{"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":"Cannabinoïde synthétique (SCRA)","origin":"synthetic","originLabel":"Synthétique","structuralClassFr":null},"originSynthesis":{"heading":"Origine (recherche pharmaceutique → marché illicite)","summaryFr":"Analogue 5-fluoropentyl de JWH-018 - synthétisé pour augmenter la pénétration cérébrale et la puissance CB1","originNote":"Recherche pharmaceutique (Makriyannis, UMass)","discovered":"2001"},"pharmacology":{"summaryFr":"AM-2201 est l'analogue fluoré (5-fluoropentyl) de JWH-018, synthétisé dans le programme SAR du groupe Alexandros Makriyannis (UMass, années 2000). Le fluor terminal augmente la lipophilie et la pénétration cérébrale : in vivo ≈ 9× plus puissant que JWH-018 (Wiley et al. 2014). Apparu sur le marché illicite européen 2010-2012 comme remplaçant de JWH-018 contrôlé. Convulsions et tachycardie sévères documentées (Schneir et Baumbacher 2012, PMID 22463729). Listé Annexe IV en France par l'**Arrêté du 27 juillet 2012** (NOR AFSP1230815A).","receptorSummaryFr":"Agoniste complet CB1 (Ki ≈ 1,0 nM) et CB2 (Ki ≈ 2,6 nM) - ≈ 9× plus puissant 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":"Apaisement","description":"Détente du corps et de l'esprit ; baisse du bruit mental sans somnolence marquée.","intensity":30},{"key":"focus","label":"Clarté","description":"Attention soutenue et pensée claire ; lucidité fonctionnelle, pas d'euphorie.","intensity":20},{"key":"sleep","label":"Sommeil","description":"Effet sédatif : aide à l'endormissement et à la continuité du sommeil profond.","intensity":50},{"key":"appetite","label":"Appétit","description":"Stimulation de la faim et de l'appréciation gustative (effet « munchies »).","intensity":55},{"key":"uplift","label":"High","description":"Euphorie et intensité sensorielle ; perception du temps et de l'espace modifiée.","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":"Stupéfiant : nommément listé","frScheduleStatus":null,"tiers":[{"jurisdiction":"international","jurisdictionLabel":"International","label":"Non listé","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"eu","jurisdictionLabel":"Union européenne","label":"Décision Conseil 2014/688/UE","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"Annexe IV : listé","reference":"Arrêté 27 juil 2012, NOR AFSP1230815A","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://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."}}