Insoluble
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |11.2°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |234.5°C
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sigmaaldrich.com/cgi-bin/hsrun/Suite7/Suite/HAHTpage/Suite.HsSigmaAdvancedSearch.formAction Aldrich MSDS]
|-
| [http://en.wikipedia.org/wiki/Directive_67/548/EEC EU classification]
| Toxic ('''T''')
[http://en.wikipedia.org/wiki/Carcinogen Carc. Cat. 2B]
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| {{NFPA 704 | Health=2 | Flammability=1 | Reactivity=0| Other=  }}
|-
| [http://en.wikipedia.org/wiki/List_of_R-phrases R-phrases]
| {{R45}}-{{R22}}-{{R68}}
|-
| [http://en.wikipedia.org/wiki/List_of_S-phrases S-phrases]
| {{S53}}-{{S45}}
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |97.8 °C
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" | CY2800000
|-
! {{chembox header}} colspan="3" | [[Safrole (data page)|Supplementary data]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and properties]]
| colspan="2" | [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant εr], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic data]]
| colspan="2" | Phase behaviour Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| colspan="2" | [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C120581&Index=0&Type=UVVis&Large=on UV], [http://www.sigmaaldrich.com/spectra/ftir/FTIR008797.PDF FT-IR Condensed Phase],
[http://www.sigmaaldrich.com/spectra/rair/RAIR014190.PDF FT-IR Raman], [http://www.sigmaaldrich.com/spectra/fnmr/FNMR011352.PDF 1H-NMR],

[http://www.aist.go.jp/RIODB/SDBS/cgi-bin/direct_frame_top.cgi?lang=eng 13C-NMR], [http://www.aist.go.jp/RIODB/SDBS/cgi-bin/direct_frame_top.cgi?lang=eng MS]
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}

== Introduction ==
Safrole is an almost colourless, oily liquid with a particularly pleasant aroma that is common constituent of many essential oils, notably those of the [http://en.wikipedia.org/wiki/Sassafras sassafras] plant in which it is present to the extent of about 75%, and also as the main component of brown camphor oil. Commonly extracted from the root-bark or fruit of the sassafras plant, it was once commonly used as a food and drink additive - used in the production of root beer and sassafras tea among others - however use was discontinued after animal tests revealed it to be a possible carcinogen.

Safrole is used chemically as a precursor in the synthesis of piperonyl butoxide; an intesticide synergist. It can also be used as a precursor for less savoury products, such as [http://en.wikipedia.org/wiki/MDMA MDMA] (more commonly known by its street name of Ecstasy) and [http://en.wikipedia.org/wiki/MDEA MDEA] (also known as Eve) - both of which have similar psychedelic and hallucinogenic effects on the human brain. Given its role as a major reactant in certain methods of synthesis of these molecules, safrole is ranked as a List I chemical by the [http://en.wikipedia.org/wiki/Drug_Enforcement_Administration DEA], and also a Table I precursor under the [http://en.wikipedia.org/wiki/United_Nations_Convention_Against_Illicit_Traffic_in_Narcotic_Drugs_and_Psychotropic_Substances United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances]

== Carcinogenic Properties ==
Studies on animals have shown that, when force fed followed by dietary administration, safrole increased the incidences of liver cell tumors in mice of both sexes. When administered at normal levels in the diet, safrole increased the incidences
of liver [http://en.wikipedia.org/wiki/Hepatocellular_carcinoma hepatocellular carcinomas] and [http://en.wikipedia.org/wiki/Cholangiocarcinoma cholangiocarcinomas] in both male and female rats, and hepatocellular carcinomas in male mice. When administered to infant mice by subcutaneous injection, safrole induced lung [http://en.wikipedia.org/wiki/Adenoma adenomas] and [http://en.wikipedia.org/wiki/Adenocarcinoma adenocarcinomas] in mice of both sexes and [http://en.wikipedia.org/wiki/Hepatoma hepatomas] in male mice.[http://ntp-server.niehs.nih.gov/ntp/roc/eleventh/profiles/s159safa.pdf]

Further studies showed that this results from metabolites of safrole forming adducts with DNA that induce chromasomal aberrations and sister chromatid exchanges. Such DNA modifications were found to eventually lead to the formation of liver tumours.[http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=text&db=pubmed&uid=11246123&dopt=Abstract]

However, the absence of evidence on safrole's carcinogenic behaivour in humans has lead safrole to be classified as only category 2b by the [http://en.wikipedia.org/wiki/International_Agency_for_Research_on_Cancer IARC].

== References ==

*"Some Naturally Occurring Substances. IARC Monographs on the Evaluation of Carcinogenic
Risk of Chemicals to Humans, vol. 10" International Agency for Research on Cancer, 353 pp.
*Daimon, H., et al., In vivo genotoxicity and DNA adduct levels in the liver of rats treated with safrole. Carcinogenesis 19, 141-146, (1998)

It:projects

2006-11-22T10:50:02Z

Bel05: /* Supplemental Project Page */

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--[[User:Rzepa|Rzepa]] 14:41, 20 October 2006 (BST)

----
[[Template:Chem-Data]]

[[Template:Chembox supplement]] - to be linked to from the supplementary section of the table in the template above, for usage see [[Template_talk:chembox_supplement|here]]

[[Template:NFPA_704]] - for notes on how to use, see [[Template_talk:NFPA_704|here]]

[[R & S Phrases]]

Talk:Safrole

2006-11-22T10:49:36Z

Bel05: Talk:Safrole moved to Talk:It:Safrole

#redirect [[Talk:It:Safrole]]

Talk:It:Safrole

2006-11-22T10:49:36Z

Bel05: Talk:Safrole moved to Talk:It:Safrole

Please note that the NFPA 704 diamond values have only been guessed by me based on the criteria listed on the [http://en.wikipedia.org/wiki/NFPA_704#Symbolism main wiki page] and what I know about this molecule --[[User:Bel05|Bel05]] 14:32, 9 November 2006 (UTC)

Safrole

2006-11-22T10:49:36Z

Bel05: Safrole moved to It:Safrole

#redirect [[It:Safrole]]

It:Safrole

2006-11-22T10:49:36Z

Bel05: Safrole moved to It:Safrole

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Safrole
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Safrole.gif|Safrole]]
|-
! {{chembox header}} colspan="3"|
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>365</size>
<color>white</color>
<script>zoom 120; wireframe on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Safrole.mol
title1
title2
22 23 0 0 0 0 0 0 0 0999 V2000
-4.1030 1.1330 0.6240 C 0 0 0 0 0 0 0 0 0 1
-3.3400 0.0700 0.5670 C 0 0 0 0 0 0 0 0 0 2
-2.6150 -0.2700 -0.7090 C 0 0 0 0 0 0 0 0 0 3
-1.1400 -0.4050 -0.4290 C 0 0 0 0 0 0 0 0 0 4
-0.6150 -1.6340 -0.0750 C 0 0 0 0 0 0 0 0 0 5
0.7370 -1.7630 0.1830 C 0 0 0 0 0 0 0 0 0 6
1.5690 -0.6600 0.0870 C 0 0 0 0 0 0 0 0 0 7
2.9130 -0.5190 0.2860 O 0 0 0 0 0 0 0 0 0 8
3.1320 0.8940 0.4470 C 0 0 0 0 0 0 0 0 0 9
2.0520 1.4940 -0.2930 O 0 0 0 0 0 0 0 0 0 10
1.0410 0.5790 -0.2690 C 0 0 0 0 0 0 0 0 0 11
-0.3150 0.6990 -0.5310 C 0 0 0 0 0 0 0 0 0 12
-4.5841 1.3583 1.4712 H 0 0 0 0 0 0 0 0 0 13
-4.2045 1.7193 -0.1797 H 0 0 0 0 0 0 0 0 0 14
-3.2387 -0.5162 1.3708 H 0 0 0 0 0 0 0 0 0 15
-2.9970 -1.2100 -1.1050 H 0 0 0 0 0 0 0 0 0 16
-2.7740 0.5240 -1.4400 H 0 0 0 0 0 0 0 0 0 17
-1.2145 -2.4313 -0.0054 H 0 0 0 0 0 0 0 0 0 18
1.1143 -2.6530 0.4390 H 0 0 0 0 0 0 0 0 0 19
3.0760 1.1730 1.4990 H 0 0 0 0 0 0 0 0 0 20
4.0940 1.1840 0.0230 H 0 0 0 0 0 0 0 0 0 21
-0.6965 1.5852 -0.7940 H 0 0 0 0 0 0 0 0 0 22
1 2 2 0 0 0
1 13 1 0 0 0
1 14 1 0 0 0
2 3 1 0 0 0
2 15 1 0 0 0
4 3 1 0 0 0
4 12 4 0 0 0
4 5 4 0 0 0
5 6 4 0 0 0
5 18 1 0 0 0
6 7 4 0 0 0
6 19 1 0 0 0
7 11 4 0 0 0
7 8 1 0 0 0
8 9 1 0 0 0
10 9 1 0 0 0
10 11 1 0 0 0
11 12 4 0 0 0
12 22 1 0 0 0
3 16 1 0 0 0
3 17 1 0 0 0
9 20 1 0 0 0
9 21 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"|5-(2-Propenyl)-1,3-benzodioxole
|-
| colspan="1" |Synonyms
| colspan="2" |Rhyuno oil
Allylcatechol methylene ether
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C10H10O2
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |C12=C(C=C(CC=C)C=C1)OCO2
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |162.188 g/mol
|-
| colspan="1" |Appearance
| colspan="2" |Colourless to slightly yellow liquid
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |94-59-7
|-
| colspan="1" |[http://en.wikipedia.org/wiki/EC-No EC number]
| colspan="2" |202-345-4
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Beilstein_database Beilstein Registry Number]
| colspan="2" |136380
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase]
| colspan="2" |1.095 g/cm3, liquid
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [http://en.wikipedia.org/wiki/Water_%28molecule%29 water]
| colspan="2" | Insoluble
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |11.2°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |234.5°C
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sigmaaldrich.com/cgi-bin/hsrun/Suite7/Suite/HAHTpage/Suite.HsSigmaAdvancedSearch.formAction Aldrich MSDS]
|-
| [http://en.wikipedia.org/wiki/Directive_67/548/EEC EU classification]
| Toxic ('''T''')
[http://en.wikipedia.org/wiki/Carcinogen Carc. Cat. 2B]
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| {{NFPA 704 | Health=2 | Flammability=1 | Reactivity=0| Other=  }}
|-
| [http://en.wikipedia.org/wiki/List_of_R-phrases R-phrases]
| {{R45}}-{{R22}}-{{R68}}
|-
| [http://en.wikipedia.org/wiki/List_of_S-phrases S-phrases]
| {{S53}}-{{S45}}
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |97.8 °C
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" | CY2800000
|-
! {{chembox header}} colspan="3" | [[Safrole (data page)|Supplementary data]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and properties]]
| colspan="2" | [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant εr], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic data]]
| colspan="2" | Phase behaviour Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| colspan="2" | [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C120581&Index=0&Type=UVVis&Large=on UV], [http://www.sigmaaldrich.com/spectra/ftir/FTIR008797.PDF FT-IR Condensed Phase],
[http://www.sigmaaldrich.com/spectra/rair/RAIR014190.PDF FT-IR Raman], [http://www.sigmaaldrich.com/spectra/fnmr/FNMR011352.PDF 1H-NMR],

[http://www.aist.go.jp/RIODB/SDBS/cgi-bin/direct_frame_top.cgi?lang=eng 13C-NMR], [http://www.aist.go.jp/RIODB/SDBS/cgi-bin/direct_frame_top.cgi?lang=eng MS]
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}

== Introduction ==
Safrole is an almost colourless, oily liquid with a particularly pleasant aroma that is common constituent of many essential oils, notably those of the [http://en.wikipedia.org/wiki/Sassafras sassafras] plant in which it is present to the extent of about 75%, and also as the main component of brown camphor oil. Commonly extracted from the root-bark or fruit of the sassafras plant, it was once commonly used as a food and drink additive - used in the production of root beer and sassafras tea among others - however use was discontinued after animal tests revealed it to be a possible carcinogen.

