Arachidoyl ethanolamide

Description

The endocannabinoids present a rich system of central cannabinoid (CB₁), peripheral cannabinoid (CB₂), and non-CB receptor-mediated pharmacology that has stimulated research in many fields including memory, weight loss and appetite, neurodegeneration, tumor surveillance, analgesia, and inflammation.^1,2 Arachidoyl ethanolamide is one of the saturated fatty acyl ethanolamides devoid of classical (CB₁/CB₂) activity. Arachidoyl ethanolamide does not bind to the murine CB₁ receptor³ and does not compete with anandamide as a substrate for the endocannabinoid hydrolytic enzyme fatty acid amide hydrolase.⁴ Non-CB receptor-mediated pharmacology of the saturated ethanolamides is still being elucidated.⁵

Uses

Arachidoyl Ethanolamide (N-(2-hydroxyethyl)-eicosanamide) is an ester product.

Definition

ChEBI: N-(icosanoyl)ethanolamine is an N-(long-chain-acyl)ethanolamine that is the ethanolamide of eicosanoic acid. It is a N-(long-chain-acyl)ethanolamine and a N-(saturated fatty acyl)ethanolamine. It is functionally related to an icosanoic acid.

References

1. Martin, B.R., Mechoulam, R., and Razdan, R.K. Discovery and characterization of endogenous cannabinoids Life Sci. 65,573-595(1999).
2. Pertwee, R.G. Pharmacology of cannabinoid receptor ligands Curr. Med. Chem. 6(8),635-664(1999).
3. Sheskin, T., Hanus, L., Slager, J., et al. Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor J. Med. Chem. 40,659-667(1997).
4. Desarnaud, F., Cadas, H., and Piomelli, D. Anandamide amidohydrolase activity in rat brain microsomes. Identification and partial characterization J. Biol. Chem. 270(11),6030-6035(1995).
5. Smart, D., Jonsson, K.O., Vandevoorde, S., et al. “Entourage” effects of N-acyl ethanolamines at human vanilloid receptors. Comparison of effects upon anandamide-induced vanilloid receptor activation and upon anandamide metabolism Br. J. Pharmacol. 136,452-458(2002).