{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"GOZGLSHDDOJPJS-HZPDHXFCSA-N","prefName":"HU-336","symbol":"HU-336","iupacName":"(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,10,10a-tetrahydrobenzo[c]chromene-1,4-dione","aliases":["HU-336","Delta8-THCQ","Δ8-THCQ","Δ8-THC quinone","delta6-Tetrahydrocannabinol quinone"],"cas":null,"pubchemCid":"11370880","chebiId":null,"smiles":"CCCCCC1=CC(=O)C2=C(C1=O)OC([C@H]3[C@H]2CC(=CC3)C)(C)C","molecularFormula":"C21H28O3","molecularWeight":328.4,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/11370880"}},"classification":{"family":"semisynthetique","familyLabel":"Semi-synthetic cannabinoid","origin":"semisynthetic","originLabel":"Semi-synthétique","structuralClassFr":null},"originSynthesis":{"heading":"Route of preparation (chemical process)","summaryFr":"No biosynthetic pathway described: HU-336 arises from the oxidation of Δ8-THC, which converts its phenolic ring into a para-quinone, obtained by chemical synthesis for research. In vaping, its measured content rises after heated aerosolisation. The 2026 authors compare this process with the oxidation of CBD to CBDQ and consider free-radical oxidation of Δ8-THC likely, without having demonstrated it. No enzymatic pathway in the plant is described in the sources consulted.","originNote":"Oxidation product of Δ8-tetrahydrocannabinol: the phenolic ring of Δ8-THC is converted into a para-quinone. No presence in the cannabis plant is reported in the sources consulted. In 2026, a study identified it as a major constituent of commercial Δ8-THC distillates and disposable vapes, where its content rises after vaping.","discovered":""},"pharmacology":{"summaryFr":"HU-336 is the para-quinone of Δ8-tetrahydrocannabinol, an oxidation product of Δ8-THC described since the 1960s, whose para-quinone structure was confirmed in 2004 by Kogan, Mechoulam and colleagues. It showed antiproliferative activity on several human cancer cell lines in vitro, markedly lower than that of HU-331, the quinone of cannabidiol. A 2021 review judges that the closed pyran ring (ring B), which prevents free rotation of the rings, is probably unfavourable to this activity. No CB1 or CB2 affinity constant was found for the molecule itself. In 2026, a study identified it as a major constituent of commercial Δ8-THC distillates and disposable vapes, where its mean content rises from 7.72 to 22.45 nmol/mg after vaping, a mean increase of 3.67-fold, reaching 30.24 mM in one cartridge. At 8.5 µM on human bronchial cells, it alters the expression of 3139 genes at 24 h, whereas Δ8-THC produces no distinct signature. No pharmacokinetic or clinical data are published in the sources consulted.","receptorSummaryFr":"No CB1 or CB2 affinity constant was found for HU-336 in the sources consulted: ChEMBL records only one measurement for this molecule, an inhibition of cell growth taken from the 2004 article. A 2021 review reports that, in 2018 work on quinones obtained by photo-oxygenation of THC and its derivatives, introducing the para-quinone moiety was accompanied by a loss of affinity for CB1 and CB2. This finding concerns a series and gives no value for HU-336 itself: no figure from that series is repeated here. The measured activities are cellular: an antiproliferative effect on several human cancer cell lines, markedly lower than that of HU-331, and, at 8.5 µM on the 16HBE human bronchial epithelial cell line, a change in the expression of 445 genes at 12 h and 3139 genes at 24 h. The 2026 authors describe it as a reactive electrophile, which could form covalent adducts with cysteine residues, without an established mechanism.","binding":[{"target":"CB1","efficacy":"modulator","relativeActivity":3,"reported":"aucune constante d'affinité retrouvée dans les sources consultées","confidence":"medium"},{"target":"CB2","efficacy":"modulator","relativeActivity":3,"reported":"aucune constante d'affinité retrouvée dans les sources consultées","confidence":"medium"}],"references":[{"label":"Kogan, Mechoulam et coll., synthèse et activité antitumorale de dérivés quinonoïdes des cannabinoïdes, Journal of Medicinal Chemistry 2004","pmid":"15239658","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/15239658/"},{"label":"Kogan, Peters et Mechoulam, les quinones cannabinoïdes : revue et observations nouvelles, Molecules 2021","pmid":"33801057","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/33801057/"},{"label":"Galal Osman et coll., produits bioactifs de la photo-oxygénation des cannabinoïdes par l'oxygène singulet, European Journal of Medicinal Chemistry 2018","pmid":"29232588","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/29232588/"},{"label":"Love et coll., réponses transcriptomiques et fonctionnelles de cellules