{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"LGEQQWMQCRIYKG-DOFZRALJSA-N","prefName":"Anandamida (N-araquidonoiletanolamina)","symbol":"AEA","iupacName":"(5Z,8Z,11Z,14Z)-N-(2-hydroxyéthyl)icosa-5,8,11,14-tétraénamide","aliases":["Anandamide","N-arachidonoyléthanolamine"],"cas":"94421-68-8","pubchemCid":"5281969","chebiId":null,"smiles":"CCCCC/C=C\\C/C=C\\C/C=C\\C/C=C\\CCCC(=O)NCCO","molecularFormula":"C22H37NO2","molecularWeight":347.53,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/5281969"}},"classification":{"family":"endocannabinoide","familyLabel":"Endocannabinoide","origin":"natural","originLabel":"Naturel","structuralClassFr":null},"originSynthesis":{"heading":"Vía biosintética (in vivo)","summaryFr":"Hidrolizada a demanda a partir del N-araquidonoil-PE de membrana (NAPE-PLD), degradada por la FAAH (hidrolasa de amidas de ácidos grasos)","originNote":"Endocannabinoide","discovered":"1992"},"pharmacology":{"summaryFr":"Primer endocannabinoide caracterizado, identificado por William Devane, Lumír Hanuš y Raphael Mechoulam en 1992 (Science 258:1946) a partir de cerebro de cerdo. El nombre procede del sánscrito « ananda », beatitud. La anandamida no se almacena - se sintetiza a demanda en la cara citosólica de la membrana neuronal (la NAPE-PLD hidroliza un precursor N-araquidonoil-PE) y se degrada en unos minutos por la FAAH (hidrolasa de amidas de ácidos grasos). Afinidad ortostérica CB1 Ki ≈ 89 nM, CB2 Ki ≈ 371 nM - agonista parcial en ambos receptores. Es además agonista de TRPV1 (lo que la convierte a la vez en endocannabinoide y en endovanilloide) y sustrato de varios CYP. Es ella, y su primo el 2-AG, la que explica por qué el cerebro humano responde a los fitocannabinoides: ya portamos el sistema. Concentraciones endógenas ~10–60 pmol·g⁻¹ en el cerebro de mamífero; modulan la percepción del dolor, el estado de ánimo, el apetito, la memoria a corto plazo, la consolidación del sueño REM, la inflamación y la fertilidad. La farmacología clínica de la inhibición de la FAAH (URB597, PF-04457845) sigue siendo prometedora, pero sufrió un revés histórico con el ensayo BIA 10-2474 de Bial (2016, Rennes) - otro inhibidor de la FAAH, cuya toxicidad fuera de diana causó un fallecimiento y varias lesiones neurológicas.","receptorSummaryFr":"Agonista parcial CB1 (Ki ≈ 89 nM), agonista parcial CB2 (Ki ≈ 371 nM), agonista TRPV1 (canal vanilloide), modulador de GPR55 y PPARα","binding":[{"target":"CB1","efficacy":"partial_agonist","relativeActivity":75,"reported":"Ki ≈ 89 nM","confidence":"medium"},{"target":"CB2","efficacy":"partial_agonist","relativeActivity":35,"reported":"Ki ≈ 371 nM","confidence":"medium"},{"target":"TRPV1","efficacy":"full_agonist","relativeActivity":65,"reported":"EC50 µM range","confidence":"medium"},{"target":"GPR55","efficacy":"modulator","relativeActivity":45,"reported":"modulateur","confidence":"medium"},{"target":"PPARα","efficacy":"full_agonist","relativeActivity":40,"reported":"agoniste","confidence":"medium"}],"references":[{"label":"Devane, Hanuš & Mechoulam - Science 1992","pmid":"1470919","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/1470919/"}]},"pharmacokinetics":null,"metabolism":null,"detection":null,"subjectiveEffects":{"profile":[{"key":"calm","label":"Calma","description":"Relajación del cuerpo y de la mente; menos ruido mental, sin somnolencia marcada.","intensity":70},{"key":"focus","label":"Claridad","description":"Atención sostenida y pensamiento claro; lucidez funcional, sin euforia.","intensity":50},{"key":"sleep","label":"Sueño","description":"Efecto sedante: favorece la conciliación del sueño y la continuidad del sueño profundo.","intensity":65},{"key":"appetite","label":"Apetito","description":"Estimulación del hambre y de la apreciación gustativa (efecto «munchies»).","intensity":60},{"key":"uplift","label":"High","description":"Euforia e intensidad sensorial; percepción del tiempo y del espacio modificada.","intensity":50}],"doseRanges":null,"humanDataCharacterised":true},"indications":{"approvedMedicines":[]},"harmProfile":{"unstudiedBanner":false,"bannerTextFr":null,"toxicologyFr":null},"legal":{"scheduleStatus":"endogenous","scheduleLabel":"Endógeno","frScheduleStatus":null,"tiers":[{"jurisdiction":"international","jurisdictionLabel":"International","label":null,"reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"eu","jurisdictionLabel":"Union européenne","label":"Endógeno - no regulado","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"Endógeno - no regulado","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Devane, Hanuš & Mechoulam - Science 1992","pmid":"1470919","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/1470919/"}],"meta":{"slug":"aea","url":"https://es.phytogrammes.com/wiki/aea","lastVerified":"2026-05-01","dataUpdatedAt":"2026-05-01","confidence":"medium","dataCompletenessPct":80,"disclaimerFr":"Contenu éditorial informatif, sans valeur d'avis médical ni juridique. Sources primaires citées par fiche. Réservé aux adultes."}}