ChemWiki - User contributions [en]

It:Tetrahydrocannabinol

2006-12-15T15:59:30Z

Sd204: /* Degradation of THC */

{| 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>
<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>water.mol
title1
title2
50 52 0 0 0 0 0 0 0 0999 V2000
-2.9910 -1.8680 -0.1160 C 0 0 0 0 0 0 0 0 0 1
-4.2620 -1.8840 0.1690 C 0 0 0 0 0 0 0 0 0 2
-5.1530 -0.6820 0.2280 C 0 0 0 0 0 0 0 0 0 3
-4.4580 0.5710 -0.3180 C 0 0 0 0 0 0 0 0 0 4
-3.0310 0.5720 0.2170 C 0 0 2 0 0 0 0 0 0 5
-3.0470 0.4240 1.2970 H 0 0 0 0 0 0 0 0 0 6
-2.2890 -0.5950 -0.4500 C 0 0 2 0 0 0 0 0 0 7
-2.3270 -0.4520 -1.5300 H 0 0 0 0 0 0 0 0 0 8
-0.8550 -0.5280 -0.0230 C 0 0 0 0 0 0 0 0 0 9
-0.0660 -1.6660 -0.1030 C 0 0 0 0 0 0 0 0 0 10
-0.6040 -2.8310 -0.5520 O 0 0 0 0 0 0 0 0 0 11
-0.4780 -2.8460 -1.5100 H 0 0 0 0 0 0 0 0 0 12
1.2680 -1.6230 0.2720 C 0 0 0 0 0 0 0 0 0 13
1.8080 -0.4340 0.7250 C 0 0 0 0 0 0 0 0 0 14
3.2590 -0.3740 1.1260 C 0 0 0 0 0 0 0 0 0 15
4.1090 -0.0010 -0.0900 C 0 0 0 0 0 0 0 0 0 16
5.5830 0.0600 0.3170 C 0 0 0 0 0 0 0 0 0 17
6.4330 0.4330 -0.8990 C 0 0 0 0 0 0 0 0 0 18
7.9070 0.4940 -0.4920 C 0 0 0 0 0 0 0 0 0 19
1.0250 0.6950 0.8110 C 0 0 0 0 0 0 0 0 0 20
-0.3250 0.6650 0.4450 C 0 0 0 0 0 0 0 0 0 21
-1.0200 1.8130 0.6050 O 0 0 0 0 0 0 0 0 0 22
-2.2470 1.8360 -0.1100 C 0 0 0 0 0 0 0 0 0 23
-1.9640 1.8830 -1.6130 C 0 0 0 0 0 0 0 0 0 24
-3.0570 3.0680 0.3000 C 0 0 0 0 0 0 0 0 0 25
-2.4330 -2.7930 -0.1070 H 0 0 0 0 0 0 0 0 0 26
-4.7100 -2.8440 0.3790 H 0 0 0 0 0 0 0 0 0 27
-6.0500 -0.8750 -0.3610 H 0 0 0 0 0 0 0 0 0 28
-5.4420 -0.5050 1.2640 H 0 0 0 0 0 0 0 0 0 29
-4.4440 0.5420 -1.4080 H 0 0 0 0 0 0 0 0 0 30
-4.9820 1.4640 0.0230 H 0 0 0 0 0 0 0 0 0 31
1.8800 -2.5110 0.2110 H 0 0 0 0 0 0 0 0 0 32
3.3900 0.3780 1.9050 H 0 0 0 0 0 0 0 0 0 33
3.5730 -1.3470 1.5040 H 0 0 0 0 0 0 0 0 0 34
3.9790 -0.7530 -0.8690 H 0 0 0 0 0 0 0 0 0 35
3.7960 0.9720 -0.4680 H 0 0 0 0 0 0 0 0 0 36
5.7140 0.8120 1.0960 H 0 0 0 0 0 0 0 0 0 37
5.8960 -0.9130 0.6950 H 0 0 0 0 0 0 0 0 0 38
6.3020 -0.3190 -1.6780 H 0 0 0 0 0 0 0 0 0 39
6.1200 1.4060 -1.2770 H 0 0 0 0 0 0 0 0 0 40
8.0370 1.2460 0.2860 H 0 0 0 0 0 0 0 0 0 41
8.2200 -0.4790 -0.1140 H 0 0 0 0 0 0 0 0 0 42
8.5120 0.7600 -1.3590 H 0 0 0 0 0 0 0 0 0 43
1.4590 1.6180 1.1660 H 0 0 0 0 0 0 0 0 0 44
-1.3930 1.0010 -1.9020 H 0 0 0 0 0 0 0 0 0 45
-2.9070 1.9010 -2.1600 H 0 0 0 0 0 0 0 0 0 46
-1.3910 2.7800 -1.8470 H 0 0 0 0 0 0 0 0 0 47
-2.4880 3.9690 0.0730 H 0 0 0 0 0 0 0 0 0 48
-3.9980 3.0840 -0.2500 H 0 0 0 0 0 0 0 0 0 49
-3.2620 3.0280 1.3700 H 0 0 0 0 0 0 0 0 0 50
1 7 1 0 0 0
1 2 1 0 0 0
1 26 1 0 0 0
2 3 1 0 0 0
2 27 1 0 0 0
9 7 1 0 0 0
9 21 1 0 0 0
9 10 1 0 0 0
10 11 1 0 0 0
10 13 1 0 0 0
11 12 1 0 0 0
13 14 1 0 0 0
13 32 1 0 0 0
14 15 1 0 0 0
14 20 1 0 0 0
20 21 1 0 0 0
20 44 1 0 0 0
21 22 1 0 0 0
22 23 1 0 0 0
3 29 1 0 0 0
3 4 1 0 0 0
3 28 1 0 0 0
4 30 1 0 0 0
4 31 1 0 0 0
4 5 1 0 0 0
5 6 1 0 0 0
5 23 1 0 0 0
5 7 1 0 0 0
7 8 1 0 0 0
15 34 1 0 0 0
15 16 1 0 0 0
15 33 1 0 0 0
16 35 1 0 0 0
16 36 1 0 0 0
16 17 1 0 0 0
17 37 1 0 0 0
17 38 1 0 0 0
17 18 1 0 0 0
18 40 1 0 0 0
18 19 1 0 0 0
18 39 1 0 0 0
19 43 1 0 0 0
19 42 1 0 0 0
19 41 1 0 0 0
23 24 1 0 0 0
23 25 1 0 0 0
24 46 1 0 0 0
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>
|-
! {{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_2.JPG|centre]]
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.

