{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"KCNFZTIIENBEPU-TUCATBTLSA-N","prefName":"Machaeriol A","symbol":"Machaeriol A","iupacName":"(6aS,9S,10aS)-6,6,9-trimethyl-3-[(E)-2-phenylethenyl]-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol","aliases":["MACHAERIOL A"],"cas":null,"pubchemCid":"10089121","chebiId":null,"smiles":"C[C@H]1CC[C@H]2[C@H](C1)c1c(O)cc(/C=C/c3ccccc3)cc1OC2(C)C","molecularFormula":"C24H28O2","molecularWeight":348.5,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/10089121"}},"classification":{"family":"mineur","familyLabel":"Minor phytocannabinoid","origin":"natural","originLabel":"Naturel","structuralClassFr":null},"originSynthesis":{"heading":"Biosynthetic pathway","summaryFr":"Biosynthetic pathway: none is described in the sources consulted for machaeriol A. Its authors classify it among the aralkyl phytocannabinoids, a rare class of phytocannabinoids produced by a higher plant, analogous to the cannabinoids of the genus Cannabis (Muhammad et al., 2023).","originNote":"Machaerium Pers. (family Fabaceae), a plant first assigned to Machaerium multiflorum. The compound was extracted from the stem bark with an ethanol extract (Muhammad et al., 2023).","discovered":""},"pharmacology":{"summaryFr":"Machaeriol A is a hexahydrodibenzopyran isolated from a plant of the genus Machaerium Pers., a legume first identified as Machaerium multiflorum, and described in 2001 by Muhammad et al. at the University of Mississippi: it is the first report of this family of compounds outside the genus Cannabis. Its structure recalls that of Δ9-THC, with a styryl chain in place of the pentyl chain. It has no CB1 affinity retained in the published studies and displaces only 24.4% of the ligand at CB2 at 10 µM, with no published Ki constant. No human data were found in the sources consulted. In France, it is classed as a narcotic under the generic clause arising from the ANSM decisions of 22 May and 3 June 2024.","receptorSummaryFr":"Machaeriol A has no CB1 affinity retained in the published studies. The 2001 binding assay judged it inactive at CB1 (Muhammad et al., 2001). In 2023 it displaced 18.4% of tritiated CP55,940 at CB1 at 10 µM and 24.4% at CB2 at the same concentration, with no published affinity constant (Muhammad et al., 2023). No functional measurement (agonist or antagonist) is published for this compound in the sources consulted. Synthetic analogues functionalized on the same scaffold, however, show CB1 and CB2 affinities (Haider et al., 2021). Outside the endocannabinoid system, machaeriol A has been tested for in vitro antibacterial activity against methicillin-resistant Staphylococcus aureus strains, without this record reproducing any values (Muhammad et al., 2020).","binding":[{"target":"CB1","efficacy":"modulator","relativeActivity":5,"reported":"aucune constante d'affinité publiée ; déplacement de 18,4 % à 10 µM (Muhammad et coll., 2023) ; aucune affinité CB1 retenue (Muhammad et coll., 2001)","confidence":"medium"},{"target":"CB2","efficacy":"modulator","relativeActivity":5,"reported":"aucune constante d'affinité publiée ; déplacement de 24,4 % à 10 µM (Muhammad et coll., 2023)","confidence":"medium"}],"references":[{"label":"Muhammad et coll., dérivés (+)-trans-hexahydrodibenzopyraniques antipaludiques de Machaerium multiflorum, Journal of Natural Products 2001","pmid":"11678659","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/11678659/"},{"label":"Muhammad et coll., affinités cannabinoïdes et opioïdes des machaeriols et machaeridiols de Machaerium Pers., Molecules 2023","pmid":"37241903","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/37241903/"},{"label":"Haider et coll., analogues du machaeriol comme modulateurs des récepteurs cannabinoïdes, ACS Omega 2021","pmid":"34395989","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/34395989/"},{"label":"Muhammad et coll., constituants antimicrobiens de Machaerium Pers. (machaeriols et machaeridiols), Molecules 2020","pmid":"33352963","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/33352963/"},{"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, Décision du 3 juin 2024 portant modification de la liste des substances classées comme stupéfiants","pmid":null,"doi":null,"url":"https://ansm.sante.fr/actualites/decision-du-03-06-2024-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":"PubChem CID 10089121 : machaeriol A (identifiants)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/10089121"}]},"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":5},{"key":"focus","label":"Clarity","description":"Sustained attention and clear thinking; functional lucidity, not euphoria.","intensity":5},{"key":"sleep","label":"Sleep","description":"Sedative effect: aids sleep onset and the continuity of deep sleep.","intensity":5},{"key":"appetite","label":"Appetite","description":"Stimulation of hunger and of taste appreciation (the “munchies” effect).","intensity":5},{"key":"uplift","label":"High","description":"Euphoria and sensory intensity; altered perception of time and space.","intensity":5}],"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":"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 European Union control measure has been identified for this compound in the sources consulted. Control therefore rests with national legislation, whose definitions can differ from one Member State to another. No European source was consulted for this compound.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"Machaeriol A is not named on the French list of narcotics. It does fall under the generic clause arising from the ANSM decisions of 22 May and 3 June 2024, which covers any substance derived from the benzo[c]chromene nucleus, hydrogenated or not on ring A, substituted at position 1 by a hydroxyl group, at position 3 by an alkenyl chain (whether or not that chain carries a ring), at position 6 by one or two alkyl groups and at position 9 by an alkyl group. Machaeriol A meets each of these conditions and falls under none of the exceptions in the text (cannabinol or CBN, cannabinolic acid or CBNA, THCV, THCA). It is therefore classed as a narcotic under this generic clause.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Muhammad et coll., dérivés (+)-trans-hexahydrodibenzopyraniques antipaludiques de Machaerium multiflorum, Journal of Natural Products 2001","pmid":"11678659","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/11678659/"},{"label":"Muhammad et coll., affinités cannabinoïdes et opioïdes des machaeriols et machaeridiols de Machaerium Pers., Molecules 2023","pmid":"37241903","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/37241903/"},{"label":"Haider et coll., analogues du machaeriol comme modulateurs des récepteurs cannabinoïdes, ACS Omega 2021","pmid":"34395989","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/34395989/"},{"label":"Muhammad et coll., constituants antimicrobiens de Machaerium Pers. (machaeriols et machaeridiols), Molecules 2020","pmid":"33352963","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/33352963/"},{"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, Décision du 3 juin 2024 portant modification de la liste des substances classées comme stupéfiants","pmid":null,"doi":null,"url":"https://ansm.sante.fr/actualites/decision-du-03-06-2024-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":"PubChem CID 10089121 : machaeriol A (identifiants)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/10089121"}],"meta":{"slug":"machaeriol-a","url":"https://en.phytogrammes.com/wiki/machaeriol-a","lastVerified":"2026-05-01","dataUpdatedAt":"2026-10-13","confidence":"high","dataCompletenessPct":90,"disclaimerFr":"Contenu éditorial informatif, sans valeur d'avis médical ni juridique. Sources primaires citées par fiche. Réservé aux adultes."}}