CBNACannabinolic acid
The acid of CBN, formed by oxidation of THCA; excluded in France from the benzo[c]chromene class.
C₂₂H₂₆O₄
CAS 2808-39-1
- Family
- PhytocannabinoidMinor
- Origin
- Degradation product
- First described
- 1965
- Molar mass
- 354.44 g/mol
Updated on
In plain terms
CBNA is the acid form of CBN. The plant does not make it directly: it appears when the acid of THC (THCA) oxidises, mostly in ageing flowers. Almost nothing is known about its effects.
Receptors and activity
Measured effects
Not characterised. No placebo-controlled human trial has measured the effects of CBNA, so no level is shown.
Levels computed from placebo-controlled human trials: difference from placebo on 100, at the dose and route stated. Read the method
Pharmacology
No biosynthetic pathway for CBNA, and therefore for CBN, has been identified; small amounts of CBNA found in some hemp samples point to oxidative degradation of THCA before decarboxylation (Maioli 2022), and a 1985 capillary gas chromatography study already classed CBN and CBNA as artefacts (Hanuš 1985). Its isolation and structure were published in 1965 by Mechoulam and Gaoni, together with those of cannabidiolic and cannabigerolic acids; a synthesis and spectroscopic characterisation were published in 2007 (Bastola 2007). Its decarboxylation gives CBN. No measurement of affinity at CB1 or CB2 receptors was found; one in vitro study reports that it mobilises intracellular calcium in human and mouse microglia (Pilchova 2026). In France, it is explicitly excluded, together with CBN, from the generic benzo[c]chromene class added to the narcotics list in 2024. No human dose has been characterised.
Key sources.
- Maioli et al. 2022, Plants: oxidative origin of CBN and CBNA (new tab)PMID 36365350
- Mechoulam & Gaoni 1965, Tetrahedron: isolation and structure of cannabinolic, cannabidiolic and cannabigerolic acids (new tab)PMID 5879350
- Hanuš & Krejčí 1985, Acta Univ Palacki Olomuc: CBN and CBNA, artefacts (new tab)PMID 3161287
- Bastola et al. 2007, Planta Med: synthesis and spectroscopic characterisation (new tab)PMID 17354173
- Pilchova et al. 2026, Cell Commun Signal: calcium in microglia (new tab)PMID 42421050
- ANSM, consolidated list of narcotics (26/06/2026) (new tab)
History
- Source
- Present in cannabis as an oxidation product of THCA
Biosynthetic pathway
No biosynthetic pathway has been identified. CBNA forms by oxidation (aromatisation) of THCA in plant material; its decarboxylation gives CBN (Maioli 2022).
Legal framework
- European Union
No EU instrument specific to the molecule. Not listed in the schedules of the 1971 Convention on Psychotropic Substances (INCB Green List, 35th edition, 2024).
- France
Explicitly excluded, together with CBN, from the generic class of benzo[c]chromene derivatives classified as narcotics (ANSM decisions of 22/05/2024 and 03/06/2024; ANSM consolidated list updated 26/06/2026). Not being a narcotic is not, in itself, an authorisation to sell. Checked on 19/10/2026.
Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.
Classification
Family, origin and source verification
- Family
Phytocannabinoid › Minor
- Presence in the plant
Artefact: formed by oxidation, light, heat or solvent
- Chemistry
Type CBN · C5 side chain · acid form
- Verification
Every fact on this entry was checked against its primary sources on 20 October 2026.
- Wikipedia (English)
No dedicated article.
References
- Maioli et al. 2022, Plants: oxidative origin of CBN and CBNA (new tab)PMID 36365350
- Mechoulam & Gaoni 1965, Tetrahedron: isolation and structure of cannabinolic, cannabidiolic and cannabigerolic acids (new tab)PMID 5879350
- Hanuš & Krejčí 1985, Acta Univ Palacki Olomuc: CBN and CBNA, artefacts (new tab)PMID 3161287
- Bastola et al. 2007, Planta Med: synthesis and spectroscopic characterisation (new tab)PMID 17354173
- Pilchova et al. 2026, Cell Commun Signal: calcium in microglia (new tab)PMID 42421050
- ANSM, consolidated list of narcotics (26/06/2026) (new tab)
Identifiers
Names
- Common name
- Cannabinolic acid
- IUPAC name
- 1-hydroxy-6,6,9-trimethyl-3-pentylbenzo[c]chromene-2-carboxylic acid
- Other names
- CBN-A
Identifiers
- Formula
- C₂₂H₂₆O₄
- CAS
- 2808-39-1
- PubChem CID
- 3081990(new tab)
- ChEBI
- 234469(new tab)
- InChIKey
- KXKOBIRSQLNUPS-UHFFFAOYSA-N
- SMILES
- CCCCCC1=
CC2= C(C3= C(C= CC(= C3) C) C(O2) (C) C) C(= C1C(= O) O) O
LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.