Background
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.
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