Machaeriol A

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.

Source

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).

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).

European Union

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.

France

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.

Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.

1. 1Muhammad et coll., dérivés (+)-trans-hexahydrodibenzopyraniques antipaludiques de Machaerium multiflorum, Journal of Natural Products 2001 (new tab)PMID 11678659
2. 2Muhammad et coll., affinités cannabinoïdes et opioïdes des machaeriols et machaeridiols de Machaerium Pers., Molecules 2023 (new tab)PMID 37241903
3. 3Haider et coll., analogues du machaeriol comme modulateurs des récepteurs cannabinoïdes, ACS Omega 2021 (new tab)PMID 34395989
4. 4Muhammad et coll., constituants antimicrobiens de Machaerium Pers. (machaeriols et machaeridiols), Molecules 2020 (new tab)PMID 33352963
5. 5ANSM, Décision du 22 mai 2024 portant modification de la liste des substances classées comme stupéfiants (clause générique benzo[c]chromène) (new tab)
6. 6ANSM, Décision du 3 juin 2024 portant modification de la liste des substances classées comme stupéfiants (new tab)
7. 7ANSM, Liste consolidée des substances classées comme stupéfiants, mise à jour du 16 février 2026 (new tab)
8. 8PubChem CID 10089121 : machaeriol A (identifiants) (new tab)

SMILES

C[C@H]1CC[C@H]2[C@H](C1)c1c(O)cc(/C=C/c3ccccc3)cc1OC2(C)C

InChIKey

KCNFZTIIENBEPU-TUCATBTLSA-N

Machine-readable entry (JSON)

LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.