{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"INXXQNIOWMOYEJ-UHFFFAOYSA-N","prefName":"CUMYL-CBMICA","symbol":"CUMYL-CBMICA","iupacName":"1-(cyclobutylmethyl)-N-(2-phenylpropan-2-yl)indole-3-carboxamide","aliases":["SGT-280","Cumyl-cbmica","GLXC-26651"],"cas":null,"pubchemCid":"155884426","chebiId":null,"smiles":"CC(C)(NC(=O)C1=CN(CC2CCC2)C2C=CC=CC=21)C1C=CC=CC=1","molecularFormula":"C23H26N2O","molecularWeight":346.5,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/155884426"}},"classification":{"family":"scra","familyLabel":"Synthetic cannabinoid (SCRA)","origin":"synthetic","originLabel":"Synthétique","structuralClassFr":null},"originSynthesis":{"heading":"Origin (pharmaceutical research → illicit market)","summaryFr":"No biosynthetic pathway: this molecule is produced by no living organism and comes solely from chemical synthesis. It results from an organic synthesis of the amide type, described here by chemical class only.","originNote":"Entirely synthetic molecule, absent from cannabis and from any other plant. It was found in herbal products (Halter et al., 2021), distributed through online shops (Haschimi et al., 2021), within the market for synthetic cannabinoids known as \"spice\" (Groth et al., 2023). It belongs to the cyclobutylmethyl (CBM) subclass of SCRAs, whose members emerged between 2019 and 2021 (Pulver et al., 2023).","discovered":""},"pharmacology":{"summaryFr":"CUMYL-CBMICA is a synthetic cannabinoid of the indole-3-carboxamide family, first identified in July 2019 by the European project ADEBAR plus. It acts on the CB1 receptor as a full agonist, with a Ki of 29.3 nM in competitive binding (Haschimi et al., 2021), a lower affinity than that of its indazole analogue, CUMYL-CBMINACA, whose Ki is 1.32 nM. It is at once the most widespread of the six SCRAs compared by Pulver et al. (2023) and the least active of them. Human data remain limited to forensic medicine observations, and the sources consulted contain neither a pharmacokinetic study nor a controlled toxicological study.","receptorSummaryFr":"A full agonist at the CB1 receptor, like the six SCRAs compared against THC by Pulver et al. (2023). In the study by Haschimi et al. (2021) on human CB1, the Ki is 29.3 nM in competitive binding, with an EC50 of 497 nM and an Emax of 168% in GTPγS. These values place the molecule clearly below its indazole analogue, CUMYL-CBMINACA, whose Ki is 1.32 nM. Cannaert et al. (2020) confirm activation of CB1 in living cells through recruitment of beta-arrestin 2. A systematic series (Janssens et al., 2023) shows that CB1 activity decreases as the ring of the side chain has fewer carbon atoms, which makes the cyclobutylmethyl version less active than its cyclopentylmethyl and cyclohexylmethyl homologues. No CB2 affinity constant is published in the sources consulted, and no other target is documented there.","binding":[{"target":"CB1","efficacy":"full_agonist","relativeActivity":76,"reported":"Ki 29,3 nM (hCB1, Haschimi et coll., 2021) ; EC50 497 nM et Emax 168 % en GTPγS (même étude)","confidence":"medium"},{"target":"CB2","efficacy":"modulator","relativeActivity":5,"reported":"aucune constante d'affinité publiée ; type d'action sur CB2 non documenté","confidence":"medium"}],"references":[{"label":"Halter et coll., identification et caractérisation du Cumyl-CBMICA, Drug Testing and Analysis, 2021","pmid":"33037749","doi":"10.1002/dta.2942","url":"https://pubmed.ncbi.nlm.nih.gov/33037749/"},{"label":"Haschimi et coll., métabolisme de phase I humain et affinité CB1 du Cumyl-CBMICA et du Cumyl-CBMINACA, Drug Testing and Analysis, 2021","pmid":"33788409","doi":"10.1002/dta.3038","url":"https://pubmed.ncbi.nlm.nih.gov/33788409/"},{"label":"Cannaert et coll., activation de CB1 in vitro par des SCRA récents dont le Cumyl-CBMICA, ACS Chemical Neuroscience, 2020","pmid":"33253529","doi":"10.1021/acschemneuro.0c00644","url":"https://pubmed.ncbi.nlm.nih.gov/33253529/"},{"label":"Janssens et coll., bibliothèque systématique de SCRA cumyle à chaînes alkyles et alicycliques, ACS Chemical Neuroscience, 2023","pmid":"36530139","doi":"10.1021/acschemneuro.2c00408","url":"https://pubmed.ncbi.nlm.nih.gov/36530139/"},{"label":"Pulver et coll., pharmacologie et prévalence en Allemagne des SCRA à chaîne cyclobutylméthyle et norbornylméthyle, Drug Testing and Analysis, 2023","pmid":"36541839","doi":"10.1002/dta.3427","url":"https://pubmed.ncbi.nlm.nih.gov/36541839/"},{"label":"Groth et coll., décès liés au « spice » autour de Munich de 2014 à 2020, International Journal of Legal Medicine, 