ChemWiki - User contributions [en]

It07:Astaxanthin

2007-12-05T14:17:48Z

Afk06: multiple references

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Astaxanthin 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Astaxanthin.png|200px|{{PAGENAME}}]] 
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 6-hydroxy-3-[(1E,3E,5E,7E,9E,11E,
13E,15E,17E)-18-(4-hydroxy-2,6,6-
trimethyl-3-oxo-1-cyclohexenyl)-
3,7,12,16-tetramethyloctadeca-1,3,
5,7,9,11,13,15,17-nonaenyl]-2,4,
4-trimethylcyclohex-2-en-1-one

|-
| Other names
| Astaxanthin
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C<sub>40</sub>H<sub>52</sub>O<sub>4</sub>
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| C\C(=C\C=C\C=C(\C)/C=C\C=C
(\C)/C=C\C1=C(C)C(=O)C(O)CC1
(C)C)/C=C\C=C(\C)/C=C \C1=C
(C)C(=O)C(O)CC1(C)C
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 596.839 g/mol
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 472-61-7
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| {{{Density}}} g/cm³ 
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| {{{Mp}}} K 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| {{{Bp}}} K
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
! {{chembox header}} | Structure
|-
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] 
| {{{Mol_Shape}}} 
|-
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination<br />geometry] 
| {{{Coordination}}} 
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| {{{Crystal_Structure}}} 
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| {{{DM}}} [[Debye|D]]
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-

== Astaxanthin ==

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'''(!) THIS ARTICLE IS NOT A SUBSTITUTE FOR A MEDICAL ADVICE. IF YOU HAVE A SPECIFIC HEALTH CONCERN PLEASE CONSULT A QUALIFIED DOCTOR OR A NUTRITIONIST.'''

Astaxanthin is a powerful antioxidant which is responsible for the red colour of salmon. Astaxanthin is said to be up to 500 times as strong as vitamin E (a common antioxidant found in vegetable oils). It is sometimes referred to as a “super-oxidant” or vitamin X.
The content of astaxanthin in wild (Pacific) salmon is typically between 14 and 40mg per kg whereas that of farmed Atlantic salmon is between 4 and 10mg per kg. Astaxanthin is also found in trout, crustaceans, and red yeast. Those seafood, however, do not synthesise astaxanthin within their own bodies – rather, they obtain them from planktons that they feed on (astaxanthin is commercially produced by extraction from microalgae).

== Chemical Properties ==

Molecular Weight: 596.839 <ref>http://chembank.broad.harvard.edu/</ref>
Melting Point: 210 - 215°C.

Astaxanthin is not soluble at room temperature but is lipophilic (fat-soluble) and is classified as a cartenoid, along with beta-carotene and lutein. More specifically, it belongs to a class of xantophyll cartenoids.

[[Image:astax.gif]] <ref name="ref2">http://www.astaxanthin.org</ref>

[[Image:beta_carotene.gif]]<ref name="ref2"/>

[[Image:lutein.gif]]<ref name="ref2"/>

Astaxanthin has a structure which is similar to that of beta-carotene and lutein, but astaxanthin also contain carbonyl and hydroxyl groups which cause greater polarities and are responsible for the different chemical properties: carbonyl groups are electron withdrawing by resonance and can thus create sites on the carbon chain which are susceptible to nucleophilic attacks.

There are two chiral centres on an astaxanthin molecule, which are labelled 3 and 3’ (the third atoms from the carbonyl oxygen of their respective six membered rings) and so there are three different enantiomers of this compound, namely 3S3’S, 3R3’S, 3R3’R. 3R3’S is not commonly seen in the nature.
Due to the nine carbon-carbon double bonds present on the carbon chain between the two carbon rings, geometrical isomerism is shown as well. At each site of double bonds, there could be an E or Z conformation (respectively trans or cis in the old fashioned way of speech). In naturally occurring astaxanthin molecules, Z isomerism has been observed at the carbon atoms 9, 13 and 15, both singly and in combination: 9Z, 13Z, 15Z,
9Z-13Z, 9Z-15Z, 13Z-15Z and 9Z-13Z-15Z. However, all-E is generally the most abundant form in nature and is the most thermodynamically stable since the repulsion between the electron densities is at minimum.

Both the hydroxyl (OH) groups could be esterified in the presence of an acid (for instance a fatty acid): hence we could have an unesterified, mono-esterified and diesterified forms of astaxanthin. It turns out that esterification of the hydroxyl groups further increases the hydrophobicity of the molecule. The unesterified forms of this compound is highly unstable and so the ones found in nature are often esterified or bound to protein molecules.

