Arachidonoyl Ethanolamide Phosphate

Arachidonoyl ethanolamide (AEA; Item No. 90050) 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 (Item No. 12068).^1,2 Since that time, a number of related endocannabinoids have been isolated, most notably 2-arachidonoyl glycerol (2-AG; Item No. 62160).² 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.³ 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.⁴ 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.

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1. Devane, W.A., Hanus, L., Breuer, A., et al. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258(5090), 1946-1949 (1992).

2. Felder, C.C., Briley, E.M., Axelrod, J., et al. Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc. Natl. Acad. Sci. USA 90(16), 7656-7660 (1993).

3. Fowler, C.J., Jonsson, K.O., Andersson, A., et al. Inhibition of C₆ glioma cell proliferation by anandamide, 1-arachidonoylglycerol, and by a water soluble phosphate ester of anandamide: Variability in response and involement of arachidonic acid. Biochem. Pharmacol. 66(5), 757-767 (2003).

4. 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(5), 659-667 (1997).