Safrole is used chemically as a precursor in the synthesis of piperonyl butoxide; an intesticide synergist. It can also be used as a precursor for less savoury products, such as [http://en.wikipedia.org/wiki/MDMA MDMA] (more commonly known by its street name of Ecstasy) and [http://en.wikipedia.org/wiki/MDEA MDEA] (also known as Eve) - both of which have similar psychedelic and hallucinogenic effects on the human brain. Given its role as a major reactant in certain methods of synthesis of these molecules, safrole is ranked as a List I chemical by the [http://en.wikipedia.org/wiki/Drug_Enforcement_Administration DEA], and also a Table I precursor under the [http://en.wikipedia.org/wiki/United_Nations_Convention_Against_Illicit_Traffic_in_Narcotic_Drugs_and_Psychotropic_Substances United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances]

=== Carcinogenic Properties ===
Studies on animals have shown that, when force fed followed by dietary administration, safrole increased the incidences of liver cell tumors in mice of both sexes. When administered at normal levels in the diet, safrole increased the incidences
of liver [http://en.wikipedia.org/wiki/Hepatocellular_carcinoma hepatocellular carcinomas] and [http://en.wikipedia.org/wiki/Cholangiocarcinoma cholangiocarcinomas] in both male and female rats, and hepatocellular carcinomas in male mice. When administered to infant mice by subcutaneous injection, safrole induced lung [http://en.wikipedia.org/wiki/Adenoma adenomas] and [http://en.wikipedia.org/wiki/Adenocarcinoma adenocarcinomas] in mice of both sexes and [http://en.wikipedia.org/wiki/Hepatoma hepatomas] in male mice.[http://ntp-server.niehs.nih.gov/ntp/roc/eleventh/profiles/s159safa.pdf]

Further studies showed that this results from metabolites of safrole forming adducts with DNA that induce chromasomal aberrations and sister chromatid exchanges. Such DNA modifications were found to eventually lead to the formation of liver tumours.[http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=text&db=pubmed&uid=11246123&dopt=Abstract]

However, the absence of evidence on safrole's carcinogenic behaivour in humans has lead safrole to be classified as only category 2b by the [http://en.wikipedia.org/wiki/International_Agency_for_Research_on_Cancer IARC].

== References ==

*"Some Naturally Occurring Substances. IARC Monographs on the Evaluation of Carcinogenic
Risk of Chemicals to Humans, vol. 10" International Agency for Research on Cancer, 353 pp.
*Daimon, H., et al., In vivo genotoxicity and DNA adduct levels in the liver of rats treated with safrole. Carcinogenesis 19, 141-146, (1998)

It:Caffeine

2006-11-22T10:44:09Z

Bel05: /* Spectra */

==Introduction==
Caffeine is one of the most widely used central nervous system stimulant. Caffeine is present in coffee, tea, chocolate, soft drinks (eg. red bull, coca-cola). Its effects (vary from person to person and are affected by the body size, and tolerance) include: reduced drowsiness, improved attention span, and faster blood circulation. When used in large doses and over a long period of time a 'dependancy' may arise, a person may even suffer from withdrawal symptoms if they stop taking it.

==Spectra==
Below are the 13C NMR and the IR spectra of caffeine
[[Image:Caffeine_NMR1.jpg|thumb|left|200|13C NMR]]
[[Image:Caffeine_IR.jpg|thumb|right|200|IR]]

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Caffeine'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Caffeine.gif]]
|-
| [[Chemical name]]
| ''1,3,7-trimethyl-2,6-dioxopurine
|-
| [[CAS nummber]]
| 58-08-2
|-
| [[Chemical formula]]
| {{{formula|C8H10N4O2
|-
| [[Molecular mass]]
| {{{mol_mass|194.1926 g/mol
|-
| [[Melting point]]
| 238 °C
|-
| [[Boiling point]]
| 178 °C
|-
| [[Water Solubility]]
| 1-5g/100 ml at 23 C
1g/5.5 ml at 88 C
|-
| [[Density]]
| 1.23
|-
| [[Comments]]
| White solid, usually powder or needle-like
Light sensitive
|-
|}

==Synthesis==
Emil Fischer was the first person to synthesise caffeine, in 1895 however his real objective was to study purines in general. The synthesis of caffeine is not an industrially used process as its extraction from coffee beans or even tea leaves is a much more cost effective process and yields 99.5% pure caffeine. A possible way to synthesis caffeine artificially, from Uracil is shown below. The first step is to methylate the uracil, there are 3 alternate ways in which this can be done the yield however is fairly poor with 10% for method 1, 20% for method 2 and 60% for method 3, the subsequent steps involve nitration, reduction (of the nitro- group), and a ring forming reaction, to form theophylline, and an another methylation to for caffeine.

[[Image:Caffsyn1.jpg|thumb|left|400|Step 1]]
[[Image:Caffsyn2.gif|thumb|left|400|Steps 2-6]]

==Metabolism==

Caffeine is completely absorbed by the stomach and small intestine within 45 minutes of ingestion. After ingestion it is taken to all the tissues in the body and is eliminated by first oreder kinetics.
The half-life of caffeine: the time required for the body to eliminate one-half of the total amount of caffeine consumed at a given time. It varies widely among individuals according to such factors such as age, liver function, pregnancy and the level of enzymes present in the liver needed for caffeine breakdown. In healthy adults, caffeine's half-life is approximately 3-4 hours. In women taking oral contraceptives this is increased to 5-10 hours, and in pregnant women the half-life is approximately 9-11 hours.

Caffeine is matabolised in the liver by the cytochrome P450 oxidase enzyme system, into three metabolic dimethylxanthines.
*Paraxanthine (84%) – Has the effect of increasing lipolysis, leading to elevated glycerol and free fatty acid levels in the blood plasma.
*Theobromine (12%) – Dilates blood vessels and increases urine volume. Theobromine is also the principal alkaloid in cocoa, and therefore chocolate.
*Theophylline (4%) – Relaxes smooth muscles of the bronchi, and is used to treat asthma. The therapeutic dose of theophylline, however, is many times greater than the levels attained from caffeine metabolism.

paraxanthine
<jmol>
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<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Tue Nov 21 11:42:09 GMT Standard Time 2006
ATOM 1 O1 MOL 1 11.959 13.788 0.003 1.00 0.00
ATOM 2 C2 MOL 1 12.065 12.554 0.001 1.00 0.00
ATOM 3 C3 MOL 1 13.350 11.903 0.000 1.00 0.00
ATOM 4 N4 MOL 1 10.933 11.727 -0.001 1.00 0.00
ATOM 5 C5 MOL 1 13.488 10.603 0.000 1.00 0.00
ATOM 6 N6 MOL 1 14.591 12.442 0.000 1.00 0.00
ATOM 7 C7 MOL 1 9.620 12.302 -0.007 1.00 0.00
ATOM 8 C8 MOL 1 11.097 10.308 0.002 1.00 0.00
ATOM 9 N9 MOL 1 12.400 9.739 0.002 1.00 0.00
ATOM 10 N10 MOL 1 14.865 10.274 -0.002 1.00 0.00
ATOM 11 C11 MOL 1 14.914 13.842 0.003 1.00 0.00
ATOM 12 C12 MOL 1 15.524 11.381 -0.002 1.00 0.00
ATOM 13 O13 MOL 1 10.102 9.571 0.003 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>

Theorombine
<jmol>
<jmolApplet>
<size>200</size>
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<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Tue Nov 21 11:49:33 GMT Standard Time 2006
ATOM 1 C1 MOL 1 12.056 15.417 0.008 1.00 0.00
ATOM 2 N2 MOL 1 12.208 13.956 0.001 1.00 0.00
ATOM 3 C3 MOL 1 13.490 13.356 -0.003 1.00 0.00
ATOM 4 C4 MOL 1 11.053 13.083 0.001 1.00 0.00
ATOM 5 C5 MOL 1 13.649 12.058 -0.003 1.00 0.00
ATOM 6 N6 MOL 1 14.753 13.991 -0.007 1.00 0.00
ATOM 7 O7 MOL 1 9.913 13.565 0.003 1.00 0.00
ATOM 8 N8 MOL 1 11.233 11.665 -0.002 1.00 0.00
ATOM 9 C9 MOL 1 12.537 11.123 -0.003 1.00 0.00
ATOM 10 N10 MOL 1 14.981 11.819 -0.001 1.00 0.00
ATOM 11 C11 MOL 1 15.648 13.065 -0.008 1.00 0.00
ATOM 12 O12 MOL 1 12.720 9.898 -0.007 1.00 0.00
ATOM 13 C13 MOL 1 15.617 10.532 0.023 1.00 0.00
TER
</inlineContents>
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Theophylline
<jmol>
<jmolApplet>
<size>200</size>
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<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Tue Nov 21 11:54:14 GMT Standard Time 2006
ATOM 1 O1 MOL 1 12.035 15.254 0.008 1.00 0.00
ATOM 2 C2 MOL 1 12.096 14.019 0.004 1.00 0.00
ATOM 3 C3 MOL 1 13.363 13.331 0.001 1.00 0.00
ATOM 4 N4 MOL 1 10.934 13.230 -0.001 1.00 0.00
ATOM 5 C5 MOL 1 13.451 12.029 0.001 1.00 0.00
ATOM 6 N6 MOL 1 14.623 13.860 -0.001 1.00 0.00
ATOM 7 C7 MOL 1 9.640 13.849 -0.007 1.00 0.00
ATOM 8 C8 MOL 1 11.052 11.811 -0.000 1.00 0.00
ATOM 9 N9 MOL 1 12.333 11.206 0.003 1.00 0.00
ATOM 10 N10 MOL 1 14.793 11.651 -0.003 1.00 0.00
ATOM 11 C11 MOL 1 15.496 12.729 -0.005 1.00 0.00
ATOM 12 O12 MOL 1 10.037 11.107 -0.004 1.00 0.00
ATOM 13 C13 MOL 1 12.471 9.778 0.008 1.00 0.00
TER</inlineContents>
</jmolApplet>
</jmol>

==Extraction==
The main methods to extract caffeine are:

1. Methylene Chloride/Ethyl Acetate Processing
The raw materials (eg. coffee beans) are softened by steam or hot water, and then methylene chloride or ethyl acetate is added which bonds with the caffeine molecules.