== Synthesis ==

In this article three active isomers are considered, which differ in the bonding of the left hand ring:
[[Image:THC_isomers.gif|centre]]

On the picture THC-A is shown as Δ1-THC, which is same as Δ9-THC since the numbering of the ring was different when this was discovered. Tetrahydrocannabinol A and B are found in hashish, while C is a synthetic one. The potency of these three isomers is similar, but by changing the alkyl group of the right hand ring an increase in effectiveness has been shown.
The synthesis of all three of them is based on the condensation of olivetol with a compound that forms the alkyl group for increase activity. An example of preparing THC-V is shown below.
[[Image:Synthesis.gif|centre]]

== 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

Due to these effects Δ9-THC is used in the medicine for several causes:
1. As an antiemetic to control nausea and vomiting associated with cancer chemotherapy.
2. As an antiemetic to control nausea and vomiting associated with the use of drugs for controlling the spread of the
AIDS virus; without which patients could regurgitate the nausea inducing drugs before being properly absorbed by the body.
3. To slow down or reverse the weight reduction syndrome of AIDS.
4. To control seizures in patients suffering from epilepsy.
5. To reduce pressure within the eyes associated with glaucoma.
6. To alleviate muscle spasms associated with multiple sclerosis.
7. To alleviate pain and muscle spasms for paraplegics and quadriplegics.

== Degradation of THC ==

Tetrahydrocannabinol undergoes oxidation to either cannabinol or 9,10-dihydroxy-tetrahydrocannabinol. Cannabinol (CBN) is also the natural degradation (oxidative) product of THC. Fresh samples of marijuana contain very little CBN but curing, or poor storage, over long periods can cause much of the THC to be oxidized to CBN. It is also possible to reduce 9,10-dihydroxy-tetrahydrocannabinol in the presence of acid to CBN.

[[Image:THC oxidation.jpg]]

Pure forms of CBN have at most 10 percent of the psychoactivity of THC. CBN seems to potentiate THC's disorienting qualities. One may feel more dizzy or drugged or generally messed up but not necessarily higher. In fact, with a high proportion of CBN, a 'high' may start well but feels as if it never quite reaches its peak, and when coming down one feels tired or sleepy.

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

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

• http://designer-drugs.com/pte/12.162.180.114/dcd/chemistry/thc/index.html

• http://www.a1b2c3.com/drugs/mj028.htm

'''Cannabis. XV. Preparation and Stability of d<sup>9</sup>-Tetrahydrocannabinol-B-Cyclodextrin inclusion complex'''
Y. Shoyama, S. Morimoto, and I. Nishioka. Journal of Natural Products, Vol 46, No.5, pp. 633-637, Sept-Oct 1983

2006-12-14T16:19:05Z

Sd204:

