ChemWiki - User contributions [en]

It:Tetrahydrocannabinol

2006-12-03T11:33:34Z

Eklp05: /* Synthesis */

{| 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 ]]
|-
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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_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.

== 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

File:THC isomers.gif

2006-12-03T11:33:11Z

Eklp05:

It:Tetrahydrocannabinol

2006-12-03T11:28:43Z

Eklp05: /* Reference */

{| 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 ]]
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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_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:

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.

== 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

It:Tetrahydrocannabinol

2006-12-03T11:27:40Z

Eklp05: /* Effects in Human */

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! {{chembox header}} | tetrahydrocannabinol
|-
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</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:

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.

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

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

It:Tetrahydrocannabinol

2006-12-03T11:25:06Z

Eklp05: /* Isomerisation */

{| 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>
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title1
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</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:

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

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

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

It:Tetrahydrocannabinol

2006-12-03T10:42:06Z

Eklp05: /* Isomerisation */

{| 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>
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title1
title2
50 52 0 0 0 0 0 0 0 0999 V2000
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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.

== 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

File:Isomerisation 2.JPG

2006-12-03T10:38:33Z

Eklp05:

It:Tetrahydrocannabinol

2006-11-07T11:49:31Z

Eklp05:

== 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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<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>
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</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 effecs 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

2006-11-07T11:48:47Z

Eklp05:

It:Tetrahydrocannabinol

2006-11-07T11:47:18Z

Eklp05: /* Introduction */

File:THC.cdx

2006-11-07T11:38:57Z

Eklp05:

It:Tetrahydrocannabinol

2006-11-07T11:38:07Z

File:Thc.gif

2006-11-04T15:18:09Z

Eklp05:

It:Tetrahydrocannabinol

2006-11-04T15:17:05Z

Eklp05: /* Introduction */

== Tetrahydrocannabinol ==

== 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.
[[Image:Cannabis.jpg|thumb|right|200|Cannabis]]
{| border="1"
|+ The table's caption
! !! !!
|-
! 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.

It:Tetrahydrocannabinol

2006-11-04T15:08:14Z

Eklp05: /* Isomerisation */

== Tetrahydrocannabinol ==

== 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.
[[Image:Cannabis.jpg|thumb|centre|200|Cannabis]]

== 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.

It:Tetrahydrocannabinol

2006-11-04T15:07:23Z

Eklp05: /* Introduction */

== Tetrahydrocannabinol ==

== 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.
[[Image:Cannabis.jpg|thumb|centre|200|Cannabis]]

== 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|Description of image]]
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.

It:Tetrahydrocannabinol

2006-11-04T15:06:58Z

2006-10-26T11:18:42Z

Eklp05: /* Functions in human body */

== Introduction ==

Anandamide (which is also known as arachidonoylethanolamide) is a naturally occurring endogenous cannabinoid neurotransmitter that plays a role in pain relief, eating and sleeping patterns, depression, memory and fertility. It can be found in the organs of both humans and animals, in particular the brain. Anandamide is responsible for the narcotic effect of marijuana, which produces a natural high. It is also found in high concentrations in chocolate. It is thought that Anandamide attaches to the protein receptor THC (tetrahydrocannabinol) on the membrane of cells and triggers a reaction inside the cells that makes us feel high. Anandamide is broken down fast naturally by the body but chocolate contains two substances, N-oleoylethanolamine and N-linoleoylethaolamine, which inhibit the natural breakdown of anandamide, hence preserving the natural high.

Anandamide got its name from the "''Sanskrit''" word "ananda", which means "bliss" i.e. a state of extreme happiness and amide. It was first isolated and structurally discovered in 1992, by Lumír Ondřej Hanuš and William Anthony Devane in the Laboratory of Raphael Mechoulam, at the Hebrew University.