2. CO2 processing
This method involves 'pressure cooking' the raw ingredients with supercritical carbon dioxide, at a high temperature and pressure, the small CO2 molecules extract the relatively small caffeine molecules, whilst the larger oils and flavouring compounds remain untouched. This makes this method popular for decaffeination of coffee.

3. Water extraction
Water extraction is similar to the methylene chloride/ ethyl acetate process, however instead of adding chemicals the raw materials are left to soak in hot water for longer, to allow the caffeine to diffuse into the water. The water is then passed through a carbon filter which removes the caffeine in the water, but as with the previous method does not affect the flavourings. The water is then passed back to the raw ingredients to allow reabsorption of these flavours.

==Effects==
Caffeine is used recreationally to help stay awake, while in medicine it is used to reduce headaches, as a cardiac stimulant, and also to increase urine production. The reason that caffeine reduces drownsiness is because it binds to the adenosine receptors of the nervous system (adenosine causes drowsiness), and therefore prevents adenosine from doing so. Caffeine also constricts the vessels for blood flow to the brain, and therefore increases its activity.
This increased activity is percieved by the pituitary gland as a sign of danger or emergency, and it releases adrenaline, which makes the heart beat faster, pupils to dilate, and the liver to release sugars (and therefore energy). Caffeine has also got an effect on dopamine release in the brain, which 'activates the pleasure center' of the brain.

==References==
1. Synthetic communications [0039-7911] Zajac yr:2003 vol:33 iss:19 pg:3291

2. [http://www.howstuffworks.com]

It:Cinnamaldehyde

2006-11-13T11:02:38Z

Bel05:

==Introduction==

{| align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"

! {{chembox header}} | Cinnamaldehyde
|-
| align="center" colspan="2" | [[Image:MFCD00007000.gif|75px|Cinnamaldehyde]]
|-
! {{chembox header}} | General
|-
| [[IUPAC nomenclature|Systematic name]]
|3-phenyl-2-propenal
|-
| Other names
|trans-cinnamaldehyde,
cinnamic aldehyde,
trans-cinnamic aldehyde
|-
|Physical Appearance
|Yellow oily liquid
|-
| [[Chemical Formula|Molecular Formula]]
|C6H5CH:CHCHO
|-
|[[Molar Mass]]
|132.16
|-
|[[Simplified molecular input line entry specification|SMILES]]
|O=C([H])/C=C/C1=CC=CC=C1
|-
|[[CAS Registry Number|CAS Number]]
|104-55-2
|-
! {{chembox header}} |Pysical Properties
|-
|[[Melting Point]]
|-7oC
|-
|[[Boiling Point]]
|248 °C(lit.)
|-
|[[Flash Point]]
|160 F
|-
|[[Density]]
|1.05 g/mL at 25 °C(lit.)
|-
|Refractive Index (n20/D)
|1.621(lit.)
|-
|Vapour Density
|4.5 (air = 1)
|-
|Vapour Pressure
|0.02 mm Hg at 20 C
|-
|Solubility
|Slight in water
|-
! {{chembox header}} | Stability
|-
|Stability
|Stable, but combustible. Incompatible
with strong bases and oxidising agents.
|-
! {{chembox header}} | Hazards and Safety
|-
|Hazard Codes
| Xi
|-
|Risk Phrases
|{{R36/37/38}}-{{R43}}
|-
|Safety Phrases
|{{R26}}-{{R36/37}}
|}

'''Cinnamaldehyde''' is an unsaturated aldehyde found in the bark of the Cinnamomum zeylanicum tree. It is a component of the spice Cinnamon, which due to its distinctive flavour and aroma is a common component of among others, foodstuffs, perfumes, and detergents. Cinnamaldehyde can be obtained naturally from the steam distillation of twigs and leaves of Cinnamomum.

==References==

[[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W228605 MSDS for Cinnamaldehyde]]
[[http://www.physchem.ox.ac.uk/MSDS/CI/cinnamaldehyde.html MSDS for Cinnamaldehyde]]

It:Safrole

2006-11-09T19:11:38Z

Bel05: /* Carcinogenic Properties */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Safrole
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Safrole.gif|Safrole]]
|-
! {{chembox header}} colspan="3"|
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>365</size>
<color>white</color>
<script>zoom 120; wireframe on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Safrole.mol
title1
title2
22 23 0 0 0 0 0 0 0 0999 V2000
-4.1030 1.1330 0.6240 C 0 0 0 0 0 0 0 0 0 1
-3.3400 0.0700 0.5670 C 0 0 0 0 0 0 0 0 0 2
-2.6150 -0.2700 -0.7090 C 0 0 0 0 0 0 0 0 0 3
-1.1400 -0.4050 -0.4290 C 0 0 0 0 0 0 0 0 0 4
-0.6150 -1.6340 -0.0750 C 0 0 0 0 0 0 0 0 0 5
0.7370 -1.7630 0.1830 C 0 0 0 0 0 0 0 0 0 6
1.5690 -0.6600 0.0870 C 0 0 0 0 0 0 0 0 0 7
2.9130 -0.5190 0.2860 O 0 0 0 0 0 0 0 0 0 8
3.1320 0.8940 0.4470 C 0 0 0 0 0 0 0 0 0 9
2.0520 1.4940 -0.2930 O 0 0 0 0 0 0 0 0 0 10
1.0410 0.5790 -0.2690 C 0 0 0 0 0 0 0 0 0 11
-0.3150 0.6990 -0.5310 C 0 0 0 0 0 0 0 0 0 12
-4.5841 1.3583 1.4712 H 0 0 0 0 0 0 0 0 0 13
-4.2045 1.7193 -0.1797 H 0 0 0 0 0 0 0 0 0 14
-3.2387 -0.5162 1.3708 H 0 0 0 0 0 0 0 0 0 15
-2.9970 -1.2100 -1.1050 H 0 0 0 0 0 0 0 0 0 16
-2.7740 0.5240 -1.4400 H 0 0 0 0 0 0 0 0 0 17
-1.2145 -2.4313 -0.0054 H 0 0 0 0 0 0 0 0 0 18
1.1143 -2.6530 0.4390 H 0 0 0 0 0 0 0 0 0 19
3.0760 1.1730 1.4990 H 0 0 0 0 0 0 0 0 0 20
4.0940 1.1840 0.0230 H 0 0 0 0 0 0 0 0 0 21
-0.6965 1.5852 -0.7940 H 0 0 0 0 0 0 0 0 0 22
1 2 2 0 0 0
1 13 1 0 0 0
1 14 1 0 0 0
2 3 1 0 0 0
2 15 1 0 0 0
4 3 1 0 0 0
4 12 4 0 0 0
4 5 4 0 0 0
5 6 4 0 0 0
5 18 1 0 0 0
6 7 4 0 0 0
6 19 1 0 0 0
7 11 4 0 0 0
7 8 1 0 0 0
8 9 1 0 0 0
10 9 1 0 0 0
10 11 1 0 0 0
11 12 4 0 0 0
12 22 1 0 0 0
3 16 1 0 0 0
3 17 1 0 0 0
9 20 1 0 0 0
9 21 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"|5-(2-Propenyl)-1,3-benzodioxole
|-
| colspan="1" |Synonyms
| colspan="2" |Rhyuno oil
Allylcatechol methylene ether
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C10H10O2
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |C12=C(C=C(CC=C)C=C1)OCO2
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |162.188 g/mol
|-
| colspan="1" |Appearance
| colspan="2" |Colourless to slightly yellow liquid
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |94-59-7
|-
| colspan="1" |[http://en.wikipedia.org/wiki/EC-No EC number]
| colspan="2" |202-345-4
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Beilstein_database Beilstein Registry Number]
| colspan="2" |136380
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase]
| colspan="2" |1.095 g/cm3, liquid
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [http://en.wikipedia.org/wiki/Water_%28molecule%29 water]
| colspan="2" | Insoluble
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |11.2°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |234.5°C
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sigmaaldrich.com/cgi-bin/hsrun/Suite7/Suite/HAHTpage/Suite.HsSigmaAdvancedSearch.formAction Aldrich MSDS]
|-
| [http://en.wikipedia.org/wiki/Directive_67/548/EEC EU classification]
| Toxic ('''T''')
[http://en.wikipedia.org/wiki/Carcinogen Carc. Cat. 2B]
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| {{NFPA 704 | Health=2 | Flammability=1 | Reactivity=0| Other=  }}
|-
| [http://en.wikipedia.org/wiki/List_of_R-phrases R-phrases]
| {{R45}}-{{R22}}-{{R68}}
|-
| [http://en.wikipedia.org/wiki/List_of_S-phrases S-phrases]
| {{S53}}-{{S45}}
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |97.8 °C
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" | CY2800000
|-
! {{chembox header}} colspan="3" | [[Safrole (data page)|Supplementary data]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and properties]]
| colspan="2" | [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant εr], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic data]]
| colspan="2" | Phase behaviour Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| colspan="2" | [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C120581&Index=0&Type=UVVis&Large=on UV], [http://www.sigmaaldrich.com/spectra/ftir/FTIR008797.PDF FT-IR Condensed Phase],
[http://www.sigmaaldrich.com/spectra/rair/RAIR014190.PDF FT-IR Raman], [http://www.sigmaaldrich.com/spectra/fnmr/FNMR011352.PDF 1H-NMR],

[http://www.aist.go.jp/RIODB/SDBS/cgi-bin/direct_frame_top.cgi?lang=eng 13C-NMR], [http://www.aist.go.jp/RIODB/SDBS/cgi-bin/direct_frame_top.cgi?lang=eng MS]
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}

== Introduction ==
Safrole is an almost colourless, oily liquid with a particularly pleasant aroma that is common constituent of many essential oils, notably those of the [http://en.wikipedia.org/wiki/Sassafras sassafras] plant in which it is present to the extent of about 75%, and also as the main component of brown camphor oil. Commonly extracted from the root-bark or fruit of the sassafras plant, it was once commonly used as a food and drink additive - used in the production of root beer and sassafras tea among others - however use was discontinued after animal tests revealed it to be a possible carcinogen.

