166100-37-4

Arachidonoyl-2'-fluoroethylamide (2-fluoro AEA) is an analog of anandamide in which the alcohol of the ethanolamide group has been removed and replaced with a fluorine atom. This substitution adds considerably increased binding affinity for the CB₁ receptor (K_is = 26.7 and 908 nM for CB₁ and CB₂, respectively). It also contributes additional selectivity, in that binding to CB₂ is decreased relative to AEA.¹ However, the in vivo activity of 2-fluoro AEA is enhanced much less than the binding affinity, because the analog remains a good substrate for FAAH and is rapidly hydrolyzed by this enzyme.

Arachidonoyl-2'-fluoroethylamide is a CB1 receptor agonist and an analog of Anandamide (A637220), which is an endogenous cannabinoid and TRPV1 receptor agonist.

1. Lin, S., Khanolkar, A.D., Fan, P., et al. Novel analogues of arachidonylethanolamide (anandamide): Affinities for the CB₁ and CB₂ cannabinoid receptors and metabolic stability J. Med. Chem. 41(27),5353-5361(1998).