(S)-(+)-Linoleyl-2'-Hydroxy-1'-Propylamide

N-Acyl ethanolamines (NAEs) have diverse biological actions that are strongly affected by the associated acyl group. Linoleoyl ethanolamide (LOEA) has potential signaling roles in aging and neurological functioning. LOEA has a weak affinity for cannabinoid (CB) receptors (Ki = 10, 25 μM for CB1, CB2, respectively) and inhibits voltage-gated K+ channels. LOEA also inhibits fatty acid amide hydrolase (FAAH; Ki = 9 μM) and is hydrolyzed by FAAH. (S)-(+)-Linoleyl-2'-hydroxy-1'-propylamide is a homolog of LOEA, characterized by the addition of an (S)-β-methyl group at the terminal ethanolamine carbon. A similar modification of arachidonoyl ethanolamide to produce S-2 methanandamide imparts higher affinity for the CB receptor. The physiological actions of this compound have not been evaluated.