{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"JHIXEZNTXMFXEK-UHFFFAOYSA-N","prefName":"Myristoylethanolamide","symbol":"MEA","iupacName":"N-(2-hydroxyéthyl)tétradécanamide","aliases":["N-myristoyléthanolamine","NMEA","N-myristoylethanolamine","14:0 NAE","myristamide MEA"],"cas":null,"pubchemCid":"8890","chebiId":null,"smiles":"CCCCCCCCCCCCCC(=O)NCCO","molecularFormula":"C16H33NO2","molecularWeight":271.4,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/8890"}},"classification":{"family":"endocannabinoide","familyLabel":"Endocannabinoid","origin":"natural","originLabel":"Naturel","structuralClassFr":"N-acyléthanolamine saturée. La molécule associe l'acide myristique, acide gras saturé linéaire à quatorze carbones, à l'éthanolamine par une liaison amide. L'absence complète d'insaturation sur la chaîne la distingue de l'anandamide, dont les quatre doubles liaisons de la chaîne arachidonique permettent le repliement nécessaire à la reconnaissance par le récepteur CB1. Elle la rapproche en revanche du palmitoyléthanolamide, homologue à seize carbones, et du stéaroyléthanolamide à dix-huit carbones."},"originSynthesis":{"heading":"Biosynthetic pathway (in vivo)","summaryFr":"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.","originNote":"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.","discovered":"La molécule appartient à la famille des N-acyléthanolamines, dont les membres ont été identifiés progressivement dans les tissus animaux à partir des années 1950, bien avant la découverte de l'anandamide en 1992. Sa pharmacologie comparée aux autres éthanolamides d'acides gras a été établie par Watanabe et collaborateurs en 1999, dans une série qui mesurait catalepsie, hypothermie et prolongation du sommeil chez la souris."},"pharmacology":{"summaryFr":"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.","receptorSummaryFr":"The compound is not a direct ligand of cannabinoid receptors: its saturated fourteen-carbon chain lacks the unsaturations that allow anandamide to bind CB1. Watanabe and colleagues verified that inactivity in mice, where myristoylethanolamide produced no catalepsy up to 40 milligrams per kilogram intravenously, unlike anandamide and its unsaturated homologues. The same study nevertheless measured a significant hypothermia at 10 milligrams per kilogram, a modest and short-lived effect. Its most plausible physiological role belongs to the so-called entourage mechanism: by occupying the same degradation enzymes as anandamide, the saturated N-acylethanolamines indirectly prolong its lifetime.","binding":[{"target":"FAAH","efficacy":"modulator","relativeActivity":45,"reported":"Substrat de la FAAH, donc inhibiteur compétitif de l'hydrolyse de l'anandamide","confidence":"medium"},{"target":"CB1","efficacy":"modulator","relativeActivity":3,"reported":"Pas de liaison directe : chaîne saturée dépourvue des insaturations requises","confidence":"medium"}],"references":[{"label":"Watanabe et coll. 1999 : effets pharmacologiques chez la souris de l'anandamide et des éthanolamides d'acides gras apparentés","pmid":"10328555","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/10328555/"},{"label":"Piomelli et coll. 2020 : structure, fonction et inhibition de l'amidase acide des N-acyléthanolamines","pmid":"32191459","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/32191459/"}]},"pharmacokinetics":"Aucune donnée de pharmacocinétique humaine n'est publiée. Les travaux disponibles reposent sur l'administration intraveineuse chez la souris, où les effets observés apparaissent dans les minutes qui suivent l'injection et restent de durée brève. Les concentrations tissulaires endogènes chez l'humain n'ont pas fait l'objet d'une quantification systématique comparable à celle de l'anandamide ou du palmitoyléthanolamide.","metabolism":"La molécule est hydrolysée en acide myristique et en éthanolamine par les deux amidases qui gouvernent le catabolisme de la famille : l'amidohydrolase des acides gras, active à pH neutre et localisée dans les membranes intracellulaires, et l'amidase acide des N-acyléthanolamines, lysosomale et préférentielle pour les substrats saturés à chaîne moyenne. C'est cette compétition pour des enzymes partagées avec l'anandamide qui fonde l'hypothèse d'un effet indirect.","detection":"La quantification s'effectue par chromatographie liquide couplée à la spectrométrie de masse en tandem, dans le cadre des méthodes lipidomiques qui dosent conjointement l'ensemble des N-acyléthanolamines d'un échantillon. Le composé n'appartient à aucun panel de dépistage toxicologique et n'a pas d'intérêt médicolégal.","subjectiveEffects":{"profile":[{"key":"calm","label":"Calm","description":"Relaxation of body and mind; reduced mental noise without marked drowsiness.","intensity":15},{"key":"focus","label":"Clarity","description":"Sustained attention and clear thinking; functional lucidity, not euphoria.","intensity":5},{"key":"sleep","label":"Sleep","description":"Sedative effect: aids sleep onset and the continuity of deep sleep.","intensity":10},{"key":"appetite","label":"Appetite","description":"Stimulation of hunger and of taste appreciation (the “munchies” effect).","intensity":5},{"key":"uplift","label":"High","description":"Euphoria and sensory intensity; altered perception of time and space.","intensity":5}],"doseRanges":null,"humanDataCharacterised":true},"indications":{"approvedMedicines":[]},"harmProfile":{"unstudiedBanner":false,"bannerTextFr":null,"toxicologyFr":"Aucun événement toxique n'est documenté. Le composé est endogène et figure de longue date parmi les ingrédients cosmétiques et détergents d'usage courant, sans signal de sécurité particulier dans ce cadre. Aucune dose humaine à visée pharmacologique n'a été caractérisée, et les seules données d'administration disponibles concernent la souris."},"legal":{"scheduleStatus":"endogenous","scheduleLabel":"Endogenous","frScheduleStatus":"endogenous","tiers":[{"jurisdiction":"international","jurisdictionLabel":"International","label":"Substance endogène ; non contrôlée","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"eu","jurisdictionLabel":"Union européenne","label":"Ingrédient cosmétique et industriel ; non contrôlé","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"Non inscrite sur les listes des stupéfiants et psychotropes","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Watanabe et coll. 1999 : effets pharmacologiques chez la souris de l'anandamide et des éthanolamides d'acides gras apparentés","pmid":"10328555","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/10328555/"},{"label":"Piomelli et coll. 2020 : structure, fonction et inhibition de l'amidase acide des N-acyléthanolamines","pmid":"32191459","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/32191459/"}],"meta":{"slug":"mea","url":"https://en.phytogrammes.com/wiki/mea","lastVerified":"2026-05-01","dataUpdatedAt":"2026-08-16","confidence":"medium","dataCompletenessPct":90,"disclaimerFr":"Contenu éditorial informatif, sans valeur d'avis médical ni juridique. Sources primaires citées par fiche. Réservé aux adultes."}}