Anandamide

Anandamide

Names
IUPAC name (5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide
Other names N-arachidonoylethanolamine arachidonoylethanolamide
Identifiers
CAS Number	94421-68-8 N
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:2700 Y
ChEMBL	ChEMBL15848 Y
ChemSpider	4445241 Y
IUPHAR/BPS	2364
MeSH	Anandamide
PubChem	5281969
UNII	UR5G69TJKH Y
InChI InChI=1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,15-16,24H,2-5,8,11,14,17-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-,16-15- Y Key: LGEQQWMQCRIYKG-DOFZRALJSA-N Y InChI=1/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,15-16,24H,2-5,8,11,14,17-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-,16-15- Key: LGEQQWMQCRIYKG-DOFZRALJBA
SMILES O=C(NCCO)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO
Properties
Chemical formula	C22H37NO2
Molar mass	347.53 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Anandamide, also known as N-arachidonoylethanolamine or AEA, is a fatty acid neurotransmitter derived from the non-oxidative metabolism of eicosatetraenoic acid (arachidonic acid) an essential ω-6 polyunsaturated fatty acid. The name is taken from the Sanskrit word ananda, which means "joy, bliss, delight", and amide. It is synthesized from N-arachidonoyl phosphatidylethanolamine by multiple pathways. It is degraded primarily by the fatty acid amide hydrolase (FAAH) enzyme, which converts anandamide into ethanolamine and arachidonic acid. As such, inhibitors of FAAH lead to elevated anandamide levels and are being pursued for therapeutic use.

Anandamide was first described in 1992 by W. A. Devane and Lumír Hanuš.

Anandamide's effects can occur in either the central or peripheral nervous system. These distinct effects are mediated primarily by CB₁cannabinoid receptors in the central nervous system, and CB₂ cannabinoid receptors in the periphery. The latter are mainly involved in functions of the immune system. Cannabinoid receptors were originally discovered as being sensitive to Δ⁹-tetrahydrocannabinol (Δ⁹-THC, commonly called THC), which is the primary psychoactive cannabinoid 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.

Anandamide has been shown to impair working memory in rats. Studies are under way to explore what role anandamide plays in human behavior, such as eating and sleep patterns, and pain relief.