{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"BUZAJRPLUGXRAB-UHFFFAOYSA-N","prefName":"AM251","symbol":"AM251","iupacName":null,"aliases":["AM-251"],"cas":"183232-66-8","pubchemCid":"2125","chebiId":null,"smiles":"CC1=C(N(N=C1C(=O)NN2CCCCC2)C3=C(C=C(C=C3)Cl)Cl)C4=CC=C(C=C4)I","molecularFormula":"C22H21Cl2IN4O","molecularWeight":555.24,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/2125"}},"classification":{"family":"ecs_tool","familyLabel":"Modulador del ECS (investigación)","origin":"synthetic","originLabel":"Synthétique","structuralClassFr":null},"originSynthesis":{"heading":"Origen (herramienta de investigación)","summaryFr":"Antagonista / agonista inverso CB1 obtenido por modificación yodada del rimonabant; síntesis orgánica (Universidad de Massachusetts)","originNote":"Investigación farmacéutica (Makriyannis)","discovered":"1996"},"pharmacology":{"summaryFr":"AM251 es el análogo yodado del rimonabant desarrollado por el grupo Makriyannis (Lan et al., J Med Chem 1999, PMID 9925732). Antagonista / agonista inverso CB1 selectivo (Ki = 7,5 nM CB1 vs 2290 nM CB2; ratio ≈ 305×). Herramienta farmacológica estándar para demostrar la mediación CB1 de un efecto observado: si el efecto queda bloqueado por AM251, es CB1-dependiente. Cabe señalar: agonista GPR55 inesperado - no utilizarlo como antagonista « limpio » en los estudios que afectan a GPR55.","receptorSummaryFr":"Antagonista / agonista inverso CB1 (Ki ≈ 7,5 nM), baja afinidad CB2 (Ki ≈ 2290 nM) - selectividad ≈ 300× por CB1","binding":[{"target":"CB1","efficacy":"inverse_agonist","relativeActivity":95,"reported":"Ki ≈ 7,5 nM","confidence":"medium"},{"target":"CB2","efficacy":"inverse_agonist","relativeActivity":20,"reported":"Ki ≈ 2290 nM","confidence":"medium"},{"target":"GPR55","efficacy":"full_agonist","relativeActivity":60,"reported":null,"confidence":"low"}],"references":[{"label":"Lan · J Med Chem 1999","pmid":"9925732","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/9925732/"}]},"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":25},{"key":"focus","label":"Claridad","description":"Atención sostenida y pensamiento claro; lucidez funcional, sin euforia.","intensity":60},{"key":"sleep","label":"Sueño","description":"Efecto sedante: favorece la conciliación del sueño y la continuidad del sueño profundo.","intensity":25},{"key":"appetite","label":"Apetito","description":"Estimulación del hambre y de la apreciación gustativa (efecto «munchies»).","intensity":15},{"key":"uplift","label":"High","description":"Euforia e intensidad sensorial; percepción del tiempo y del espacio modificada.","intensity":20}],"doseRanges":null,"humanDataCharacterised":true},"indications":{"approvedMedicines":[]},"harmProfile":{"unstudiedBanner":false,"bannerTextFr":null,"toxicologyFr":null},"legal":{"scheduleStatus":"unscheduled","scheduleLabel":"No listado","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":"No listado","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"Herramienta de investigación, no listado","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Lan · J Med Chem 1999","pmid":"9925732","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/9925732/"}],"meta":{"slug":"am251","url":"https://es.phytogrammes.com/wiki/am251","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."}}