{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"XFHZHCKWTBGPFD-UHFFFAOYSA-N","prefName":"CB-25","symbol":"CB-25","iupacName":"N-cyclopropyl-11-(3-hydroxy-5-pentylphenoxy)undecanamide","aliases":["CCG-208736","DB-221616","NS00017326","orb1944655"],"cas":null,"pubchemCid":"11654304","chebiId":null,"smiles":"CCCCCC1=CC(=CC(=C1)OCCCCCCCCCCC(=O)NC2CC2)O","molecularFormula":"C25H41NO3","molecularWeight":403.6,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/11654304"}},"classification":{"family":"ecs_tool","familyLabel":"ECS modulator (research)","origin":"synthetic","originLabel":"Synthétique","structuralClassFr":null},"originSynthesis":{"heading":"Origin (research tool)","summaryFr":"No biosynthetic pathway. The molecule is a chemical synthesis product belonging to the family of olivetol-type alkylated resorcinols. No living organism is reported to produce it in the sources consulted.","originNote":"A fully synthetic molecule. No plant source is reported in the sources consulted. It belongs to the series of ligands derived from olivetol and resorcinol, which combines a 5-pentylresorcinol core, one hydroxyl of which is etherified, with an alkyloxy chain ending in an N-cyclopropyl amide.","discovered":""},"pharmacology":{"summaryFr":"CB-25 is a synthetic ligand of the cannabinoid receptors CB1 and CB2, described in 2005 by Brizzi et al. in the Journal of Medicinal Chemistry. The original study reports a Ki of 5.2 nM at CB1 and 13.0 nM at CB2 in human receptors, with affinity constants clearly lower than those of anandamide. In functional tests, it behaves mainly as a partial agonist of CB1 on mouse brain membranes, and as an inverse agonist in a cyclic AMP test on N18TG2 cells. At CB2, it behaves as a neutral antagonist (Cascio et al., 2006). In rodents, it produces dose-dependent nociception in healthy rats and attenuates both phases of the formalin test in mice. No human data are published in the sources consulted.","receptorSummaryFr":"A synthetic ligand of the human cannabinoid receptors CB1 and CB2, with a Ki of 5.2 nM at CB1 and 13.0 nM at CB2 (Brizzi et al., 2005). At CB1 it behaves mainly as a partial agonist: on mouse brain membranes, it stimulates GTPγS binding with an EC50 of 100 nM and a maximal stimulation of 48%. In N18TG2 cells, it increases forskolin-induced cyclic AMP, with an EC50 of about 20 nM, which corresponds to inverse agonist behaviour. At human CB1 expressed in CHO cells, it inhibits cyclic AMP formation with an EC50 of 1600 nM, that is 68% of the effect of CP-55,940. At CB2, it shows no agonist activity and antagonises CP-55,940-stimulated GTPγS binding on human CB2 membranes: it behaves as a neutral antagonist (Cascio et al., 2006). The authors report affinity constants clearly lower than those of anandamide, and close to those of WIN 55-212 (Brizzi et al., 2005). It also inhibits anandamide membrane transport, with an IC50 of 17 µM in RBL-2H3 cells (ChEMBL data from the same article).","binding":[{"target":"CB1","efficacy":"partial_agonist","relativeActivity":90,"reported":"Ki 5,2 nM sur CB1 humain exprimé dans des cellules COS (Brizzi et coll., 2005)","confidence":"medium"},{"target":"CB2","efficacy":"antagonist","relativeActivity":84,"reported":"Ki 13,0 nM sur CB2 humain exprimé dans des cellules COS (Brizzi et coll., 2005) ; antagonisme neutre fonctionnel (Cascio et coll., 2006)","confidence":"medium"}],"references":[{"label":"Brizzi A et coll., conception, synthèse et études de liaison de nouveaux ligands des récepteurs cannabinoïdes, J Med Chem 2005","pmid":"16279794","doi":"10.1021/jm0501533","url":"https://pubmed.ncbi.nlm.nih.gov/16279794/"},{"label":"Cascio MG et coll., pharmacologie in vitro et in vivo de ligands cannabinoïdes synthétiques dérivés de l'olivétol ou du résorcinol, Br J Pharmacol 2006","pmid":"16953186","doi":"10.1038/sj.bjp.0706888","url":"https://pubmed.ncbi.nlm.nih.gov/16953186/"},{"label":"ChEMBL, fiche du composé CHEMBL225506 (constantes Ki sur CB1 et CB2 humains, document CHEMBL1139484)","pmid":null,"doi":null,"url":"https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL225506/"},{"label":"PubChem, notice du composé CB-25 (CID 11654304)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/11654304"},{"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":"INCB, Liste verte 2026 (substances 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":5},{"key":"focus","label":"Clarity","description":"Sustained attention and clear thinking; functional lucidity, not euphoria.","intensity":2},{"key":"sleep","label":"Sleep","description":"Sedative effect: aids sleep onset and the continuity of deep sleep.","intensity":3},{"key":"appetite","label":"Appetite","description":"Stimulation of hunger and of taste appreciation (the “munchies” effect).","intensity":2},{"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 harmonised control measure at European Union level was found for this molecule in the sources consulted. Any control therefore falls under national legislation, without the countries concerned being specified here.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"CB-25 is not named in the consolidated list of substances classified as narcotics published by ANSM (update of 16 February 2026). Its structure does not meet the definition of the generic families of that list: it is neither a tetrahydrocannabinol nor one of its derivatives, it has neither the benzo[c]chromene skeleton, nor an indole or indazole nucleus, nor a cyclohexyl ring linked to the phenol. It is therefore not classified as a narcotic in France.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Brizzi A et coll., conception, synthèse et études de liaison de nouveaux ligands des récepteurs cannabinoïdes, J Med Chem 2005","pmid":"16279794","doi":"10.1021/jm0501533","url":"https://pubmed.ncbi.nlm.nih.gov/16279794/"},{"label":"Cascio MG et coll., pharmacologie in vitro et in vivo de ligands cannabinoïdes synthétiques dérivés de l'olivétol ou du résorcinol, Br J Pharmacol 2006","pmid":"16953186","doi":"10.1038/sj.bjp.0706888","url":"https://pubmed.ncbi.nlm.nih.gov/16953186/"},{"label":"ChEMBL, fiche du composé CHEMBL225506 (constantes Ki sur CB1 et CB2 humains, document CHEMBL1139484)","pmid":null,"doi":null,"url":"https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL225506/"},{"label":"PubChem, notice du composé CB-25 (CID 11654304)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/11654304"},{"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":"INCB, Liste verte 2026 (substances 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":"cb-25","url":"https://en.phytogrammes.com/wiki/cb-25","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."}}