{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"ABBDMPBQHOHMJZ-UHFFFAOYSA-N","prefName":"CUMYL-FUBINACA","symbol":"CUMYL-FUBINACA","iupacName":"1-[(4-fluorophenyl)methyl]-N-(2-phenylpropan-2-yl)indazole-3-carboxamide","aliases":["SGT-149","Cumyl-fubinaca"],"cas":null,"pubchemCid":"117650352","chebiId":null,"smiles":"CC(C)(C1=CC=CC=C1)NC(=O)C2=NN(C3=CC=CC=C32)CC4=CC=C(C=C4)F","molecularFormula":"C24H22FN3O","molecularWeight":387.4,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/117650352"}},"classification":{"family":"scra","familyLabel":"Synthetic cannabinoid (SCRA)","origin":"synthetic","originLabel":"Synthétique","structuralClassFr":null},"originSynthesis":{"heading":"Origin (pharmaceutical research → illicit market)","summaryFr":"No biosynthetic pathway: the molecule exists in no living organism and comes exclusively from organic synthesis of the indazole-3-carboxamide class, by forming an amide bond between an indazole-3-carboxylic acid derivative bearing the fluorobenzyl group and an amine with a cumyl head. Manufacture is described here by chemical class only.","originNote":"An entirely synthetic molecule, absent from cannabis as from any living organism. It was spotted on websites and forums of users of new synthetic products during web-crawler monitoring conducted from November 2017 to May 2019, published by Zangani and colleagues in 2020, without appearing, in spring 2019, in the databases of the European drugs observatory or of the United Nations Office on Drugs and Crime.","discovered":""},"pharmacology":{"summaryFr":"CUMYL-FUBINACA (SGT-149) is a synthetic indazole-3-carboxamide that combines a 4-fluorobenzyl tail with a cumyl head. Its only experimental pharmacological characterisation found comes from Longworth and colleagues (ACS Chemical Neuroscience, 2017), who evaluated it alongside nine other carboxamides with a cumyl head: the whole series behaves there as potent and efficacious agonists at CB1 and CB2, with EC50 values of 0.43 to 12.3 nM at CB1 and a functional selectivity of 3.1 to 53 fold for CB1. No affinity constant has been found, nor any in vivo, metabolism or toxicology study concerning this molecule; no poisoning has been attributed to it in the indexed literature. It was spotted on user websites and forums during monitoring conducted from November 2017 to May 2019. Absent from the international schedules, it is nevertheless classified as a narcotic in France through the generic clause covering 3-carboxamide indazole derivatives. Human data are lacking, and no safe amount is defined.","receptorSummaryFr":"An agonist at the CB1 and CB2 receptors, with a functional preference for CB1. No affinity constant (Ki) was found in the indexed literature. The only functional data found come from the study by Longworth and colleagues (2017), which evaluated ten carboxamides with a cumyl head, this one included, in a fluorometric membrane potential assay in AtT-20 cells: the whole series behaves there as potent and efficacious agonists, with EC50 values of 0.43 to 12.3 nM at CB1 and of 11.3 to 122 nM at CB2, a selectivity of 3.1 to 53 fold in favour of CB1. According to the summary by Angerer and colleagues (2019), all these derivatives, with the exception of CUMYL-FUBICA, activate CB1 and CB2 with a potency greater than that of the reference agonist CP-55,940. In modelling, a one-microsecond molecular dynamics simulation of the CB1 receptor bound to this molecule, placed by molecular docking, shows, as for the other new psychoactive substances studied, a larger distance than for classical cannabinoids between the carbonyl of its linker and residue S383 of transmembrane helix 7, interpreted as a weaker interaction with that helix (Dutta and Shukla, 2025). No data found concern TRPV1, GPR55 or PPARγ.","binding":[{"target":"CB1","efficacy":"full_agonist","relativeActivity":75,"reported":"Aucune constante d'affinité retrouvée ; agoniste puissant et efficace en essai de potentiel de membrane sur cellules AtT-20, EC50 de la série cumyle comprises entre 0,43 et 12,3 nM (Longworth et coll., 2017)","confidence":"medium"},{"target":"CB2","efficacy":"full_agonist","relativeActivity":55,"reported":"Aucune constante d'affinité retrouvée ; EC50 de la série cumyle comprises entre 11,3 et 122 nM, sélectivité fonctionnelle de 3,1 à 53 fois pour CB1 (Longworth et coll., 2017)","confidence":"medium"}],"references":[{"label":"Longworth et coll., pharmacologie des carboxamides à tête cumyle CUMYL-BICA, CUMYL-PICA, CUMYL-5F-PICA, CUMYL-5F-PINACA et analogues, ACS Chemical Neuroscience 2017","pmid":"28792725","doi":"10.1021/acschemneuro.7b00267","url":"https://pubmed.ncbi.nlm.nih.gov/28792725/"},{"label":"Angerer et coll., le 5F-Cumyl-PINACA dans les e-liquides et synthèse de la pharmacologie des dérivés cumyle, Forensic Toxicology 2019","pmid":"30636986","doi":"10.1007/s11419-018-0451-8","url":"https://pubmed.ncbi.nlm.nih.gov/30636986/"},{"label":"Zangani et coll., les cannabinoïdes de synthèse recensés en ligne par le robot NPS.Finder, Current Neuropharmacology 2020","pmid":"32116194","doi":"10.2174/1570159X18666200302125146","url":"https://pubmed.ncbi.nlm.nih.gov/32116194/"},{"label":"Dutta et Shukla, cinétique de liaison et signalisation des nouveaux produits de synthèse au récepteur CB1 par dynamique moléculaire, eLife 