Cannabinoid

Tetrahydrocannabutol

Also called THCB, Tetrahydrocannabinol-C4, delta-9-tetrahydrocannabinol-c4, THC-C4

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

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Dosage

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Mixing

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Overview

Tetrahydrocannabutol (THCB) is a phytocannabinoid. PW

Δ⁹-Tetrahydrocannabutol (Δ⁹-THCB, THC-B, tetrahydrocannabinol-C4, THC-C4, (C4)-Δ⁹-THC, or butyl-THC) is a phytocannabinoid found in cannabis that is a homologue of tetrahydrocannabinol (THC), the main active component of Cannabis. Structurally, they are only different by the pentyl side chain being replaced by a butyl side chain. THCB was studied by Roger Adams as early as 1942[1][2] WP

History

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Legal status

Legality

THCB is not scheduled internationally under the Convention on Psychotropic Substances, but may be controlled under analogue law in some individual jurisdictions as a homologue of THC. WP

Pharmacology

Δ⁹-THCB, showed an affinity for the human CB₁ (Ki = 15 nM) and CB₂ receptors (Ki = 51 nM) comparable to that of Δ⁹-THC. The formalin test in vivo was performed on Δ⁹-THCB in order to reveal possible analgesic and anti-inflammatory properties. The tetrad test in mice showed a partial agonistic activity of Δ⁹-THCB toward the CB₁ receptor. THCB has rarely been isolated from cannabis samples, but appears to be less commonly present than THC or THCV. It is metabolized in a similar manner to THC.[1][3][4] WP

In an analysis by the University of Rhode Island on phytocannabinoids it was found that THC-Butyl had the highest 3C-like protease inhibitor activity against COVID-19 out of all the phytocannabinoids tested within that study but not as high as the antiviral drug GC376 (81% THCB vs. 100% GC376).[5] WP

Chemistry

Formula: C20H28O2 PC
CAS number: 60008-00-6 PC
Molar mass (g/mol): 300.4 PC
IUPAC name (computed by PubChem): (6aR,10aR)-3-butyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol PC
SMILES: CCCCC1=CC(=C2[C@@H]3C=C(CC[C@H]3C(OC2=C1)(C)C)C)O PC
InChIKey: QHCQSGYWGBDSIY-HZPDHXFCSA-N PC
PubChem CID: 6453891

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Pop culture

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References

Journal / agency Linciano P, Citti C, Luongo L, Belardo C, Maione S, Vandelli MA, Forni F, Gigli G, Laganà A, Montone CM, Cannazza G. Isolation of a High-Affinity Cannabinoid for the Human CB1 Receptor from a Medicinal Cannabis sativa Variety: Δ⁹-Tetrahydrocannabutol, the Butyl Homologue of Δ⁹-Tetrahydrocannabinol. Journal of Natural Products. January 2020. doi:10.1021/acs.jnatprod.9b00876 · PMID 31891265
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
Journal / agency Harvey DJ. Characterization of the butyl homologues of delta1-tetrahydrocannabinol, cannabinol and cannabidiol in samples of cannabis by combined gas chromatography and mass spectrometry. The Journal of Pharmacy and Pharmacology. April 1976. doi:10.1111/j.2042-7158.1976.tb04153.x · PMID 6715
Journal / agency Brown NK, Harvey DJ. In vivo metabolism of the n-butyl-homologues of delta 9-tetrahydrocannabinol and delta 8-tetrahydrocannabinol by the mouse. Xenobiotica; the Fate of Foreign Compounds in Biological Systems. April 1988. doi:10.3109/00498258809041678 · PMID 2840781
Journal / agency Liu C, Puopolo T, Li H, Cai A, Seeram NP, Ma H. Identification of SARS-CoV-2 Main Protease Inhibitors from a Library of Minor Cannabinoids by Biochemical Inhibition Assay and Surface Plasmon Resonance Characterized Binding Affinity. Molecules. September 2022. doi:10.3390/molecules27186127 · PMID 36144858 · PMC9502466

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.