Chemistry:Tetrahydrocannabinol-C4
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| Formula | C20H28O2 |
| Molar mass | 300.442 g·mol−1 |
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Δ9-Tetrahydrocannabutol, tetrahydrocannabinol-C4, THC-C4, Δ9-THCB, (C4)-Δ9-THC, or butyl-THC, is a homologue of tetrahydrocannabinol (THC), the active component of cannabis.[1] They are only different by the pentyl side chain being replaced by a butyl side chain. 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] The propyl analog, THCV, is a cannabinoid receptor type 1 and cannabinoid receptor type 2 antagonist,[2] while THC is a CB1 agonist. THCB has rarely been isolated from cannabis samples,[1][3] but appears to be less commonly present than THC or THCV. It is metabolised in a similar manner to THC.[4] Similarly to THC, it has 7 double bond isomers and 30 stereoisomers.[5] The Δ8 isomer is known as a synthetic cannabinoid under the code name JWH-130.[6]
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.
See also
References
- ↑ 1.0 1.1 1.2 1.3 1.4 Linciano, Pasquale; Citti, Cinzia; Luongo, Livio; Belardo, Carmela; Maione, Sabatino; Vandelli, Maria Angela; Forni, Flavio; Gigli, Giuseppe et al. (2020-01-24). "Isolation of a High-Affinity Cannabinoid for the Human CB1 Receptor from a Medicinal Cannabis sativa Variety: Δ 9 -Tetrahydrocannabutol, the Butyl Homologue of Δ 9 -Tetrahydrocannabinol" (in en). Journal of Natural Products 83 (1): 88–98. doi:10.1021/acs.jnatprod.9b00876. ISSN 0163-3864. PMID 31891265. https://pubs.acs.org/doi/10.1021/acs.jnatprod.9b00876.
- ↑ "Evidence that the plant cannabinoid Delta9-tetrahydrocannabivarin is a cannabinoid CB1 and CB2 receptor antagonist". British Journal of Pharmacology 146 (7): 917–26. December 2005. doi:10.1038/sj.bjp.0706414. PMID 16205722.
- ↑ "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 28 (4): 280–5. April 1976. doi:10.1111/j.2042-7158.1976.tb04153.x. PMID 6715.
- ↑ "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 18 (4): 417–27. April 1988. doi:10.3109/00498258809041678. PMID 2840781.
- ↑ "Verschil THC Olie, CBD olie, wietolie, hennepolie en cannabisolie?". http://www.dutch-headshop.com/nl/verschil-thc-olie-cannabisolie-cbd-olie-wietolie-hennepolie-a-176.html.
- ↑ "The Structure-Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation". Perspectives in Medicinal Chemistry 8: 17–39. 2016. doi:10.4137/PMC.S32171. PMID 27398024.
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