Minor phytocannabinoid
UnscheduledCBECannabielsoin
(5aS,6S,9R,9aR)-6-methyl-3-pentyl-9-prop-1-en-2-yl-7,8,9,9a-tetrahydro-5aH-dibenzofuran-1,6-diol
Aliases.cannabielsoin · CBE-C5 · Cannabielsoin A · S-CBE
An oxidation product of CBD with a benzofuran ring, a weak and biased CB1 agonist.
Updated on
Level of detail
Harm-reduction warning
No characterised human dose: animal / in vitro data only. Effect profile, safety margin and acute toxicity are not documented in human clinical practice. Extremely potent compound: severe effects, seizures and deaths reported in the literature.
Identifiers
- Formula
- C₂₁H₃₀O₃
- Molar mass
- 330.50 g·mol⁻¹
- CAS
- 52025-76-0
- PubChem CID
- 162113
- First described
- Décrite dans les années 1970 comme produit d'oxydation du cannabidiol, puis identifiée en 1988 comme métabolite du CBD formé par les enzymes microsomales hépatiques.
- Origin
- A minor molecule arising from the oxidation of cannabidiol (CBD); it is found in trace amounts in hemp that has aged or been exposed to air and light, as well as as a metabolite of CBD in mammals.
- InChIKey
- RBEAVAMWZAJWOI-MTOHEIAKSA-N
In plain terms
Cannabielsoin (CBE) is a minor cannabinoid that appears when CBD oxidises on contact with air and light, or when the body transforms it.
Receptors and activity
- CB1EC50 ≈ 3,7 µM (1,23 µg/mL, dosage AMPc)Partial agonist
- CB1 β-arrestineModulator
- Agonist
- Partial agonist
- Antagonist
- Modulator
- Inverse agonist
Hover over a row for the precise value (Ki, EC50…)
Subjective signature
Hover over an axis to read its definition.
- Calm38
- Clarity20
- Sleep30
- Appetite20
- High18
Editorial estimate, not clinical.
Pharmacology
Cannabielsoin (CBE) is a minor cannabinoid arising from the oxidation of cannabidiol, recognisable by its distinctive dibenzofuran ring. A 2024 in vitro study describes it as a weak and biased agonist at the CB1 receptor (EC50 ≈ 3.7 µM in the cAMP assay), with no activity on the β-arrestin pathway, which clearly distinguishes it from the CBD it derives from. It also appears as a hepatic metabolite of CBD, formed via an epoxide intermediate by the cytochrome P-450 system.
Key sources.
- Cannabielsoin (CBE), a CBD Oxidation Product, Is a Biased CB1 Agonist : Biomedicines 2024PMID 39062125
- Identification of cannabielsoin, a new metabolite of cannabidiol formed by guinea-pig hepatic microsomal enzymesPMID 3254981
- Cannabielsoin as a new metabolite of cannabidiol in mammals : Life Sciences 1991
- PubChem CID 162113 : Cannabielsoin
Biosynthetic pathway
Cannabielsoin is formed by oxidation of cannabidiol: CBD is first converted into an epoxide (1S,2R-epoxy-CBD) which spontaneously rearranges by closing a furan ring to give cannabielsoin. A second pathway starts from cannabidiolic acid (CBDA), oxidised to cannabielsoinic acid (CBEA) and then decarboxylated.
Legal framework
France
Cannabielsoin is not a THC-type cannabinoid: its benzofuran ring does not fall under the generic clause covering benzo[c]chromene derivatives. A minor molecule not designated by name by the French narcotics regulations; its status follows the general regime applicable to cannabis derivatives, with no specific text scheduling it to date.
European Union
No specific listing at European Union level; a minor cannabinoid that is not listed, liable to be monitored as a new psychoactive substance should a pattern of use develop.
Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.
Structural classification
- Class
- Minor phytocannabinoid
- Origin
- A minor molecule arising from the oxidation of cannabidiol (CBD); it is found in trace amounts in hemp that has aged or been exposed to air and light, as well as as a metabolite of CBD in mammals.
- Status
- Unscheduled
Cannabinoïde de type cannabielsoïne, bâti sur un noyau dibenzofuranique (benzofurane) qui distingue cette famille des cannabinoïdes classiques à noyau résorcinol ou benzo[c]chromène.
Metabolism
La cannabielsoïne est elle-même un métabolite du CBD : sa formation est localisée dans les microsomes hépatiques et dépend du système mono-oxygénase à cytochrome P-450, avec besoin de NADPH et d'oxygène moléculaire, via l'intermédiaire époxyde.
References
- 1.Cannabielsoin (CBE), a CBD Oxidation Product, Is a Biased CB1 Agonist : Biomedicines 2024PMID 39062125
- 2.Identification of cannabielsoin, a new metabolite of cannabidiol formed by guinea-pig hepatic microsomal enzymesPMID 3254981
- 3.Cannabielsoin as a new metabolite of cannabidiol in mammals : Life Sciences 1991
- 4.PubChem CID 162113 : Cannabielsoin
Structured data
- InChIKey
- RBEAVAMWZAJWOI-MTOHEIAKSA-N
- SMILES
- CCCCCC1=CC(=C2[C@H]3[C@@H](CC[C@]([C@H]3OC2=C1)(C)O)C(=C)C)O
- Formula
- C21H30O3
- Molar mass
- 330.50 g·mol⁻¹
- CAS
- 52025-76-0
- PubChem CID
- 162113
LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.