Safrole is used chemically as a precursor in the synthesis of piperonyl butoxide; an intesticide synergist. It can also be used as a precursor for less savoury products, such as [http://en.wikipedia.org/wiki/MDMA MDMA] (more commonly known by its street name of Ecstasy) and [http://en.wikipedia.org/wiki/MDEA MDEA] (also known as Eve) - both of which have similar psychedelic and hallucinogenic effects on the human brain. Given its role as a major reactant in certain methods of synthesis of these molecules, safrole is ranked as a List I chemical by the [http://en.wikipedia.org/wiki/Drug_Enforcement_Administration DEA], and also a Table I precursor under the [http://en.wikipedia.org/wiki/United_Nations_Convention_Against_Illicit_Traffic_in_Narcotic_Drugs_and_Psychotropic_Substances United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances]

=== Carcinogenic Properties ===
Studies on animals have shown that, when force fed followed by dietary administration, safrole increased the incidences of liver cell tumors in mice of both sexes. When administered at normal levels in the diet, safrole increased the incidences
of liver [http://en.wikipedia.org/wiki/Hepatocellular_carcinoma hepatocellular carcinomas] and [http://en.wikipedia.org/wiki/Cholangiocarcinoma cholangiocarcinomas] in both male and female rats, and hepatocellular carcinomas in male mice. When administered to infant mice by subcutaneous injection, safrole induced lung [http://en.wikipedia.org/wiki/Adenoma adenomas] and [http://en.wikipedia.org/wiki/Adenocarcinoma adenocarcinomas] in mice of both sexes and [http://en.wikipedia.org/wiki/Hepatoma hepatomas] in male mice.[http://ntp-server.niehs.nih.gov/ntp/roc/eleventh/profiles/s159safa.pdf]

Further studies showed that this results from metabolites of safrole forming adducts with DNA that induce chromasomal aberrations and sister chromatid exchanges. Such DNA modifications were found to eventually lead to the formation of liver tumours.[http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=text&db=pubmed&uid=11246123&dopt=Abstract]

However, the absence of evidence on safrole's carcinogenic behaivour in humans has lead safrole to be classified as only category 2b by the [http://en.wikipedia.org/wiki/International_Agency_for_Research_on_Cancer IARC].

== References ==

*"Some Naturally Occurring Substances. IARC Monographs on the Evaluation of Carcinogenic
Risk of Chemicals to Humans, vol. 10" International Agency for Research on Cancer, 353 pp.
*Daimon, H., et al., In vivo genotoxicity and DNA adduct levels in the liver of rats treated with safrole. Carcinogenesis 19, 141-146, (1998)

It:Safrole

2006-11-09T19:08:35Z

Bel05:

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Safrole
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Safrole.gif|Safrole]]
|-
! {{chembox header}} colspan="3"|
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>365</size>
<color>white</color>
<script>zoom 120; wireframe on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Safrole.mol
title1
title2
22 23 0 0 0 0 0 0 0 0999 V2000
-4.1030 1.1330 0.6240 C 0 0 0 0 0 0 0 0 0 1
-3.3400 0.0700 0.5670 C 0 0 0 0 0 0 0 0 0 2
-2.6150 -0.2700 -0.7090 C 0 0 0 0 0 0 0 0 0 3
-1.1400 -0.4050 -0.4290 C 0 0 0 0 0 0 0 0 0 4
-0.6150 -1.6340 -0.0750 C 0 0 0 0 0 0 0 0 0 5
0.7370 -1.7630 0.1830 C 0 0 0 0 0 0 0 0 0 6
1.5690 -0.6600 0.0870 C 0 0 0 0 0 0 0 0 0 7
2.9130 -0.5190 0.2860 O 0 0 0 0 0 0 0 0 0 8
3.1320 0.8940 0.4470 C 0 0 0 0 0 0 0 0 0 9
2.0520 1.4940 -0.2930 O 0 0 0 0 0 0 0 0 0 10
1.0410 0.5790 -0.2690 C 0 0 0 0 0 0 0 0 0 11
-0.3150 0.6990 -0.5310 C 0 0 0 0 0 0 0 0 0 12
-4.5841 1.3583 1.4712 H 0 0 0 0 0 0 0 0 0 13
-4.2045 1.7193 -0.1797 H 0 0 0 0 0 0 0 0 0 14
-3.2387 -0.5162 1.3708 H 0 0 0 0 0 0 0 0 0 15
-2.9970 -1.2100 -1.1050 H 0 0 0 0 0 0 0 0 0 16
-2.7740 0.5240 -1.4400 H 0 0 0 0 0 0 0 0 0 17
-1.2145 -2.4313 -0.0054 H 0 0 0 0 0 0 0 0 0 18
1.1143 -2.6530 0.4390 H 0 0 0 0 0 0 0 0 0 19
3.0760 1.1730 1.4990 H 0 0 0 0 0 0 0 0 0 20
4.0940 1.1840 0.0230 H 0 0 0 0 0 0 0 0 0 21
-0.6965 1.5852 -0.7940 H 0 0 0 0 0 0 0 0 0 22
1 2 2 0 0 0
1 13 1 0 0 0
1 14 1 0 0 0
2 3 1 0 0 0
2 15 1 0 0 0
4 3 1 0 0 0
4 12 4 0 0 0
4 5 4 0 0 0
5 6 4 0 0 0
5 18 1 0 0 0
6 7 4 0 0 0
6 19 1 0 0 0
7 11 4 0 0 0
7 8 1 0 0 0
8 9 1 0 0 0
10 9 1 0 0 0
10 11 1 0 0 0
11 12 4 0 0 0
12 22 1 0 0 0
3 16 1 0 0 0
3 17 1 0 0 0
9 20 1 0 0 0
9 21 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"|5-(2-Propenyl)-1,3-benzodioxole
|-
| colspan="1" |Synonyms
| colspan="2" |Rhyuno oil
Allylcatechol methylene ether
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C10H10O2
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |C12=C(C=C(CC=C)C=C1)OCO2
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |162.188 g/mol
|-
| colspan="1" |Appearance
| colspan="2" |Colourless to slightly yellow liquid
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |94-59-7
|-
| colspan="1" |[http://en.wikipedia.org/wiki/EC-No EC number]
| colspan="2" |202-345-4
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Beilstein_database Beilstein Registry Number]
| colspan="2" |136380
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase]
| colspan="2" |1.095 g/cm3, liquid
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [http://en.wikipedia.org/wiki/Water_%28molecule%29 water]
| colspan="2" | Insoluble
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |11.2°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |234.5°C
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sigmaaldrich.com/cgi-bin/hsrun/Suite7/Suite/HAHTpage/Suite.HsSigmaAdvancedSearch.formAction Aldrich MSDS]
|-
| [http://en.wikipedia.org/wiki/Directive_67/548/EEC EU classification]
| Toxic ('''T''')
[http://en.wikipedia.org/wiki/Carcinogen Carc. Cat. 2B]
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| {{NFPA 704 | Health=2 | Flammability=1 | Reactivity=0| Other=  }}
|-
| [http://en.wikipedia.org/wiki/List_of_R-phrases R-phrases]
| {{R45}}-{{R22}}-{{R68}}
|-
| [http://en.wikipedia.org/wiki/List_of_S-phrases S-phrases]
| {{S53}}-{{S45}}
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |97.8 °C
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" | CY2800000
|-
! {{chembox header}} colspan="3" | [[Safrole (data page)|Supplementary data]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and properties]]
| colspan="2" | [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant εr], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic data]]
| colspan="2" | Phase behaviour Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| colspan="2" | [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C120581&Index=0&Type=UVVis&Large=on UV], [http://www.sigmaaldrich.com/spectra/ftir/FTIR008797.PDF FT-IR Condensed Phase],
[http://www.sigmaaldrich.com/spectra/rair/RAIR014190.PDF FT-IR Raman], [http://www.sigmaaldrich.com/spectra/fnmr/FNMR011352.PDF 1H-NMR],

[http://www.aist.go.jp/RIODB/SDBS/cgi-bin/direct_frame_top.cgi?lang=eng 13C-NMR], [http://www.aist.go.jp/RIODB/SDBS/cgi-bin/direct_frame_top.cgi?lang=eng MS]
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}

== Introduction ==
Safrole is an almost colourless, oily liquid with a particularly pleasant aroma that is common constituent of many essential oils, notably those of the [http://en.wikipedia.org/wiki/Sassafras sassafras] plant in which it is present to the extent of about 75%, and also as the main component of brown camphor oil. Commonly extracted from the root-bark or fruit of the sassafras plant, it was once commonly used as a food and drink additive - used in the production of root beer and sassafras tea among others - however use was discontinued after animal tests revealed it to be a possible carcinogen.

Safrole is used chemically as a precursor in the synthesis of piperonyl butoxide; an intesticide synergist. It can also be used as a precursor for less savoury products, such as [http://en.wikipedia.org/wiki/MDMA MDMA] (more commonly known by its street name of Ecstasy) and [http://en.wikipedia.org/wiki/MDEA MDEA] (also known as Eve) - both of which have similar psychedelic and hallucinogenic effects on the human brain. Given its role as a major reactant in certain methods of synthesis of these molecules, safrole is ranked as a List I chemical by the [http://en.wikipedia.org/wiki/Drug_Enforcement_Administration DEA], and also a Table I precursor under the [http://en.wikipedia.org/wiki/United_Nations_Convention_Against_Illicit_Traffic_in_Narcotic_Drugs_and_Psychotropic_Substances United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances]

=== Carcinogenic Properties ===
Studies on animals have shown that, when force fed followed by dietary administration, safrole increased the incidences of liver cell tumors in mice of both sexes. When administered at normal levels in the diet, safrole increased the incidences
of liver [http://en.wikipedia.org/wiki/Hepatocellular_carcinoma hepatocellular carcinomas] and [http://en.wikipedia.org/wiki/Cholangiocarcinoma cholangiocarcinomas] in both male and female rats, and hepatocellular carcinomas in male mice. When administered to infant mice by subcutaneous injection, safrole induced lung [http://en.wikipedia.org/wiki/Adenoma adenomas] and [http://en.wikipedia.org/wiki/Adenocarcinoma adenocarcinomas] in mice of both sexes and http://en.wikipedia.org/wiki/Hepatoma hepatomas] in male mice.[http://ntp-server.niehs.nih.gov/ntp/roc/eleventh/profiles/s159safa.pdf]
Further studies showed that this is a result of covalently interactions with liver cell DNA. Upon division, sister chromatid exchanges (among others aberations to normal cellular operation) were detected. Such DNA modifications were found to eventually lead to the formation of liver tumours.[http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=text&db=pubmed&uid=11246123&dopt=Abstract]

However, the absence of evidence on safrole's carcinogenic behaivour in humans has lead safrole to be classified as only category 2b by the [http://en.wikipedia.org/wiki/International_Agency_for_Research_on_Cancer IARC].