==

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Anandamide'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:anandamide-struct.gif]]
|-
!{{chembox header}}| General
|-
! Systematic Chemical name
| (5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)
icosa-5,8,11,14-tetraenamide
|-
!Synonyms
| Arachidonylethanolamide(AEA)
Arachidonic acid N-(hydroxyethyl)amide
|-
!Appearance
|Light yellow oil
|-
! Chemical formula
|C22H37NO2
|-
! Molecular Weight
| 347.54
|-
! CAS number
| 94421-68-8
|-
! Smile string
|CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(NCCO)=O
|-
!{{chembox header}}| Physical Properties
|-
!Solubility
|Soluble in ethanol
|-
!Density
|0.92g/mL (at 25oC)
|-
!{{chembox header}}|Safety
|-
!Precautions
|Keep away from skin and eyes
|-
|}

<jmol>
<jmolApplet>
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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>HEADER NONAME 19-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 19-Oct-06 0 NONE 4
ATOM 1 C 0 10.383 0.053 -2.692 0.00 0.00 C+0
ATOM 2 C 0 9.332 1.090 -2.291 0.00 0.00 C+0
ATOM 3 C 0 8.617 0.627 -1.021 0.00 0.00 C+0
ATOM 4 C 0 7.566 1.665 -0.620 0.00 0.00 C+0
ATOM 5 C 0 6.851 1.202 0.651 0.00 0.00 C+0
ATOM 6 C 0 5.816 2.224 1.045 0.00 0.00 C+0
ATOM 7 C 0 4.578 1.853 1.262 0.00 0.00 C+0
ATOM 8 C 0 4.223 0.388 1.280 0.00 0.00 C+0
ATOM 9 C 0 3.509 0.060 2.566 0.00 0.00 C+0
ATOM 10 C 0 2.354 -0.557 2.535 0.00 0.00 C+0
ATOM 11 C 0 1.817 -1.084 1.229 0.00 0.00 C+0
ATOM 12 C 0 1.480 -2.546 1.379 0.00 0.00 C+0
ATOM 13 C 0 0.288 -2.980 1.053 0.00 0.00 C+0
ATOM 14 C 0 -0.688 -2.059 0.368 0.00 0.00 C+0
ATOM 15 C 0 -1.192 -2.711 -0.894 0.00 0.00 C+0
ATOM 16 C 0 -2.480 -2.834 -1.099 0.00 0.00 C+0
ATOM 17 C 0 -3.458 -2.180 -0.157 0.00 0.00 C+0
ATOM 18 C 0 -4.447 -1.330 -0.958 0.00 0.00 C+0
ATOM 19 C 0 -5.440 -0.666 -0.002 0.00 0.00 C+0
ATOM 20 C 0 -6.413 0.171 -0.791 0.00 0.00 C+0
ATOM 21 N 0 -7.385 0.854 -0.154 0.00 0.00 N+0
ATOM 22 C 0 -8.332 1.668 -0.921 0.00 0.00 C+0
ATOM 23 C 0 -9.325 2.332 0.036 0.00 0.00 C+0
ATOM 24 O 0 -8.631 3.253 0.879 0.00 0.00 O+0
ATOM 25 O 0 -6.322 0.231 -1.999 0.00 0.00 O+0
ATOM 26 H 0 11.109 -0.059 -1.886 0.00 0.00 H+0
ATOM 27 H 0 9.896 -0.905 -2.877 0.00 0.00 H+0
ATOM 28 H 0 10.893 0.382 -3.597 0.00 0.00 H+0
ATOM 29 H 0 9.819 2.047 -2.106 0.00 0.00 H+0
