624. Anandamide

Nomenclature

CAS number: 94421-68-8
(5Z,8Z,11Z,14Z)-N-(2-Hydroxyethyl)-5,8,11,14-eicosatetraenamide; arachidonylethanolamide; N-arachidonoylethanolamide; N-(2-hydroxyethyl)arachidonamide.
C22H37NO2; mol wt 347.53.
C 76.03%, H 10.73%, N 4.03%, O 9.21%.

Description and 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) DOI PubMed. Identification in chocolate and cocoa: E. di Tomaso et al., Nature 382, 677 (1996) DOI PubMed. Pharmacology: P. B. Smith et al., J. Pharmacol. Exp. Ther. 270, 219 (1994) PubMed. Biosynthetic studies: W. A. Devane, J. Axelrod, Proc. Natl. Acad. Sci. USA 91, 6698 (1994) DOI PubMed; V. Di Marzo et al., Nature 372, 686 (1994) DOI PubMed. LC/MS/MS determn and distribution in human tissues: C. C. Felder et al., FEBS Lett. 393, 231 (1996) DOI PubMed. Review: V. Di Marzo, A. Fontana, Prostaglandins Leukotrienes Essent. Fatty Acids 53, 1-11 (1995) DOI PubMed. Review of pharmacology: K. Smita et al., Fundam. Clin. Pharmacol. 21, 1-8 (2007) DOI PubMed; of regulatory role in food intake: R. Capasso, A. A. Izzo, J. Neuroendocrinol. 20, Suppl. 1, 39-46 (2008) DOI PubMed.

Chemical structure