== Extraction ==

Although astaxanthin is found in many algae, the green algae Haematococcus pluvialis is mainly used as a commercial source since it has the ability to synthesise and store a greater amount of this pigment than others. It has been found that limiting the growth of H. pluvialis aided the development of further astaxanthin.

== Oxygen Quenching ==

Astaxanthin, when it is in crystalline form, is so susceptible to oxidation that it would only require a trace of oxygen in order to decompose.
An oxygen molecule is reactive due to its two free radicals (which are believed to be the cause of cancer). Astaxanthin (and other cartenoids) limit the activity of these oxygen molecules by taking away their energy and absorbing it themselves. They then release that energy in the form of heat, relaxing to the ground states.

The quenching constant of astaxanthin is reported to be 2.4 × 1010 Lmol-1sec-1 whereas that of beta-carotene is 1.4 × 1010 Lmol-1sec-1.

== Risks ==

Negative side effects of astaxanthin are not currently known.

== References ==
<references/>

Choi, Y. E ; Yun, Y.-S.; Park, J. M.
Biotechnol. Prog.; (Article); 2002; 18(6); 1170-1175.

Wu, T.-H.; Liao, J.-H.; Hou, W.-C.; Huang, F.-Y.; Maher, T. J.; Hu, C.-C.
J. Agric. Food Chem.; (Article); 2006; 54(6); 2418-2423.

Hussein, G.; Sankawa, U.; Goto, H.; Matsumoto, K.; Watanabe, H.
J. Nat. Prod.; (Review); 2006; 69(3); 443-449