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} | Lysergic Acid Diethylamide
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:LSD.cdx|LSD Structure]]
|-
! align="center" colspan="2" bgcolor="#ffffff" | <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>water.mol
title1
title2
50 52 0 0 0 0 0 0 0 0999 V2000
-2.9910 -1.8680 -0.1160 C 0 0 0 0 0 0 0 0 0 1
-4.2620 -1.8840 0.1690 C 0 0 0 0 0 0 0 0 0 2
-5.1530 -0.6820 0.2280 C 0 0 0 0 0 0 0 0 0 3
-4.4580 0.5710 -0.3180 C 0 0 0 0 0 0 0 0 0 4
-3.0310 0.5720 0.2170 C 0 0 2 0 0 0 0 0 0 5
-3.0470 0.4240 1.2970 H 0 0 0 0 0 0 0 0 0 6
-2.2890 -0.5950 -0.4500 C 0 0 2 0 0 0 0 0 0 7
-2.3270 -0.4520 -1.5300 H 0 0 0 0 0 0 0 0 0 8
-0.8550 -0.5280 -0.0230 C 0 0 0 0 0 0 0 0 0 9
-0.0660 -1.6660 -0.1030 C 0 0 0 0 0 0 0 0 0 10
-0.6040 -2.8310 -0.5520 O 0 0 0 0 0 0 0 0 0 11
-0.4780 -2.8460 -1.5100 H 0 0 0 0 0 0 0 0 0 12
1.2680 -1.6230 0.2720 C 0 0 0 0 0 0 0 0 0 13
1.8080 -0.4340 0.7250 C 0 0 0 0 0 0 0 0 0 14
3.2590 -0.3740 1.1260 C 0 0 0 0 0 0 0 0 0 15
4.1090 -0.0010 -0.0900 C 0 0 0 0 0 0 0 0 0 16
5.5830 0.0600 0.3170 C 0 0 0 0 0 0 0 0 0 17
6.4330 0.4330 -0.8990 C 0 0 0 0 0 0 0 0 0 18
7.9070 0.4940 -0.4920 C 0 0 0 0 0 0 0 0 0 19
1.0250 0.6950 0.8110 C 0 0 0 0 0 0 0 0 0 20
-0.3250 0.6650 0.4450 C 0 0 0 0 0 0 0 0 0 21
-1.0200 1.8130 0.6050 O 0 0 0 0 0 0 0 0 0 22
-2.2470 1.8360 -0.1100 C 0 0 0 0 0 0 0 0 0 23
-1.9640 1.8830 -1.6130 C 0 0 0 0 0 0 0 0 0 24
-3.0570 3.0680 0.3000 C 0 0 0 0 0 0 0 0 0 25
-2.4330 -2.7930 -0.1070 H 0 0 0 0 0 0 0 0 0 26
-4.7100 -2.8440 0.3790 H 0 0 0 0 0 0 0 0 0 27
-6.0500 -0.8750 -0.3610 H 0 0 0 0 0 0 0 0 0 28
-5.4420 -0.5050 1.2640 H 0 0 0 0 0 0 0 0 0 29
-4.4440 0.5420 -1.4080 H 0 0 0 0 0 0 0 0 0 30
-4.9820 1.4640 0.0230 H 0 0 0 0 0 0 0 0 0 31
1.8800 -2.5110 0.2110 H 0 0 0 0 0 0 0 0 0 32
3.3900 0.3780 1.9050 H 0 0 0 0 0 0 0 0 0 33
3.5730 -1.3470 1.5040 H 0 0 0 0 0 0 0 0 0 34
3.9790 -0.7530 -0.8690 H 0 0 0 0 0 0 0 0 0 35
3.7960 0.9720 -0.4680 H 0 0 0 0 0 0 0 0 0 36
5.7140 0.8120 1.0960 H 0 0 0 0 0 0 0 0 0 37
5.8960 -0.9130 0.6950 H 0 0 0 0 0 0 0 0 0 38
6.3020 -0.3190 -1.6780 H 0 0 0 0 0 0 0 0 0 39
6.1200 1.4060 -1.2770 H 0 0 0 0 0 0 0 0 0 40
8.0370 1.2460 0.2860 H 0 0 0 0 0 0 0 0 0 41
8.2200 -0.4790 -0.1140 H 0 0 0 0 0 0 0 0 0 42
8.5120 0.7600 -1.3590 H 0 0 0 0 0 0 0 0 0 43
1.4590 1.6180 1.1660 H 0 0 0 0 0 0 0 0 0 44
-1.3930 1.0010 -1.9020 H 0 0 0 0 0 0 0 0 0 45
-2.9070 1.9010 -2.1600 H 0 0 0 0 0 0 0 0 0 46
-1.3910 2.7800 -1.8470 H 0 0 0 0 0 0 0 0 0 47
-2.4880 3.9690 0.0730 H 0 0 0 0 0 0 0 0 0 48
-3.9980 3.0840 -0.2500 H 0 0 0 0 0 0 0 0 0 49
-3.2620 3.0280 1.3700 H 0 0 0 0 0 0 0 0 0 50
1 7 1 0 0 0
1 2 1 0 0 0
1 26 1 0 0 0
2 3 1 0 0 0
2 27 1 0 0 0
9 7 1 0 0 0
9 21 1 0 0 0
9 10 1 0 0 0
10 11 1 0 0 0
10 13 1 0 0 0
11 12 1 0 0 0
13 14 1 0 0 0
13 32 1 0 0 0
14 15 1 0 0 0
14 20 1 0 0 0
20 21 1 0 0 0
20 44 1 0 0 0
21 22 1 0 0 0
22 23 1 0 0 0
3 29 1 0 0 0
3 4 1 0 0 0
3 28 1 0 0 0
4 30 1 0 0 0
4 31 1 0 0 0
4 5 1 0 0 0
5 6 1 0 0 0
5 23 1 0 0 0
5 7 1 0 0 0
7 8 1 0 0 0
15 34 1 0 0 0
15 16 1 0 0 0
15 33 1 0 0 0
16 35 1 0 0 0
16 36 1 0 0 0
16 17 1 0 0 0
17 37 1 0 0 0
17 38 1 0 0 0
17 18 1 0 0 0
18 40 1 0 0 0
18 19 1 0 0 0
18 39 1 0 0 0
19 43 1 0 0 0
19 42 1 0 0 0
19 41 1 0 0 0
23 24 1 0 0 0
23 25 1 0 0 0
24 46 1 0 0 0
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>
|-
! {{chembox header}} | General
|-
! CAS Registry Number
|50-37-3
|-
! Chemical Name
|Lysergic Acid Diethylamide||
|-
! IUPAC Name
|(6aR,9R)-N,N-Diethyl-7-methyl-4,6,6a,7,8,9-
hexahydroindolo-[4,3-fg]quinoline-9-carboxamide
|-
! Molecular Formula
|C20H25N3O||
|-
! Molecular Weight
|323.43g/mol||
|-
! Structure Keyword
|Stereo compound||
|-
! Type of Substance
|Heterocyclic||
|}

