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Cannabinoid

Tetrahydrocannabiphorol

Also called THCP, 3-Heptyl-delta-1-thc, Tetrahydrocannabinol-C7

Original Wikipedia articleen.wikipedia.org/wiki/Tetrahydrocannabiphorol revision used (24 October 2026)

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Overview

Tetrahydrocannabiphorol (THCP) is a potent phytocannabinoid that is structurally similar to delta-9-THC, the main psychoactive compound in cannabis. Like THC, THCP is a CB1 and CB2 receptor agonist with psychoactive effects. Initial in-vitro binding assay studies suggest that THCP may be up to 30 times more potent than delta-9-THC, potentially leading to more pronounced psychoactive effects. However, the full extent of THCP's psychoactivity and how it compares to THC is still being researched.[1][2] PW

Tetrahydrocannabiphorol (THCP) is a potent phytocannabinoid, a CB₁ and CB₂ receptor agonist which was known as a synthetic homologue of tetrahydrocannabinol (THC), but for the first time in 2019 was isolated as a trace natural product from Cannabis sativa.[3][4][5] WP

THCP is structurally similar to Δ⁹-THC, the main active component of cannabis, but with the pentyl side chain extended to heptyl. Since it has a longer side chain, its cannabinoid effects are "far higher than Δ⁹-THC itself." Tetrahydrocannabiphorol has a reported binding affinity of 1.2 nM at CB₁, approximately 33 times that of Δ⁹-THC (40 nM at CB₁), however this does not mean it's 33x stronger per milligram.[1] WP

THCP was studied by Roger Adams as early as 1942.[6] WP

History

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Pharmacology

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Chemistry

Formula
C23H34O2 PC
CAS number
54763-99-4 PC
Molar mass (g/mol)
342.5 PC
IUPAC name (computed by PubChem)
(6aR,10aR)-3-heptyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol PC
SMILES
CCCCCCCC1=CC(=C2[C@@H]3C=C(CC[C@H]3C(OC2=C1)(C)C)C)O PC
InChIKey
OJTMRZHYTZMJKX-RTBURBONSA-N PC
PubChem CID
6453074

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References

  1. Journal / agency Citti C, Linciano P, Russo F, Luongo L, Iannotta M, Maione S, Laganà A, Capriotti AL, Forni F, Vandelli MA, Gigli G, Cannazza G. A novel phytocannabinoid isolated from Cannabis sativa L. with an in vivo cannabimimetic activity higher than Δ⁹-tetrahydrocannabinol: Δ⁹-Tetrahydrocannabiphorol. Scientific Reports. December 2019. doi:10.1038/s41598-019-56785-1 · PMID 31889124 · PMC6937300
  2. Other https://www.livescience.com/new-potent-cannabinoid.html
  3. Journal / agency Harvey DJ. Identification of hepatic metabolites of n-heptyl-delta-1-tetrahydrocannabinol in the mouse. Xenobiotica; the Fate of Foreign Compounds in Biological Systems. March 1985. doi:10.3109/00498258509045349 · PMID 2992174
  4. Journal / agency Bueno J, Greenbaum EA. (-)-trans-Δ⁹-Tetrahydrocannabiphorol Content of Cannabis sativa Inflorescence from Various Chemotypes. Journal of Natural Products. February 2021. doi:10.1021/acs.jnatprod.0c01034 · PMID 33565878
  5. Journal / agency Linciano P, Russo F, Citti C, Tolomeo F, Paris R, Fulvio F, Pecchioni N, Vandelli MA, Laganà A, Capriotti AL, Biagini G, Carbone L, Gigli G, Cannazza G. The novel heptyl phorolic acid cannabinoids content in different Cannabis sativa L. accessions. Talanta. December 2021. doi:10.1016/j.talanta.2021.122704 · PMID 34517579
  6. Journal / agency Adams R, Loewe S, Smith CM, McPhee WD. Tetrahydrocannabinol Homologs and Analogs with Marihuana Activity. XIII¹. Journal of the American Chemical Society. 1942. doi:10.1021/ja01255a061

Text and values on this page are quoted from PsychonautWiki (CC BY-SA 4.0), Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.