{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"DULWRYKFTVFPTL-UHFFFAOYSA-N","prefName":"THJ-2201","symbol":"THJ-2201","iupacName":"[1-(5-fluoropentyl)indazol-3-yl]-naphthalen-1-ylmethanone","aliases":["THJ-2201","AM-2201 indazole analog","[1-(5-fluoropentyl)-1H-indazol-3-yl](naphthalen-1-yl)methanone"],"cas":"1801552-01-1","pubchemCid":"91864533","chebiId":null,"smiles":"C1=CC=C2C(=C1)C=CC=C2C(=O)C3=NN(C4=CC=CC=C43)CCCCCF","molecularFormula":"C23H21FN2O","molecularWeight":360.4,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/91864533"}},"classification":{"family":"scra","familyLabel":"Synthetic cannabinoid (SCRA)","origin":"synthetic","originLabel":"Synthétique","structuralClassFr":"Naphtoylindazole terminalement fluorée. Le cœur est un indazole, le lien une cétone en position 3, la queue une chaîne 5-fluoropentyle sur l'azote en position 1, et la tête un naphtalène rattaché en position 1. Le THJ-2201 combine ainsi deux stratégies de contournement : le remplacement isostère indole vers indazole, et la fluoration terminale de la chaîne latérale, deux modifications qui préservent ou renforcent l'activité tout en produisant une entité chimique nouvelle."},"originSynthesis":{"heading":"Origin (pharmaceutical research → illicit market)","summaryFr":"No biological route: THJ-2201 is a naphthoylindazole obtained by synthesis. The skeleton combines an indazole core bearing a 5-fluoropentyl chain on the nitrogen at position 1, and at position 3 a ketone function linking a naphthalene ring. It is described here by chemical class only.","originNote":"A wholly synthetic molecule with no natural occurrence. Manufactured outside any pharmaceutical circuit, it is distributed as a powder then sprayed onto inert plant supports or incorporated into vaping liquids. The only lawful productions are laboratory analytical standards.","discovered":"Identifié en 2014 sur les marchés européen et nord-américain, en même temps que le THJ-018 dont il est l'analogue terminalement fluoré. Il reprend le squelette de l'AM-2201 en substituant un noyau indazole au noyau indole. Sa diffusion a été rapide : le système d'information des laboratoires forensiques américains a enregistré 220 signalements, et l'agence antidrogue américaine l'a inscrit à son tableau I dès janvier 2015, en raison du nombre d'événements indésirables rapportés."},"pharmacology":{"summaryFr":"THJ-2201 is a full synthetic agonist of cannabinoid receptors, of the naphthoylindazole family. It is to AM-2201 what THJ-018 is to JWH-018: the indole core is replaced by an indazole, an isosteric substitution that preserves activity while changing the declared chemical class. Hess and colleagues (2016) class it among the full agonists of CB1 and CB2, of low nanomolar to subnanomolar affinity. Its diffusion was rapid and its consequences documented: 220 reports to the American forensic laboratory information system and a Schedule I listing as early as January 2015, prompted by numerous adverse events. Diao and colleagues (2016) characterised its metabolism on human hepatocytes and observed 27 metabolites, dominated by an oxidative defluorination followed by carboxylation or glucuronidation; in silico prediction clearly underestimated that defluorination. No human data on dose or tolerance exist.","receptorSummaryFr":"A full agonist of CB1 and CB2 receptors, of very high affinity. Hess and colleagues (2016) place it among the full agonists of both subtypes, with affinities measured by radioligand binding in the low nanomolar to subnanomolar range, several orders of magnitude beyond Δ9-THC. As for the rest of the series, no activity was demonstrated at the GPR18 receptor.","binding":[{"target":"CB1","efficacy":"full_agonist","relativeActivity":95,"reported":null,"confidence":"low"},{"target":"CB2","efficacy":"full_agonist","relativeActivity":93,"reported":null,"confidence":"low"}],"references":[{"label":"Hess et coll. 2016 : évaluation pharmacologique des cannabinoïdes de synthèse du « spice »","pmid":"27429655","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/27429655/"},{"label":"Diao et coll. 2016 : métabolisme du THJ-018 et du THJ-2201 sur hépatocytes humains","pmid":"26430074","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/26430074/"}]},"pharmacokinetics":"Aucune