{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"UFDYTRQMIXJHTH-UHFFFAOYSA-N","prefName":"HU-345","symbol":"HU-345","iupacName":"6,6,9-trimethyl-3-pentylbenzo[c]chromene-1,4-dione","aliases":["CBNQ","6,6,9-trimethyl-3-pentyl-1H-benzo[c]chromene-1,4(6H)-dione"],"cas":null,"pubchemCid":"11198119","chebiId":null,"smiles":"CCCCCC1=CC(=O)C2=C(C1=O)OC(C3=C2C=C(C=C3)C)(C)C","molecularFormula":"C21H24O3","molecularWeight":324.4,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/11198119"}},"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: the molecule is obtained by chemical synthesis, through oxidation of cannabinol. No living organism is reported to produce it in the sources consulted.","originNote":"Semi-synthetic molecule: it derives from cannabinol (CBN) by oxidation of its phenol ring. It is not described as a constituent of cannabis in the sources consulted.","discovered":""},"pharmacology":{"summaryFr":"HU-345, or cannabinolquinone (CBNQ), is a quinone derivative of cannabinol (CBN), obtained by chemical oxidation and described in a patent application from the Hebrew University of Jerusalem filed in 2005. The patent, which groups HU-345 with other cannabinoid quinones, reports that they do not bind the CB1 and CB2 receptors up to 15 µM and that no measurable psychotropic effect is observed. In cell culture, growth of Raji lymphoma cells is inhibited by more than 50% at 6.25 µg/mL, and that of Jurkat and DU-145 cell lines at 12.5 µg/mL. In a 2020 study of phytocannabinoid oxidation, its EC50 at PPAR-γ is 23.1 µM, whereas cannabinol exceeds 25 µM. No pharmacokinetic, metabolic or human toxicology data are published in the sources consulted.","receptorSummaryFr":"No measurable affinity for the CB1 or CB2 receptors: the patent, which groups HU-345 with other cannabinoid quinones, reports that they do not bind these receptors up to 15 µM. At the nuclear receptor PPAR-γ, the EC50 is 23.1 µM (Caprioglio et al., 2020), whereas the cannabinol from which it derives exceeds 25 µM. No data were found for GPR55 or GPR18 in the sources consulted.","binding":[{"target":"CB1","efficacy":"modulator","relativeActivity":2,"reported":"Aucune liaison mesurable jusqu'à 15 µM pour l'ensemble des quinones du brevet, dont HU-345 (brevet US 8 497 299, Mechoulam et coll.)","confidence":"medium"},{"target":"CB2","efficacy":"modulator","relativeActivity":2,"reported":"Aucune liaison mesurable jusqu'à 15 µM pour l'ensemble des quinones du brevet, dont HU-345 (brevet US 8 497 299, Mechoulam et coll.)","confidence":"medium"},{"target":"PPAR-γ","efficacy":"full_agonist","relativeActivity":5,"reported":"CE50 de 23,1 µM (activation de PPAR-γ en test luciférase, Caprioglio et coll., 2020)","confidence":"medium"}],"references":[{"label":"Kogan NM et coll., Cannabinoid quinones: a review and novel observations, Molecules, 2021","pmid":"33801057","doi":"10.3390/molecules26061761","url":"https://pubmed.ncbi.nlm.nih.gov/33801057/"},{"label":"Caprioglio D et coll., The oxidation of phytocannabinoids to cannabinoquinoids, J Nat Prod, 2020","pmid":"32315173","doi":"10.1021/acs.jnatprod.9b01284","url":"https://pubmed.ncbi.nlm.nih.gov/32315173/"},{"label":"Mechoulam R, Kogan NM et coll., Compositions including quinonoid derivatives of cannabinoids for therapeutic use, brevet US 8 497 299 B2 (Yissum), 2013","pmid":null,"doi":null,"url":"https://patents.google.com/patent/US8497299B2/en"},{"label":"ChEMBL, fiche CHEMBL127671 (activités enregistrées pour HU-345, dont PPAR-γ)","pmid":null,"doi":null,"url":"https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL127671/"},{"label":"PubChem, composé CID 11198119 (HU-345)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/11198119"},{"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":"ANSM, décision du 22 mai 2024 portant modification de la liste des substances classées comme stupéfiants (clause du noyau 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":"OICS, liste verte 2026 des substances placées sous contrôle international","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"}]},"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":3},{"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":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":"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 has been identified for this molecule in the sources consulted: its status falls under national legislation. At international level, it is not listed in the 2026 green list of the INCB.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"HU-345 is not named in any annex of the order of 22 February 1990 nor in the ANSM consolidated list updated on 16 February 2026. It is not covered by the entry for tetrahydrocannabinols, their esters, ethers and salts. Its classification therefore depends on the generic clause for the benzo[c]chromene nucleus, introduced by the ANSM decision of 22 May 2024. That clause covers any derivative of this nucleus, not, partly or fully hydrogenated on ring A, substituted or not at positions 1, 2, 3, 4, 6 or 9 by the groups it lists, and expressly excludes cannabinol. HU-345 has an aromatic ring A and carries a pentyl chain at position 3, two methyls at position 6 and a methyl at position 9, which matches the list. However, its positions 1 and 4 carry quinone ketone functions, which the list does not provide for (at position 1: hydroxyl, esterified or not, or alkoxy; at position 2 or 4: carboxyl), and the text of the clause does not say whether these substitutions exclude the molecule. Its status therefore remains uncertain at this stage and must be verified before any decision. This absence of classification does not amount to 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 NM et coll., Cannabinoid quinones: a review and novel observations, Molecules, 2021","pmid":"33801057","doi":"10.3390/molecules26061761","url":"https://pubmed.ncbi.nlm.nih.gov/33801057/"},{"label":"Caprioglio D et coll., The oxidation of phytocannabinoids to cannabinoquinoids, J Nat Prod, 2020","pmid":"32315173","doi":"10.1021/acs.jnatprod.9b01284","url":"https://pubmed.ncbi.nlm.nih.gov/32315173/"},{"label":"Mechoulam R, Kogan NM et coll., Compositions including quinonoid derivatives of cannabinoids for therapeutic use, brevet US 8 497 299 B2 (Yissum), 2013","pmid":null,"doi":null,"url":"https://patents.google.com/patent/US8497299B2/en"},{"label":"ChEMBL, fiche CHEMBL127671 (activités enregistrées pour HU-345, dont PPAR-γ)","pmid":null,"doi":null,"url":"https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL127671/"},{"label":"PubChem, composé CID 11198119 (HU-345)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/11198119"},{"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":"ANSM, décision du 22 mai 2024 portant modification de la liste des substances classées comme stupéfiants (clause du noyau 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":"OICS, liste verte 2026 des substances placées sous contrôle international","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"}],"meta":{"slug":"hu-345","url":"https://en.phytogrammes.com/wiki/hu-345","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."}}