183323-26-4

Arachidonoyl ethanolamide (AEA; ) was the first endogenous cannabinoid (CB) to be isolated and characterized as an agonist acting on the same receptors (CB₁ and CB₂) as Δ⁹-THC . Since that time, a number of related endocannabinoids have been isolated, most notably 2-arachidonoyl glycerol (2-AG; ). The phosphate ester of AEA, AEA-P, has been tested as a water soluble prodrug version of AEA in the treatment of C₆ glioma cells in vivo. Here it acts with essentially the same potency as AEA. However, when tested for inhibition of AEA binding to isolated rat brain CB₁ receptors, AEA-P is about 5-fold less potent as an agonist with a K_i of about 200 nM. The phosphate esters of AEA and its analogs are also structural variants of lysophosphatidic acid (LPA). However, the effects of AEA-P on the various LPA receptors have not been tested.

ChEBI: Phospho-anandamide is a phosphoethanolamine and a N-acylethanolamine phosphate.