=Introduction=

First synthesised in 1938 Lysergic Acid Diethylamide is a pyschoactive compound more commonly known as the abbreviation LSD. It is a non-toxic, non-addictive drug that mimics serotonin in the brain.

=History=

LSD was first synthesised in 1938 by Dr. Alfred Hoffman, a Chemist in the pharmacological department in Sandoz Laboratories, Basel, Switzerland. It was initially developed while he was studying derivatives of lysergic acid, systematically reacting the carboxylic acid group with various reagents, to produce the corresponding amides, anhydrides, esters, etc. The reaction of diethylamine with this group produced what was then named LSD-25, however no real benefits of the compound were found and its study was discontinued.

Interest in the drug resumed 5 years later when Dr Hoffman synthesised LSD-25 again so that a sample could be given to the pharmocological department for further testing, when it was thought to be a potential treatment for schizophrenia. Although initial observations on the benefits were highly optimistic, empirical data developed subsequently proved much less promising.

Although LSD is relatively non-toxic and non-addictive, various governments around the world outlawed it after a number of fatal accidents were reported. Such accidents involved, for example, people under the influence of LSD jumping to their deaths off buildings believing they could fly. Research in the 1960's and 70's showed that there was also a considerable psychological risk with the drug and that high doses, especially in inappropriate settings, often caused panic reactions.
Scientific study finally ceased around mid 1970's as research funding declined, due to political reasons.

=How does LSD work?=

Although the mechanism by which LSD causes such profound affects on the human perception still hasn't been established
LSD has a very similar molecular structure to a hormone secreted in the brain called Serotoninwhich is why the body mistakes LSD for serotonin. LSD stimulates centers of the sympathetic nervous system in the midbrain by binding with the 5-HT receptors in the brain. Due to its higher affinity for these receptors serotonin is prevented from sending neural messages in the presence of LSD.

The common functional group found in Serotonin and LSD is the Indole ring (shown in blue below) that is characteristic of the tryptamine molecules and is also found in many other psychodelic compounds such as Psilocybin and Ergoline, which are alkaloids that occur naturally in fungi and plants.

[[Image:LSD Serotonin comparison.jpg|centre]]

The indole ring has a great influence on the electron density and dipole moment of both molecules and is likely to be responsible for the binding ability of both molecules to the 5-HT receptors.

=Synthesis of LSD=

LSD is synthesised with the following reagents:

[[Image:Example.jpg]]

File:LSD.cdx

2006-12-14T16:12:40Z

Sd204:

2006-12-14T15:47:56Z

Sd204:

It:Lysergic Acid Diethylamide

2006-12-14T15:47:31Z

Sd204:

=Introduction=

First synthesised in 1938 Lysergic Acid Diethylamide is a pyschoactive compound more commonly known as the abbreviation LSD. It is a non-toxic, non-addictive drug that mimics serotonin in the brain.

=History=

LSD was first synthesised in 1938 by Dr. Alfred Hoffman, a Chemist in the pharmacological department in Sandoz Laboratories, Basel, Switzerland. It was initially developed while he was studying derivatives of lysergic acid, systematically reacting the carboxylic acid group with various reagents, to produce the corresponding amides, anhydrides, esters, etc. The reaction of diethylamine with this group produced what was then named LSD-25, however no real benefits of the compound were found and its study was discontinued.

Interest in the drug resumed 5 years later when Dr Hoffman synthesised LSD-25 again so that a sample could be given to the pharmocological department for further testing, when it was thought to be a potential treatment for schizophrenia. Although initial observations on the benefits were highly optimistic, empirical data developed subsequently proved much less promising.

Although LSD is relatively non-toxic and non-addictive, various governments around the world outlawed it after a number of fatal accidents were reported. Such accidents involved, for example, people under the influence of LSD jumping to their deaths off buildings believing they could fly. Research in the 1960's and 70's showed that there was also a considerable psychological risk with the drug and that high doses, especially in inappropriate settings, often caused panic reactions.
Scientific study finally ceased around mid 1970's as research funding declined, due to political reasons.

