OEAOleoylethanolamide

Formula

C₂₀H₃₉NO₂

Molar mass

325.50 g·mol⁻¹

CAS

111-58-0

PubChem CID

5283454

First described

Décrit comme médiateur lipidique de la satiété par l'équipe de Daniele Piomelli au début des années 2000, au sein de la famille des N-acyléthanolamines endogènes.

Origin

An endogenous molecule present in mammals, produced notably in the mucosa of the small intestine. Also offered as a food supplement.

InChIKey

BOWVQLFMWHZBEF-KTKRTIGZSA-N

Editorial estimate, not clinical.

Oleoylethanolamide (OEA) is an endogenous N-acylethanolamine, a congener of anandamide and the oleic analogue of PEA. Despite this kinship, it barely activates the CB1 and CB2 cannabinoid receptors: its mechanism rests chiefly on activation of the nuclear receptor PPAR-α, of which it is a high-affinity endogenous ligand, with a contribution from the GPR119 receptors and the TRPV1 channel. Produced in the small intestine in response to feeding, it acts as a local lipid satiety signal transmitted by vagal afferents.

Oleoylethanolamide is synthesised on demand in cell membranes: a phospholipid precursor, N-oleoyl-phosphatidylethanolamine (NAPE), is cleaved by a specific phospholipase D (NAPE-PLD) that releases OEA. Its intestinal production is stimulated by dietary fat intake. It is then degraded by fatty acid amide hydrolase (FAAH), the same enzyme as for anandamide.

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

Class

Endocannabinoid

Origin

An endogenous molecule present in mammals, produced notably in the mucosa of the small intestine. Also offered as a food supplement.

Status

Endogenous

N-acyléthanolamine (NAE) mono-insaturée : l'acide oléique (C18:1, cis-9) lié par une fonction amide à l'éthanolamine. C'est le congénère mono-insaturé de l'anandamide (AEA) et l'analogue oléique du palmitoyléthanolamide (PEA).

Médiateur lipidique produit et agissant localement, à demi-vie courte : il est rapidement hydrolysé par la FAAH, ce qui limite sa durée d'action après une libération endogène.

Dégradé par hydrolyse enzymatique via la FAAH (et, accessoirement, la NAAA), qui scinde la liaison amide en acide oléique et éthanolamine.

1. 1.PubChem CID 5283454 : Oleoylethanolamide
2. 2.GPR119 and GPR55 as Receptors for Fatty Acid Ethanolamides, OEA and PEA (Int. J. Mol. Sci. 2021)
3. 3.Central mechanisms mediating the hypophagic effects of oleoylethanolamide (Front. Pharmacol. 2015)
4. 4.A systematic review of OEA, a high-affinity endogenous ligand of PPAR-α (Clin. Exp. Pharmacol. Physiol. 2020)