Anandamide

Title: Anandamide
CAS Registry Number: 94421-68-8
CAS Name: (5Z,8Z,11Z,14Z)-N-(2-Hydroxyethyl)-5,8,11,14-eicosatetraenamide
Additional Names: arachidonylethanolamide; N-(2-hydroxyethyl)arachidonamide
Molecular Formula: C22H37NO2
Molecular Weight: 347.53
Percent Composition: C 76.03%, H 10.73%, N 4.03%, O 9.21%
Literature References: Endogenous ligand for the mammalian cannabinoid receptor; derivative of arachidonic acid, q.v. Name coined from the Sanskrit word "ananda," meaning bliss. Identification in pig brain: W. A. Devane et al., Science 258, 1946 (1992). Identification in chocolate and cocoa: E. di Tomaso et al., Nature 382, 677 (1996). Pharmacology: P. B. Smith et al., J. Pharmacol. Exp. Ther. 270, 219 (1994). Biosynthetic studies: W. A. Devane, J. Axelrod, Proc. Natl. Acad. Sci. USA 91, 6698 (1994); V. Di Marzo et al., Nature 372, 686 (1994). LC/MS/MS determn and distribution in human tissues: C. C. Felder et al., FEBS Lett. 393, 231 (1996). Review: V. Di Marzo, A. Fontana, Prostaglandins Leukotrienes Essent. Fatty Acids 53, 1-11 (1995).
Anatoxins Anazolene Sodium Ancitabine Ancymidol Andrographis

Anandamide
Anandamide skeletal.svg
Identifiers
CAS number 94421-68-8 N
PubChem 5281969
ChemSpider 4445241 YesY
UNII UR5G69TJKH YesY
MeSH Anandamide
ChEBI CHEBI:2700 YesY
ChEMBL CHEMBL15848 YesY
IUPHAR ligand 737
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C22H37NO2
Molar mass 347.53 g/mol
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Anandamide, also known as N-arachidonoylethanolamine or AEA, is an endogenous cannabinoid neurotransmitter. The name is taken from the Sanskrit word ananda, which means "bliss, delight", and amide.[1][2] It is synthesized from N-arachidonoyl phosphatidylethanolamine by multiple pathways.[3] 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.[4][5]