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From the plant

CBECannabielsoin

A dibenzofuran oxidation product of CBD, also an animal metabolite of CBD; a partial CB1 agonist in vitro (one study).

Unscheduled
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.

C₂₁H₃₀O₃

CAS 52025-76-0

Family
PhytocannabinoidMinor
Origin
Degradation product
Molar mass
330.50 g/mol

Updated on

In plain terms

Cannabielsoin (CBE) forms when CBD oxidises, in cannabis as well as in the body of some animals given CBD. A single laboratory study has tested it at the CB1 receptor, which it activates weakly. No human study has been published.

Receptors and activity

Target network

CB1Partial agonistEC50 = 3.7 µM · humaninhibition of forskolin-stimulated cAMP, CHO-K1 (cAMP Hunter); about 60% of the CP55940 Emax at 12 µM
  • Activates
  • Blocks or inhibits

The lower the cited value, the closer the target sits to CBE: one ring per factor of 100. A target with no measured value stays on the edge.

Where these targets live

Where each target has been found in humans, according to the cited studies. The map shows the target, not an effect of CBE.

Brain, side view
Body, front view
Blood

CB1CB1 found in 7 regions of the body

  1. Basal gangliadenseMost dense in basal ganglia outflow nuclei1
  2. CerebellumdenseVery dense in the cerebellum1
  3. HippocampusdenseVery high concentrations in the hippocampus2
  4. AmygdaladenseHigh concentrations in the amygdala2
  5. CortexpresentPresent throughout the neocortex2
  6. Adipose tissuepresentExpressed in adipose tissue3
  7. GutpresentColonic epithelium, smooth muscle and plexus4

Map sources

  1. Herkenham M et al. Cannabinoid receptor localization in brain. Proc Natl Acad Sci U S A, 1990 (new tab)
  2. Glass M et al. Cannabinoid receptors in the human brain: a detailed anatomical and quantitative autoradiographic study in the fetal, neonatal and adult human brain. Neuroscience, 1997 (new tab)
  3. Engeli S et al. Activation of the peripheral endocannabinoid system in human obesity. Diabetes, 2005 (new tab)
  4. Wright K et al. Differential expression of cannabinoid receptors in the human colon: cannabinoids promote epithelial wound healing. Gastroenterology, 2005 (new tab)

Cited values

  1. CB1Partial agonistEC50 = 3.7 µM · human24 out of 100

    Haghdoost et al. 2024, Biomedicines (funded by Charlotte's Web) (new tab) · inhibition of forskolin-stimulated cAMP, CHO-K1 (cAMP Hunter); about 60% of the CP55940 Emax at 12 µM

  2. CB1 (β-arrestine)Antagonistno measured value cited

    no agonism up to 12 µM; reduces the response to CP55940 from 1.34 µM, 35% of the max. effect of AM281 at 12 µM, IC50 not calculable (mouse CB1; Haghdoost 2024)

Bar length follows the measured value (Ki, Kd, EC50 or IC50), on one scale shared by every entry, from 100 µM to 0.1 nM. A target with no cited value has no bar.

Pharmacology

Cannabielsoin (CBE) was detected in 1973 in Lebanese hashish, and its configuration (5aS,6S,9R,9aR) established in 1974 (Radwan 2021). It derives from CBD by epoxidation followed by intramolecular cyclisation, which form its dibenzofuran nucleus (Caprioglio 2022); Cannabis sativa cell cultures also carry out this transformation (Hartsel 1983). In the guinea pig it is a hepatic metabolite of CBD formed by cytochrome P450 (Yamamoto 1988, 1991); in mice it had little effect on pentobarbital-induced sleep and on body temperature (Yamamoto 1988). Its formation in humans is not established. In the only in vitro receptor study, funded by Charlotte's Web, (5aS,6S,9R,9aR)-CBE acted as a partial agonist of human CB1 in a cAMP assay (EC50 = 3.72 µM, versus 0.3 nM for CP55940), without recruiting β-arrestin up to 12 µM (Haghdoost 2024).

Key sources.

History

Source
Present in cannabis as an oxidation product of CBD; also a metabolite of CBD in several mammals

Biosynthetic pathway

No plant-specific enzymatic pathway has been identified. Cannabielsoin derives from CBD by epoxidation followed by intramolecular cyclisation (Caprioglio 2022); in the guinea pig, this transformation involves cytochrome P450 and 1S,2R-epoxide intermediates (Yamamoto 1991). Cannabis sativa cell cultures also convert CBD into CBE (Hartsel 1983). A route through cannabielsoic acid (CBEA), formed by oxidation of CBDA and then decarboxylated, has been proposed (Haghdoost 2024).

Classification

Family, origin and source verification

Family

Phytocannabinoid › Minor

Presence in the plant

Artefact: formed by oxidation, light, heat or solvent

Chemistry

Type CBE · C5 side chain · neutral form

Verification

Every fact on this entry was checked against its primary sources on 20 October 2026.

Wikipedia (English)

Cannabielsoin (new tab)

Article paired by the molecule's structure (InChIKey), revision read on 19 October 2026. Read as a second opinion, never cited as a source.

References

  1. Haghdoost et al. 2024, Biomedicines: CBE, biased CB1 agonist (funded by Charlotte's Web) (new tab)PMID 39062125
  2. Yamamoto et al. 1988, J Pharmacobiodyn 11:833: CBE, metabolite of CBD (guinea pig microsomes) (new tab)PMID 3254981
  3. Yamamoto et al. 1991, Pharmacol Biochem Behav 40:541: CBE, metabolite of CBD in mammals (new tab)PMID 1806944
  4. Hartsel et al. 1983, Planta Med 48:17: biotransformation of CBD into CBE by cell cultures (new tab)PMID 17404934
  5. Radwan et al. 2021, Molecules: CBE type (new tab)PMID 34066753
  6. Caprioglio et al. 2022, Biomolecules: formation of CBE from CBD (new tab)PMID 36008978

Identifiers

Names

Common name
Cannabielsoin
IUPAC name
(5aS,6S,9R,9aR)-6-methyl-3-pentyl-9-prop-1-en-2-yl-7,8,9,9a-tetrahydro-5aH-dibenzofuran-1,6-diol
Other names
CBE-C5 · Cannabielsoin A · S-CBE

Identifiers

Formula
C₂₁H₃₀O₃
CAS
52025-76-0
PubChem CID
162113(new tab)
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

Machine-readable entry (JSON)

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