2007-11-20T17:45:15Z

Afk06: /* Anandamide */

= Anandamide =

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 250px"
! {{chembox header}} | '''Anandamide''' 
|-
| align="center" colspan="2" bgcolor="#ffffff" | <jmol>
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<inlineContents>HEADER NONAME 18-Oct-07 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 18-Oct-07 0 NONE 4
ATOM 1 C 0 12.110 -0.512 -0.273 0.00 0.00 C+0
ATOM 2 C 0 11.045 -0.120 0.753 0.00 0.00 C+0
ATOM 3 C 0 9.873 0.557 0.039 0.00 0.00 C+0
ATOM 4 C 0 8.808 0.950 1.064 0.00 0.00 C+0
ATOM 5 C 0 7.654 1.617 0.360 0.00 0.00 C+0
ATOM 6 C 0 6.438 1.155 0.515 0.00 0.00 C+0
ATOM 7 C 0 5.284 1.822 -0.189 0.00 0.00 C+0
ATOM 8 C 0 4.537 0.801 -1.008 0.00 0.00 C+0
ATOM 9 C 0 3.250 0.636 -0.834 0.00 0.00 C+0
ATOM 10 C 0 2.503 -0.385 -1.652 0.00 0.00 C+0
ATOM 11 C 0 1.774 -1.331 -0.733 0.00 0.00 C+0
ATOM 12 C 0 0.483 -1.508 -0.864 0.00 0.00 C+0
ATOM 13 C 0 -0.245 -2.454 0.055 0.00 0.00 C+0
ATOM 14 C 0 -1.384 -1.728 0.724 0.00 0.00 C+0
ATOM 15 C 0 -2.603 -2.200 0.636 0.00 0.00 C+0
ATOM 16 C 0 -3.742 -1.474 1.304 0.00 0.00 C+0
ATOM 17 C 0 -4.829 -1.171 0.272 0.00 0.00 C+0
ATOM 18 C 0 -5.985 -0.433 0.950 0.00 0.00 C+0
ATOM 19 C 0 -7.056 -0.135 -0.067 0.00 0.00 C+0
ATOM 20 O 0 -6.909 -0.478 -1.221 0.00 0.00 O+0
ATOM 21 N 0 -8.178 0.514 0.306 0.00 0.00 N+0
ATOM 22 C 0 -9.219 0.804 -0.683 0.00 0.00 C+0
ATOM 23 C 0 -10.375 1.541 -0.004 0.00 0.00 C+0
ATOM 24 O 0 -9.923 2.817 0.454 0.00 0.00 O+0
ATOM 25 H 0 12.944 -0.994 0.237 0.00 0.00 H+0
ATOM 26 H 0 11.679 -1.202 -0.998 0.00 0.00 H+0
ATOM 27 H 0 12.465 0.381 -0.787 0.00 0.00 H+0
ATOM 28 H 0 10.689 -1.012 1.268 0.00 0.00 H+0
ATOM 29 H 0 11.475 0.571 1.479 0.00 0.00 H+0
ATOM 30 H 0 10.229 1.450 -0.476 0.00 0.00 H+0
ATOM 31 H 0 9.442 -0.133 -0.687 0.00 0.00 H+0
ATOM 32 H 0 8.453 0.057 1.579 0.00 0.00 H+0
ATOM 33 H 0 9.239 1.640 1.790 0.00 0.00 H+0
ATOM 34 H 0 7.830 2.475 -0.271 0.00 0.00 H+0
ATOM 35 H 0 6.262 0.297 1.146 0.00 0.00 H+0
ATOM 36 H 0 4.612 2.258 0.549 0.00 0.00 H+0
ATOM 37 H 0 5.663 2.606 -0.844 0.00 0.00 H+0
ATOM 38 H 0 5.064 0.204 -1.738 0.00 0.00 H+0
ATOM 39 H 0 2.723 1.233 -0.103 0.00 0.00 H+0
ATOM 40 H 0 1.784 0.121 -2.297 0.00 0.00 H+0
ATOM 41 H 0 3.208 -0.945 -2.266 0.00 0.00 H+0
ATOM 42 H 0 2.317 -1.862 0.035 0.00 0.00 H+0
ATOM 43 H 0 -0.059 -0.977 -1.632 0.00 0.00 H+0
ATOM 44 H 0 -0.637 -3.292 -0.522 0.00 0.00 H+0
ATOM 45 H 0 0.444 -2.826 0.814 0.00 0.00 H+0
ATOM 46 H 0 -1.195 -0.819 1.275 0.00 0.00 H+0
ATOM 47 H 0 -2.791 -3.110 0.085 0.00 0.00 H+0
ATOM 48 H 0 -4.156 -2.098 2.096 0.00 0.00 H+0
ATOM 49 H 0 -3.376 -0.540 1.732 0.00 0.00 H+0
ATOM 50 H 0 -4.415 -0.546 -0.520 0.00 0.00 H+0
ATOM 51 H 0 -5.195 -2.104 -0.156 0.00 0.00 H+0
ATOM 52 H 0 -6.400 -1.058 1.742 0.00 0.00 H+0
ATOM 53 H 0 -5.620 0.500 1.378 0.00 0.00 H+0
ATOM 54 H 0 -8.295 0.788 1.229 0.00 0.00 H+0
ATOM 55 H 0 -8.804 1.428 -1.474 0.00 0.00 H+0
ATOM 56 H 0 -9.584 -0.130 -1.110 0.00 0.00 H+0
ATOM 57 H 0 -11.187 1.679 -0.718 0.00 0.00 H+0
ATOM 58 H 0 -10.732 0.956 0.843 0.00 0.00 H+0
ATOM 59 H 0 -10.680 3.247 0.875 0.00 0.00 H+0
CONECT 1 2 25 26 27 NONE 64
CONECT 2 1 3 28 29 NONE 65
CONECT 3 2 4 30 31 NONE 66
CONECT 4 3 5 32 33 NONE 67
CONECT 5 4 6 34 0 NONE 68
CONECT 6 5 7 35 0 NONE 69
CONECT 7 6 8 36 37 NONE 70
CONECT 8 7 9 38 0 NONE 71
CONECT 9 8 10 39 0 NONE 72
CONECT 10 9 11 40 41 NONE 73
CONECT 11 10 12 42 0 NONE 74
CONECT 12 11 13 43 0 NONE 75
CONECT 13 12 14 44 45 NONE 76
CONECT 14 13 15 46 0 NONE 77
CONECT 15 14 16 47 0 NONE 78
CONECT 16 15 17 48 49 NONE 79
CONECT 17 16 18 50 51 NONE 80
CONECT 18 17 19 52 53 NONE 81
CONECT 19 18 20 21 0 NONE 82
CONECT 20 19 0 0 0 NONE 83
CONECT 21 19 22 54 0 NONE 84
CONECT 22 21 23 55 56 NONE 85
CONECT 23 22 24 57 58 NONE 86
CONECT 24 23 59 0 0 NONE 87
END NONE 88
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[http://www.gynx.org/imperial/anandamide.pdb Anandamide]
A 3D representation of the 'I' shape conformer.

|-
! {{chembox header}} | Structure
|-
|align="center" colspan="1" |
|[[Image:Anandamide_1.png|thumb|center|Anandamide]]


|-
! {{chembox header}} | Identifiers
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| Eicosa-5,8,11,14-tetraenoic acid (2-hydroxy-ethyl)-amide
(5Z, 8Z, 11Z, 14Z)-N-(2-hydroxyethyl)-5,8,11,14-eicosatetraenamide

|-
| Other names
| Anandamide<br>Arachidonoylethanolamide (AEA)
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C<sub>22</sub>H<sub>37</sub>NO<sub>2</sub>

|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CCCCC\C=C/C\C=C/C\C=C
/C\C=C/CCCC(NCCO)=O
|-

| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 94421-68-8
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 347.54 gmol<sup>-1</sup>
|-
| Appearance
| Light yellow oil
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| 0.92g/ml
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) (soluble in ethanol)
|-



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

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

'''Anandamide''' (a name deriving from the Sanskrit word "ananda," meaning bliss), also known as '''arachidonoylethanolamide (AEA)''', is a neurotransmitter present in animal and human organs, commonly in the brain. More specifically, anandamide is a cannabanoid; it binds to the cannabanoid receptor in mammalian brains, the same receptor that the psychoactive ingredient in marijuana targets.

