(±)5(6)-EET Ethanolamide

Arachidonyl ethanolamide (AEA, Cay-90050) is an endogenous lipid neurotransmitter with cannabinergic activity, binding to both the central cannabinoid (CB1) and peripheral cannabinoid (CB2) receptors. Fatty acid amide hydrolase (FAAH) is the enzyme responsible for the hydrolysis and inactivation of AEA. Metabolism of AEA by cyclooxygenase-2, leading to formation of prostaglandin ethanolamides, and by lipoxygenases has also been documented. (±)5(6)-EET ethanolamide is a cytochrome P450 (CYP450) metabolite of AEA, although specific stereochemistry rather than a racemic mixture ensues from enzymatic metabolism. (±)5(6)-EET ethanolamide is a potent and selective agonist of CB2 (Ki = 8.9 nM for CB2, 11.4 µM for CB1), effectively suppressing forskolin-stimulated accumulation of cAMP through this Gi-coupled receptor (IC50 = 9.8 nM).