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From the plant

CBRCannabiripsol

A dihydroxylated hexahydrocannabinol isolated in 1979, with weak micromolar affinity for CB1 and CB2.

FranceNarcotic: generic clauseInternationalUnscheduled
Level of detail

C₂₁H₃₂O₄

CAS 72236-32-9

Family
PhytocannabinoidMinor
Origin
Origin not established
Molar mass
348.50 g/mol

Updated on

In plain terms

Cannabiripsol is a rare cannabinoid of cannabis, isolated in 1979 from a South African variety. It is a close relative of THC carrying two more hydroxyl groups. In the laboratory it binds the CB1 receptor about 300 times less well than THC, and it produced no THC-like effect in mice at the dose tested.

Receptors and activity

Target network

CB1Binding (function not established)Ki = 5.7 µM · human[3H]CP-55,940 displacement, HEK293-hCB1 membranes (± 1324 nM); Δ9-THC 18 nM in the same assay; efficacy not measured
  • Binds or modulates

The lower the cited value, the closer the target sits to CBR: 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 CBR.

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. CB1Binding (function not established)Ki = 5.7 µM · human21 out of 100

    Radwan et al. 2015, J Nat Prod (new tab) · [3H]CP-55,940 displacement, HEK293-hCB1 membranes (± 1324 nM); Δ9-THC 18 nM in the same assay; efficacy not measured

  2. CB2Binding (function not established)Ki = 2.1 µM · human28 out of 100

    Radwan et al. 2015, J Nat Prod (new tab) · [3H]CP-55,940 displacement, HEK293-hCB2 membranes (± 353 nM); Δ9-THC 42 nM in the same assay; efficacy not measured

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

Cannabiripsol is a minor cannabinoid of Cannabis sativa, described in 1979 by Boeren, ElSohly and Turner as (−)-(6aR,9S,10S,10aR)-9,10-dihydroxy-hexahydrocannabinol, isolated from a South African variant and confirmed by synthesis; no formation origin has been established. It keeps the benzo[c]chromene nucleus of THC, but its terpene ring is saturated and carries a vicinal diol. Re-isolated in 2015 from high-potency cannabis, it showed weak affinity for human CB1 (Ki 5668 ± 1324 nM) and CB2 (Ki 2143 ± 353 nM) receptors, against 18 and 42 nM for Δ9-THC in the same assay, and no significant effect in the mouse tetrad at 20 mg/kg (Radwan 2015). CAS numbers 99623-72-0 and 99623-73-1, sometimes associated with cannabiripsol and its propyl homologue, are probably erroneous according to ElSohly and Slade (2005), who trace them to a faulty structure in a 1985 publication; the number used here, 72236-32-9, is the one PubChem links to the correct structure.

Key sources.

History

Source
A minor constituent of Cannabis sativa, described in a South African variant (1979) and re-isolated from high-potency cannabis (2015); origin not established.

Biosynthetic pathway

No enzyme or formation mechanism has been established: the inventories report its isolation without assigning it an origin. Structurally, it is a hexahydrocannabinol bearing a vicinal diol at positions 9 and 10.

Classification

Family, origin and source verification

Family

Phytocannabinoid › Minor

Presence in the plant

Present in the plant; origin not established

Chemistry

Miscellaneous · C5 side chain · neutral form

Verification

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

Wikipedia (English)

Cannabiripsol (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. Boeren, ElSohly & Turner 1979, Experientia 35:1278-9: isolation of cannabiripsol from a South African variant (new tab)PMID 499397
  2. Radwan et al. 2015, J Nat Prod: re-isolation; CB1/CB2 Ki (table 3) and mouse tetrad (table 4) (new tab)PMID 26000707
  3. Husni et al. 2014, Med Chem Res: binding method (HEK293 hCB1/hCB2, [3H]CP-55,940) (new tab)PMID 25419092
  4. ElSohly & Slade 2005, Life Sci: erroneous CAS numbers assigned to cannabiripsol (new tab)PMID 16199061
  5. Radwan et al. 2021, Molecules: inventory of cannabis cannabinoids (new tab)PMID 34066753
  6. ANSM, decision of 22/05/2024 (benzo[c]chromene class) and consolidated list of 26/06/2026 (new tab)
  7. PubChem CID 192007: cannabiripsol (new tab)

Identifiers

Names

Common name
Cannabiripsol
IUPAC name
(6aR,9S,10S,10aR)-6,6,9-trimethyl-3-pentyl-7,8,10,10a-tetrahydro-6aH-benzo[c]chromene-1,9,10-triol
Other names
CBR-C5 · (6aR,9S,10S,10aR)-9,10-dihydroxy-hexahydrocannabinol

Identifiers

Formula
C₂₁H₃₂O₄
CAS
72236-32-9
PubChem CID
192007(new tab)
InChIKey
TZGCTXUTNDNTTE-DYZHCLJRSA-N
SMILES
CCCCCC1=CC(=C2[C@H]3[C@@H](CC[C@]([C@H]3O)(C)O)C(OC2=C1)(C)C)O

Machine-readable entry (JSON)

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