(S)-(-)-Eicosapentaenyl-1'-Hydroxy-2'-Propylamide

N-Acyl ethanolamines (NAEs) have diverse biological actions that are strongly affected by the associated acyl group. Eicosapentaenoyl ethanolamide (EPEA) has potential signaling roles in aging, cancer, inflammation, and neurological development.^1,2,3,4 At least some of EPEA’s effects are mediated through cannabinoid (CB) receptors, while some NAEs also act as vanilloid receptor agonists.^1,5 S-(−)-Eicosapentaenyl-1’-droxy-2’-propylamide is a homolog of EPEA, characterized by the addition of an (S)-α-metl group at the metlene 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 drolysis.⁶ The psiological actions of this compound have not been evaluated.