== Biosynthesis of Anandamide ==

There are two ways to synthesise anandamide. One is through the formation from free arachidonic acid and ethanolamine; the other is the formation from N-arachidonoyl phosphatidylethanolamine (PE), through the action of an enzyme called phosphodiesterase. These pathways, however, do not appear to generate a large amount of anandamide under physiological conditions. The generation of anandamide from free arachidonic acid and ethanolamine is catalyzed by a degrading enzyme anandamide amidohydrolase or a fatty acid amide hydrolase working in reverse. This requires large amounts of substrates. For the second pathway, arachidonic acids esterified at the 1-position of glycerophospholipids, which are mostly esterified at the 2-position, are used for the formation of N-arachidonoyl PE, a stored precursor form of anandamide. The reaction schemes of the second pathway are shown in the diagrams below:
[[Image:formation_1.gif]]

''Diagram 1:'' The synthesis of N-acyl PE through a series of reactions from Ca2+ ions and the enzyme transacylase.
[[Image:formation_2.gif]]

''Diagram 2:'' The second step of the biosynthesis involves the hydrolysis of the N-acyl-phosphatidylethanolamine by the enzyme phosphodiesterase.

[http://www.gynx.org/imperial/anandamide.pdb Anandamide]

== Possible Conformers ==

[[Image:Anandamide_1.png|center|Anandamide]]
[[Image:choco.gif|center|Anandamide]]
[[Image:structureanadamide.jpg|center|Anandamide]]

<center>[http://www.gynx.org/imperial/anandamide.svg Anandamide SVG (maybe)]</center>


==''' References '''==
1. T. Sugiura, Y. Kobayashi, S. Oka and K. Waku, Prostaglandins Leukotrienes and Essential Fatty Acids, 2002, 66, 173-192.