ATOM 30 H 0 8.606 1.201 -3.097 0.00 0.00 H+0
ATOM 31 H 0 8.130 -0.330 -1.206 0.00 0.00 H+0
ATOM 32 H 0 9.343 0.516 -0.215 0.00 0.00 H+0
ATOM 33 H 0 8.053 2.622 -0.435 0.00 0.00 H+0
ATOM 34 H 0 6.840 1.776 -1.426 0.00 0.00 H+0
ATOM 35 H 0 6.364 0.245 0.466 0.00 0.00 H+0
ATOM 36 H 0 7.577 1.091 1.456 0.00 0.00 H+0
ATOM 37 H 0 6.094 3.262 1.148 0.00 0.00 H+0
ATOM 38 H 0 3.813 2.596 1.429 0.00 0.00 H+0
ATOM 39 H 0 3.573 0.162 0.436 0.00 0.00 H+0
ATOM 40 H 0 5.133 -0.207 1.208 0.00 0.00 H+0
ATOM 41 H 0 3.950 0.334 3.514 0.00 0.00 H+0
ATOM 42 H 0 1.786 -0.687 3.444 0.00 0.00 H+0
ATOM 43 H 0 0.918 -0.531 0.956 0.00 0.00 H+0
ATOM 44 H 0 2.570 -0.962 0.451 0.00 0.00 H+0
ATOM 45 H 0 2.223 -3.235 1.754 0.00 0.00 H+0
ATOM 46 H 0 0.005 -3.998 1.277 0.00 0.00 H+0
ATOM 47 H 0 -1.528 -1.859 1.033 0.00 0.00 H+0
ATOM 48 H 0 -0.190 -1.122 0.119 0.00 0.00 H+0
ATOM 49 H 0 -0.491 -3.078 -1.630 0.00 0.00 H+0
ATOM 50 H 0 -2.841 -3.403 -1.943 0.00 0.00 H+0
ATOM 51 H 0 -4.002 -2.948 0.393 0.00 0.00 H+0
ATOM 52 H 0 -2.918 -1.544 0.544 0.00 0.00 H+0
ATOM 53 H 0 -3.903 -0.562 -1.508 0.00 0.00 H+0
ATOM 54 H 0 -4.987 -1.965 -1.660 0.00 0.00 H+0
ATOM 55 H 0 -5.983 -1.434 0.548 0.00 0.00 H+0
ATOM 56 H 0 -4.899 -0.030 0.700 0.00 0.00 H+0
ATOM 57 H 0 -7.459 0.806 0.812 0.00 0.00 H+0
ATOM 58 H 0 -7.788 2.436 -1.471 0.00 0.00 H+0
ATOM 59 H 0 -8.872 1.032 -1.622 0.00 0.00 H+0
ATOM 60 H 0 -10.082 2.865 -0.540 0.00 0.00 H+0
ATOM 61 H 0 -9.805 1.569 0.648 0.00 0.00 H+0
ATOM 62 H 0 -9.291 3.648 1.464 0.00 0.00 H+0
CONECT 1 2 26 27 28 NONE 67
CONECT 2 1 3 29 30 NONE 68
CONECT 3 2 4 31 32 NONE 69
CONECT 4 3 5 33 34 NONE 70
CONECT 5 4 6 35 36 NONE 71
CONECT 6 5 7 37 0 NONE 72
CONECT 7 6 8 38 0 NONE 73
CONECT 8 7 9 39 40 NONE 74
CONECT 9 8 10 41 0 NONE 75
CONECT 10 9 11 42 0 NONE 76
CONECT 11 10 12 43 44 NONE 77
CONECT 12 11 13 45 0 NONE 78
CONECT 13 12 14 46 0 NONE 79
CONECT 14 13 15 47 48 NONE 80
CONECT 15 14 16 49 0 NONE 81
CONECT 16 15 17 50 0 NONE 82
CONECT 17 16 18 51 52 NONE 83
CONECT 18 17 19 53 54 NONE 84
CONECT 19 18 20 55 56 NONE 85
CONECT 20 19 21 25 0 NONE 86
CONECT 21 20 22 57 0 NONE 87
CONECT 22 21 23 58 59 NONE 88
CONECT 23 22 24 60 61 NONE 89
CONECT 24 23 62 0 0 NONE 90
CONECT 25 20 0 0 0 NONE 91
END NONE 92
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[[User:Smbc05|Smbc05]] 14:53, 20 October 2006 (BST)