=How does LSD work?=

Although the mechanism by which LSD causes such profound affects on the human perception still hasn't been established
LSD has a very similar molecular structure to a hormone secreted in the brain called Serotoninwhich is why the body mistakes LSD for serotonin. LSD stimulates centers of the sympathetic nervous system in the midbrain by binding with the 5-HT receptors in the brain. Due to its higher affinity for these receptors serotonin is prevented from sending neural messages in the presence of LSD.

The common functional group found in Serotonin and LSD is the Indole ring (shown in blue below) that is characteristic of the tryptamine molecules and is also found in many other psychodelic compounds such as Psilocybin and Ergoline, which are alkaloids that occur naturally in fungi and plants.

[[Image:LSD Serotonin comparison.jpg|centre]]

The indole ring has a great influence on the electron density and dipole moment of both molecules and is likely to be responsible for the binding ability of both molecules to the 5-HT receptors.

=Synthesis of LSD=

LSD is synthesised with the following reagents:

[[Image:Example.jpg]]

It:Lysergic Acid Diethylamide

2006-12-14T14:47:36Z

Sd204:

=Introduction=

First synthesised in 1938 Lysergic Acid Diethylamide is a pyschoactive compound more commonly known as the abbreviation LSD. It is a non-toxic, non-addictive drug that mimics serotonin in the brain.

=History=

LSD was first synthesised in 1938 by Dr. Alfred Hoffman, a Chemist in the pharmacological department in Sandoz Laboratories, Basel, Switzerland. It was initially developed while he was studying derivatives of lysergic acid, systematically reacting the carboxylic acid group with various reagents, to produce the corresponding amides, anhydrides, esters, etc. The reaction of diethylamine with this group produced what was then named LSD-25, however no real benefits of the compound were found and its study was discontinued.

Interest in the drug resumed 5 years later when Dr Hoffman synthesised LSD-25 again so that a sample could be given to the pharmocological department for further testing, when it was thought to be a potential treatment for schizophrenia. Although initial observations on the benefits were highly optimistic, empirical data developed subsequently proved much less promising.

Although LSD is relatively non-toxic and non-addictive, various governments around the world outlawed it after a number of fatal accidents were reported. Such accidents involved, for example, people under the influence of LSD jumping to their deaths off buildings believing they could fly. Research in the 1960's and 70's showed that there was also a considerable psychological risk with the drug and that high doses, especially in inappropriate settings, often caused panic reactions.
Scientific study finally ceased around mid 1970's as research funding declined, due to political reasons.

=How does LSD work?=

Although the mechanism by which LSD causes such profound affects on the human perception still hasn't been established
LSD has a very similar molecular structure to a hormone secreted in the brain called Serotoninwhich is why the body mistakes LSD for serotonin. LSD stimulates centers of the sympathetic nervous system in the midbrain by binding with the 5-HT receptors in the brain. Due to its higher affinity for these receptors serotonin is prevented from sending neural messages in the presence of LSD.

The common functional group found in Serotonin and LSD is the Indole ring (shown in blue below) that is characteristic of the tryptamine molecules and is also found in many other psychodelic compounds such as Psilocybin and Ergoline, which are alkaloids that occur naturally in fungi and plants.

[[Image:LSD Serotonin comparison.jpg|centre]]

The indole ring has a great influence on the electron density and dipole moment of both molecules and will

=Synthesis of LSD=

LSD is synthesised by the

File:LSD Serotonin comparison.jpg

2006-12-14T14:40:01Z

Sd204:

It:Lysergic Acid Diethylamide

2006-12-14T14:38:39Z

Sd204:

[[Image:LSD Serotonin comparison.jpg|centre]]

=Introduction=

First synthesised in 1938 Lysergic Acid Diethylamide is a pyschoactive compound more commonly known as the abbreviation LSD. It is a non-toxic, non-addictive drug that mimics serotonin in the brain.

=History=

LSD was first synthesised in 1938 by Dr. Alfred Hoffman, a Chemist in the pharmacological department in Sandoz Laboratories, Basel, Switzerland. It was initially developed while he was studying derivatives of lysergic acid, systematically reacting the carboxylic acid group with various reagents, to produce the corresponding amides, anhydrides, esters, etc. The reaction of diethylamine with this group produced what was then named LSD-25, however no real benefits of the compound were found and its study was discontinued.

Interest in the drug resumed 5 years later when Dr Hoffman synthesised LSD-25 again so that a sample could be given to the pharmocological department for further testing, when it was thought to be a potential treatment for schizophrenia. Although initial observations on the benefits were highly optimistic, empirical data developed subsequently proved much less promising.

Although LSD is relatively non-toxic and non-addictive, various governments around the world outlawed it after a number of fatal accidents were reported. Such accidents involved, for example, people under the influence of LSD jumping to their deaths off buildings believing they could fly. Research in the 1960's and 70's showed that there was also a considerable psychological risk with the drug and that high doses, especially in inappropriate settings, often caused panic reactions.
Scientific study finally ceased around mid 1970's as research funding declined, due to political reasons.

