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Synthetic

9-nor-9b-HHC9-nor-9beta-hydroxy-hexahydrocannabinol

Synthetic classical cannabinoid (1976), analgesic in animals; the chemical ancestor of CP-47,497.

FranceNarcotic: generic clauseInternationalUnscheduled
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.

C₂₀H₃₀O₃

CAS 52171-85-4

Family
Synthetic CB receptor agonistResearch ligand or medicine
Molar mass
318.50 g/mol

Updated on

In plain terms

9-nor-9β-HHC is a laboratory molecule created in the 1970s by simplifying the structure of THC. It does not exist in hemp and is not described as a consumer product. In animals, it relieved pain as potently as morphine in some tests; no study has been carried out in humans.

Receptors and activity

Target network

CB1Agonistno measured value
  • Activates

The lower the cited value, the closer the target sits to 9-nor-9b-HHC: 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 9-nor-9b-HHC.

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. CB1Agonistno measured value cited
  2. CB2Agonistno measured value cited
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

9-nor-9β-HHC (9-nor-9β-hydroxyhexahydrocannabinol) is a classical dibenzopyran-type cannabinoid lacking the C9 methyl, which is replaced by a β-oriented hydroxyl. Wilson and May described it in 1976 together with its 9α epimer: both produced ataxia in dogs and reduced spontaneous activity in mice, but only the 9β epimer was analgesic, with a potency comparable to that of morphine. In the mouse tail-flick test, racemic 9β was roughly equipotent with morphine (ED50 of 7.12 mg/kg); naloxone antagonised this effect, with no cross-tolerance to morphine, which according to the authors suggests properties shared with narcotic analgesics but important differences (Bloom et al., 1977). The (−) enantiomer did not suppress withdrawal signs in morphine-dependent monkeys and caused hypotension and bradycardia in anaesthetised dogs (Martin et al., 1977). In mice, a mixture of its epimers was at least as potent as Δ9-THC on locomotor activity, immobility and temperature, with no effect in the hot-plate test (Skinner et al., 1979, as reported by the EMCDDA). Pfizer derived from it analgesics ten times more potent than morphine (Johnson et al., 1981), then CP-47,497, showing that the pyran ring was not necessary (Melvin et al., 1984). No published affinity constant and no human data were found.

Key sources.

History

Source
Synthetic: a research ligand prepared in the laboratory; no natural occurrence or conversion from a plant extract is documented

Origin

Laboratory synthesis

No known biosynthesis: the molecule has only been described as a synthetic product (Wilson and May, 1976). No source documents its preparation from a plant-extracted cannabinoid or its presence in cannabis.

Classification

Family, origin and source verification

Family

Synthetic CB receptor agonist › Research ligand or medicine

Chemistry

C5 side chain · neutral form

Class

classical

Verification

Checked on 20 October 2026; some points still await human review.

Wikipedia (English)

9-Nor-9β-hydroxyhexahydrocannabinol (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. Wilson RS, May EL. 9-Nor-9-hydroxyhexahydrocannabinols. Synthesis, some behavioral and analgesic properties, and comparison with the tetrahydrocannabinols. J Med Chem 1976;19:1165-1167 (new tab)PMID 978681
  2. Bloom AS, Dewey WL, Harris LS, Brosius KK. 9-nor-9beta-hydroxyhexahydrocannabinol, a cannabinoid with potent antinociceptive activity: comparisons with morphine. J Pharmacol Exp Ther 1977;200:263-270 (new tab)PMID 839438
  3. Martin BR et al. A potent antinociceptive cannabinoid which lacks opiate substitution properties in monkeys. Res Commun Chem Pathol Pharmacol 1977;16:187-190 (new tab)PMID 402685
  4. Johnson MR et al. Potent analgetics derived from 9-nor-9 beta-hydroxyhexahydrocannabinol. NIDA Res Monogr 1981;34:68-74 (new tab)PMID 6111753
  5. Melvin LS, Johnson MR, Harbert CA, Milne GM, Weissman A. A cannabinoid derived prototypical analgesic. J Med Chem 1984;27:67-71 (new tab)PMID 6690685
  6. Berglund BA et al. Development of a novel class of monocyclic and bicyclic alkyl amides that exhibit CB1 and CB2 cannabinoid receptor affinity and receptor activation. Drug Des Discov 2000;16:281-294 (new tab)PMID 10807034
  7. Pertwee RG et al. IUPHAR LXXIX. Cannabinoid receptors and their ligands: beyond CB1 and CB2. Pharmacol Rev 2010;62:588-631 (new tab)PMID 21079038
  8. EMCDDA (Ujváry et al.), Hexahydrocannabinol (HHC) and related substances, technical report, 2023 (table 6, « 11-nor-9-OH-HHC ») (new tab)
  9. ANSM, consolidated list of substances classified as narcotics, updated 26/06/2026 (benzo[c]chromene class, annex IV) (new tab)
  10. PubChem CID 6452587; GSRS UNII NA3QQQ5D4S (CAS 52171-85-4, racemic) (new tab)

Identifiers

Names

Common name
9-nor-9beta-hydroxy-hexahydrocannabinol
IUPAC name
6,6-dimethyl-3-pentyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromene-1,9-diol
Other names
9-nor-9b-OH-HHC · 9-nor-9β-hydroxyhexahydrocannabinol · 9-Hydroxy-9-norhexahydrocannabinol · 9-nor-9-hydroxyhexahydrocannabinol

Identifiers

Formula
C₂₀H₃₀O₃
CAS
52171-85-4
PubChem CID
6452587(new tab)
InChIKey
AAIHVZNCFQTVCA-UHFFFAOYSA-N
SMILES
CCCCCC1=CC2=C(C3CC(CCC3C(O2)(C)C)O)C(=C1)O

Machine-readable entry (JSON)

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