(+-)8(9)-EET Ethanolamide

Arachidonoyl ethanolamide (AEA; anandamide) is an endogenous lipid neurotransmitter with cannabinergic activity, binding to both the central cannabinoid (CB1) and peripheral cannabinoid (CB2) receptors.{2713,14062} Fatty acid amide hydrolase (FAAH) is the enzyme responsible for the hydrolysis and inactivation of AEA.{13132} Metabolism of AEA by COX-2, lipoxygenases, and cytochrome P450 (CYP450) enzymes has also been documented.{12168,14767} (+-)8(9)-EET ethanolamide is a CYP450 metabolite of AEA, although specific stereochemistry rather than a racemic mixture would likely ensue from enzymatic metabolism.{14767} Human liver microsomes metabolize AEA to 5,6-, 8,9-, 11,12-, and 14,15-EET ethanolamides in a time and protein concentration dependent manner.{14767} (+-)8(9)-EET reduces glomerular filtration rate through cyclooxygenase dependent preglomerular vasoconstriction.{1111} The physiological actions of (+-)8(9)-EET ethanolamide have not been examined.