=How does LSD work?=

Although the mechanism by which LSD causes such profound affects on the human perception still hasn't been established
LSD has a very similar molecular structure to a hormone secreted in the brain called Serotoninwhich is why the body mistakes LSD for serotonin. LSD stimulates centers of the sympathetic nervous system in the midbrain by binding with the 5-HT receptors in the brain. Due to its higher affinity for these receptors serotonin is prevented from sending neural messages in the presence of LSD.

The common functional group found in Serotonin and LSD is the Indole ring (shown in blue below) that is characteristic of the tryptamine molecules and is also found in many other psychodelic compounds such as Psilocybin and Ergoline, which are alkaloids that occur naturally in fungi and plants.

The indole ring has a great influence on the electron density and dipole moment of both molecules and will

=Synthesis of LSD=

LSD is synthesised by the

2006-12-13T21:53:10Z

Sd204:

It:Lysergic Acid Diethylamide

2006-12-13T21:50:56Z

Sd204:

It:Lysergic Acid Diethylamide

2006-12-13T18:15:52Z

Sd204:

It:Lysergic Acid Diethylamide

2006-12-13T17:51:27Z

Sd204:

It:projects

2006-12-13T17:29:09Z

Sd204: /* Supplemental Project Page */

__FORCETOC__

'''''You MUST use the Edit buttons on the right to edit this content. Do NOT use the Edit button on the top of this page.'''''
== Sandbox (Play-Pen) ==

This is an area where you can play without worrying what you do. Enter it by pressing the [Edit] button '''on the right''' and '''not''' at the top. Go here for a [http://en.wikipedia.org/wiki/Wikipedia:Cheatsheet ''cheat sheet''] summary of how to create a Wiki page. It's a free-for-all in here! Learn how to use a Wiki by coming here! PS This is how to do Greek: Α, α, β Δ, δ
Try copying/pasting some of the [http://www.ch.ic.ac.uk/local/it/lab1.html examples in the course work] into this page. See the effect by selecting '''Show Preview'''. No not use '''Save Page''' so as to leave this area uncluttered for others.
----
{|
|NEW: This demonstrates the use of Jmol loading discrete molecule files (rather than having to paste them into the wiki page). Upload the molecule file, and invoke it as shown here. Use it for eg loading large proteins etc. Sorry about the delay in getting this working, but the cause was pretty unobvious.--[[User:Rzepa|Rzepa]] 16:07, 4 December 2006 (UTC)
<center><jmol>
<jmolApplet>
<title>Pentahelicene</title><color>yellow</color>
<uploadedFileContents>Pentahelicene.mol</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>console</script>
<text>open a console window</text>
</jmolButton>
</jmol></center>
-----
<center><jmol><jmolAppletButton><title>Show Pentahelicene in popup window</title><color>cyan</color>
<uploadedFileContents>Pentahelicene.mol</uploadedFileContents></jmolAppletButton>
</jmol></center>