== References ==

*"Some Naturally Occurring Substances. IARC Monographs on the Evaluation of Carcinogenic
Risk of Chemicals to Humans, vol. 10" International Agency for Research on Cancer, 353 pp.
*Daimon, H., et al., In vivo genotoxicity and DNA adduct levels in the liver of rats treated with safrole. Carcinogenesis 19, 141-146, (1998)

It:Safrole

2006-11-09T18:10:04Z

Bel05:

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Safrole
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Safrole.gif|Safrole]]
|-
! {{chembox header}} colspan="3"|
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>365</size>
<color>white</color>
<script>zoom 120; wireframe on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>Safrole.mol
title1
title2
22 23 0 0 0 0 0 0 0 0999 V2000
-4.1030 1.1330 0.6240 C 0 0 0 0 0 0 0 0 0 1
-3.3400 0.0700 0.5670 C 0 0 0 0 0 0 0 0 0 2
-2.6150 -0.2700 -0.7090 C 0 0 0 0 0 0 0 0 0 3
-1.1400 -0.4050 -0.4290 C 0 0 0 0 0 0 0 0 0 4
-0.6150 -1.6340 -0.0750 C 0 0 0 0 0 0 0 0 0 5
0.7370 -1.7630 0.1830 C 0 0 0 0 0 0 0 0 0 6
1.5690 -0.6600 0.0870 C 0 0 0 0 0 0 0 0 0 7
2.9130 -0.5190 0.2860 O 0 0 0 0 0 0 0 0 0 8
3.1320 0.8940 0.4470 C 0 0 0 0 0 0 0 0 0 9
2.0520 1.4940 -0.2930 O 0 0 0 0 0 0 0 0 0 10
1.0410 0.5790 -0.2690 C 0 0 0 0 0 0 0 0 0 11
-0.3150 0.6990 -0.5310 C 0 0 0 0 0 0 0 0 0 12
-4.5841 1.3583 1.4712 H 0 0 0 0 0 0 0 0 0 13
-4.2045 1.7193 -0.1797 H 0 0 0 0 0 0 0 0 0 14
-3.2387 -0.5162 1.3708 H 0 0 0 0 0 0 0 0 0 15
-2.9970 -1.2100 -1.1050 H 0 0 0 0 0 0 0 0 0 16
-2.7740 0.5240 -1.4400 H 0 0 0 0 0 0 0 0 0 17
-1.2145 -2.4313 -0.0054 H 0 0 0 0 0 0 0 0 0 18
1.1143 -2.6530 0.4390 H 0 0 0 0 0 0 0 0 0 19
3.0760 1.1730 1.4990 H 0 0 0 0 0 0 0 0 0 20
4.0940 1.1840 0.0230 H 0 0 0 0 0 0 0 0 0 21
-0.6965 1.5852 -0.7940 H 0 0 0 0 0 0 0 0 0 22
1 2 2 0 0 0
1 13 1 0 0 0
1 14 1 0 0 0
2 3 1 0 0 0
2 15 1 0 0 0
4 3 1 0 0 0
4 12 4 0 0 0
4 5 4 0 0 0
5 6 4 0 0 0
5 18 1 0 0 0
6 7 4 0 0 0
6 19 1 0 0 0
7 11 4 0 0 0
7 8 1 0 0 0
8 9 1 0 0 0
10 9 1 0 0 0
10 11 1 0 0 0
11 12 4 0 0 0
12 22 1 0 0 0
3 16 1 0 0 0
3 17 1 0 0 0
9 20 1 0 0 0
9 21 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"|5-(2-Propenyl)-1,3-benzodioxole
|-
| colspan="1" |Synonyms
| colspan="2" |Rhyuno oil
Allylcatechol methylene ether
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C10H10O2
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |C12=C(C=C(CC=C)C=C1)OCO2
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |162.188 g/mol
|-
| colspan="1" |Appearance
| colspan="2" |Colourless to slightly yellow liquid
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |94-59-7
|-
| colspan="1" |[http://en.wikipedia.org/wiki/EC-No EC number]
| colspan="2" |202-345-4
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Beilstein_database Beilstein Registry Number]
| colspan="2" |136380
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase]
| colspan="2" |1.095 g/cm3, liquid
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [http://en.wikipedia.org/wiki/Water_%28molecule%29 water]
| colspan="2" | Sparingly soluble (0.16 g/L)
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |11.2°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |234.5°C
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sigmaaldrich.com/cgi-bin/hsrun/Suite7/Suite/HAHTpage/Suite.HsSigmaAdvancedSearch.formAction Aldrich MSDS]
|-
| [http://en.wikipedia.org/wiki/Directive_67/548/EEC EU classification]
| Toxic ('''T''')
[http://en.wikipedia.org/wiki/Carcinogen Carc. Cat. 2B]
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| {{NFPA 704 | Health=2 | Flammability=1 | Reactivity=0| Other=  }}
|-
| [http://en.wikipedia.org/wiki/List_of_R-phrases R-phrases]
| {{R45}}-{{R22}}-{{R68}}
|-
| [http://en.wikipedia.org/wiki/List_of_S-phrases S-phrases]
| {{S53}}-{{S45}}
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |97.8 °C
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" | CY2800000
|-
! {{chembox header}} colspan="3" | [[Safrole (data page)|Supplementary data]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and properties]]
| colspan="2" | [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant εr], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic data]]
| colspan="2" | Phase behaviour Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| colspan="2" | [http://webbook.nist.gov/cgi/cbook.cgi?Spec=C120581&Index=0&Type=UVVis&Large=on UV], [http://www.sigmaaldrich.com/spectra/ftir/FTIR008797.PDF FT-IR Condensed Phase],
[http://www.sigmaaldrich.com/spectra/rair/RAIR014190.PDF FT-IR Raman], [http://www.sigmaaldrich.com/spectra/fnmr/FNMR011352.PDF 1H-NMR],

[http://www.aist.go.jp/RIODB/SDBS/cgi-bin/direct_frame_top.cgi?lang=eng 13C-NMR], [http://www.aist.go.jp/RIODB/SDBS/cgi-bin/direct_frame_top.cgi?lang=eng MS]
|-
| {{chembox header}} colspan="3"| Except where noted otherwise, data are given for materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)] [http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]
|-
|}

==Introduction==
Safrole is an almost colourless, oily liquid with a particularly pleasant aroma that is common constituent of many essential oils, notably those of the [http://en.wikipedia.org/wiki/Sassafras sassafras] plant in which it is present to the extent of about 75%, and also as the main component of brown camphor oil. Commonly extracted from the root-bark or fruit of the sassafras plant, it was once commonly used as a food and drink additive - used in the production of root beer and sassafras tea among others - however use was discontinued after animal tests revealed it to be a possible carcinogen.

Safrole is used chemically as a precursor in the synthesis of piperonyl butoxide; an intesticide synergist. It can also be used as a precursor for less savoury products, such as [http://en.wikipedia.org/wiki/MDMA MDMA] (more commonly known by its street name of Ecstasy) and [http://en.wikipedia.org/wiki/MDEA MDEA] (also known as Eve) - both of which have similar psychedelic and hallucinogenic effects on the human brain. Given its role as a major reactant in certain methods of synthesis of these molecules, safrole is ranked as a List I chemical by the [http://en.wikipedia.org/wiki/Drug_Enforcement_Administration DEA], and also a Table I precursor under the [http://en.wikipedia.org/wiki/United_Nations_Convention_Against_Illicit_Traffic_in_Narcotic_Drugs_and_Psychotropic_Substances United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances]

User:Bel05

2006-11-09T17:25:10Z

Bel05:

=Current Contributions:=
*Schwarz's Reagent Chembox table including 2D and 3D structures
*NFPA 704 fire diamond template
*R & S Phrases templates
*Safrole (in progress)
*Tetrahydrocannabinol 3D structure

User:Bel05

2006-11-09T17:24:28Z

Bel05:

R & S Phrases

2006-11-09T17:23:30Z

Bel05:

This page lists all of the R & S phrases used to describe hazardous chemicals in their wiki template form. To use them in your articles, simply type, for example <nowiki>{{</nowiki>R22}} into the edit window and you will end up with {{R22}}, which will describe the phrase when you hover the cursor over it. --[[User:Bel05|Bel05]] 17:23, 9 November 2006 (UTC)

==R Phrases==
{{R1}}, {{R2}}, {{R3}}, {{R4}}, {{R5}}, {{R6}}, {{R7}}, {{R8}}, {{R9}}, {{R10}}, {{R11}}, {{R12}}, {{R14}}, {{R15}}, {{R16}}, {{R17}}, {{R18}}, {{R19}}, {{R20}}, {{R21}}, {{R22}}, {{R23}}, {{R24}}, {{R25}}, {{R26}}, {{R27}}, {{R28}}, {{R29}}, {{R30}}, {{R31}}, {{R32}}, {{R33}}, {{R34}}, {{R35}}, {{R36}}, {{R37}}, {{R38}}, {{R39}}, {{R40}}, {{R41}}, {{R42}}, {{R43}}, {{R44}}, {{R45}}, {{R46}}, {{R48}}, {{R49}}, {{R50}}, {{R51}}, {{R52}}, {{R53}}, {{R54}}, {{R55}}, {{R56}}, {{R57}}, {{R58}}, {{R59}}, {{R60}}, {{R61}}, {{R62}}, {{R63}}, {{R64}}, {{R65}}, {{R66}} {{R67}}, {{R68}}

==Combined R Phrases==
{{R14/15}}, {{R15/29}}, {{R20/21}}, {{R20/21/22}}, {{R20/22}}, {{R21/22}}, {{R23/24}}, {{R23/24/25}}, {{R23/25}}, {{R24/25}}, {{R26/27}}, {{R26/27/28}}, {{R26/28}}, {{R27/28}}, {{R36/37}}, {{R36/37/38}}, {{R36/38}}, {{R37/38}}, {{R39/23}}, {{R39/23/24}}, {{R39/23/24/25}}, {{R39/23/25}}, {{R39/24}}, {{R39/24/25}}, {{R39/25}}, {{R39/26}}, {{R39/26/27}}, {{R39/26/27/28}}, {{R39/26/28}}, {{R39/27}}, {{R39/27/28}}, {{R39/28}}, {{R42/43}}, {{R48/20}}, {{R48/20/21}}, {{R48/20/21/22}}, {{R48/20/22}}, {{R48/21}}, {{R48/21/22}}, {{R48/22}}, {{R48/23}}, {{R48/23/24}}, {{R48/23/24/25}}, {{R48/23/25}}, {{R48/24}}, {{R48/24/25}}, {{R48/25}}, {{R50/53}}, {{R51/53}}, {{R52/53}}, {{R68/20}}, {{R68/20/21}}, {{R68/20/21/22}}, {{R68/20/22}}, {{R68/21}}, {{R68/21/22}}, {{R68/22}}