2023","pmid":"37072496","doi":"10.1007/s00414-023-02995-2","url":"https://pubmed.ncbi.nlm.nih.gov/37072496/"},{"label":"Gampfer et coll., cytotoxicité de NPS sur cellules HepG2 par criblage à haut contenu, Toxicology, 2022","pmid":"35842060","doi":"10.1016/j.tox.2022.153258","url":"https://pubmed.ncbi.nlm.nih.gov/35842060/"},{"label":"ANSM, Liste consolidée des substances classées comme stupéfiants, mise à jour du 16 février 2026 (annexe IV, dérivés du 3-carboxamide indole)","pmid":null,"doi":null,"url":"https://ansm.sante.fr/uploads/2026/02/17/20260217-stupefiants-liste-consolidee.pdf"},{"label":"INCB, Green List 2026 (substances des tableaux de la Convention de 1971)","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"},{"label":"PubChem, Cumyl-CBMICA, CID 155884426","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/155884426"}]},"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":5},{"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":12},{"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":"No harmonised control measure at Union level is documented in the sources consulted, so control remains national. The molecule was the subject of a formal notification to the European early warning system of the EMCDDA (now EUDA) after its identification in 2019 (Halter et al., 2021). In Germany, the 2020 reform of the new psychoactive substances act placed all SCRAs with a cyclobutylmethyl side chain under control (Pulver et al., 2023).","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"This molecule is not named in the consolidated list of narcotics published by ANSM, updated on 16 February 2026. It does, however, fall within the generic clause for \"3-carboxamide indole derivatives\" in annex IV of the order of 22 February 1990. Each condition of that definition is met: the indole nitrogen carries a cycloalkylmethyl group (cyclobutylmethyl), the carboxamide bridge carries a cumyl-type substituent, and the indole ring may or may not be further substituted. It is therefore classed as a narcotic through the generic clause. Production, possession, transfer and use fall under the criminal regime for narcotics.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Halter et coll., identification et caractérisation du Cumyl-CBMICA, Drug Testing and Analysis, 2021","pmid":"33037749","doi":"10.1002/dta.2942","url":"https://pubmed.ncbi.nlm.nih.gov/33037749/"},{"label":"Haschimi et coll., métabolisme de phase I humain et affinité CB1 du Cumyl-CBMICA et du Cumyl-CBMINACA, Drug Testing and Analysis, 2021","pmid":"33788409","doi":"10.1002/dta.3038","url":"https://pubmed.ncbi.nlm.nih.gov/33788409/"},{"label":"Cannaert et coll., activation de CB1 in vitro par des SCRA récents dont le Cumyl-CBMICA, ACS Chemical Neuroscience, 2020","pmid":"33253529","doi":"10.1021/acschemneuro.0c00644","url":"https://pubmed.ncbi.nlm.nih.gov/33253529/"},{"label":"Janssens et coll., bibliothèque systématique de SCRA cumyle à chaînes alkyles et alicycliques, ACS Chemical Neuroscience, 2023","pmid":"36530139","doi":"10.1021/acschemneuro.2c00408","url":"https://pubmed.ncbi.nlm.nih.gov/36530139/"},{"label":"Pulver et coll., pharmacologie et prévalence en Allemagne des SCRA à chaîne cyclobutylméthyle et norbornylméthyle, Drug Testing and Analysis, 2023","pmid":"36541839","doi":"10.1002/dta.3427","url":"https://pubmed.ncbi.nlm.nih.gov/36541839/"},{"label":"Groth et coll., décès liés au « spice » autour de Munich de 2014 à 2020, International Journal of Legal Medicine, 2023","pmid":"37072496","doi":"10.1007/s00414-023-02995-2","url":"https://pubmed.ncbi.nlm.nih.gov/37072496/"},{"label":"Gampfer et coll., cytotoxicité de NPS sur cellules HepG2 par criblage à haut contenu, Toxicology, 2022","pmid":"35842060","doi":"10.1016/j.tox.2022.153258","url":"https://pubmed.ncbi.nlm.nih.gov/35842060/"},{"label":"ANSM, Liste consolidée des substances classées comme stupéfiants, mise à jour du 16 février 2026 (annexe IV, dérivés du 3-carboxamide indole)","pmid":null,"doi":null,"url":"https://ansm.sante.fr/uploads/2026/02/17/20260217-stupefiants-liste-consolidee.pdf"},{"label":"INCB, Green List 2026 (substances des tableaux de la Convention de 1971)","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"},{"label":"PubChem, Cumyl-CBMICA, CID 155884426","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/155884426"}],"meta":{"slug":"cumyl-cbmica","url":"https://en.phytogrammes.com/wiki/cumyl-cbmica","lastVerified":"2026-05-01","dataUpdatedAt":"2026-10-13","confidence":"high","dataCompletenessPct":90,"disclaimerFr":"Contenu éditorial informatif, sans valeur d'avis médical ni juridique. Sources primaires citées par fiche. Réservé aux adultes."}}