Anandamide
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| Anandamide | |
|---|---|
| Chemical name | (5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl) icosa-5,8,11,14-tetraenamide or arachidonoylethanolamide |
| Chemical formula | C22H37NO2 |
| Molecular mass | 347.53 g/mol |
| CAS number | 94421-68-8 |
| SMILES | CCCCC\C=C/C\C=C/C\C=C /C\C=C/CCCC(NCCO)=O |
| Image:Anandamide structure.png | |
Anandamide, also known as arachidonylethanolamide or arachidonoylethanolamine or AEA, is a naturally occurring endogenous cannabinoid neurotransmitter found in the brain of animals, as well as other organs. It was isolated, and its structure elucidated by William Devane and Lumír Hanuš in the Laboratory of Raphael Mechoulam, at the Hebrew University in Jerusalem in 1992. The name is taken from the Sanskrit word ananda, which means "bliss", and amide.
Anandamide's effects can be either central, in the brain, or peripheral, in other parts of the body. These distinct effects are mediated by the CB1 receptor in the nervous system, and the CB2 receptor in the periphery. The latter is mainly involved in functions of the immune system.
These receptors are part of the largest known family of receptors, the G protein-coupled receptors, which - in this case - has a distinctive pattern in which the receptor molecule spans the cell membrane seven times over. The CB1 receptor is one of the most numerous in the nervous system.
Anandamide receptors were originally discovered as being sensitive to Δ9-tetrahydrocannabinol (Δ9-THC), which is among the psychoactive cannabinoids found in cannabis. The discovery of anandamide came from research into CB1 and CB2, as it was inevitable that a naturally occurring (endogenous) chemical would be found to affect these receptors.
Endogenous cannabinoids occur in minute quantities in cocoa (fermented Theobroma cacao) beans, in sea urchin roeTemplate:Ref, and in chocolate, though there is some controversy over whether they have any effects on the body in these quantities.
Anandamide receptors have been shown to be involved in the management of short term memoryTemplate:Ref. Studies are under way to explore what role anandamide plays in human behavior, such as eating and sleep patterns, and the part it plays in pain relief.
Anandamide is also important for implantation of the early stage embryo in its blastocyst form into the uterus. Therefore cannabinoids like Δ9-THC might interfere with the earliest stages of human pregnancyTemplate:Ref.
Moreover, anandamide is thought to be an endogenous ligand for vanilloid receptors (which are involved in the transduction of acute and inflammatory pain signals), activating the receptor in a PKC-dependent (protein kinase C-dependent) manner.
See also
- Tetrahydrocannabinol (THC)
References
- Template:Note Bisogno T, Ventriglia M, Milone A, Mosca M, Cimino G, Di Marzo V. Occurrence and metabolism of anandamide and related acyl-ethanolamides in ovaries of the sea urchin Paracentrotus lividus. Biochim Biophys Acta. 1997 Apr 21;1345(3):338-48. PMID 9150253
- Template:Note Sinan Bir L, Ercan S. Effects of intrathecal anandamide on somatosensory evoked responses in rats. Exp Neurol. 2006 Feb;197(2):386-390. PMID 16289169
- Template:Note Piomelli D. THC: moderation during implantation. Nat Med. 2004 Jan;10(1):19-20. PMID 14702623
Template:Cannabinoidsde:Anandamid it:Anandamide nl:Anandamide pl:Anandamid fi:Anandamidi sv:Anandamid