Δ9-Tetrahydrocannabutol (tetrahydrocannabinol-C4, THC-C4, Δ⁹-THCB, (C4)-Δ⁹-THC, butyl-THC) is a

phytocannabinoid Cannabinoids () are several structural classes of compounds found in the cannabis plant primarily and most animal organisms (although insects lack such receptors) or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tet ...

found in

cannabis ''Cannabis'' () is a genus of flowering plants in the family Cannabaceae. The number of species within the genus is disputed. Three species may be recognized: '' Cannabis sativa'', '' C. indica'', and '' C. ruderalis''. Alternative ...

that is a homologue of

tetrahydrocannabinol Tetrahydrocannabinol (THC) is the principal psychoactive constituent of cannabis and one of at least 113 total cannabinoids identified on the plant. Although the chemical formula for THC (C21H30O2) describes multiple isomers, the term ''THC' ...

(THC), the main active component of Cannabis. Structurally, they are only different by the

pentyl Pentyl is a five-carbon alkyl group or substituent with chemical formula -C5H11. It is the substituent form of the alkane pentane. In older literature, the common non-systematic name amyl was often used for the pentyl group. Conversely, the name ...

side chain In organic chemistry and biochemistry, a side chain is a chemical group that is attached to a core part of the molecule called the "main chain" or backbone. The side chain is a hydrocarbon branching element of a molecule that is attached to a ...

being replaced by a

butyl In organic chemistry, butyl is a four- carbon alkyl radical or substituent group with general chemical formula , derived from either of the two isomers (''n''-butane and isobutane) of butane. The isomer ''n''-butane can connect in two ways, gi ...

side chain.

Pharmacology

Δ9-THCB, showed an affinity for the human CB1 (''K''i = 15 nM) and CB2 receptors (''K''i = 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. In an analysis by the

University of Rhode Island The University of Rhode Island (URI) is a public land-grant research university with its main campus in Kingston, Rhode Island, United States. It is the flagship public research as well as the land-grant university of the state of Rhode Isla ...

phytocannabinoids Cannabinoids () are several structural classes of compounds found in the cannabis plant primarily and most animal organisms (although insects lack such receptors) or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tet ...

it was found that THC-Butyl had the highest

3C-like protease The 3C-like protease (3CLpro) or main protease (Mpro), formally known as C30 endopeptidase or 3-chymotrypsin-like protease, is the main protease found in coronaviruses. It cleaves the coronavirus polyprotein at eleven conserved sites. It is a c ...

inhibitor activity against

COVID-19 Coronavirus disease 2019 (COVID-19) is a contagious disease caused by a virus, the severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2). The first known case was identified in Wuhan, China, in December 2019. The disease quickly ...

out of all the phytocannabinoids tested within that study but not as high as the antiviral drug

GC376 GC376 is a broad-spectrum antiviral medication under development by the biopharmaceutical company Anivive Lifesciences for therapeutic uses in humans and animals. Anivive licensed the exclusive worldwide patent rights to GC376 from Kansas State ...

(81% THCB vs 100% GC376).

Chemistry

Similarly to THC, it has 7 double bond isomers and 30 stereoisomers. The Δ⁸ isomer is known as a synthetic cannabinoid under the code name JWH-130, and the ring-opened analogue cannibidibutol is also known. Cannabidibutol_structure

]

]

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.

References

{{Cannabinoids Terpeno-phenolic compounds Cannabinoids Diterpenes Benzochromenes Tetrahydrocannabinol

Pharmacology

Chemistry

Legality

See also

References