bronchiques humaines au Δ8-THC vapoté et à son produit d'oxydation, le Δ8-THCQ, Scientific Reports 2026","pmid":"42141046","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/42141046/"},{"label":"ANSM, décision du 22 mai 2024 portant modification de la liste des substances classées comme stupéfiants (clause générique benzo[c]chromène)","pmid":null,"doi":null,"url":"https://ansm.sante.fr/actualites/decision-du-22-05-2024-portant-modification-de-la-liste-des-substances-classees-comme-stupefiants"},{"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":"OICS, liste verte 2026 des substances psychotropes placées sous contrôle international (convention de 1971)","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"},{"label":"ChEMBL, CHEMBL2111830 : mesures enregistrées pour HU-336","pmid":null,"doi":null,"url":"https://www.ebi.ac.uk/chembl/api/data/activity.json?molecule_chembl_id=CHEMBL2111830"},{"label":"PubChem CID 11370880 : HU-336 (identifiants)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/11370880"}]},"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":"evolving","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 targets this molecule; its control falls to national legislation. It does not appear in the schedules of the 1971 Convention: the 2026 INCB Green List names, under tetrahydrocannabinol, only specifically named dibenzopyran-1-ol isomers, including Δ8-THC. HU-336, with molecular formula C21H28O3, is not one of these isomers.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"HU-336 is named in no annex of the order of 22 February 1990, nor in the ANSM consolidated list updated on 16 February 2026. It is not named in the annex III entry on tetrahydrocannabinols, their esters, ethers and salts. The generic clause for the benzo[c]chromene nucleus, from the ANSM decision of 22 May 2024 (annex IV), covers any derivative of that nucleus, fully or partially hydrogenated on ring A, substituted or not at position 1, 2, 3, 4, 6 or 9 by the groups it lists. HU-336 has a partially hydrogenated ring A, a pentyl chain at position 3, two methyls at position 6 and a methyl at position 9, which match that list. However, its positions 1 and 4 carry quinone ketone functions, which the clause does not provide for (at position 1: a hydroxyl function, esterified or not, or an alkoxy; at position 4: a carboxyl function), and its quinone ring is no longer aromatic. The text does not settle whether these substitutions exclude the molecule, so its status remains uncertain at this stage. This absence of scheduling is not an authorisation: no authorised medical, food or cosmetic use is documented in the sources consulted.","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 quinonoïdes des cannabinoïdes, Journal of Medicinal Chemistry 2004","pmid":"15239658","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/15239658/"},{"label":"Kogan, Peters et Mechoulam, les quinones cannabinoïdes : revue et observations nouvelles, Molecules 2021","pmid":"33801057","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/33801057/"},{"label":"Galal Osman et coll., produits bioactifs de la photo-oxygénation des cannabinoïdes par l'oxygène singulet, European Journal of Medicinal Chemistry 2018","pmid":"29232588","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/29232588/"},{"label":"Love et coll., réponses transcriptomiques et fonctionnelles de cellules bronchiques humaines au Δ8-THC vapoté et à son produit d'oxydation, le Δ8-THCQ, Scientific Reports 2026","pmid":"42141046","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/42141046/"},{"label":"ANSM, décision du 22 mai 2024 portant modification de la liste des substances classées comme stupéfiants (clause générique benzo[c]chromène)","pmid":null,"doi":null,"url":"https://ansm.sante.fr/actualites/decision-du-22-05-2024-portant-modification-de-la-liste-des-substances-classees-comme-stupefiants"},{"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":"OICS, liste verte 2026 des substances psychotropes placées sous contrôle international (convention de 1971)","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"},{"label":"ChEMBL, CHEMBL2111830 : mesures enregistrées pour HU-336","pmid":null,"doi":null,"url":"https://www.ebi.ac.uk/chembl/api/data/activity.json?molecule_chembl_id=CHEMBL2111830"},{"label":"PubChem CID 11370880 : HU-336 (identifiants)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/11370880"}],"meta":{"slug":"hu-336","url":"https://en.phytogrammes.com/wiki/hu-336","lastVerified":"2026-05-01","dataUpdatedAt":"2026-10-12","confidence":"high","dataCompletenessPct":90,"disclaimerFr":"Contenu éditorial informatif, sans valeur d'avis médical ni juridique. Sources primaires citées par fiche. Réservé aux adultes."}}