2. H. H. O. Schmid, Chemistry and Physics of Lipids, 2000, 108, 71-87.

3. M. J. O'Neil, The Merck Index Thirteenth Edition, 2001, p105

2007-11-20T17:19:46Z

Afk06: /* Anandamide */

= Anandamide =

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 250px"
! {{chembox header}} | {{Anandamide}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>250</size>
<color>black</color>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 18-Oct-07 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 18-Oct-07 0 NONE 4
ATOM 1 C 0 12.110 -0.512 -0.273 0.00 0.00 C+0
ATOM 2 C 0 11.045 -0.120 0.753 0.00 0.00 C+0
ATOM 3 C 0 9.873 0.557 0.039 0.00 0.00 C+0
ATOM 4 C 0 8.808 0.950 1.064 0.00 0.00 C+0
ATOM 5 C 0 7.654 1.617 0.360 0.00 0.00 C+0
ATOM 6 C 0 6.438 1.155 0.515 0.00 0.00 C+0
ATOM 7 C 0 5.284 1.822 -0.189 0.00 0.00 C+0
ATOM 8 C 0 4.537 0.801 -1.008 0.00 0.00 C+0
ATOM 9 C 0 3.250 0.636 -0.834 0.00 0.00 C+0
ATOM 10 C 0 2.503 -0.385 -1.652 0.00 0.00 C+0
ATOM 11 C 0 1.774 -1.331 -0.733 0.00 0.00 C+0
ATOM 12 C 0 0.483 -1.508 -0.864 0.00 0.00 C+0
ATOM 13 C 0 -0.245 -2.454 0.055 0.00 0.00 C+0
ATOM 14 C 0 -1.384 -1.728 0.724 0.00 0.00 C+0
ATOM 15 C 0 -2.603 -2.200 0.636 0.00 0.00 C+0
ATOM 16 C 0 -3.742 -1.474 1.304 0.00 0.00 C+0
ATOM 17 C 0 -4.829 -1.171 0.272 0.00 0.00 C+0
ATOM 18 C 0 -5.985 -0.433 0.950 0.00 0.00 C+0
ATOM 19 C 0 -7.056 -0.135 -0.067 0.00 0.00 C+0
ATOM 20 O 0 -6.909 -0.478 -1.221 0.00 0.00 O+0
ATOM 21 N 0 -8.178 0.514 0.306 0.00 0.00 N+0
ATOM 22 C 0 -9.219 0.804 -0.683 0.00 0.00 C+0
ATOM 23 C 0 -10.375 1.541 -0.004 0.00 0.00 C+0
ATOM 24 O 0 -9.923 2.817 0.454 0.00 0.00 O+0
ATOM 25 H 0 12.944 -0.994 0.237 0.00 0.00 H+0
ATOM 26 H 0 11.679 -1.202 -0.998 0.00 0.00 H+0
ATOM 27 H 0 12.465 0.381 -0.787 0.00 0.00 H+0
ATOM 28 H 0 10.689 -1.012 1.268 0.00 0.00 H+0
ATOM 29 H 0 11.475 0.571 1.479 0.00 0.00 H+0
ATOM 30 H 0 10.229 1.450 -0.476 0.00 0.00 H+0
ATOM 31 H 0 9.442 -0.133 -0.687 0.00 0.00 H+0
ATOM 32 H 0 8.453 0.057 1.579 0.00 0.00 H+0
ATOM 33 H 0 9.239 1.640 1.790 0.00 0.00 H+0
ATOM 34 H 0 7.830 2.475 -0.271 0.00 0.00 H+0
ATOM 35 H 0 6.262 0.297 1.146 0.00 0.00 H+0
ATOM 36 H 0 4.612 2.258 0.549 0.00 0.00 H+0
ATOM 37 H 0 5.663 2.606 -0.844 0.00 0.00 H+0
ATOM 38 H 0 5.064 0.204 -1.738 0.00 0.00 H+0
ATOM 39 H 0 2.723 1.233 -0.103 0.00 0.00 H+0
ATOM 40 H 0 1.784 0.121 -2.297 0.00 0.00 H+0
ATOM 41 H 0 3.208 -0.945 -2.266 0.00 0.00 H+0
ATOM 42 H 0 2.317 -1.862 0.035 0.00 0.00 H+0
ATOM 43 H 0 -0.059 -0.977 -1.632 0.00 0.00 H+0
ATOM 44 H 0 -0.637 -3.292 -0.522 0.00 0.00 H+0
ATOM 45 H 0 0.444 -2.826 0.814 0.00 0.00 H+0
ATOM 46 H 0 -1.195 -0.819 1.275 0.00 0.00 H+0
ATOM 47 H 0 -2.791 -3.110 0.085 0.00 0.00 H+0
ATOM 48 H 0 -4.156 -2.098 2.096 0.00 0.00 H+0
ATOM 49 H 0 -3.376 -0.540 1.732 0.00 0.00 H+0
ATOM 50 H 0 -4.415 -0.546 -0.520 0.00 0.00 H+0
ATOM 51 H 0 -5.195 -2.104 -0.156 0.00 0.00 H+0
ATOM 52 H 0 -6.400 -1.058 1.742 0.00 0.00 H+0
ATOM 53 H 0 -5.620 0.500 1.378 0.00 0.00 H+0
ATOM 54 H 0 -8.295 0.788 1.229 0.00 0.00 H+0
ATOM 55 H 0 -8.804 1.428 -1.474 0.00 0.00 H+0
ATOM 56 H 0 -9.584 -0.130 -1.110 0.00 0.00 H+0
ATOM 57 H 0 -11.187 1.679 -0.718 0.00 0.00 H+0
ATOM 58 H 0 -10.732 0.956 0.843 0.00 0.00 H+0
ATOM 59 H 0 -10.680 3.247 0.875 0.00 0.00 H+0
CONECT 1 2 25 26 27 NONE 64
CONECT 2 1 3 28 29 NONE 65
CONECT 3 2 4 30 31 NONE 66
CONECT 4 3 5 32 33 NONE 67
CONECT 5 4 6 34 0 NONE 68
CONECT 6 5 7 35 0 NONE 69
CONECT 7 6 8 36 37 NONE 70
CONECT 8 7 9 38 0 NONE 71
CONECT 9 8 10 39 0 NONE 72
CONECT 10 9 11 40 41 NONE 73
CONECT 11 10 12 42 0 NONE 74
CONECT 12 11 13 43 0 NONE 75
CONECT 13 12 14 44 45 NONE 76
CONECT 14 13 15 46 0 NONE 77
CONECT 15 14 16 47 0 NONE 78
CONECT 16 15 17 48 49 NONE 79
CONECT 17 16 18 50 51 NONE 80
CONECT 18 17 19 52 53 NONE 81
CONECT 19 18 20 21 0 NONE 82
CONECT 20 19 0 0 0 NONE 83
CONECT 21 19 22 54 0 NONE 84
CONECT 22 21 23 55 56 NONE 85
CONECT 23 22 24 57 58 NONE 86
CONECT 24 23 59 0 0 NONE 87
END NONE 88
</inlineContents>
</jmolApplet>
</jmol>
[http://www.gynx.org/imperial/anandamide.pdb Anandamide]
This 3D representation is of the 'I' shape conformer.