==S Phrases==
{{S1}}, {{S2}}, {{S3}}, {{S4}}, {{S5}}, {{S6}}, {{S7}}, {{S8}}, {{S9}}, {{S12}}, {{S13}}, {{S14}}, {{S15}}, {{S16}}, {{S17}}, {{S18}}, {{S20}}, {{S21}}, {{S22}}, {{S23}}, {{S24}}, {{S25}}, {{S26}}, {{S27}}, {{S28}}, {{S29}}, {{S33}}, {{S35}}, {{S36}}, {{S37}}, {{S38}}, {{S39}}, {{S40}}, {{S41}}, {{S42}}, {{S43}}, {{S45}}, {{S46}}, {{S47}}, {{S48}}, {{S49}}, {{S50}}, {{S51}}, {{S52}}, {{S53}}, {{S56}}, {{S57}}, {{S59}}, {{S60}}, {{S61}}, {{S62}}, {{S63}}, {{S64}}

==Combined S Phrases==
{{S1/2}}, {{S3/7}}, {{S3/9/14}}, {{S3/9/14/49}}, {{S3/9/49}}, {{S3/14}}, {{S7/8}}, {{S7/9}}, {{S7/47}}, {{S20/21}}, {{S24/25}}, {{S27/28}}, {{S29/35}}, {{S29/56}}, {{S36/37}}, {{S36/37/39}}, {{S36/39}}, {{S37/39}}, {{S47/49}}

R & S Phrases

2006-11-09T17:20:29Z

Bel05:

This page lists all of the R & S phrases used to describe hazardous chemicals in their wiki template form. To use them in your articles, simply type, for example <nowiki>{{</nowiki>R22}} into the edit window and you will end up with {{R22}}, which will describe the phrase when you hover the cursor over it.

==R Phrases==
{{R1}}, {{R2}}, {{R3}}, {{R4}}, {{R5}}, {{R6}}, {{R7}}, {{R8}}, {{R9}}, {{R10}}, {{R11}}, {{R12}}, {{R14}}, {{R15}}, {{R16}}, {{R17}}, {{R18}}, {{R19}}, {{R20}}, {{R21}}, {{R22}}, {{R23}}, {{R24}}, {{R25}}, {{R26}}, {{R27}}, {{R28}}, {{R29}}, {{R30}}, {{R31}}, {{R32}}, {{R33}}, {{R34}}, {{R35}}, {{R36}}, {{R37}}, {{R38}}, {{R39}}, {{R40}}, {{R41}}, {{R42}}, {{R43}}, {{R44}}, {{R45}}, {{R46}}, {{R48}}, {{R49}}, {{R50}}, {{R51}}, {{R52}}, {{R53}}, {{R54}}, {{R55}}, {{R56}}, {{R57}}, {{R58}}, {{R59}}, {{R60}}, {{R61}}, {{R62}}, {{R63}}, {{R64}}, {{R65}}, {{R66}} {{R67}}, {{R68}}

==Combined R Phrases==
{{R14/15}}, {{R15/29}}, {{R20/21}}, {{R20/21/22}}, {{R20/22}}, {{R21/22}}, {{R23/24}}, {{R23/24/25}}, {{R23/25}}, {{R24/25}}, {{R26/27}}, {{R26/27/28}}, {{R26/28}}, {{R27/28}}, {{R36/37}}, {{R36/37/38}}, {{R36/38}}, {{R37/38}}, {{R39/23}}, {{R39/23/24}}, {{R39/23/24/25}}, {{R39/23/25}}, {{R39/24}}, {{R39/24/25}}, {{R39/25}}, {{R39/26}}, {{R39/26/27}}, {{R39/26/27/28}}, {{R39/26/28}}, {{R39/27}}, {{R39/27/28}}, {{R39/28}}, {{R42/43}}, {{R48/20}}, {{R48/20/21}}, {{R48/20/21/22}}, {{R48/20/22}}, {{R48/21}}, {{R48/21/22}}, {{R48/22}}, {{R48/23}}, {{R48/23/24}}, {{R48/23/24/25}}, {{R48/23/25}}, {{R48/24}}, {{R48/24/25}}, {{R48/25}}, {{R50/53}}, {{R51/53}}, {{R52/53}}, {{R68/20}}, {{R68/20/21}}, {{R68/20/21/22}}, {{R68/20/22}}, {{R68/21}}, {{R68/21/22}}, {{R68/22}}

==S Phrases==
{{S1}}, {{S2}}, {{S3}}, {{S4}}, {{S5}}, {{S6}}, {{S7}}, {{S8}}, {{S9}}, {{S12}}, {{S13}}, {{S14}}, {{S15}}, {{S16}}, {{S17}}, {{S18}}, {{S20}}, {{S21}}, {{S22}}, {{S23}}, {{S24}}, {{S25}}, {{S26}}, {{S27}}, {{S28}}, {{S29}}, {{S33}}, {{S35}}, {{S36}}, {{S37}}, {{S38}}, {{S39}}, {{S40}}, {{S41}}, {{S42}}, {{S43}}, {{S45}}, {{S46}}, {{S47}}, {{S48}}, {{S49}}, {{S50}}, {{S51}}, {{S52}}, {{S53}}, {{S56}}, {{S57}}, {{S59}}, {{S60}}, {{S61}}, {{S62}}, {{S63}}, {{S64}}

==Combined S Phrases==
{{S1/2}}, {{S3/7}}, {{S3/9/14}}, {{S3/9/14/49}}, {{S3/9/49}}, {{S3/14}}, {{S7/8}}, {{S7/9}}, {{S7/47}}, {{S20/21}}, {{S24/25}}, {{S27/28}}, {{S29/35}}, {{S29/56}}, {{S36/37}}, {{S36/37/39}}, {{S36/39}}, {{S37/39}}, {{S47/49}}

Template:S47/49

2006-11-09T17:19:56Z

Bel05:

S47/49

Template:S37/39

2006-11-09T17:19:39Z

Bel05:

S37/39

Template:S36/39

2006-11-09T17:19:10Z

Bel05:

S36/39

Template:S36/37/39

2006-11-09T17:18:55Z

Bel05:

S36/37/39

Template:S36/37

2006-11-09T17:18:40Z

Bel05:

S36/37

Template:S29/56

2006-11-09T17:18:20Z

Bel05:

S29/56

Template:S29/35

2006-11-09T17:17:39Z

Bel05:

S29/35

Template:S27/28

2006-11-09T17:17:15Z

Bel05:

<span class="abbr" style="color: blue; border-bottom: 1px dotted blue" title="After contact with skin, take off immediately all contaminated clothing, and wash immediately with plenty of ... (to be specified by the manufacturer)">S27/28

It:Tetrahydrocannabinol

2006-11-09T17:16:50Z

Bel05:

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} | tetrahydrocannabinol
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:THC.cdx|250px|Tetrahydrocannabinic Acid B ]]
|-
! align="center" colspan="2" bgcolor="#ffffff" | <jmol>
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<size>200</size>
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|-
! {{chembox header}} | General
|-
! Beilstein Registry Number
| 4693381 ||
|-
! CAS Registry Number
|1972-08-3
|-
! Chemical Name
|Tetrahydrocannabinol ||
|-
! Autoname
|6,6,9-trimethyl-3-pentyl-6a,7,8,
10a-tetrahydro-6H-benzo[c]chromen-1-ol
|-
! Molecular Formula
|C21H30O2||
|-
! Molecular Weight
|314.47 g/mol||
|-
! Structure Keyword
|Stereo compound||
|-
! Type of Substance
|Heterocyclic||
|}

== Introduction ==

Cannabis has around 60 different psychoactive chemicals of which tetrahydrocannabinol (THC) is the main one that acts on the nervous system. It is known as the source of the marijuana drug. It was first isolated by Raphael Mechoulam and Yechiel Gaoni from Weizmann Institute in Rehovot in 1964.

== Properties ==

THC has a good solubility in organic solvents, e.g. hexane or ethanol, but not in water. If the glassy solid is warmed it becomes viscous and sticky.

== Isomerisation ==

There are two isomers of THC found in marijuana: Δ8- and Δ9-tetrahydrocannabinol. Δ8-THC compromises around 10% of total tetrahydrocannabinol, which might be formed by isomerisation since it has similar pharmacological activity to Δ9-THC.
[[Image:Isomerisation.jpg|thumb|centre|1000|Isomerization (General)]]
The most reactive sites for Δ8- THC are at C-7 and for Δ9-THC at C-8; and C-11 for both isomers. Secondary alcohols such as hydroxysteroids are oxidized to the equivalent ketones by the enzyme dehydrogenases in cytosol and microsomes. However, it was discovered that microsomal alcohol oxygenase (MALCO) can also oxidise 7 - and 7 -hydroxy- 8-THC to 7-oxo- 8-THC. In humans it is catalysed by CYP3A4.

== Effects in Human ==

Tetrahydrocannabinol binds to the cannabinoid receptor CB1, which is located in the brain. Even at low doses it has analgesic effects.

Its effects are:

• Relaxation
• Euphoria
• Altered space-time perception
• Alteration of visual, auditory and olfactory senses
• Disorientation
• Fatigue
• Appetite simulation
• Anti-emetic effects

== Reference ==
• http://dmd.aspetjournals.org/cgi/content/full/29/11/1485#F1

• http://en.wikipedia.org/wiki/Tetrahydrocannabinol

It:Tetrahydrocannabinol

2006-11-09T17:13:43Z

Bel05: Correct 3D structure

== Introduction ==

Cannabis has around 60 different psychoactive chemicals of which tetrahydrocannabinol (THC) is the main one that acts on the nervous system. It is known as the source of the marijuana drug. It was first isolated by Raphael Mechoulam and Yechiel Gaoni from Weizmann Institute in Rehovot in 1964.

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24 47 1 0 0 0
24 45 1 0 0 0
25 50 1 0 0 0
25 48 1 0 0 0
25 49 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} | tetrahydrocannabinol
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:THC.cdx|250px|Tetrahydrocannabinic Acid B ]]
|-
! {{chembox header}} | General
|-
! Beilstein Registry Number
| 4693381 ||
|-
! CAS Registry Number
|1972-08-3
|-
! Chemical Name
|Tetrahydrocannabinol ||
|-
! Autoname
|6,6,9-trimethyl-3-pentyl-6a,7,8,
10a-tetrahydro-6H-benzo[c]chromen-1-ol
|-
! Molecular Formula
|C21H30O2||
|-
! Molecular Weight
|314.47 g/mol||
|-
! Structure Keyword
|Stereo compound||
|-
! Type of Substance
|Heterocyclic||
|}

== Properties ==

THC has a good solubility in organic solvents, e.g. hexane or ethanol, but not in water. If the glassy solid is warmed it becomes viscous and sticky.

