{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"QXACEHWTBCFNSA-ATVHPVEESA-N","prefName":"Cannabinerol","symbol":"CBNR","iupacName":"2-[(2Z)-3,7-dimethylocta-2,6-dienyl]-5-pentylbenzene-1,3-diol","aliases":["CBNR","Cannabinérol","Cannabinerol","cis-CBG","(Z)-cannabigérol"],"cas":null,"pubchemCid":"21959679","chebiId":null,"smiles":"CCCCCC1=CC(=C(C(=C1)O)C/C=C(/C)\\CCC=C(C)C)O","molecularFormula":"C21H32O2","molecularWeight":316.5,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/21959679"}},"classification":{"family":"mineur","familyLabel":"Minor phytocannabinoid","origin":"natural","originLabel":"Naturel","structuralClassFr":null},"originSynthesis":{"heading":"Biosynthetic pathway","summaryFr":"Biosynthetic pathway: cannabinerol is the analogue of cannabigerol in which the resorcinol is alkylated by a neryl unit rather than a geranyl one. Its acid form would be cannabinerolic acid, an isomer of cannabigerolic acid. The share of this pathway in the plant is not quantified in the sources consulted.","originNote":"Described in recent literature as a little-known phytocannabinoid of Cannabis sativa L. It is the geometric isomer of cannabigerol: the terpene chain is of the neryl type (Z double bond) instead of geranyl (E double bond).","discovered":""},"pharmacology":{"summaryFr":"Cannabinerol (CBNR) is the (Z) isomer of cannabigerol: its terpene chain is of the neryl type instead of geranyl. Long overlooked, it has been the subject since 2022 of transcriptomic work by a team in Messina. In the NSC-34 line, the expression profile suggests activation of the CB1 receptor and of the kinase Akt between 20 and 7.5 µM, with a rise in Neurod1 and Map2 pointing to early neuronal differentiation; a 2024 study describes the regulation of synaptic genes, including subunits of calcium, sodium and potassium channels. In a cellular model of Alzheimer's disease, pretreatment limited the loss of viability induced by the β-amyloid peptide. These results remain preliminary: no binding affinity, no animal data and no human data have been published.","receptorSummaryFr":"No affinity constant at CB1 or CB2 has been published for cannabinerol. The first study, on motor-neuron-like NSC-34 cells, interprets the transcriptomic profile as activation of the CB1 receptor followed by phosphorylation of the kinase Akt, especially between 20 and 7.5 µM, with signals of early neuronal differentiation. This is an inference from gene expression, not a binding measurement.","binding":[{"target":"CB1","efficacy":"modulator","relativeActivity":15,"reported":"activation suggérée par transcriptomique sur cellules NSC-34 ; aucune constante d'affinité publiée","confidence":"medium"},{"target":"CB2","efficacy":"modulator","relativeActivity":5,"reported":"aucune constante d'affinité publiée","confidence":"medium"}],"references":[{"label":"Valeri et coll., cannabinérol et analyse transcriptomique sur cellules NSC-34 : la dose fait-elle la différenciation neuronale, International Journal of Molecular Sciences 2022","pmid":"35886896","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/35886896/"},{"label":"Artimagnella et coll., le cannabinérol (CBNR) influence des gènes synaptiques associés au cytosquelette et aux canaux ioniques dans la lignée NSC-34, Biomedicines 2024","pmid":"38255294","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/38255294/"},{"label":"Chiricosta et coll., le cannabinérol prévient les dysfonctions du réticulum endoplasmique et des mitochondries dans un modèle in vitro de maladie d'Alzheimer, Cells 2024","pmid":"38920643","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/38920643/"},{"label":"Légifrance, annexe IV de l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants","pmid":null,"doi":null,"url":"https://www.legifrance.gouv.fr/loda/article_lc/LEGIARTI000020689963/"},{"label":"PubChem CID 21959679 : cannabinérol (identifiants)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/21959679"}]},"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":6},{"key":"focus","label":"Clarity","description":"Sustained attention and clear thinking; functional lucidity, not euphoria.","intensity":4},{"key":"sleep","label":"Sleep","description":"Sedative effect: aids sleep onset and the continuity of deep sleep.","intensity":4},{"key":"appetite","label":"Appetite","description":"Stimulation of hunger and of taste appreciation (the “munchies” effect).","intensity":4},{"key":"uplift","label":"High","description":"Euphoria and sensory intensity; altered perception of time and space.","intensity":2}],"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":"unscheduled","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 control measure of its own at European Union level. The molecule appears in no schedule of the 1961 Convention on Narcotic Drugs or of the 1971 Convention on Psychotropic Substances. It holds no marketing authorisation and no novel food authorisation under Regulation (EU) 2015/2283: it circulates only as a chemical or reference standard intended for research.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"Unscheduled substance. Cannabinerol is named in no annex of the order of 22 February 1990 and falls under no generic clause. It is not a tetrahydrocannabinol and does not derive from the benzo[c]chromene nucleus targeted by the ANSM decision of 22 May 2024: its skeleton is that of cannabigerol, a resorcinol carrying an open terpene chain, with no pyran ring.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Valeri et coll., cannabinérol et analyse transcriptomique sur cellules NSC-34 : la dose fait-elle la différenciation neuronale, International Journal of Molecular Sciences 2022","pmid":"35886896","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/35886896/"},{"label":"Artimagnella et coll., le cannabinérol (CBNR) influence des gènes synaptiques associés au cytosquelette et aux canaux ioniques dans la lignée NSC-34, Biomedicines 2024","pmid":"38255294","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/38255294/"},{"label":"Chiricosta et coll., le cannabinérol prévient les dysfonctions du réticulum endoplasmique et des mitochondries dans un modèle in vitro de maladie d'Alzheimer, Cells 2024","pmid":"38920643","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/38920643/"},{"label":"Légifrance, annexe IV de l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants","pmid":null,"doi":null,"url":"https://www.legifrance.gouv.fr/loda/article_lc/LEGIARTI000020689963/"},{"label":"PubChem CID 21959679 : cannabinérol (identifiants)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/21959679"}],"meta":{"slug":"cbnr","url":"https://en.phytogrammes.com/wiki/cbnr","lastVerified":"2026-05-01","dataUpdatedAt":"2026-10-11","confidence":"high","dataCompletenessPct":90,"disclaimerFr":"Contenu éditorial informatif, sans valeur d'avis médical ni juridique. Sources primaires citées par fiche. Réservé aux adultes."}}