|-
! {{chembox header}} | Structure
|-
|align="center" colspan="1" |
|[[Image:Anandamide_1.png|thumb|center|Anandamide]]


|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| Eicosa-5,8,11,14-tetraenoic acid (2-hydroxy-ethyl)-amide
(5Z, 8Z, 11Z, 14Z)-N-(2-hydroxyethyl)-5,8,11,14-eicosatetraenamide

|-
| Other names
| Anandamide<br>Arachidonoylethanolamide (AEA)
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C<sub>22</sub>H<sub>37</sub>NO<sub>2</sub>

|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CCCCC\C=C/C\C=C/C\C=C
/C\C=C/CCCC(NCCO)=O
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 347.54 gmol<sup>-1</sup>

|-
| Appearance
| Light yellow oil
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 94421-68-8
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| 0.92g/ml
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) (soluble in ethanol)
|-



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

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

'''Anandamide''' (a name deriving from the Sanskrit word "ananda," meaning bliss), also known as '''arachidonoylethanolamide (AEA)''', is a neurotransmitter present in animal and human organs, commonly in the brain. More specifically, anandamide is a cannabanoid; it binds to the cannabanoid receptor in mammalian brains, the same receptor that the psychoactive ingredient in marijuana targets.

== '''Biosynthesis of anandamide''' ==

There are two ways to synthesise anandamide. One is through the formation from free arachidonic acid and ethanolamine; the other is the formation from N-arachidonoyl phosphatidylethanolamine (PE), through the action of an enzyme called phosphodiesterase. These pathways, however, do not appear to generate a large amount of anandamide under physiological conditions. The generation of anandamide from free arachidonic acid and ethanolamine is catalyzed by a degrading enzyme anandamide amidohydrolase or a fatty acid amide hydrolase working in reverse. This requires large amounts of substrates. For the second pathway, arachidonic acids esterified at the 1-position of glycerophospholipids, which are mostly esterified at the 2-position, are used for the formation of N-arachidonoyl PE, a stored precursor form of anandamide. The reaction schemes of the second pathway are shown in the diagrams below:
[[Image:formation_1.gif]]

''Diagram 1:'' The synthesis of N-acyl PE through a series of reactions from Ca2+ ions and the enzyme transacylase.
[[Image:formation_2.gif]]

''Diagram 2:'' The second step of the biosynthesis involves the hydrolysis of the N-acyl-phosphatidylethanolamine by the enzyme phosphodiesterase.

[http://www.gynx.org/imperial/anandamide.pdb Anandamide]

This 3D representation is of the 'I' shape conformer.

[[Image:Anandamide_1.png|center|Anandamide]]
[[Image:choco.gif|center|Anandamide]]
[[Image:structureanadamide.jpg|center|Anandamide]]

<center>[http://www.gynx.org/imperial/anandamide.svg Anandamide SVG (maybe)]</center>


==''' References '''==
1. T. Sugiura, Y. Kobayashi, S. Oka and K. Waku, Prostaglandins Leukotrienes and Essential Fatty Acids, 2002, 66, 173-192.