== Isomerisation ==

There are two isomers of THC found in marijuana: Δ8- and Δ9-tetrahydrocannabinol. Δ8-THC compromises around 10% of total tetrahydrocannabinol, which might be formed by isomerisation since it has similar pharmacological activity to Δ9-THC.
[[Image:Isomerisation.jpg|thumb|centre|1000|Isomerization (General)]]
The most reactive sites for Δ8- THC are at C-7 and for Δ9-THC at C-8; and C-11 for both isomers. Secondary alcohols such as hydroxysteroids are oxidized to the equivalent ketones by the enzyme dehydrogenases in cytosol and microsomes. However, it was discovered that microsomal alcohol oxygenase (MALCO) can also oxidise 7 - and 7 -hydroxy- 8-THC to 7-oxo- 8-THC. In humans it is catalysed by CYP3A4.

== Effects in Human ==

Tetrahydrocannabinol binds to the cannabinoid receptor CB1, which is located in the brain. Even at low doses it has analgesic effects.

Its effects are:

• Relaxation
• Euphoria
• Altered space-time perception
• Alteration of visual, auditory and olfactory senses
• Disorientation
• Fatigue
• Appetite simulation
• Anti-emetic effects

== Reference ==
• http://dmd.aspetjournals.org/cgi/content/full/29/11/1485#F1

• http://en.wikipedia.org/wiki/Tetrahydrocannabinol

It:Tetrahydrocannabinol

2006-11-09T16:58:54Z

Bel05: /* Effects in Human */

== Introduction ==

Cannabis has around 60 different psychoactive chemicals of which tetrahydrocannabinol (THC) is the main one that acts on the nervous system. It is known as the source of the marijuana drug. It was first isolated by Raphael Mechoulam and Yechiel Gaoni from Weizmann Institute in Rehovot in 1964.

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY THCANB
COMPND UNNAMED
AUTHOR GENERATED BY CONQUEST
CRYST1 16.514 14.324 8.744 90.00 90.00 90.00 P 21 21 21 4
ATOM 1 C1 UNK 0 1 6.351 -1.377 2.224 1.00 0.00
ATOM 2 C2 UNK 0 1 7.331 -0.232 2.255 1.00 0.00
ATOM 3 C3 UNK 0 1 6.789 1.038 1.665 1.00 0.00
ATOM 4 C4 UNK 0 1 5.342 1.235 2.129 1.00 0.00
ATOM 5 C5 UNK 0 1 4.782 2.606 1.863 1.00 0.00
ATOM 6 C6 UNK 0 1 0.725 3.242 3.129 1.00 0.00
ATOM 7 C7 UNK 0 1 6.913 -2.729 2.642 1.00 0.00
ATOM 8 C8 UNK 0 1 2.555 1.548 2.365 1.00 0.00
ATOM 9 C9 UNK 0 1 5.522 3.721 2.601 1.00 0.00
ATOM 10 C10 UNK 0 1 4.627 2.915 0.430 1.00 0.00
ATOM 11 C11 UNK 0 1 -1.171 0.901 3.136 1.00 0.00
ATOM 12 C12 UNK 0 1 -1.950 1.345 2.024 1.00 0.00
ATOM 13 C13 UNK 0 1 -3.504 1.417 2.346 1.00 0.00
ATOM 14 C14 UNK 0 1 -4.138 0.493 2.632 1.00 0.00
ATOM 15 C15 UNK 0 1 -5.702 0.573 2.682 1.00 0.00
ATOM 16 C16 UNK 0 1 1.224 1.858 2.734 1.00 0.00
ATOM 17 C17 UNK 0 1 0.304 0.821 2.659 1.00 0.00
ATOM 18 C18 UNK 0 1 0.743 -0.411 2.144 1.00 0.00
ATOM 19 C19 UNK 0 1 2.028 -0.649 1.753 1.00 0.00
ATOM 20 C20 UNK 0 1 3.025 0.324 1.883 1.00 0.00
ATOM 21 C21 UNK 0 1 4.472 0.135 1.527 1.00 0.00
ATOM 22 C22 UNK 0 1 5.057 -1.187 1.922 1.00 0.00
ATOM 23 H1 UNK 0 1 1.668 -2.449 1.128 1.00 0.00
ATOM 24 H2 UNK 0 1 2.593 3.939 3.069 1.00 0.00
ATOM 25 H3 UNK 0 1 0.083 -1.146 2.055 1.00 0.00
ATOM 26 H4 UNK 0 1 4.475 0.158 0.481 1.00 0.00
ATOM 27 H5 UNK 0 1 4.442 -1.962 1.915 1.00 0.00
ATOM 28 H6 UNK 0 1 8.141 -0.516 1.749 1.00 0.00
ATOM 29 H7 UNK 0 1 7.596 -0.014 3.192 1.00 0.00
ATOM 30 H8 UNK 0 1 6.771 0.931 0.603 1.00 0.00
ATOM 31 H9 UNK 0 1 7.349 1.819 1.836 1.00 0.00
ATOM 32 H10 UNK 0 1 5.318 1.132 3.148 1.00 0.00
ATOM 33 H11 UNK 0 1 7.894 -2.593 2.886 1.00 0.00
ATOM 34 H12 UNK 0 1 6.837 -3.337 1.871 1.00 0.00
ATOM 35 H13 UNK 0 1 6.424 -3.080 3.436 1.00 0.00
ATOM 36 H14 UNK 0 1 6.457 3.810 2.230 1.00 0.00
ATOM 37 H15 UNK 0 1 5.565 3.495 3.568 1.00 0.00
ATOM 38 H16 UNK 0 1 5.037 4.584 2.475 1.00 0.00
ATOM 39 H17 UNK 0 1 5.516 2.908 -0.026 1.00 0.00
ATOM 40 H18 UNK 0 1 4.195 3.796 0.306 1.00 0.00
ATOM 41 H19 UNK 0 1 4.046 2.206 0.000 1.00 0.00
ATOM 42 H20 UNK 0 1 -1.239 1.547 3.847 1.00 0.00
ATOM 43 H21 UNK 0 1 -1.470 0.000 3.366 1.00 0.00
ATOM 44 H22 UNK 0 1 -1.800 0.745 1.259 1.00 0.00
ATOM 45 H23 UNK 0 1 -1.651 2.278 1.793 1.00 0.00
ATOM 46 H24 UNK 0 1 -3.914 1.690 1.408 1.00 0.00
ATOM 47 H25 UNK 0 1 -3.650 2.163 2.938 1.00 0.00
ATOM 48 H26 UNK 0 1 -3.815 0.372 3.611 1.00 0.00
ATOM 49 H27 UNK 0 1 -3.815 -0.258 2.116 1.00 0.00
ATOM 50 H28 UNK 0 1 -6.028 -0.301 3.025 1.00 0.00
ATOM 51 H29 UNK 0 1 -6.011 0.673 1.723 1.00 0.00
ATOM 52 H30 UNK 0 1 -6.011 1.303 3.227 1.00 0.00
ATOM 53 O1 UNK 0 1 3.466 2.620 2.497 1.00 0.00
ATOM 54 O2 UNK 0 1 2.360 -1.829 1.222 1.00 0.00
ATOM 55 O3 UNK 0 1 -0.386 3.517 3.355 1.00 0.00
ATOM 56 O4 UNK 0 1 1.666 4.181 3.217 1.00 0.00
CONECT 1 2 7 22
CONECT 2 1 3 28 29
CONECT 3 2 4 30 31
CONECT 4 3 5 21 32
CONECT 5 4 9 10 53
CONECT 6 16 55 56
CONECT 7 1 33 34 35
CONECT 8 16 20 53
CONECT 9 5 36 37 38
CONECT 10 5 39 40 41
CONECT 11 12 17 42 43
CONECT 12 11 13 44 45
CONECT 13 12 14 46 47
CONECT 14 13 15 48 49
CONECT 15 14 50 51 52
CONECT 16 6 8 17
CONECT 17 11 16 18
CONECT 18 17 19 25
CONECT 19 18 20 54
CONECT 20 8 19 21
CONECT 21 4 20 22 26
CONECT 22 1 21 27
CONECT 23 54
CONECT 24 56
CONECT 25 18
CONECT 26 21
CONECT 27 22
CONECT 28 2
CONECT 29 2
CONECT 30 3
CONECT 31 3
CONECT 32 4
CONECT 33 7
CONECT 34 7
CONECT 35 7
CONECT 36 9
CONECT 37 9
CONECT 38 9
CONECT 39 10
CONECT 40 10
CONECT 41 10
CONECT 42 11
CONECT 43 11
CONECT 44 12
CONECT 45 12
CONECT 46 13
CONECT 47 13
CONECT 48 14
CONECT 49 14
CONECT 50 15
CONECT 51 15
CONECT 52 15
CONECT 53 5 8
CONECT 54 19 23
CONECT 55 6
CONECT 56 6 24
MASTER 0 0 0 0 0 0 0 0 56 0 56 0
END</inlineContents>
</jmolApplet>
</jmol>

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} | tetrahydrocannabinol
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:THC.cdx|250px|Tetrahydrocannabinic Acid B ]]
|-
! {{chembox header}} | General
|-
! Beilstein Registry Number
| 4693381 ||
|-
! CAS Registry Number
|1972-08-3, 3556-79-4, 6087-73-6, 6465-30-1, 16849-50-6, 17766-02-8, 26906-54-7, 43009-38-7, 69855-10-3 ||
|-
! Chemical Name
|Tetrahydrocannabinol ||
|-
! Autoname
|6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol ||
|-
! Molecular Formula
|C21H30O2||
|-
! Molecular Weight
|314.47 g/mol||
|-
! Structure Keyword
|Stereo compound||
|-
! Type of Substance
|Heterocyclic||
|}

== Properties ==

THC has a good solubility in organic solvents, e.g. hexane or ethanol, but not in water. If the glassy solid is warmed it becomes viscous and sticky.

== Isomerisation ==

There are two isomers of THC found in marijuana: Δ8- and Δ9-tetrahydrocannabinol. Δ8-THC compromises around 10% of total tetrahydrocannabinol, which might be formed by isomerisation since it has similar pharmacological activity to Δ9-THC.
[[Image:Isomerisation.jpg|thumb|centre|1000|Isomerization (General)]]
The most reactive sites for Δ8- THC are at C-7 and for Δ9-THC at C-8; and C-11 for both isomers. Secondary alcohols such as hydroxysteroids are oxidized to the equivalent ketones by the enzyme dehydrogenases in cytosol and microsomes. However, it was discovered that microsomal alcohol oxygenase (MALCO) can also oxidise 7 - and 7 -hydroxy- 8-THC to 7-oxo- 8-THC. In humans it is catalysed by CYP3A4.

