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| Formula | C20H28O2 |
| Molar mass | 300.442 g·mol−1 |
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Δ9-Tetrahydrocannabutol (Δ9-THCB,THC-B,tetrahydrocannabinol-C4,THC-C4,(C4)-Δ9-THC, orbutyl-THC) is aphytocannabinoid found incannabis that is ahomologue oftetrahydrocannabinol (THC), the main active component of Cannabis.[1] Structurally, they are only different by thepentylside chain being replaced by abutyl side chain. THCB was studied byRoger Adams as early as 1942[2]
Δ9-THCB, showed an affinity for the human CB1 (Ki = 15 nM) and CB2 receptors (Ki = 51 nM) comparable to that of Δ9-THC.[1] The formalin test in vivo was performed on Δ9-THCB in order to reveal possible analgesic and anti-inflammatory properties.[1] The tetrad test in mice showed a partial agonistic activity of Δ9-THCB toward the CB1 receptor.[1] THCB has rarely been isolated from cannabis samples,[1][3] but appears to be less commonly present than THC or THCV. It is metabolized in a similar manner to THC.[4]
In an analysis by theUniversity of Rhode Island onphytocannabinoids it was found that THC-Butyl had the highest3C-like protease inhibitor activity againstCOVID-19 out of all the phytocannabinoids tested within that study but not as high as theantiviral drugGC376 (81% THCB vs. 100% GC376).[5]
Similarly to THC, it has 7 double bond isomers and 30 stereoisomers.[6] The Δ8 isomer is known as a synthetic cannabinoid under the code nameJWH-130,[7] and the ring-opened analoguecannibidibutol (CBDB) is also known.[8] THC-Butyl can be synthesized from4-butylresorcinol.[citation needed]
THCB is not scheduled internationally under theConvention on Psychotropic Substances, but may be controlled under analogue law in some individual jurisdictions as a homologue of THC.