2. H. H. O. Schmid, Chemistry and Physics of Lipids, 2000, 108, 71-87.

3. M. J. O'Neil, The Merck Index Thirteenth Edition, 2001, p105

It07a:Anandamide

2007-11-20T17:17:03Z

Afk06: /* Anandamide */

= Anandamide =

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 250px"
! {{chembox header}} | {{Anandamide}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>250</size>
<color>black</color>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 18-Oct-07 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 18-Oct-07 0 NONE 4
ATOM 1 C 0 12.110 -0.512 -0.273 0.00 0.00 C+0
ATOM 2 C 0 11.045 -0.120 0.753 0.00 0.00 C+0
ATOM 3 C 0 9.873 0.557 0.039 0.00 0.00 C+0
ATOM 4 C 0 8.808 0.950 1.064 0.00 0.00 C+0
ATOM 5 C 0 7.654 1.617 0.360 0.00 0.00 C+0
ATOM 6 C 0 6.438 1.155 0.515 0.00 0.00 C+0
ATOM 7 C 0 5.284 1.822 -0.189 0.00 0.00 C+0
ATOM 8 C 0 4.537 0.801 -1.008 0.00 0.00 C+0
ATOM 9 C 0 3.250 0.636 -0.834 0.00 0.00 C+0
ATOM 10 C 0 2.503 -0.385 -1.652 0.00 0.00 C+0
ATOM 11 C 0 1.774 -1.331 -0.733 0.00 0.00 C+0
ATOM 12 C 0 0.483 -1.508 -0.864 0.00 0.00 C+0
ATOM 13 C 0 -0.245 -2.454 0.055 0.00 0.00 C+0
ATOM 14 C 0 -1.384 -1.728 0.724 0.00 0.00 C+0
ATOM 15 C 0 -2.603 -2.200 0.636 0.00 0.00 C+0
ATOM 16 C 0 -3.742 -1.474 1.304 0.00 0.00 C+0
ATOM 17 C 0 -4.829 -1.171 0.272 0.00 0.00 C+0
ATOM 18 C 0 -5.985 -0.433 0.950 0.00 0.00 C+0
ATOM 19 C 0 -7.056 -0.135 -0.067 0.00 0.00 C+0
ATOM 20 O 0 -6.909 -0.478 -1.221 0.00 0.00 O+0
ATOM 21 N 0 -8.178 0.514 0.306 0.00 0.00 N+0
ATOM 22 C 0 -9.219 0.804 -0.683 0.00 0.00 C+0
ATOM 23 C 0 -10.375 1.541 -0.004 0.00 0.00 C+0
ATOM 24 O 0 -9.923 2.817 0.454 0.00 0.00 O+0
ATOM 25 H 0 12.944 -0.994 0.237 0.00 0.00 H+0
ATOM 26 H 0 11.679 -1.202 -0.998 0.00 0.00 H+0
ATOM 27 H 0 12.465 0.381 -0.787 0.00 0.00 H+0
ATOM 28 H 0 10.689 -1.012 1.268 0.00 0.00 H+0
ATOM 29 H 0 11.475 0.571 1.479 0.00 0.00 H+0
ATOM 30 H 0 10.229 1.450 -0.476 0.00 0.00 H+0
ATOM 31 H 0 9.442 -0.133 -0.687 0.00 0.00 H+0
ATOM 32 H 0 8.453 0.057 1.579 0.00 0.00 H+0
ATOM 33 H 0 9.239 1.640 1.790 0.00 0.00 H+0
ATOM 34 H 0 7.830 2.475 -0.271 0.00 0.00 H+0
ATOM 35 H 0 6.262 0.297 1.146 0.00 0.00 H+0
ATOM 36 H 0 4.612 2.258 0.549 0.00 0.00 H+0
ATOM 37 H 0 5.663 2.606 -0.844 0.00 0.00 H+0
ATOM 38 H 0 5.064 0.204 -1.738 0.00 0.00 H+0
ATOM 39 H 0 2.723 1.233 -0.103 0.00 0.00 H+0
ATOM 40 H 0 1.784 0.121 -2.297 0.00 0.00 H+0
ATOM 41 H 0 3.208 -0.945 -2.266 0.00 0.00 H+0
ATOM 42 H 0 2.317 -1.862 0.035 0.00 0.00 H+0
ATOM 43 H 0 -0.059 -0.977 -1.632 0.00 0.00 H+0
ATOM 44 H 0 -0.637 -3.292 -0.522 0.00 0.00 H+0
ATOM 45 H 0 0.444 -2.826 0.814 0.00 0.00 H+0
ATOM 46 H 0 -1.195 -0.819 1.275 0.00 0.00 H+0
ATOM 47 H 0 -2.791 -3.110 0.085 0.00 0.00 H+0
ATOM 48 H 0 -4.156 -2.098 2.096 0.00 0.00 H+0
ATOM 49 H 0 -3.376 -0.540 1.732 0.00 0.00 H+0
ATOM 50 H 0 -4.415 -0.546 -0.520 0.00 0.00 H+0
ATOM 51 H 0 -5.195 -2.104 -0.156 0.00 0.00 H+0
ATOM 52 H 0 -6.400 -1.058 1.742 0.00 0.00 H+0
ATOM 53 H 0 -5.620 0.500 1.378 0.00 0.00 H+0
ATOM 54 H 0 -8.295 0.788 1.229 0.00 0.00 H+0
ATOM 55 H 0 -8.804 1.428 -1.474 0.00 0.00 H+0
ATOM 56 H 0 -9.584 -0.130 -1.110 0.00 0.00 H+0
ATOM 57 H 0 -11.187 1.679 -0.718 0.00 0.00 H+0
ATOM 58 H 0 -10.732 0.956 0.843 0.00 0.00 H+0
ATOM 59 H 0 -10.680 3.247 0.875 0.00 0.00 H+0
CONECT 1 2 25 26 27 NONE 64
CONECT 2 1 3 28 29 NONE 65
CONECT 3 2 4 30 31 NONE 66
CONECT 4 3 5 32 33 NONE 67
CONECT 5 4 6 34 0 NONE 68
CONECT 6 5 7 35 0 NONE 69
CONECT 7 6 8 36 37 NONE 70
CONECT 8 7 9 38 0 NONE 71
CONECT 9 8 10 39 0 NONE 72
CONECT 10 9 11 40 41 NONE 73
CONECT 11 10 12 42 0 NONE 74
CONECT 12 11 13 43 0 NONE 75
CONECT 13 12 14 44 45 NONE 76
CONECT 14 13 15 46 0 NONE 77
CONECT 15 14 16 47 0 NONE 78
CONECT 16 15 17 48 49 NONE 79
CONECT 17 16 18 50 51 NONE 80
CONECT 18 17 19 52 53 NONE 81
CONECT 19 18 20 21 0 NONE 82
CONECT 20 19 0 0 0 NONE 83
CONECT 21 19 22 54 0 NONE 84
CONECT 22 21 23 55 56 NONE 85
CONECT 23 22 24 57 58 NONE 86
CONECT 24 23 59 0 0 NONE 87
END NONE 88
</inlineContents>
</jmolApplet>
</jmol>
[http://www.gynx.org/imperial/anandamide.pdb Anandamide]
This 3D representation is of the 'I' shape conformer.

