{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"VAKGBPSFDNTMDJ-UHFFFAOYSA-N","prefName":"THJ-018","symbol":"THJ-018","iupacName":"naphthalen-1-yl-(1-pentylindazol-3-yl)methanone","aliases":["THJ-018","(naphthalen-1-yl)(1-pentyl-1H-indazol-3-yl)methanone","1-naphthalenyl(1-pentyl-1H-indazol-3-yl)-methanone"],"cas":"1364933-55-0","pubchemCid":"124518671","chebiId":null,"smiles":"CCCCCN1C2=CC=CC=C2C(=N1)C(=O)C3=CC=CC4=CC=CC=C43","molecularFormula":"C23H22N2O","molecularWeight":342.4,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/124518671"}},"classification":{"family":"scra","familyLabel":"Synthetic cannabinoid (SCRA)","origin":"synthetic","originLabel":"Synthétique","structuralClassFr":"Naphtoylindazole. Le cœur est un indazole, le lien une fonction cétone en position 3, la queue une chaîne n-pentyle sur l'azote en position 1, et la tête un naphtalène rattaché en position 1. Le THJ-018 est l'homologue indazole du JWH-018 : le remplacement d'un carbone du cycle à cinq chaînons par un azote constitue une substitution isostère, qui conserve la géométrie du pharmacophore tout en changeant la classe chimique déclarée."},"originSynthesis":{"heading":"Origin (pharmaceutical research → illicit market)","summaryFr":"No biological route: THJ-018 is a naphthoylindazole obtained by synthesis. The skeleton combines an indazole core bearing a pentyl chain on the nitrogen at position 1, and at position 3 a ketone function linking the naphthalene ring. It is described here by chemical class only.","originNote":"A wholly synthetic molecule with no natural occurrence. It is produced outside any pharmaceutical circuit, imported as a powder, then deposited on an inert plant support or incorporated into vaping liquids. The only lawful productions are laboratory analytical standards.","discovered":"Le THJ-018 a été identifié sur le marché européen et nord-américain en 2014, aux côtés de son analogue fluoré le THJ-2201. Il procède d'une logique de contournement devenue classique : reprendre le JWH-018, agoniste de première génération largement classé, et remplacer son noyau indole par un noyau indazole, isostère qui modifie l'identité chimique sans détruire l'activité pharmacologique."},"pharmacology":{"summaryFr":"THJ-018 is a synthetic agonist of cannabinoid receptors of the naphthoylindazole family, a direct analogue of JWH-018 from which it differs only by the replacement of the indole core with an indazole core. That isosteric substitution, without major consequence for activity, sufficed to place it outside the scope of listings by name targeting JWH-018: it illustrates the very mechanism of the race between legislator and clandestine laboratories. Hess and colleagues (2016) class it among the full agonists of CB1 and CB2 receptors, with affinities in the low nanomolar to subnanomolar range, far above that of Δ9-THC. Its metabolism has been characterised on human hepatocytes by Diao and colleagues (2016), who identified thirteen metabolites, hydroxylation of the N-pentyl chain followed by oxidation or glucuronidation constituting the major routes. No human data on dose, tolerance or safety exist.","receptorSummaryFr":"A full agonist of CB1 and CB2 receptors, of high affinity. In the pharmacological evaluation of Hess and colleagues (2016), which measured by radioligand binding a broad series of synthetic cannabinoids seized in spice products, most of the compounds studied, including THJ-018, behave as full agonists at both subtypes with affinities in the low nanomolar to subnanomolar range. No interaction was demonstrated at GPR18 in this series.","binding":[{"target":"CB1","efficacy":"full_agonist","relativeActivity":92,"reported":null,"confidence":"low"},{"target":"CB2","efficacy":"full_agonist","relativeActivity":90,"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 : ni biodisponibilité, ni Tmax, ni demi-vie ne sont établis. La voie d'exposition dominante est l'inhalation de végétaux imprégnés, à laquelle s'ajoute le vapotage de liquides. Comme pour l'ensemble des agonistes de synthèse fumés, l'installation des effets est rapide et la durée courte, ce qui favorise les réadministrations rapprochées et les surdoses.","metabolism":"Diao et collaborateurs (2016) ont incubé le THJ-018 sur hépatocytes humains et détecté treize métabolites en spectrométrie de masse haute résolution. Les voies majeures sont l'hydroxylation de la chaîne N-pentyle, suivie d'une oxydation supplémentaire ou d'une glucuronidation. La formation d'un dihydrodiol sur le noyau naphtalène a également été observée, comme pour le THJ-2201. La prédiction in silico par MetaSite concordait bien avec les métabolites réellement observés pour ce composé.","detection":"Le THJ-018 n'est pas détecté par les immunoessais cannabis urinaires, qui ciblent le métabolite carboxylique du THC. L'identification exige une chromatographie liquide couplée à la spectrométrie de masse haute résolution ou en tandem. Les marqueurs urinaires recommandés par Diao et collaborateurs sont les métabolites hydroxylés de la chaîne pentyle et leurs conjugués glucuronides, la molécule mère n'étant que fugacement présente.","subjectiveEffects":{"profile":[{"key":"calm","label":"Calm","description":"Relaxation of body and mind; reduced mental noise without marked drowsiness.","intensity":18},{"key":"focus","label":"Clarity","description":"Sustained attention and clear thinking; functional lucidity, not euphoria.","intensity":10},{"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":75}],"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":"La classe des naphtoylindazoles partage le profil de risque des agonistes complets de synthèse : tachycardie, hypertension, agitation, convulsions, vomissements incoercibles et épisodes psychotiques. Aucun essai de tolérance humaine n'a jamais été conduit sur le THJ-018 et aucune dose sûre n'est caractérisée. Le risque est aggravé par l'hétérogénéité de l'imprégnation des supports végétaux, qui rend la dose réellement inhalée imprévisible."},"legal":{"scheduleStatus":"controlled-clause","scheduleLabel":"Narcotic: generic clause","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":"No harmonised control measure at Union level: THJ-018 does not appear in the annex to framework decision 2004/757/JHA, unlike its more widely diffused fluorinated analogue. It is monitored by the early warning system of the European drugs agency and controlled nationally in several Member States. It appears neither in the schedules of the convention of 1961 nor in those of the convention of 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, without listing by name. The arrêté of 31 March 2017, which amends Annex IV of the arrêté of 22 February 1990, added twelve chemical families of synthetic cannabinoids, among them that of indazol-3-yl methanones. THJ-018, a ketone linking an indazole substituted at position 1 to a naphthalene, meets that definition. 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-018","url":"https://en.phytogrammes.com/wiki/thj-018","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."}}