{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"UYBGHBAVRNATET-VQTJNVASSA-N","prefName":"Cannabidiol dimethyl ether","symbol":"CBDD","iupacName":"1,3-dimethoxy-2-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylbenzene","aliases":["CBDD","Cannabidiol diméthyl éther","Cannabidiol dimethyl ether","CBD-2',6'-diméthyl éther"],"cas":"1242-67-7","pubchemCid":"3081957","chebiId":null,"smiles":"CCCCCC1=CC(=C(C(=C1)OC)[C@@H]2C=C(CC[C@H]2C(=C)C)C)OC","molecularFormula":"C23H34O2","molecularWeight":342.5,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/3081957"}},"classification":{"family":"semisynthetique","familyLabel":"Semi-synthetic cannabinoid","origin":"semisynthetic","originLabel":"Semi-synthétique","structuralClassFr":null},"originSynthesis":{"heading":"Route of preparation (chemical process)","summaryFr":"Route of preparation: CBDD is obtained by methylation of the two phenol groups of cannabidiol, itself extracted from hemp. This is a chemical transformation of the etherification class, with no enzymatic equivalent described in the plant for the dimethylated derivative.","originNote":"A derivative of cannabidiol in which the two phenolic hydroxyls are masked by methyl groups. It is studied as a research tool, mainly by the Japanese team of Shuso Takeda and Kazuhito Watanabe.","discovered":""},"pharmacology":{"summaryFr":"Cannabidiol-2',6'-dimethyl ether (CBDD) is the cannabidiol derivative whose two phenolic hydroxyls are methylated. In 2009 Takeda's team showed that this methylation strengthens the inhibition of 15-lipoxygenase: the IC50 falls from 2.56 µM for CBD to 0.28 µM for CBDD, with a selectivity above 700 over 5-lipoxygenase. Because 15-lipoxygenase takes part in the formation of oxidised LDL, CBDD was proposed as a prototype for atherosclerosis research, and a 2011 study confirms that it selectively blocks this pathway in vitro. In apolipoprotein E-deficient mice, however, it stimulated body weight gain. Its metabolism in the guinea pig goes through an epoxide, 1S,2R-epoxy-CBDD. No human data exist.","receptorSummaryFr":"The described target of CBDD is not a cannabinoid receptor but an enzyme, 15-lipoxygenase. Cannabidiol inhibits it with an IC50 of 2.56 µM; CBDD is about nine times more potent, with an IC50 of 0.28 µM, and its selectivity, expressed as the ratio of IC50 values between 5-lipoxygenase and 15-lipoxygenase, exceeds 700. A 2011 study shows that it selectively inhibits the formation of oxidised LDL through the 15-lipoxygenase pathway. No CB1 or CB2 affinity was found in the sources consulted.","binding":[{"target":"15-lipoxygénase","efficacy":"antagonist","relativeActivity":85,"reported":"CI50 0,28 µM (2,56 µM pour le CBD) ; rapport de sélectivité 5-LOX/15-LOX supérieur à 700 (Takeda et coll., 2009)","confidence":"medium"}],"references":[{"label":"Takeda et coll., le cannabidiol-2',6'-diméthyl éther, dérivé du cannabidiol, est un inhibiteur puissant et sélectif de la 15-lipoxygénase, Drug Metabolism and Disposition 2009","pmid":"19406952","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/19406952/"},{"label":"Takeda et coll., le cannabidiol-2',6'-diméthyl éther protège efficacement de l'oxydation des lipoprotéines de basse densité par la 15-lipoxygénase in vitro, Biological and Pharmaceutical Bulletin 2011","pmid":"21804214","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/21804214/"},{"label":"Takeda et coll., le cannabidiol-2',6'-diméthyl éther stimule la prise de poids chez des souris déficientes en apolipoprotéine E, Journal of Toxicological Sciences 2015","pmid":"26558454","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/26558454/"},{"label":"Gohda et coll., métabolisme in vivo et in vitro de l'éther monométhylique et de l'éther diméthylique du cannabidiol chez le cobaye, Chemical and Pharmaceutical Bulletin 1990","pmid":"2208386","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/2208386/"},{"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 3081957 : cannabidiol diméthyl éther (identifiants)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/3081957"}]},"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. CBDD is named in no annex of the order of 22 February 1990. The generic clause of Annex IV targets the ethers of tetrahydrocannabinols: CBDD is an ether of cannabidiol, not of a tetrahydrocannabinol, and it lacks the benzo[c]chromene nucleus targeted by the ANSM decision of 22 May 2024. 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":"Takeda et coll., le cannabidiol-2',6'-diméthyl éther, dérivé du cannabidiol, est un inhibiteur puissant et sélectif de la 15-lipoxygénase, Drug Metabolism and Disposition 2009","pmid":"19406952","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/19406952/"},{"label":"Takeda et coll., le cannabidiol-2',6'-diméthyl éther protège efficacement de l'oxydation des lipoprotéines de basse densité par la 15-lipoxygénase in vitro, Biological and Pharmaceutical Bulletin 2011","pmid":"21804214","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/21804214/"},{"label":"Takeda et coll., le cannabidiol-2',6'-diméthyl éther stimule la prise de poids chez des souris déficientes en apolipoprotéine E, Journal of Toxicological Sciences 2015","pmid":"26558454","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/26558454/"},{"label":"Gohda et coll., métabolisme in vivo et in vitro de l'éther monométhylique et de l'éther diméthylique du cannabidiol chez le cobaye, Chemical and Pharmaceutical Bulletin 1990","pmid":"2208386","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/2208386/"},{"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 3081957 : cannabidiol diméthyl éther (identifiants)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/3081957"}],"meta":{"slug":"cbdd","url":"https://en.phytogrammes.com/wiki/cbdd","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."}}