{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"MPJURNPNPDQYSY-LEWJYISDSA-N","prefName":"Cannabidiol-dimethylheptyl","symbol":"CBD-DMH","iupacName":"5-(2-methyloctan-2-yl)-2-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]benzene-1,3-diol","aliases":["CBD-DMH","Cannabidiol-diméthylheptyl","Cannabidiol-dimethylheptyl","DMH-CBD","1',1'-diméthylheptyl-cannabidiol"],"cas":"97452-63-6","pubchemCid":"126670","chebiId":null,"smiles":"CCCCCCC(C)(C)C1=CC(=C(C(=C1)O)[C@@H]2C=C(CC[C@H]2C(=C)C)C)O","molecularFormula":"C25H38O2","molecularWeight":370.6,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/126670"}},"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 comes from no living organism. It is obtained by organic synthesis, by coupling a resorcinol bearing a dimethylheptyl chain to the terpene fragment of cannabidiol.","originNote":"A fully synthetic molecule: an analogue of cannabidiol in which the pentyl chain is replaced by a 1,1-dimethylheptyl chain. It does not occur in hemp and serves only as a research tool.","discovered":""},"pharmacology":{"summaryFr":"Cannabidiol-dimethylheptyl (CBD-DMH) is a synthetic analogue of cannabidiol carrying the 1,1-dimethylheptyl chain. Studied from the 1980s as an anticonvulsant more active than CBD, it was the subject in 1988 of a pharmacokinetic study in dogs: terminal half-life of 2 hours, clearance of 8.3 litres per hour and low, variable oral bioavailability, from 3 to 43 % in the animals where it was detectable. Its pharmacology diverges from that of CBD: in 2019 Tham and colleagues showed that it acts at CB1 as a mixed agonist and positive allosteric modulator, whereas CBD is a negative modulator there. In 2023 Bouma and colleagues described at CB2 a dual binding mode, allosteric and orthosteric, absent in cannabidiol. No human data exist.","receptorSummaryFr":"Despite an almost identical structure, CBD-DMH does not behave like cannabidiol. At the human CB1 receptor, CBD is a negative allosteric modulator, whereas CBD-DMH is a mixed agonist and positive allosteric modulator. At CB2, a 2019 study describes it as a positive allosteric modulator of the cyclic AMP pathway and a negative modulator of β-arrestin 1 recruitment. A 2023 study details this dual binding mode: CBD-DMH allosterically modulates radioligand binding and reduces G protein activation by CP55,940, anandamide and 2-AG, while also binding competitively and acting as a partial agonist. Cannabidiol shows none of these behaviours at CB2.","binding":[{"target":"CB1","efficacy":"modulator","relativeActivity":45,"reported":"agoniste mixte et modulateur allostérique positif (Tham et coll., 2019)","confidence":"medium"},{"target":"CB2","efficacy":"modulator","relativeActivity":50,"reported":"liaison allostérique et orthostérique, agonisme partiel sur l'activation des protéines G (Bouma et coll., 2023)","confidence":"medium"}],"references":[{"label":"Tham et coll., pharmacologie allostérique et orthostérique du cannabidiol et du cannabidiol-diméthylheptyl sur les récepteurs cannabinoïdes de type 1 et 2, British Journal of Pharmacology 2019","pmid":"29981240","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/29981240/"},{"label":"Bouma et coll., double pharmacologie allostérique et orthostérique de l'analogue synthétique cannabidiol-diméthylheptyl, mais pas du cannabidiol, sur le récepteur CB2, Biochemical Pharmacology 2023","pmid":"37972874","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/37972874/"},{"label":"Samara et coll., pharmacocinétique de l'homologue diméthylheptyle du cannabidiol chez le chien, Drug Metabolism and Disposition 1988","pmid":"2907468","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/2907468/"},{"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 126670 : cannabidiol-diméthylheptyl (identifiants)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/126670"}]},"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. CBD-DMH is named in no annex of the order of 22 February 1990 and falls under no generic clause: it is not a tetrahydrocannabinol and it lacks the benzo[c]chromene nucleus targeted by the ANSM decision of 22 May 2024, its open skeleton being that of cannabidiol. This absence of scheduling is not an authorisation: the molecule has no status as a medicine, food ingredient or cosmetic.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Tham et coll., pharmacologie allostérique et orthostérique du cannabidiol et du cannabidiol-diméthylheptyl sur les récepteurs cannabinoïdes de type 1 et 2, British Journal of Pharmacology 2019","pmid":"29981240","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/29981240/"},{"label":"Bouma et coll., double pharmacologie allostérique et orthostérique de l'analogue synthétique cannabidiol-diméthylheptyl, mais pas du cannabidiol, sur le récepteur CB2, Biochemical Pharmacology 2023","pmid":"37972874","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/37972874/"},{"label":"Samara et coll., pharmacocinétique de l'homologue diméthylheptyle du cannabidiol chez le chien, Drug Metabolism and Disposition 1988","pmid":"2907468","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/2907468/"},{"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 126670 : cannabidiol-diméthylheptyl (identifiants)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/126670"}],"meta":{"slug":"cbd-dmh","url":"https://en.phytogrammes.com/wiki/cbd-dmh","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."}}