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. (R)-(+)-Docosahexaenyl-1'-hydroxy-2'-propylamide is a homolog of DHEA, 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. The physiological actions of this compound have not been evaluated.

(S)-(−)-Docosahexaenyl-1'-hydroxy-2'-propylamide is the enantiomer of (R)-(−)-Docosahexaenyl-1'-hydroxy-2'-propylamide. (R)-(-)-Docosahexaenyl-2'-hydroxy-1'-propylamide is a homolog of dehydroepiandrosterone (DHEA). This compound is characterized by the addition of an (R)-β-methyl group to the terminal ethanolamine carbon atom.

(S)-(+)-Docosahexaenyl-2'-hydroxy-1'-propylamide (N-Docosahexacnoylethanolamide(22:6)) is a homologue of dehydroepiandrosterone (DHEA). This compound can block Shaker-related voltage-gated potassium channels and inhibits Kv1.2 K+ currents with an IC50 value of 1.5 μM.

(R)-(-)-Docosahexaenyl-2'-hydroxy-1'-propylamide is a homolog of dehydroepiandrosterone (DHEA), characterized by the addition of an (R)-β-methyl group at the terminal ethanolamine carbon atom.