== Main Project Page ==
'''Please do not edit this page itself'''. Click on one of the titles to start editing.
{| summary="CIT Project Titles" border="1"
! bgcolor="cyan" |Project<br /> Number
! bgcolor="cyan" |General Keywords
|-
| bgcolor="#CCFF00" |01
| bgcolor="#CCFF00" | [[it:Lignocaine|Lignocaine (used in dentistry as a "local")]]
|-
| bgcolor="#CCFF00" |02
| bgcolor="#66FF99" | [[it:Piperine|Piperine (active ingredient of both black and white pepper)]]
|-
| bgcolor="#CCFF00" |03
| bgcolor="#CCFF00" | [[it:Rapamycin|Rapamycin (prevents transplant rejection)]]
|-
| bgcolor="#CCFF00" |04
| bgcolor="#66FF99" | [[it:Gossypol|Gossypol (male birth control)]]
|-
| bgcolor="#CCFF00" |05
| bgcolor="#CCFF00" | [[it:Gentamycin|Gentamicin A (aminoglycoside antibiotic)]]
|-
| bgcolor="#CCFF00" |06
| bgcolor="#66FF99" | [[it:Herceptin|Herceptin (topical anticancer drug)]]
|-
| bgcolor="#CCFF00" |07
| bgcolor="#CCFF00" | [[it:Gingerone|Zingerone (the characteristic smell of ginger)]]
|-
| bgcolor="#CCFF00" |08
| bgcolor="#66FF99" | [[it:Sucralose|Sucralose (non-metabolizable sweetening agent)]]
|-
| bgcolor="#CCFF00" |09
| bgcolor="#CCFF00" | [[it:Bufotoxin|Bufotoxin (active component of the toad ''Bufo vulgaris'')]]
|-
| bgcolor="#CCFF00" |10
| bgcolor="#66FF99" | [[it:Roaccutane|Roaccutane (treatment for severe acne)]]
|-
| bgcolor="#CCFF00" |11
| bgcolor="#CCFF00" | [[it:Sibutramine|Sibutramine (appetite suppresor)]]
|-
| bgcolor="#CCFF00" |12
| bgcolor="#66FF99" | [[it:Anandamide|Anandamide (the "feel-good" factor in chocolate)]]
|-
| bgcolor="#CCFF00" |13
| bgcolor="#CCFF00" | [[it:h3nbh3|Ammonia-borane: H<sub>3</sub>N-BH<sub>3</sub> (Hydrogen storage molecule?)]]
|-
| bgcolor="#CCFF00" |14
| bgcolor="#66FF99" | [[it:Methoxsalen|Methoxsalen (Treatment of psoriasis)]]
|-
| bgcolor="#CCFF00" |15
| bgcolor="#CCFF00" | [[it:Hycocine|Hyoscine (From Mandrake and Witches Henbane, pre-med before surgery)]]
|-
| bgcolor="#CCFF00" |16
| bgcolor="#66FF99" | [[it:Capreomycin|Capreomycin (Drug-resistant TB)]]
|-
| bgcolor="#CCFF00" |17
| bgcolor="#CCFF00" | [[it:wilkinson|Wilkinson's catalyst]]
|-
| bgcolor="#CCFF00" |18
| bgcolor="#66FF99" | [[it:Jacobsen|Jacobsen's epoxidation catalyst]]
|-
| bgcolor="#CCFF00" |19
| bgcolor="#CCFF00" | [[it:Methylaluminoxane|Methylaluminoxane: MAO - hugely important ethylene polymerisation cocatalyst]]
|-
| bgcolor="#CCFF00" |20
| bgcolor="#66FF99" | [[it:Schwartz|Schwartz reagent for the hydrozirconation of alkenes and alkynes]]
|-
| bgcolor="#CCFF00" |21
| bgcolor="#CCFF00" | [[it:Schrock|Schrock metathesis catalyst]]
|-
| bgcolor="#CCFF00" |22
| bgcolor="#66FF99" | [[it:knots|Molecular-scale knots (nanoscale devices)]]
|-
|bgcolor="#CCFF00" |23
| bgcolor="#CCFF00" | [[it:Vioxx|Vioxx (treatment of osteoarthritis symptoms and pain)]]
|-
| bgcolor="#CCFF00" |24
| bgcolor="#66FF99" | [[it:Sertraline|Sertraline HCl (anti-depression)]]
|-
| bgcolor="#CCFF00" |25
| bgcolor="#CCFF00" | [[it:Ceftriaxone|Ceftriaxone (Gonorrhoea)]]
|-
| bgcolor="#CCFF00" |26
| bgcolor="#66FF99" | [[it:Zithromycin|Zithromycin (anti-infective)]]
|-
| bgcolor="#CCFF00" |27
| bgcolor="#CCFF00" | [[it:Lipitor|Lipitor (Cholesterol reducing agent)]]
|-
| bgcolor="#CCFF00" |28
| bgcolor="#66FF99" | [[it:Cyameluric Acid|Cyameluric acid (Linus Pauling's last idea!)]]
|}

== Supplemental Project Page ==

This area is for people who wish to create their own projects if none of the above appeal to them. Click on the '''Edit''' button to the right to open up an editable page,
then add an entry below as follows