2025","pmid":"41181929","doi":"10.7554/eLife.98798","url":"https://pubmed.ncbi.nlm.nih.gov/41181929/"},{"label":"ANSM, Liste consolidée des substances classées comme stupéfiants, mise à jour du 16 février 2026 (annexe IV, famille des dérivés du 3-carboxamide indazole)","pmid":null,"doi":null,"url":"https://ansm.sante.fr/uploads/2026/02/17/20260217-stupefiants-liste-consolidee.pdf"},{"label":"Légifrance, arrêté du 31 mars 2017 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants","pmid":null,"doi":null,"url":"https://www.legifrance.gouv.fr/jorf/id/JORFARTI000034372042"},{"label":"OICS, Liste verte des substances psychotropes sous contrôle international, édition 2026","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"},{"label":"PubChem, CUMYL-FUBINACA, CID 117650352","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/117650352"}]},"pharmacokinetics":null,"metabolism":null,"detection":null,"subjectiveEffects":{"profile":[{"key":"calm","label":"Calm","description":"Relaxation of body and mind; reduced mental noise without marked drowsiness.","intensity":8},{"key":"focus","label":"Clarity","description":"Sustained attention and clear thinking; functional lucidity, not euphoria.","intensity":3},{"key":"sleep","label":"Sleep","description":"Sedative effect: aids sleep onset and the continuity of deep sleep.","intensity":8},{"key":"appetite","label":"Appetite","description":"Stimulation of hunger and of taste appreciation (the “munchies” effect).","intensity":10},{"key":"uplift","label":"High","description":"Euphoria and sensory intensity; altered perception of time and space.","intensity":10}],"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":"unscheduled","scheduleLabel":"Unscheduled","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":"The molecule does not appear in the 2026 Green List of the International Narcotics Control Board, which reproduces the schedules of the 1971 Convention on Psychotropic Substances, and no harmonised control measure of the European Union targeting it has been identified. At the time of the survey published by Zangani and colleagues (2020), it appeared neither in the database of the European drugs observatory (status at 1 April 2019) nor in that of UNODC (status at 13 June 2019). Its control therefore rests with national legislation, according to their generic definitions.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"The molecule is not named in the consolidated list of narcotics published by ANSM (update of 16 February 2026), but it meets each of the conditions of the family of 3-carboxamide indazole derivatives listed in annex IV of the decree of 22 February 1990, a family added to that annex by the decree of 31 March 2017: a halobenzyl substituent, here 4-fluorobenzyl, on the nitrogen at position 1 of the indazole nucleus; an indazole nucleus with no other substituent, which the definition allows since it covers the nucleus whether substituted or not; a carboxamide nitrogen bearing a cumyl-type substituent. Its close analogues CUMYL-PINACA, 5F-CUMYL-PINACA and CUMYL-THPINACA are moreover cited as examples of this family. It therefore falls under the narcotics regime, and no product sold here contains it.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Longworth et coll., pharmacologie des carboxamides à tête cumyle CUMYL-BICA, CUMYL-PICA, CUMYL-5F-PICA, CUMYL-5F-PINACA et analogues, ACS Chemical Neuroscience 2017","pmid":"28792725","doi":"10.1021/acschemneuro.7b00267","url":"https://pubmed.ncbi.nlm.nih.gov/28792725/"},{"label":"Angerer et coll., le 5F-Cumyl-PINACA dans les e-liquides et synthèse de la pharmacologie des dérivés cumyle, Forensic Toxicology 2019","pmid":"30636986","doi":"10.1007/s11419-018-0451-8","url":"https://pubmed.ncbi.nlm.nih.gov/30636986/"},{"label":"Zangani et coll., les cannabinoïdes de synthèse recensés en ligne par le robot NPS.Finder, Current Neuropharmacology 2020","pmid":"32116194","doi":"10.2174/1570159X18666200302125146","url":"https://pubmed.ncbi.nlm.nih.gov/32116194/"},{"label":"Dutta et Shukla, cinétique de liaison et signalisation des nouveaux produits de synthèse au récepteur CB1 par dynamique moléculaire, eLife 2025","pmid":"41181929","doi":"10.7554/eLife.98798","url":"https://pubmed.ncbi.nlm.nih.gov/41181929/"},{"label":"ANSM, Liste consolidée des substances classées comme stupéfiants, mise à jour du 16 février 2026 (annexe IV, famille des dérivés du 3-carboxamide indazole)","pmid":null,"doi":null,"url":"https://ansm.sante.fr/uploads/2026/02/17/20260217-stupefiants-liste-consolidee.pdf"},{"label":"Légifrance, arrêté du 31 mars 2017 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants","pmid":null,"doi":null,"url":"https://www.legifrance.gouv.fr/jorf/id/JORFARTI000034372042"},{"label":"OICS, Liste verte des substances psychotropes sous contrôle international, édition 2026","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"},{"label":"PubChem, CUMYL-FUBINACA, CID 117650352","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/117650352"}],"meta":{"slug":"cumyl-fubinaca","url":"https://en.phytogrammes.com/wiki/cumyl-fubinaca","lastVerified":"2026-05-01","dataUpdatedAt":"2026-10-12","confidence":"high","dataCompletenessPct":90,"disclaimerFr":"Contenu éditorial informatif, sans valeur d'avis médical ni juridique. Sources primaires citées par fiche. Réservé aux adultes."}}