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From the plant

THCPTetrahydrocannabiphorol

Heptyl (C7) homologue of Δ9-THC, present in trace amounts; CB1 Ki of 1.2 nM in vitro.

Narcotic: generic clause
Level of detail

C₂₃H₃₄O₂

CAS 54763-99-4

Family
PhytocannabinoidMinor
Origin
Decarboxylation
Molar mass
342.52 g/mol

Updated on

In plain terms

THCP is a THC whose side chain has seven carbons instead of five. The plant contains only traces of it. In the laboratory it binds the CB1 receptor much more strongly than THC according to published measurements, but no human study has measured what this changes in use.

Receptors and activity

Target network

CB1AgonistKi = 1.2 nM · human[3H]CP55940 or [3H]WIN 55212-2 displacement, purified human CB1; THC-like profile in the mouse tetrad test; CB1 activation in β-arrestin 2 recruitment (Janssens et al. 2024)
  • Activates

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

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. CB1AgonistKi = 1.2 nM · human82 out of 100

    Citti et al. 2019, Sci Rep 9:20335 (new tab) · [3H]CP55940 or [3H]WIN 55212-2 displacement, purified human CB1; THC-like profile in the mouse tetrad test; CB1 activation in β-arrestin 2 recruitment (Janssens et al. 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

Δ9-Tetrahydrocannabiphorol (Δ9-THCP) is the heptyl-chain (C7) homologue of Δ9-THC. Citti, Cannazza and colleagues isolated it in 2019 from the Italian medicinal cannabis variety FM2, together with cannabidiphorol, and confirmed its structure by stereoselective synthesis. It is present there only in trace amounts: about 29 µg/g in FM2, and 0.0023% to 0.0136% (w/w) in the inflorescences of Δ9-THC-dominant chemotypes (Bueno and Greenbaum 2021). In vitro, it bound human CB1 and CB2 receptors with Ki values of 1.2 and 6.2 nM; the authors compare the CB1 Ki with a literature value of 40 nM for Δ9-THC, a ratio of about 33, without a measurement in the same assay. In mice, it produced a THC-like profile in the tetrad test at 2.5 to 10 mg/kg, and in a β-arrestin 2 recruitment assay it showed a higher CB1 activation potential than Δ9-THC (Janssens et al. 2024). No human study has measured its effects; a case report describes a psychotic episode after a reported intake of 8 mg (Greer et al. 2025). In France, it has been a controlled narcotic since 3 June 2024 through the generic class of benzo[c]chromene derivatives.

Key sources.

History

Source
Cannabis sativa L.: a constituent present in trace amounts. Isolated from the Italian medicinal variety FM2, where its content was estimated at about 29 µg/g (Citti et al. 2019), then quantified at 0.0023% to 0.0136% (w/w) in the 13 inflorescence samples from Δ9-THC-dominant chemotypes, and not detected in a CBD-dominant chemotype (Bueno and Greenbaum 2021). Its acid, THCPA, was quantified in 49 samples from four chemotypes (Linciano et al. 2021).

Biosynthetic pathway

Δ9-THCP is the neutral form produced by decarboxylation of its acid, THCPA, which fresh inflorescence contains (Linciano et al. 2021). The enzyme or starter unit that supplies the heptyl chain has not been characterised in the plant.

Classification

Family, origin and source verification

Family

Phytocannabinoid › Minor

Presence in the plant

Neutral form: decarboxylation of a plant acid

Chemistry

Type Δ9-THC · C7 side chain · neutral form

Verification

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

Wikipedia (English)

Tetrahydrocannabiphorol (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. Citti C. et al., isolation of Δ9-tetrahydrocannabiphorol and cannabidiphorol from the FM2 variety; Ki CB1 1.2 nM and CB2 6.2 nM; tetrad in mice, Sci Rep 2019, 9:20335 (new tab)PMID 31889124
  2. Bueno J., Greenbaum E. A., Δ9-THCP content of inflorescences of different chemotypes, J Nat Prod 2021, 84:531-536 (new tab)PMID 33565878
  3. Linciano P. et al., phorolic cannabinoid acid content (CBDPA, THCPA) in 49 Cannabis sativa L. samples, Talanta 2021, 235:122704 (new tab)PMID 34517579
  4. Janssens L. K. et al., intrinsic CB1 activity of hemp-derived and semi-synthetic cannabinoids (β-arrestin 2 recruitment), Arch Toxicol 2024, 98:2619-2630 (new tab)PMID 38735004
  5. James K. M. et al., in vitro metabolism (human liver microsomes) of Δ9-THCB, Δ9-THCH and Δ9-THCP, J Anal Toxicol 2026, 50:bkag045 (new tab)PMID 42286420
  6. Greer D. et al., psychosis and suicide attempt after a single use of Δ9-THCP: case report, PCN Rep 2025, 4:e70060 (new tab)PMID 39906186
  7. Muir L. S. et al., LC-MS-MS analysis of THC isomers, analogues, homologues and metabolites in blood and urine, J Anal Toxicol 2025, 49:322-331 (new tab)PMID 40098275
  8. ANSM, decision of 22/05/2024 amending the list of substances classified as narcotics (generic benzo[c]chromene class) (new tab)
  9. ANSM, « ANSM adds new cannabinoids to the list of narcotics », 24/05/2024, updated 11/03/2025 (THCP cited among the benzo[c]chromene family) (new tab)
  10. ANSM, consolidated list of substances classified as narcotics (26/06/2026) (new tab)
  11. GSRS UNII WTK87HN3LG and PubChem CID 6453074: tetrahydrocannabiphorol, CAS 54763-99-4 (new tab)

Identifiers

Names

Common name
Tetrahydrocannabiphorol
IUPAC name
(6aR,10aR)-3-heptyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
Other names
Δ9-THCP

Identifiers

Formula
C₂₃H₃₄O₂
CAS
54763-99-4
PubChem CID
6453074(new tab)
InChIKey
OJTMRZHYTZMJKX-RTBURBONSA-N
SMILES
CCCCCCCC1=CC(=C2[C@@H]3C=C(CC[C@H]3C(OC2=C1)(C)C)C)O

Machine-readable entry (JSON)

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

In the Journal