{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"QYNCMPYNYFYQFE-JENMUQSASA-N","prefName":"Hexahydrocannabivarin","symbol":"HHCV","iupacName":"(6aR,10aR)-6,6,9-trimethyl-3-propyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol","aliases":["hexahydrocannabivarin","HHCV","HHC-V","hexahydrocannabivarine"],"cas":null,"pubchemCid":"175224406","chebiId":null,"smiles":"CCCc1cc2OC(C)(C)[C@@H]3CCC(C)C[C@H]3c2c(O)c1","molecularFormula":"C19H28O2","molecularWeight":288.4,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/175224406"}},"classification":{"family":"semisynthetique","familyLabel":"Semi-synthetic cannabinoid","origin":"semisynthetic","originLabel":"Semi-synthétique","structuralClassFr":"Cannabinoïde semi-synthétique de la série hexahydro, à chaîne latérale propyle. Le squelette benzo[c]chromène est saturé sur le cycle carboné, ce qui supprime la double liaison du tétrahydrocannabinol et crée un centre stéréogène en position 9, d'où l'existence des épimères 9R et 9S. La chaîne latérale compte trois carbones au lieu des cinq du HHC, relation identique à celle qui unit le THCV au THC. Ce composé n'est donc pas une molécule unique en pratique, mais un couple d'épimères en proportions variables."},"originSynthesis":{"heading":"Route of preparation (chemical process)","summaryFr":"No documented plant enzymatic route for this compound. It is obtained by hydrogenation of the double bond of the carbon ring of a tetrahydrocannabivarin, which turns the tetrahydro skeleton into a hexahydro skeleton. That saturation creates a stereogenic centre at position 9 and therefore generates two epimers. The molecule is described here by chemical class only.","originNote":"A semi-synthetic compound, with no natural occurrence documented at a significant level. It is obtained by catalytic hydrogenation of a tetrahydrocannabivarin, itself arising from the cyclisation of cannabidivarin or of a related feedstock, on the model of the channel that produces HHC from hemp cannabidiol.","discovered":"L'hexahydrocannabivarine est apparue dans le sillage commercial de l'hexahydrocannabinol, dont elle est l'homologue à chaîne propyle. Sa place relève moins d'une découverte scientifique que d'une logique de marché : après le classement du HHC dans plusieurs pays européens à partir de 2023, les homologues de chaîne latérale ont été proposés comme substituts. La revue de référence sur l'hexahydrocannabinol et les cannabinoïdes semi-synthétiques apparentés, publiée par Ujváry en 2024, replace ces dérivés dans leur contexte chimique et réglementaire."},"pharmacology":{"summaryFr":"Hexahydrocannabivarin is the propyl-chain homologue of hexahydrocannabinol, obtained by hydrogenation of the carbon ring of a tetrahydrocannabivarin. Its appearance illustrates a mechanism that has become routine on the semi-synthetic cannabinoid market: when a molecule is scheduled, its side-chain homologues are offered as substitutes, without any new data accompanying that displacement. An important structural caveat must be set out at once, and it holds for this whole family: hydrogenation creates a stereogenic centre at position 9 and produces a mixture of 9R and 9S epimers whose proportions vary from lot to lot, and which are not pharmacologically equivalent. For hexahydrocannabinol, the 9R epimer is a partial CB1 agonist comparable to Δ9-THC in nature but lesser in potency, while the 9S is markedly less active. What is bought under a single name is therefore in reality a mixture of variable composition. For hexahydrocannabivarin specifically, no affinity or efficacy has been measured, and the shortening of the side chain leads one to expect a potency lower still. No human data exist.","receptorSummaryFr":"No measured affinity or efficacy value is published for hexahydrocannabivarin itself. What is known comes from the class: the epimers of hexahydrocannabinol are partial CB1 agonists comparable to Δ9-THC but less potent, the 9S epimer being the less active of the two. Shortening the side chain from five to three carbons moreover reduces affinity in the classical cannabinoid series, which leads one to expect a potency lower than that of HHC without the measurement having been made.","binding":[{"target":"CB1","efficacy":"partial_agonist","relativeActivity":25,"reported":null,"confidence":"low"},{"target":"CB2","efficacy":"partial_agonist","relativeActivity":20,"reported":null,"confidence":"low"}],"references":[{"label":"Ujváry 