donnée de pharmacocinétique humaine publiée : biodisponibilité, Tmax et demi-vie ne sont pas caractérisés. L'exposition se fait par inhalation de végétaux imprégnés ou par vapotage. La défluoration oxydative étant une voie métabolique majeure, une partie de l'exposition se poursuit sous forme de métabolites eux-mêmes actifs sur les récepteurs, ce qui complique toute lecture simple de la durée d'effet.","metabolism":"Diao et collaborateurs (2016) ont détecté 27 métabolites après incubation sur hépatocytes humains. Les voies dominantes sont la défluoration oxydative, suivie d'une carboxylation ou d'une glucuronidation, et la glucuronidation des métabolites hydroxylés. Un dihydrodiol se forme également sur le noyau naphtalène. La prédiction in silico par MetaSite sous-estimait nettement l'importance de la défluoration oxydative, ce qui souligne la nécessité de la caractérisation expérimentale pour cette classe.","detection":"Non détecté par les immunoessais cannabis urinaires. L'identification repose sur la chromatographie liquide couplée à la spectrométrie de masse haute résolution. Diao et collaborateurs recommandent de cibler les métabolites de défluoration oxydative et leurs conjugués plutôt que la molécule mère : ce sont eux qui signent une consommation de THJ-2201, et ils permettent de la distinguer d'une exposition au THJ-018.","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":8},{"key":"sleep","label":"Sleep","description":"Sedative effect: aids sleep onset and the continuity of deep sleep.","intensity":30},{"key":"appetite","label":"Appetite","description":"Stimulation of hunger and of taste appreciation (the “munchies” effect).","intensity":40},{"key":"uplift","label":"High","description":"Euphoria and sensory intensity; altered perception of time and space.","intensity":80}],"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":"L'inscription au tableau I américain en janvier 2015 a été motivée par de nombreux événements indésirables rapportés, sur fond de 220 signalements aux laboratoires forensiques. Le profil de risque est celui des agonistes complets de synthèse : tachycardie, hypertension, agitation, convulsions, vomissements et épisodes psychotiques, avec un potentiel de dépendance et un syndrome de sevrage. Aucune dose humaine sûre n'est établie et l'hétérogénéité d'imprégnation des supports végétaux rend la dose inhalée imprévisible."},"legal":{"scheduleStatus":"controlled-named","scheduleLabel":"Narcotic: named in schedule","frScheduleStatus":"controlled-clause","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":"THJ-2201 is monitored by the early warning system of the European drugs agency and controlled nationally in many Member States, without a harmonised measure at Union level under framework decision 2004/757/JHA. Outside the Union, it has been listed in Schedule I in the United States since January 2015, classified as Class B in the United Kingdom, in Schedule II in Canada, and in Annex II in Germany. It does not appear in the schedules of the international conventions of 1961 and 1971.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"A narcotic in France by generic clause. The arrêté of 31 March 2017, amending Annex IV of the arrêté of 22 February 1990, introduced twelve chemical families of synthetic cannabinoids, including that of indazol-3-yl methanones: THJ-2201, a ketone linking an N-substituted indazole to a naphthalene, meets it. Production, possession, transfer and use are criminally punishable.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Hess et coll. 2016 : évaluation pharmacologique des cannabinoïdes de synthèse du « spice »","pmid":"27429655","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/27429655/"},{"label":"Diao et coll. 2016 : métabolisme du THJ-018 et du THJ-2201 sur hépatocytes humains","pmid":"26430074","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/26430074/"}],"meta":{"slug":"thj-2201","url":"https://en.phytogrammes.com/wiki/thj-2201","lastVerified":"2026-05-01","dataUpdatedAt":"2026-08-14","confidence":"medium","dataCompletenessPct":90,"disclaimerFr":"Contenu éditorial informatif, sans valeur d'avis médical ni juridique. Sources primaires citées par fiche. Réservé aux adultes."}}