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

N-Acyl ethanolamines (NAEs) have diverse biological actions that are strongly affected by the associated acyl group. Docosahexaenoyl ethanolamide (DHEA) has potential signaling roles in cancer, inflammation, and neurological development and functioning. At least some of DHEA's effects are mediated through cannabinoid (CB) receptors, while some NAEs also act as vanilloid receptor agonists and voltage-gated K+ channel blockers. (S)-(-)-Docosahexaenyl-1'-hydroxy-2'-propylamide is a homolog of DHEA, 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.