|-
! {{chembox header}} | Structure
|-
|align="center" colspan="1" |
|[[Image:Anandamide_1.png|thumb|center|Anandamide]]


|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| Eicosa-5,8,11,14-tetraenoic acid (2-hydroxy-ethyl)-amide
(5Z, 8Z, 11Z, 14Z)-N-(2-hydroxyethyl)-5,8,11,14-eicosatetraenamide

|-
| Other names
| Anandamide<br>Arachidonoylethanolamide (AEA)
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C<sub>22</sub>H<sub>37</sub>NO<sub>2</sub>

|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CCCCC\C=C/C\C=C/C\C=C
/C\C=C/CCCC(NCCO)=O
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 347.54 gmol<sup>-1</sup>

|-
| Appearance
| Light yellow oil
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 94421-68-8
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| 0.92g/ml
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) (soluble in ethanol)
|-



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

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

'''Anandamide''' (a name deriving from the Sanskrit word "ananda," meaning bliss), also known as '''arachidonoylethanolamide (AEA)''', is a neurotransmitter present in animal and human organs, commonly in the brain. More specifically, anandamide is a cannabanoid; it binds to the cannabanoid receptor in mammalian brains, the same receptor that the psychoactive ingredient in marijuana targets.

== '''Biosynthesis of anandamide''' ==

There are two ways to synthesise anandamide. One is through the formation from free arachidonic acid and ethanolamine; the other is the formation from N-arachidonoyl phosphatidylethanolamine (PE), through the action of an enzyme called phosphodiesterase. These pathways, however, do not appear to generate a large amount of anandamide under physiological conditions. The generation of anandamide from free arachidonic acid and ethanolamine is catalyzed by a degrading enzyme anandamide amidohydrolase or a fatty acid amide hydrolase working in reverse. This requires large amounts of substrates. For the second pathway, arachidonic acids esterified at the 1-position of glycerophospholipids, which are mostly esterified at the 2-position, are used for the formation of N-arachidonoyl PE, a stored precursor form of anandamide. The reaction schemes of the second pathway are shown in the diagrams below:
[[Image:formation_1.gif]]

''Diagram 1:'' The synthesis of N-acyl PE through a series of reactions from Ca2+ ions and the enzyme transacylase.
[[Image:formation_2.gif]]

''Diagram 2:'' The second step of the biosynthesis involves the hydrolysis of the N-acyl-phosphatidylethanolamine by the enzyme phosphodiesterase.

[http://www.gynx.org/imperial/anandamide.pdb Anandamide]

This 3D representation is of the 'I' shape conformer.

[[Image:Anandamide_1.png|center|Anandamide]]
[[Image:choco.gif|thumb|center|Anandamide]]
[[Image:structureanadamide.jpg|center|Anandamide]]

<center>[http://www.gynx.org/imperial/anandamide.svg Anandamide SVG (maybe)]</center>


==''' References '''==
1. T. Sugiura, Y. Kobayashi, S. Oka and K. Waku, Prostaglandins Leukotrienes and Essential Fatty Acids, 2002, 66, 173-192.

2. H. H. O. Schmid, Chemistry and Physics of Lipids, 2000, 108, 71-87.

3. M. J. O'Neil, The Merck Index Thirteenth Edition, 2001, p105