{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"MCVPMHDADNVRKF-UHFFFAOYSA-N","prefName":"Nabitan","symbol":"Nabitan","iupacName":"[5,5-dimethyl-8-(3-methyloctan-2-yl)-2-prop-2-ynyl-3,4-dihydro-1H-chromeno[4,3-c]pyridin-10-yl] 4-piperidin-1-ylbutanoate","aliases":["NABITAN","Nabitan [INN]","Nabitanum","Nabutan","Benzopyranoperidine","JO7BOR6B3O"],"cas":"66556-74-9","pubchemCid":"39503","chebiId":null,"smiles":"CCCCCC(C)C(C)C1=CC2=C(C3=C(CCN(C3)CC#C)C(O2)(C)C)C(=C1)OC(=O)CCCN4CCCCC4","molecularFormula":"C35H52N2O3","molecularWeight":548.8,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/39503"}},"classification":{"family":"ecs_tool","familyLabel":"ECS modulator (research)","origin":"synthetic","originLabel":"Synthétique","structuralClassFr":null},"originSynthesis":{"heading":"Origin (research tool)","summaryFr":"No biosynthetic pathway is known in the sources consulted. Obtained by chemical synthesis, described here by chemical class only: a benzopyrano-pyridine derivative of the tricyclic THC skeleton.","originNote":"Presented as an analogue of delta-9-THC in the 1978 clinical literature (Jochimsen et al.), and listed among the cannabinoids studied by the 2001 review (Campbell et al.). No source consulted reports it in a plant.","discovered":""},"pharmacology":{"summaryFr":"Nabitan, also called benzopyranoperidine, is an analogue of delta-9-THC described in the clinical literature. A double-blind crossover trial published in 1978 compared, in 35 patients with cancer pain, two oral doses, 2 and 4 mg, with codeine (60 and 120 mg) and with placebo: the molecule was no more effective than placebo, and pain perception appeared even increased at both doses. The 2001 systematic review (Campbell et al.) reports the same lack of superiority over placebo. No binding affinity constant for the CB1 or CB2 receptors is published in the sources consulted, and no pharmacokinetic or human safety data were found in those sources.","receptorSummaryFr":"No binding affinity constant for the CB1 or CB2 receptors was found in the sources consulted: ChEMBL holds no measured activity for this molecule. It is presented as an analogue of delta-9-THC (Jochimsen et al., 1978), which does not establish whether it is an agonist or an antagonist.","binding":[{"target":"CB1","efficacy":"modulator","relativeActivity":5,"reported":"aucune constante d'affinité publiée","confidence":"medium"}],"references":[{"label":"Jochimsen et coll., effet de la benzopyranoperidine sur la douleur, essai croisé en double aveugle, Clin Pharmacol Ther, 1978","pmid":"354840","doi":"10.1002/cpt1978242223","url":"https://pubmed.ncbi.nlm.nih.gov/354840/"},{"label":"Campbell et coll., revue systématique des cannabinoïdes dans la douleur, BMJ, 2001","pmid":"11440935","doi":"10.1136/bmj.323.7303.13","url":"https://pubmed.ncbi.nlm.nih.gov/11440935/"},{"label":"PubChem, notice du composé nabitan (CID 39503)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/39503"},{"label":"ChEMBL, fiche CHEMBL2110593 (stade clinique maximal)","pmid":null,"doi":null,"url":"https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL2110593/"},{"label":"ANSM, liste consolidée des substances classées comme stupéfiants (mise à jour du 16 février 2026)","pmid":null,"doi":null,"url":"https://ansm.sante.fr/uploads/2026/02/17/20260217-stupefiants-liste-consolidee.pdf"},{"label":"ANSM, décision du 22 mai 2024 modifiant la liste des substances classées comme stupéfiants","pmid":null,"doi":null,"url":"https://ansm.sante.fr/actualites/decision-du-22-05-2024-portant-modification-de-la-liste-des-substances-classees-comme-stupefiants"},{"label":"INCB, Green List 2026 (tableaux des conventions de 1961 et 1971)","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"}]},"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":10},{"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":5},{"key":"appetite","label":"Appetite","description":"Stimulation of hunger and of taste appreciation (the “munchies” effect).","intensity":3},{"key":"uplift","label":"High","description":"Euphoria and sensory intensity; altered perception of time and space.","intensity":3}],"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":"evolving","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 European Union level was found for this molecule in the sources consulted: control currently rests with national regimes. No marketing authorisation is documented in the sources consulted.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"Nabitan is not named under any of its names or codes in the ANSM consolidated list of narcotics (updated 16 February 2026). It also does not appear in the INCB Green List 2026. The generic clause for the benzo[c]chromene nucleus (ANSM decision of 22 May 2024) is close to its structure, but its ring A contains a nitrogen atom in place of a carbon of the skeleton: the text does not allow certainty on whether this difference takes it outside the definition. The French status is therefore marked as evolving, without a firm classification.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Jochimsen et coll., effet de la benzopyranoperidine sur la douleur, essai croisé en double aveugle, Clin Pharmacol Ther, 1978","pmid":"354840","doi":"10.1002/cpt1978242223","url":"https://pubmed.ncbi.nlm.nih.gov/354840/"},{"label":"Campbell et coll., revue systématique des cannabinoïdes dans la douleur, BMJ, 2001","pmid":"11440935","doi":"10.1136/bmj.323.7303.13","url":"https://pubmed.ncbi.nlm.nih.gov/11440935/"},{"label":"PubChem, notice du composé nabitan (CID 39503)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/39503"},{"label":"ChEMBL, fiche CHEMBL2110593 (stade clinique maximal)","pmid":null,"doi":null,"url":"https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL2110593/"},{"label":"ANSM, liste consolidée des substances classées comme stupéfiants (mise à jour du 16 février 2026)","pmid":null,"doi":null,"url":"https://ansm.sante.fr/uploads/2026/02/17/20260217-stupefiants-liste-consolidee.pdf"},{"label":"ANSM, décision du 22 mai 2024 modifiant la liste des substances classées comme stupéfiants","pmid":null,"doi":null,"url":"https://ansm.sante.fr/actualites/decision-du-22-05-2024-portant-modification-de-la-liste-des-substances-classees-comme-stupefiants"},{"label":"INCB, Green List 2026 (tableaux des conventions de 1961 et 1971)","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"}],"meta":{"slug":"nabitan","url":"https://en.phytogrammes.com/wiki/nabitan","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."}}