{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"RSUMDJRTAFBISX-UHFFFAOYSA-N","prefName":"CB-13","symbol":"CB-13","iupacName":"naphthalen-1-yl-(4-pentoxynaphthalen-1-yl)methanone","aliases":["CB 13","CB13 compound","CRA-13","CRA13","SAB-378","NVP-SAB378","naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone"],"cas":"432047-72-8","pubchemCid":"9799417","chebiId":"CHEBI:185985","smiles":"CCCCCOC1=CC=C(C2=CC=CC=C21)C(=O)C3=CC=CC4=CC=CC=C43","molecularFormula":"C26H24O2","molecularWeight":368.5,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/9799417","chebi":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:CHEBI:185985"}},"classification":{"family":"scra","familyLabel":"Synthetic cannabinoid (SCRA)","origin":"synthetic","originLabel":"Synthétique","structuralClassFr":null},"originSynthesis":{"heading":"Origin (pharmaceutical research → illicit market)","summaryFr":"No biosynthetic pathway: CB-13 is not reported in hemp or in any living organism in the sources consulted. It is obtained by fully synthetic means, in the chemical class of naphthyl diaryl ketones. Described here by chemical class only.","originNote":"Laboratory. No natural occurrence is reported in the sources consulted: the molecule comes from pharmaceutical research, and its documented use is that of a research compound.","discovered":""},"pharmacology":{"summaryFr":"CB-13 is a synthetic molecule of the naphthyl diaryl ketone class, described in 2007 by the Novartis Institutes for BioMedical Research (Dziadulewicz et al., 2007). It binds human CB1 and CB2 receptors, with an IC50 of 15.0 nM at CB1 and 98 nM at CB2, and behaves as an agonist in functional tests. In mice, central effects appear only at a dose about ten times the median effective dose on allodynia (Slivicki et al., 2022). A phase I trial with single oral doses, in 63 healthy male volunteers divided into seven cohorts, describes it as reasonably well tolerated, with mild to moderate, dose-dependent adverse effects (Gardin et al., 2009). Repeated doses in mice, by contrast, lead to analgesic tolerance and signs of central nervous system activity (Slivicki et al., 2022). In the sources consulted, no recreational use is documented.","receptorSummaryFr":"Dual agonist of human CB1 and CB2 receptors. In the displacement assay of [3H]CP-55940 on human CB1, the IC50 is 15.0 nM; in the reversal assay of forskolin-induced cAMP, the EC50 is 6.1 nM on CB1 and 27.9 nM on CB2, the displacement IC50 on CB2 being 98 nM (Dziadulewicz et al., 2007, ChEMBL data). Maximal efficacy reaches 104.7% on CB1 and 88.4% on CB2, expressed relative to CP-55940, the reference agonist of the assay. In human sensory neurons pre-exposed to PGE2, the molecule reduces membrane excitability (Ford et al., 2021), and in mice it inhibits the high-voltage-activated calcium current of small dorsal root ganglion neurons (Ford et al., 2022). Outside the endocannabinoid system, the only data in the sources consulted are cytochrome P450 inhibition assays (see metabolism).","binding":[{"target":"CB1","efficacy":"full_agonist","relativeActivity":82,"reported":"CI50 = 15,0 nM (déplacement de [3H]CP-55940, CB1 humain) ; CE50 = 6,1 nM (inversion de l'AMPc, Dziadulewicz et coll., 2007)","confidence":"medium"},{"target":"CB2","efficacy":"full_agonist","relativeActivity":65,"reported":"CI50 = 98 nM (déplacement de [3H]CP-55940, CB2 humain) ; CE50 = 27,9 nM (Dziadulewicz et coll., 2007)","confidence":"medium"}],"references":[{"label":"Dziadulewicz et coll., naphtyl-(4-pentyloxynaphtyl)méthanone, agoniste double CB1/CB2, J Med Chem 2007","pmid":"17630726","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/17630726/"},{"label":"Gardin et coll., pharmacocinétique et tolérance en dose unique chez l'humain, Drug Metab Dispos 2009","pmid":"19144772","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/19144772/"},{"label":"Trevaskis et coll., effet alimentaire et transport lymphatique, Pharm Res 2009","pmid":"19280324","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/19280324/"},{"label":"Cluny et coll., SAB378, agoniste CB1/CB2 périphérique et motilité intestinale, J Pharmacol Exp Ther 2010","pmid":"20571060","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/20571060/"},{"label":"Pryce et coll., agonistes CB1 exclus du système nerveux central et spasticité, FASEB J 2014","pmid":"24121462","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/24121462/"},{"label":"Pryce et Baker, antidote à l'intoxication cannabinoïde et hypothermie induite par CB-13, Br J Pharmacol 2017","pmid":"28800377","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/28800377/"},{"label":"Slivicki et coll., analgésie périphérique de CB-13 et tolérance à doses répétées, Pain 2022","pmid":"34961756","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/34961756/"},{"label":"Ford NC et coll., neurones sensitifs CB1 et analgésie de CB-13, Br J Anaesth 2022","pmid":"34844727","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/34844727/"},{"label":"Ford ZK et coll., CB1 dans les ganglions rachidiens humains et effets de CB13, Front Pain Res 2021","pmid":"35295508","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/35295508/"},{"label":"Hur et coll., potentiel d'abus de AM-1248, CB-13 et PB-22, Biomol Ther 2021","pmid":"33935046","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/33935046/"},{"label":"Ummadisetty et coll., CB13 et douleur après brûlure chez le rat, Br J Pharmacol 