*<nowiki> [[it:name_of_project|Descriptive name of intended project]]</nowiki>
*This will produce the effect: [[it:name_of_project|Descriptive name of intended project]]
----
*[[it:sitagliptin_page|Sitagliptin]]
*[[it:Retinal|Retinal, molecule of sight]]
*[[it:Tamoxifen|Tamoxifen, breast cancer treatment]]
*[[it:Morphine|Morphine, painkiller]]
*[[it:Pelargonidin|Pelargonidin, colouring in nature]]
*[[it:Propanil|Propanil, weedkiller]]
*[[it:Ranitidine|Ranitidine, antiulcerative]]
*[[it:chlorphentermine|chlorphentermine, anorectic]]
*[[it:Serotonin|Serotonin, The 'HAPPY' Drug]]
*[[it:Amphidinolide T1|Amphidinolide T1]]
*[[it:Rosiglitazone|Rosiglitazone, drug that is currently used to treat diabetes.]]
*[[it:Furosemide|Furosemide]]
*[[it:Tryptophan|Tryptophan]]
*[[it:methylpentynol|methylpentynol, tranquilliser.]]
*[[it:Ferrocene|Ferrocene]]
*[[it:Scopolamine|Scopolamine, the (Former) Truth Drug]]
*[[it:Camptothecin|Camptothecin,Anti-cancer agent ]]
*[[it:Salmeterol|Salmeterol, an agonist used to treat asthma]]
*[[it:Psilocin|Psilocin]]
*[[it:Epibatidine|Epibatidine]]
*[[it:Beta Carotene|Beta Carotene]]
*[[it:Thyroxine|Thyroxine, the Thyroid Hormone]]
*[[it:Tetrahydrocannabinol|Tetrahydrocannabinol]]
*[[it:Linalool|Linalool(A component of essential oil)]]
*[[it:Dihydroartemisinin| Dihydroartemisinin, An Active Anti-Malarial]]
*[[it:Acrolein|Acrolein]]
*[[it:Cinnamaldehyde|Cinnamaldehyde: The smell and taste in the spice cinnamon]]
*[[it:Melatonin|Melatonin: The All-Natural Nightcap]]
*[[it:Benzylpiperazine|Benzylpiperazine (BZP): Party Pills]]
*[[it:Vanillin|Vanillin, flavouring used in food]]
*[[it:Gingerol|Gingerol, precursor of Zingerone]]
*[[it:MSG|MSG; because everyone loves the flavour]]
*[[it:DDT|DDT, Pesticide]]
*[[it:Oseltamivir|Oseltamivir, neuraminidase inhibitor]]
*[[it:Caffeine|Caffeine]]
*[[it:Fullerene]]
*[[it:Histrionicotoxin]]
*[[it:limonene]]
*[[it:Capsanthin]]
*[[it:Safrole|Safrole: A formerly popular food and drinks additive]]
*[[it:Adenosine_Triphosphate|Adenosine Triphosphate (ATP), Energy source in muscles]]
*[[it:Aspartame|Aspartame: Artificial sweetener]]
*[[it:Astemizole|Astemizole:non-sedating anti-histamine]]
*[[it:Flucloxacillin|Flucloxacillin:antibiotic]]
*[[it:Quinine|Quinine: The Perfect Tonic for Any Fever]]
*[[it:Caramel|Caramel]]
*[[it:Azithromycin|Azithromycin]]
*[[it:Artemisinin|Artemisinin: An antimalarial drug]]
*[[it:Bradykinin|Bradykinin]]
*[[it:Carminic_acid|Carminic acid, Red colouring agent]]
*[[it:Oxytocin|Oxytocin: The Hormone of Love]]
*[[it:Carmoisine|Carmoisine]]
*[[it:Ziegler-Natta|Ziegler-Natta]]
*[[it:Cyclamate|Cyclamate]]
*[[it:Polyurethane|Polyurethane]]
*[[it:sexithiophene|sexithiophene]]
*[[it:Polydimethylsiloxane|Polydimethylsiloxane: Silicon-based organic polymer]]
*[[it:Lycopene|Lycopene: the red antioxidant molecule]]
*[[it:Crystal Meth|Crystal Meth]]
*[[it:Mustard Gas|Mustard Gas]]
*[[it:Saxitoxin|Shellfish Poison]]
*[[it:Luminol|Luminol: Chemiluminescence Reactions]]
*[[it:Tumor Necrosis Factor|Tumour Necrosis Factor]]
*[[it:Tamiflu|Tamiflu: Antiviral]]
*[[it:Warfarin|Warfarin: Blood thinner]]
*[[it:Vitamin C|Ascorbic acid: Vitamin C]]
*[[it:Hexahelicene|Hexahelicene]]
*[[it:Cocaine|Cocaine]]
*[[it:Eucalyptol|Eucalyptol: The main component of eucalyptus oil]]
*[[it:dichlorodifluromethane| Dichlorodifluromethane]]
*[[it:Theobromine| Theobromine: The key ingredient for chocolate!!]]
*[[it:Maraviroc|Maraviroc: A Potent CCR5 Antagonist for treatment of HIV]]
*[[it:Aspirin]]
*[[it:DEET|DEET]]
*[[it:PhenylButazone|PhenylButazone]]
*[[it:Epinephrine|Epinephrine]]
*[[it:Phenylmercury Acetate|Phenylmurcury Acetate]]
*[[it:Methyltestosterone|Methyltestosterone]]
*[[it:Carboplatin|Carboplatin]]
*[[it:Osmium Tetroxide|Osmium Tetroxide]]
*[[it:TNT|TNT]]
*[[it:Ethenzamide|Ethenzamide]]
*[[it:Cis-platin|Cis-platin]]
*[[it:arsine|arsine]]
*[[it:Vitamin E|Vitamin E: An Important Antioxidant]]
*[[it:Acrylamide|Acrylamide]]
*[[it:Lysergic Acid Diethylamide|Lysergic Acid Diethylamide]]

=== Wiki Utillities ===
Utilities have been written to help the conversion of material from HTML.
# [http://diberri.dyndns.org/wikipedia/html2wiki/ A HTML2Wiki Converter]
----

No wiki2html converter suitable for use has yet been identified.

=== Wiki Templates ===

[[Template:DOI]] and [[Template:Doi-inline]] are providea as (protected) templates for your use. Many other templates exist, often to be found on e.g. Wikipedia pages. You may decide one of these is of particular use, or of interest. If so, you can install it on the wiki here for you and others to use. Add below a line that looks like Template:Template-name, save, and click on the red text to create the new template. If you prefer the task of adding useful templates to that of adding information about molecules, then you will be given full credit for performing this valuable service for others! --Rzepa 14:41, 20 October 2006 (BST)

[[Template:Chem-Data]]

[[Template:Drug-Box]] - For pharmaceutical drugs just copy variable names and code generates tables

[[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]]