2024 : l'hexahydrocannabinol et les cannabinoïdes semi-synthétiques apparentés, revue générale","pmid":"37269160","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/37269160/"},{"label":"PubChem CID 175224406 : hexahydrocannabivarine","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/175224406"}]},"pharmacokinetics":"Aucune donnée, ni chez l'animal ni chez l'humain. Par analogie avec l'hexahydrocannabinol, dont la toxicologie analytique a été étudiée sur échantillons humains et sur fraction S9 de foie humain, on attend une forte lipophilie et une métabolisation hépatique importante ; rien de tout cela n'a été vérifié pour l'homologue propyle, et la variabilité épimérique complique par avance toute caractérisation.","metabolism":"Aucune étude publiée. Pour l'hexahydrocannabinol, la voie principale est l'hydroxylation en position 11 conduisant au 11-hydroxy-hexahydrocannabinol actif, puis l'oxydation en acide 11-nor-9-carboxylique, chacun de ces métabolites existant sous forme d'épimères. Une séquence analogue est attendue ici, avec les mêmes réserves : il s'agit d'une extrapolation de classe, non d'une observation.","detection":"Non détecté par les immunoessais cannabis usuels. L'identification repose sur la chromatographie liquide ou gazeuse couplée à la spectrométrie de masse haute résolution, avec une difficulté propre à cette famille : séparer les épimères et distinguer les métabolites hexahydro de ceux du THC, dont ils sont proches en masse et en fragmentation. Les méthodes développées pour l'hexahydrocannabinol servent de point de départ.","subjectiveEffects":{"profile":[{"key":"calm","label":"Calm","description":"Relaxation of body and mind; reduced mental noise without marked drowsiness.","intensity":30},{"key":"focus","label":"Clarity","description":"Sustained attention and clear thinking; functional lucidity, not euphoria.","intensity":15},{"key":"sleep","label":"Sleep","description":"Sedative effect: aids sleep onset and the continuity of deep sleep.","intensity":30},{"key":"appetite","label":"Appetite","description":"Stimulation of hunger and of taste appreciation (the “munchies” effect).","intensity":30},{"key":"uplift","label":"High","description":"Euphoria and sensory intensity; altered perception of time and space.","intensity":35}],"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":"Aucune donnée de toxicologie propre. Les risques rapportés avec l'hexahydrocannabinol, tremblements, vomissements, anxiété, confusion, malaise, tachycardie, douleur thoracique et hypertension, constituent la référence la plus proche disponible, l'intensité variant avec la teneur du produit. L'absence d'étalonnage de la teneur et la variabilité du rapport des épimères rendent tout dosage illusoire pour la personne qui consomme."},"legal":{"scheduleStatus":"evolving","scheduleLabel":"Status changing","frScheduleStatus":"controlled-clause","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 Union level and no listing under the international conventions of 1961 and 1971. Hexahydrocannabinol has been monitored by the Union's early warning system since 21 October 2022, the first semi-synthetic cannabinoid to be so; chain homologues fall under national responses, heterogeneous from one Member State to another.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"The decision of the ANSM of 13 June 2023 placed hexahydrocannabinol and two of its derivatives, the acetate (HHC-O) and hexahydrocannabiphorol (HHCP), on the list of narcotics. Hexahydrocannabivarin is not named there. It does, however, fall under the generic clause targeting derivatives of the benzo[c]chromene core, introduced by the decision of the ANSM of 22 May 2024, its hexahydrobenzo[c]chromen-1-ol skeleton meeting that definition.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Ujváry 2024 : l'hexahydrocannabinol et les cannabinoïdes semi-synthétiques apparentés, revue générale","pmid":"37269160","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/37269160/"},{"label":"PubChem CID 175224406 : hexahydrocannabivarine","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/175224406"}],"meta":{"slug":"hhcv","url":"https://en.phytogrammes.com/wiki/hhcv","lastVerified":"2026-05-01","dataUpdatedAt":"2026-08-14","confidence":"medium","dataCompletenessPct":90,"disclaimerFr":"Contenu éditorial informatif, sans valeur d'avis médical ni juridique. Sources primaires citées par fiche. Réservé aux adultes."}}