== Effects in Human ==

Tetrahydrocannabinol binds to the cannabinoid receptor CB1, which is located in the brain. Even at low doses it has analgesic effects.

Its effects are:

• Relaxation
• Euphoria
• Altered space-time perception
• Alteration of visual, auditory and olfactory senses
• Disorientation
• Fatigue
• Appetite simulation
• Anti-emetic effects

== Reference ==
• http://dmd.aspetjournals.org/cgi/content/full/29/11/1485#F1

• http://en.wikipedia.org/wiki/Tetrahydrocannabinol

It:Tetrahydrocannabinol

2006-11-09T16:58:40Z

Bel05: /* Effects in Human */

== Introduction ==

Cannabis has around 60 different psychoactive chemicals of which tetrahydrocannabinol (THC) is the main one that acts on the nervous system. It is known as the source of the marijuana drug. It was first isolated by Raphael Mechoulam and Yechiel Gaoni from Weizmann Institute in Rehovot in 1964.

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY THCANB
COMPND UNNAMED
AUTHOR GENERATED BY CONQUEST
CRYST1 16.514 14.324 8.744 90.00 90.00 90.00 P 21 21 21 4
ATOM 1 C1 UNK 0 1 6.351 -1.377 2.224 1.00 0.00
ATOM 2 C2 UNK 0 1 7.331 -0.232 2.255 1.00 0.00
ATOM 3 C3 UNK 0 1 6.789 1.038 1.665 1.00 0.00
ATOM 4 C4 UNK 0 1 5.342 1.235 2.129 1.00 0.00
ATOM 5 C5 UNK 0 1 4.782 2.606 1.863 1.00 0.00
ATOM 6 C6 UNK 0 1 0.725 3.242 3.129 1.00 0.00
ATOM 7 C7 UNK 0 1 6.913 -2.729 2.642 1.00 0.00
ATOM 8 C8 UNK 0 1 2.555 1.548 2.365 1.00 0.00
ATOM 9 C9 UNK 0 1 5.522 3.721 2.601 1.00 0.00
ATOM 10 C10 UNK 0 1 4.627 2.915 0.430 1.00 0.00
ATOM 11 C11 UNK 0 1 -1.171 0.901 3.136 1.00 0.00
ATOM 12 C12 UNK 0 1 -1.950 1.345 2.024 1.00 0.00
ATOM 13 C13 UNK 0 1 -3.504 1.417 2.346 1.00 0.00
ATOM 14 C14 UNK 0 1 -4.138 0.493 2.632 1.00 0.00
ATOM 15 C15 UNK 0 1 -5.702 0.573 2.682 1.00 0.00
ATOM 16 C16 UNK 0 1 1.224 1.858 2.734 1.00 0.00
ATOM 17 C17 UNK 0 1 0.304 0.821 2.659 1.00 0.00
ATOM 18 C18 UNK 0 1 0.743 -0.411 2.144 1.00 0.00
ATOM 19 C19 UNK 0 1 2.028 -0.649 1.753 1.00 0.00
ATOM 20 C20 UNK 0 1 3.025 0.324 1.883 1.00 0.00
ATOM 21 C21 UNK 0 1 4.472 0.135 1.527 1.00 0.00
ATOM 22 C22 UNK 0 1 5.057 -1.187 1.922 1.00 0.00
ATOM 23 H1 UNK 0 1 1.668 -2.449 1.128 1.00 0.00
ATOM 24 H2 UNK 0 1 2.593 3.939 3.069 1.00 0.00
ATOM 25 H3 UNK 0 1 0.083 -1.146 2.055 1.00 0.00
ATOM 26 H4 UNK 0 1 4.475 0.158 0.481 1.00 0.00
ATOM 27 H5 UNK 0 1 4.442 -1.962 1.915 1.00 0.00
ATOM 28 H6 UNK 0 1 8.141 -0.516 1.749 1.00 0.00
ATOM 29 H7 UNK 0 1 7.596 -0.014 3.192 1.00 0.00
ATOM 30 H8 UNK 0 1 6.771 0.931 0.603 1.00 0.00
ATOM 31 H9 UNK 0 1 7.349 1.819 1.836 1.00 0.00
ATOM 32 H10 UNK 0 1 5.318 1.132 3.148 1.00 0.00
ATOM 33 H11 UNK 0 1 7.894 -2.593 2.886 1.00 0.00
ATOM 34 H12 UNK 0 1 6.837 -3.337 1.871 1.00 0.00
ATOM 35 H13 UNK 0 1 6.424 -3.080 3.436 1.00 0.00
ATOM 36 H14 UNK 0 1 6.457 3.810 2.230 1.00 0.00
ATOM 37 H15 UNK 0 1 5.565 3.495 3.568 1.00 0.00
ATOM 38 H16 UNK 0 1 5.037 4.584 2.475 1.00 0.00
ATOM 39 H17 UNK 0 1 5.516 2.908 -0.026 1.00 0.00
ATOM 40 H18 UNK 0 1 4.195 3.796 0.306 1.00 0.00
ATOM 41 H19 UNK 0 1 4.046 2.206 0.000 1.00 0.00
ATOM 42 H20 UNK 0 1 -1.239 1.547 3.847 1.00 0.00
ATOM 43 H21 UNK 0 1 -1.470 0.000 3.366 1.00 0.00
ATOM 44 H22 UNK 0 1 -1.800 0.745 1.259 1.00 0.00
ATOM 45 H23 UNK 0 1 -1.651 2.278 1.793 1.00 0.00
ATOM 46 H24 UNK 0 1 -3.914 1.690 1.408 1.00 0.00
ATOM 47 H25 UNK 0 1 -3.650 2.163 2.938 1.00 0.00
ATOM 48 H26 UNK 0 1 -3.815 0.372 3.611 1.00 0.00
ATOM 49 H27 UNK 0 1 -3.815 -0.258 2.116 1.00 0.00
ATOM 50 H28 UNK 0 1 -6.028 -0.301 3.025 1.00 0.00
ATOM 51 H29 UNK 0 1 -6.011 0.673 1.723 1.00 0.00
ATOM 52 H30 UNK 0 1 -6.011 1.303 3.227 1.00 0.00
ATOM 53 O1 UNK 0 1 3.466 2.620 2.497 1.00 0.00
ATOM 54 O2 UNK 0 1 2.360 -1.829 1.222 1.00 0.00
ATOM 55 O3 UNK 0 1 -0.386 3.517 3.355 1.00 0.00
ATOM 56 O4 UNK 0 1 1.666 4.181 3.217 1.00 0.00
CONECT 1 2 7 22
CONECT 2 1 3 28 29
CONECT 3 2 4 30 31
CONECT 4 3 5 21 32
CONECT 5 4 9 10 53
CONECT 6 16 55 56
CONECT 7 1 33 34 35
CONECT 8 16 20 53
CONECT 9 5 36 37 38
CONECT 10 5 39 40 41
CONECT 11 12 17 42 43
CONECT 12 11 13 44 45
CONECT 13 12 14 46 47
CONECT 14 13 15 48 49
CONECT 15 14 50 51 52
CONECT 16 6 8 17
CONECT 17 11 16 18
CONECT 18 17 19 25
CONECT 19 18 20 54
CONECT 20 8 19 21
CONECT 21 4 20 22 26
CONECT 22 1 21 27
CONECT 23 54
CONECT 24 56
CONECT 25 18
CONECT 26 21
CONECT 27 22
CONECT 28 2
CONECT 29 2
CONECT 30 3
CONECT 31 3
CONECT 32 4
CONECT 33 7
CONECT 34 7
CONECT 35 7
CONECT 36 9
CONECT 37 9
CONECT 38 9
CONECT 39 10
CONECT 40 10
CONECT 41 10
CONECT 42 11
CONECT 43 11
CONECT 44 12
CONECT 45 12
CONECT 46 13
CONECT 47 13
CONECT 48 14
CONECT 49 14
CONECT 50 15
CONECT 51 15
CONECT 52 15
CONECT 53 5 8
CONECT 54 19 23
CONECT 55 6
CONECT 56 6 24
MASTER 0 0 0 0 0 0 0 0 56 0 56 0
END</inlineContents>
</jmolApplet>
</jmol>

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} | tetrahydrocannabinol
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:THC.cdx|250px|Tetrahydrocannabinic Acid B ]]
|-
! {{chembox header}} | General
|-
! Beilstein Registry Number
| 4693381 ||
|-
! CAS Registry Number
|1972-08-3, 3556-79-4, 6087-73-6, 6465-30-1, 16849-50-6, 17766-02-8, 26906-54-7, 43009-38-7, 69855-10-3 ||
|-
! Chemical Name
|Tetrahydrocannabinol ||
|-
! Autoname
|6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol ||
|-
! Molecular Formula
|C21H30O2||
|-
! Molecular Weight
|314.47 g/mol||
|-
! Structure Keyword
|Stereo compound||
|-
! Type of Substance
|Heterocyclic||
|}

== Properties ==

THC has a good solubility in organic solvents, e.g. hexane or ethanol, but not in water. If the glassy solid is warmed it becomes viscous and sticky.

== Isomerisation ==

There are two isomers of THC found in marijuana: Δ8- and Δ9-tetrahydrocannabinol. Δ8-THC compromises around 10% of total tetrahydrocannabinol, which might be formed by isomerisation since it has similar pharmacological activity to Δ9-THC.
[[Image:Isomerisation.jpg|thumb|centre|1000|Isomerization (General)]]
The most reactive sites for Δ8- THC are at C-7 and for Δ9-THC at C-8; and C-11 for both isomers. Secondary alcohols such as hydroxysteroids are oxidized to the equivalent ketones by the enzyme dehydrogenases in cytosol and microsomes. However, it was discovered that microsomal alcohol oxygenase (MALCO) can also oxidise 7 - and 7 -hydroxy- 8-THC to 7-oxo- 8-THC. In humans it is catalysed by CYP3A4.

== Effects in Human ==

Tetrahydrocannabinol binds to the cannabinoid receptor CB1, which is located in the brain. Even at low doses it has analgesic effects.

Its effecTs are:

• Relaxation
• Euphoria
• Altered space-time perception
• Alteration of visual, auditory and olfactory senses
• Disorientation
• Fatigue
• Appetite simulation
• Anti-emetic effects

== Reference ==
• http://dmd.aspetjournals.org/cgi/content/full/29/11/1485#F1

• http://en.wikipedia.org/wiki/Tetrahydrocannabinol

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