2026","pmid":"41787689","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/41787689/"},{"label":"Hassan et coll., métabolites oxydés de CRA13 et analogues, Bioorg Med Chem 2018","pmid":"30217464","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/30217464/"},{"label":"Hassan et coll., jeu de données RMN de métabolites oxydés de CRA13, Data Brief 2018","pmid":"30364648","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/30364648/"},{"label":"Alvarez-Fuentes et coll., dosage RP-HPLC de CB13 en nanoparticules PLGA, ScientificWorldJournal 2012","pmid":"22792051","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/22792051/"},{"label":"ChEMBL, CHEMBL244403 (données d'activité du document CHEMBL1148711)","pmid":null,"doi":null,"url":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL244403"},{"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":"Arrêté du 31 mars 2017 modifiant l'arrêté du 22 février 1990 (Légifrance)","pmid":null,"doi":null,"url":"https://www.legifrance.gouv.fr/jorf/id/JORFARTI000034372042"},{"label":"INCB, Liste verte 2026 (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, CID 9799417","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/9799417"}]},"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":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":"controlled-named","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 European Union control measure has been identified for this compound in the sources consulted, so control rests on national legislation. No notification to the EU early warning system could be confirmed from a consulted source.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"Narcotic in France, by named listing. CB-13 (or CRA-13 or SAB-378), or naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl) methanone, is listed in Annex IV of the order of 22 February 1990 fixing the list of substances classified as narcotics, as amended by the order of 31 March 2017 (ANSM consolidated list, updated 16 February 2026). This annex covers substances classified in France but not under the international conventions, and the cannabinoid block also covers their isomers, stereoisomers, esters, ethers and salts.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Dziadulewicz et coll., naphtyl-(4-pentyloxynaphtyl)méthanone, agoniste double CB1/CB2, J Med Chem 2007","pmid":"17630726","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/17630726/"},{"label":"Gardin et coll., pharmacocinétique et tolérance en dose unique chez l'humain, Drug Metab Dispos 2009","pmid":"19144772","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/19144772/"},{"label":"Trevaskis et coll., effet alimentaire et transport lymphatique, Pharm Res 2009","pmid":"19280324","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/19280324/"},{"label":"Cluny et coll., SAB378, agoniste CB1/CB2 périphérique et motilité intestinale, J Pharmacol Exp Ther 2010","pmid":"20571060","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/20571060/"},{"label":"Pryce et coll., agonistes CB1 exclus du système nerveux central et spasticité, FASEB J 2014","pmid":"24121462","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/24121462/"},{"label":"Pryce et Baker, antidote à l'intoxication cannabinoïde et hypothermie induite par CB-13, Br J Pharmacol 2017","pmid":"28800377","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/28800377/"},{"label":"Slivicki et coll., analgésie périphérique de CB-13 et tolérance à doses répétées, Pain 2022","pmid":"34961756","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/34961756/"},{"label":"Ford NC et coll., neurones sensitifs CB1 et analgésie de CB-13, Br J Anaesth 2022","pmid":"34844727","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/34844727/"},{"label":"Ford ZK et coll., CB1 dans les ganglions rachidiens humains et effets de CB13, Front Pain Res 2021","pmid":"35295508","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/35295508/"},{"label":"Hur et coll., potentiel d'abus de AM-1248, CB-13 et PB-22, Biomol Ther 2021","pmid":"33935046","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/33935046/"},{"label":"Ummadisetty et coll., CB13 et douleur après brûlure chez le rat, Br J Pharmacol 2026","pmid":"41787689","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/41787689/"},{"label":"Hassan et coll., métabolites oxydés de CRA13 et analogues, Bioorg Med Chem 2018","pmid":"30217464","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/30217464/"},{"label":"Hassan et coll., jeu de données RMN de métabolites oxydés de CRA13, Data Brief 2018","pmid":"30364648","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/30364648/"},{"label":"Alvarez-Fuentes et coll., dosage RP-HPLC de CB13 en nanoparticules PLGA, ScientificWorldJournal 2012","pmid":"22792051","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/22792051/"},{"label":"ChEMBL, CHEMBL244403 (données d'activité du document CHEMBL1148711)","pmid":null,"doi":null,"url":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL244403"},{"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":"Arrêté du 31 mars 2017 modifiant l'arrêté du 22 février 1990 (Légifrance)","pmid":null,"doi":null,"url":"https://www.legifrance.gouv.fr/jorf/id/JORFARTI000034372042"},{"label":"INCB, Liste verte 2026 (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, CID 9799417","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/9799417"}],"meta":{"slug":"cb-13","url":"https://en.phytogrammes.com/wiki/cb-13","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."}}