{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"ALQFAGFPQCBPED-UHFFFAOYSA-N","prefName":"AM-2201 (1-(5-fluoropentyl)-3-(1-naphthoyl)indole)","symbol":"AM-2201","iupacName":"[1-(5-fluoropentyl)-1H-indol-3-yl](naphthalen-1-yl)methanone","aliases":["1-(5-fluoropentyl)-3-(1-naphthoyl)indole"],"cas":"335161-24-5","pubchemCid":"53393997","chebiId":null,"smiles":"C1=CC=C2C(=C1)C=CC=C2C(=O)C3=CN(C4=CC=CC=C43)CCCCCF","molecularFormula":"C24H22FNO","molecularWeight":359.44,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/53393997"}},"classification":{"family":"scra","familyLabel":"Cannabinoide sintético (SCRA)","origin":"synthetic","originLabel":"Synthétique","structuralClassFr":null},"originSynthesis":{"heading":"Origen (investigación farmacéutica → mercado ilícito)","summaryFr":"Análogo 5-fluoropentilo de JWH-018 - sintetizado para aumentar la penetración cerebral y la potencia CB1","originNote":"Investigación farmacéutica (Makriyannis, UMass)","discovered":"2001"},"pharmacology":{"summaryFr":"El AM-2201 es el análogo fluorado (5-fluoropentilo) de JWH-018, sintetizado en el programa SAR del grupo de Alexandros Makriyannis (UMass, años 2000). El flúor terminal aumenta la lipofilia y la penetración cerebral: in vivo ≈ 9× más potente que el JWH-018 (Wiley et al. 2014). Apareció en el mercado ilícito europeo 2010-2012 como sustituto del JWH-018 controlado. Convulsiones y taquicardia graves documentadas (Schneir y Baumbacher 2012, PMID 22463729). Listado en el Anexo IV en Francia por el **Arrêté (orden ministerial) del 27 de julio de 2012** (NOR AFSP1230815A).","receptorSummaryFr":"Agonista completo CB1 (Ki ≈ 1,0 nM) y CB2 (Ki ≈ 2,6 nM) - ≈ 9× más potente que JWH-018 in vivo","binding":[{"target":"CB1","efficacy":"full_agonist","relativeActivity":98,"reported":"Ki ≈ 1,0 nM","confidence":"medium"},{"target":"CB2","efficacy":"full_agonist","relativeActivity":95,"reported":"Ki ≈ 2,6 nM","confidence":"medium"}],"references":[{"label":"Schneir · Ann Emerg Med 2012","pmid":"22463729","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/22463729/"}]},"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":30},{"key":"focus","label":"Claridad","description":"Atención sostenida y pensamiento claro; lucidez funcional, sin euforia.","intensity":20},{"key":"sleep","label":"Sueño","description":"Efecto sedante: favorece la conciliación del sueño y la continuidad del sueño profundo.","intensity":50},{"key":"appetite","label":"Apetito","description":"Estimulación del hambre y de la apreciación gustativa (efecto «munchies»).","intensity":55},{"key":"uplift","label":"High","description":"Euforia e intensidad sensorial; percepción del tiempo y del espacio modificada.","intensity":95}],"doseRanges":null,"humanDataCharacterised":false},"indications":{"approvedMedicines":[]},"harmProfile":{"unstudiedBanner":true,"bannerTextFr":"Aucune dose humaine caractérisée : données animales / in vitro uniquement. Profil d'effet, marge de sécurité et toxicité aiguë non documentés en clinique humaine.","toxicologyFr":null},"legal":{"scheduleStatus":"controlled-named","scheduleLabel":"Estupefaciente: listado nominalmente","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":"Decisión del Consejo 2014/688/UE","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"Estupefaciente listado nominalmente","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Schneir · Ann Emerg Med 2012","pmid":"22463729","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/22463729/"}],"meta":{"slug":"am-2201","url":"https://es.phytogrammes.com/wiki/am-2201","lastVerified":"2026-05-01","dataUpdatedAt":"2026-05-01","confidence":"medium","dataCompletenessPct":90,"disclaimerFr":"Contenu éditorial informatif, sans valeur d'avis médical ni juridique. Sources primaires citées par fiche. Réservé aux adultes."}}