(S)-(-)-Linoleyl-1'-Hydroxy-2'-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 and 25 μM for CB1 and CB2, respectively). It also inhibits fatty acid amide hydrolase (FAAH; Ki = 9 μM) and is hydrolyzed by FAAH, and inhibits voltage-gated K+ channels. (S)-(-)-Linoleyl-1'-hydroxy-2'-propylamide is a homolog of LOEA, characterized by the addition of an (S)-α-methyl group at the methylene carbon adjacent to the amide nitrogen. A similar modification of arachidonoyl ethanolamide to produce S-1 methanandamide results in a diminished affinity for the CB receptor but greatly improved metabolic stability to aminopeptidase hydrolysis. The physiological actions of this compound have not been evaluated.