MEAMyristoylethanolamide

Formula

C₁₆H₃₃NO₂

Molar mass

271.40 g·mol⁻¹

CAS

-

PubChem CID

8890

Origin

An endogenous compound present in trace amounts in animal tissues, where it is produced by the same enzymatic machinery as the other N-acylethanolamines. The molecule is also manufactured industrially, under various trade names, as a surfactant and thickening agent for cosmetics and detergency, a use unrelated to its biological function.

InChIKey

JHIXEZNTXMFXEK-UHFFFAOYSA-N

Editorial estimate, not clinical.

Myristoylethanolamide is the saturated fourteen-carbon member of the N-acylethanolamine family, the one that counts anandamide among its unsaturated members and palmitoylethanolamide among its best studied saturated ones. It shares with them the biosynthetic route, which passes through a phospholipid precursor cleaved by a specific phospholipase D, as well as the degradation enzymes, fatty acid amide hydrolase and N-acylethanolamine acid amidase. It does not share their receptor pharmacology: the absence of unsaturations on its chain deprives it of the affinity for the CB1 receptor that characterises anandamide. Watanabe and colleagues documented that dissociation in 1999 on three murine models. Myristoylethanolamide produced no catalepsy up to 40 milligrams per kilogram intravenously, when anandamide acted with a median effective dose of 6.0 milligrams per kilogram; nor did it prolong pentobarbital-induced sleep. It did by contrast provoke, like anandamide and its oleic and linoleic homologues, a significant but weak hypothermia at 10 milligrams per kilogram. That profile places the molecule in the role of an indirect modulator rather than a messenger: it competes for the degradation enzymes of the active endocannabinoids, the so-called entourage mechanism, without carrying a cannabinoid effect of its own.

The molecule is a saturated member of the N-acylethanolamine family, formed from myristic acid, a saturated fourteen-carbon fatty acid. Its production follows the route common to that family: a phospholipid precursor, N-acyl-phosphatidylethanolamine, is built by transfer of an acyl chain onto the amine function of a phosphatidylethanolamine, then releases the corresponding ethanolamide under the action of a specific phospholipase D. Degradation falls to fatty acid amide hydrolase and to N-acylethanolamine acid amidase.

Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.

Class

Endocannabinoid

Origin

An endogenous compound present in trace amounts in animal tissues, where it is produced by the same enzymatic machinery as the other N-acylethanolamines. The molecule is also manufactured industrially, under various trade names, as a surfactant and thickening agent for cosmetics and detergency, a use unrelated to its biological function.

Status

Endogenous

1. 1.Watanabe et coll. 1999 : effets pharmacologiques chez la souris de l'anandamide et des éthanolamides d'acides gras apparentésPMID 10328555
2. 2.Piomelli et coll. 2020 : structure, fonction et inhibition de l'amidase acide des N-acyléthanolaminesPMID 32191459