==Structure==
Anandamide is fat-soluble due to its long hydrocarbon tail. It can pass through the hydrocarbon-rich curtain which isolates the brain from the bloodstream easily. Unlike THC, anandamide breaks down very quickly in the body; which is also the reason why anandamide does not produce an everlasting natural 'high'. [http://antoine.frostburg.edu/chem/senese/101/features/anandamide.shtml]

With the long unsaturated hydrocarbon chain, anandamide possesses a very flexible structure of 16 torsion angles allowing hundreds of conformers. However, researchs showed that the molecule lacks internal folding of the aliphatic chain and its structure is somewhere between linear and U-shaped. This may explain the function of anandamide as a ligand for cannabinoid receptors such as CB1 and CB2.
{|
|-
| align="center" colspan="2" bgcolor="#ffffff" |[[Image: Prefered_conformation_of_anandamide.jpg]] ||Summary of NMR-based structural calculation of AEA conformations in chloroform solution, 32 sets of conformational families were generated and grouped together with the cutoff energy of 36 kcal/mol, showing that AEA mainly assumes 36% of the conformers in extended pseudo helical shapes (A in a side view and a top view), 17% in the twisted “U”-shapes” (B), 17% in the “L” shapes, 6% in “Γ” shapes, and 24% in “C” shapes (E). The energy differences among these conformers are about 0.2~2.5 kcal/mol.
|-
|}
==Functions in human body==
Anandamide has certain functions in our body, and it is not as simple as producing happiness. Anandamide is synthesized in those areas in the brain that are important in memory and higher thought processes, as well as areas which control movements. Anandamide or N-arachidonoylethanolamine (AnNH) plays important roles in the nervous and immune system. Anandamide receptors were originally found due to sensitivity to Δ9-tetrahydrocannabinol (Δ9-THC), which is a component of marijuana. The chemical affects the short term memory and some human behaviour like sleeping and eating pattern and also in pain relieves. It was also found out that anadamide plays an important role in implantation of the embryo stage; hence Δ9-THC might obstruct the early stages of pregnancy.

Other than the brain, anandamide can also be found in other parts of the body, such as in the uterus. In fact, the highest concentration of anandamide found in our body is not the brain, but in the uterus just before the implantation of the embryo; and its concentration varies with the receptivity of the uterus. Anandamide acts as a chemical messenger between the embryo and uterus during the implantation of the embryo in the uterine wall, which means one of the first communications that occurs between the mother and child is carried out by anandamide. [http://antoine.frostburg.edu/chem/senese/101/features/anandamide.shtml]

'''The ligand binds to two receptors'''

Cannabinoid CB1 receptors (G-protein-coupled receptors) are found on presynaptic membranes in the brain in the nervous system. The effects are:

• Induce inhibition of forskolin-induced cAMP accumulation
• Inhibition of N-type Ca+ channels
• Activation of mitogen-activated protein kinase signal transduction pathway
• Increase in protein tyrosine phosphorylation

Cannabinoid CB2 receptors are present not in the brain in the periphery but also on cells of the immune system. The effects are:

• Inhibition of aldenylate cyclase
• Activation of the mitogen- activated proeteinkinase signaling

[http://www.jbc.org/cgi/reprint/273/48/32332.pdf]

==Anandamide and Chocolate==
In 1996, Daniele Piomelli and co-workers at the Neurosciences Institute in San Diego discovered three other compounds in dark chocolate which were very similar to anandamide. Other compounds such as N-acylethanolamines were also found to block the breakdown of anandamide. Due to the inhibitation of the natural breakdown of anadamide, it may stick around in our body longer, making us feel good longer when we eat chocolate. Hence, the pleasure of chocolate is a result of the total effect of anandamide and anandamide-preserving N-acylethanolamines. [http://www.exploratorium.edu/exploring/exploring_chocolate/choc_8.html]

==Future use==
A new family of therapeutic drugs may be developed from the discovery of Anandamide.

==Reference==
http://en.wikipedia.org/wiki/Anandamide

http://antoine.frostburg.edu/chem/senese/101/features/anandamide.shtml

http://www.exploratorium.edu/exploring/exploring_chocolate/choc_8.html

Sigma-Aldrich Online MSDS: http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/A0580

C. Bonechi, A. B. V. B. M. F. A. D. C. R. (2001). Conformational analysis of N-arachidonylethanolamide (anandamide) using nuclear magnetic resonance and theoretical calculations. Magn. Res. Chem. 39: 432-437.

Chen, J.-Z., X.-W. Han, et al. (2005). "Preferred conformations of endogenous cannabinoid ligand anandamide." Life Sciences 76(18): 2053-2069.