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

N-Acyl ethanolamines 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.^1,2 LOEA has a weak affinity for cannabinoid (CB) receptors (K_i = 10, 25 μM for CB₁, CB₂, respectively). ³ Although hydrolized by fatty acid amide hydrolase (FAAH; K_i = 9 μM) it also inhibits FAAH and inhibits voltage-gated K⁺ channels.^3,4,5,6 (R)-(+)-Linoleyl-1’-hydroxy-2’-propylamide is a homolog of LOEA, characterized by the addition of an (R)-α-methyl group at the methylene carbon adjacent to the amide nitrogen. A similar modification of arachidonoyl ethanolamide to produce R-1 methanandamide imparts higher affinity for the CB receptor as well as improved metabolic stability.⁷ The physiological actions of this compound have not been evaluated.