{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"WDXXEUARVHTWQF-DLBZAZTESA-N","prefName":"Cannabidiol hydroxyquinone","symbol":"HU-331","iupacName":"3-hydroxy-2-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylcyclohexa-2,5-diene-1,4-dione","aliases":["HU-331","Cannabidiol hydroxyquinone","CBDHQ","CBD-quinone","Quinone du cannabidiol"],"cas":"137252-25-6","pubchemCid":"11393311","chebiId":"CHEBI:197014","smiles":"CCCCCC1=CC(=O)C(=C(C1=O)O)[C@@H]2C=C(CC[C@H]2C(=C)C)C","molecularFormula":"C21H28O3","molecularWeight":328.4,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/11393311","chebi":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:CHEBI:197014"}},"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: HU-331 derives from cannabidiol by oxidation of the resorcinol core into a quinone. This is a chemical transformation of the oxidation class, not an enzymatic pathway of the plant.","originNote":"An oxidation product of cannabidiol: the resorcinol core of CBD is converted into a hydroxy-para-quinone. It was prepared and studied at the Hebrew University of Jerusalem, hence the prefix HU.","discovered":""},"pharmacology":{"summaryFr":"HU-331, or cannabidiol hydroxyquinone, is the para-quinone obtained by oxidation of cannabidiol, described in 2004 by Kogan, Mechoulam and colleagues together with the quinones of Δ8-THC and cannabinol. All three compounds showed antiproliferative activity on human cancer cell lines in vitro. Later work identified its mechanism: a highly specific inhibition of topoisomerase II, with no cell cycle arrest, no apoptosis of tumour cells and no production of reactive oxygen species. A 2014 study specifies that it is a catalytic inhibitor of topoisomerase IIα, which does not cause DNA strand breaks. In mice bearing tumour grafts, a 2007 comparison describes it as less cardiotoxic than doxorubicin; in HT-29 colon carcinoma, tumour weight in the treated group was 54 % lower than in the control group. No human trial has been conducted.","receptorSummaryFr":"The described target of HU-331 is not a cannabinoid receptor but an enzyme, DNA topoisomerase II, which it inhibits with no significant effect on topoisomerase I. A 2014 biochemical study on purified human topoisomerase IIα classes it among catalytic inhibitors: it blocks DNA relaxation at micromolar concentrations without causing strand breaks, through non-competitive inhibition of the ATPase activity that is sensitive to reducing agents. It is also antiangiogenic: it inhibits angiogenesis from 300 nM by directly inducing apoptosis of vascular endothelial cells.","binding":[{"target":"Topoisomérase IIα","efficacy":"antagonist","relativeActivity":80,"reported":"inhibiteur catalytique : bloque la relaxation de l'ADN à des concentrations micromolaires sans cassures, inhibition non compétitive de l'ATPase (Regal et coll., 2014)","confidence":"medium"},{"target":"Angiogenèse (cellules endothéliales)","efficacy":"antagonist","relativeActivity":60,"reported":"inhibition significative dès 300 nM sur anneau aortique de rat (Kogan et coll., 2006)","confidence":"medium"}],"references":[{"label":"Kogan, Mechoulam et coll., synthèse et activité antitumorale de dérivés quinoniques de cannabinoïdes, Journal of Medicinal Chemistry 2004","pmid":"15239658","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/15239658/"},{"label":"Kogan et coll., HU-331, nouvel inhibiteur de la topoisomérase II anticancéreux dérivé d'un cannabinoïde, Molecular Cancer Therapeutics 2007","pmid":"17237277","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/17237277/"},{"label":"Kogan et coll., une quinone cannabinoïde anticancéreuse, HU-331, est plus puissante et moins cardiotoxique que la doxorubicine : étude comparative in vivo, Journal of Pharmacology and Experimental Therapeutics 2007","pmid":"17478614","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/17478614/"},{"label":"Regal et coll., HU-331 est un inhibiteur catalytique de la topoisomérase IIα, Chemical Research in Toxicology 2014","pmid":"25409338","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/25409338/"},{"label":"Kogan et coll., une quinone cannabinoïde inhibe l'angiogenèse en ciblant les cellules endothéliales vasculaires, Molecular Pharmacology 2006","pmid":"16571653","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/16571653/"},{"label":"Trac et coll., le produit d'oxydation du cannabidiol HU-331, quinone cannabinoïde anticancéreuse potentielle : revue narrative, Journal of Cannabis Research 2021","pmid":"33892826","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/33892826/"},{"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 11393311 : HU-331 (identifiants)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/11393311"}]},"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":2},{"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":2},{"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":0}],"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. HU-331 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. This absence of scheduling is not an authorisation: the molecule is neither an authorised medicine nor an ingredient permitted in food or cosmetics, and its use belongs exclusively to research.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Kogan, Mechoulam et coll., synthèse et activité antitumorale de dérivés quinoniques de cannabinoïdes, Journal of Medicinal Chemistry 2004","pmid":"15239658","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/15239658/"},{"label":"Kogan et coll., HU-331, nouvel inhibiteur de la topoisomérase II anticancéreux dérivé d'un cannabinoïde, Molecular Cancer Therapeutics 2007","pmid":"17237277","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/17237277/"},{"label":"Kogan et coll., une quinone cannabinoïde anticancéreuse, HU-331, est plus puissante et moins cardiotoxique que la doxorubicine : étude comparative in vivo, Journal of Pharmacology and Experimental Therapeutics 2007","pmid":"17478614","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/17478614/"},{"label":"Regal et coll., HU-331 est un inhibiteur catalytique de la topoisomérase IIα, Chemical Research in Toxicology 2014","pmid":"25409338","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/25409338/"},{"label":"Kogan et coll., une quinone cannabinoïde inhibe l'angiogenèse en ciblant les cellules endothéliales vasculaires, Molecular Pharmacology 2006","pmid":"16571653","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/16571653/"},{"label":"Trac et coll., le produit d'oxydation du cannabidiol HU-331, quinone cannabinoïde anticancéreuse potentielle : revue narrative, Journal of Cannabis Research 2021","pmid":"33892826","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/33892826/"},{"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 11393311 : HU-331 (identifiants)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/11393311"}],"meta":{"slug":"hu-331","url":"https://en.phytogrammes.com/wiki/hu-331","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."}}