(±)-2-Methyl Arachidonoyl-2'-Fluoroethylamide

(±)-2-Methyl arachidonoyl-2'-fluoroethylamide (2-Methyl-2'-fluoro AEA) is an analog of anandamide (AEA) in which the alcohol of the ethanolamide group has been removed and replaced with a fluorine atom. This substitution confers considerably increased binding affinity for the CB₁ receptor (K_i = 5.7 nM in rat brain). It also confers 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. 2-Methyl-2'-fluoro AEA is further modified by the addition of an α-methyl group at the C-2 position of arachidonic acid. This substitution confers enhanced metabolic stability. 2-Methyl-2'-fluoro AEA can fully substitute for Δ⁹-THC in animal self-administration tests, whereas AEA and 2-fluoro AEA cannot.²

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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).

2. Ryan, W.J., Banner, K., Crocker, P.J., et al. Synthesis of (+)- and (−)-2-methylarachidonyl-2'-fluoroethylamide (O-689). Bioorg. Med. Chem. Lett. 7, 2669-2672 (1997).