Tetrahydrocannabutol: Difference between revisions
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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.<ref name=":0" /> The formalin test in vivo was performed on Δ9-THCB in order to reveal possible analgesic and anti-inflammatory properties.<ref name=":0" /> The tetrad test in mice showed a partial agonistic activity of Δ9-THCB toward the CB1 receptor.<ref name=":0" /> THCB has rarely been isolated from cannabis samples,<ref name=":0" /><ref>{{cite journal | vauthors = Harvey DJ | title = Characterization of the butyl homologues of delta1-tetrahydrocannabinol, cannabinol and cannabidiol in samples of cannabis by combined gas chromatography and mass spectrometry | journal = The Journal of Pharmacy and Pharmacology | volume = 28 | issue = 4 | pages = 280–5 | date = April 1976 | pmid = 6715 | doi = 10.1111/j.2042-7158.1976.tb04153.x | s2cid = 32734030 }}</ref> but appears to be less commonly present than THC or THCV. It is metabolized in a similar manner to THC.<ref>{{cite journal | vauthors = Brown NK, Harvey DJ | title = In vivo metabolism of the n-butyl-homologues of delta 9-tetrahydrocannabinol and delta 8-tetrahydrocannabinol by the mouse | journal = Xenobiotica; the Fate of Foreign Compounds in Biological Systems | volume = 18 | issue = 4 | pages = 417–27 | date = April 1988 | pmid = 2840781 | doi = 10.3109/00498258809041678 }}</ref> |
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.<ref name=":0" /> The formalin test in vivo was performed on Δ9-THCB in order to reveal possible analgesic and anti-inflammatory properties.<ref name=":0" /> The tetrad test in mice showed a partial agonistic activity of Δ9-THCB toward the CB1 receptor.<ref name=":0" /> THCB has rarely been isolated from cannabis samples,<ref name=":0" /><ref>{{cite journal | vauthors = Harvey DJ | title = Characterization of the butyl homologues of delta1-tetrahydrocannabinol, cannabinol and cannabidiol in samples of cannabis by combined gas chromatography and mass spectrometry | journal = The Journal of Pharmacy and Pharmacology | volume = 28 | issue = 4 | pages = 280–5 | date = April 1976 | pmid = 6715 | doi = 10.1111/j.2042-7158.1976.tb04153.x | s2cid = 32734030 }}</ref> but appears to be less commonly present than THC or THCV. It is metabolized in a similar manner to THC.<ref>{{cite journal | vauthors = Brown NK, Harvey DJ | title = In vivo metabolism of the n-butyl-homologues of delta 9-tetrahydrocannabinol and delta 8-tetrahydrocannabinol by the mouse | journal = Xenobiotica; the Fate of Foreign Compounds in Biological Systems | volume = 18 | issue = 4 | pages = 417–27 | date = April 1988 | pmid = 2840781 | doi = 10.3109/00498258809041678 }}</ref> |
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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). <ref> |
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). <ref>{{cite journal | doi=10.3390/molecules27186127 | doi-access=free | title=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 | year=2022 | last1=Liu | first1=Chang | last2=Puopolo | first2=Tess | last3=Li | first3=Huifang | last4=Cai | first4=Ang | last5=Seeram | first5=Navindra P. | last6=Ma | first6=Hang | journal=Molecules | volume=27 | issue=18 | page=6127 | pmid=36144858 }}</ref> |
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== Chemistry == |
== Chemistry == |
Revision as of 01:11, 12 March 2023
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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, butyl-THC) is a phytocannabinoid found in cannabis that is a homologue of tetrahydrocannabinol (THC), the main active component of Cannabis.[1] Structurally, they are only different by the pentyl side chain being replaced by a butyl side chain.
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.[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][2] but appears to be less commonly present than THC or THCV. It is metabolized in a similar manner to THC.[3]
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). [4]
Chemistry
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] and the ring-opened analogue cannibidibutol is also known.[7]
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
- ^ a b c d e Linciano, Pasquale; Citti, Cinzia; Luongo, Livio; Belardo, Carmela; Maione, Sabatino; Vandelli, Maria Angela; Forni, Flavio; Gigli, Giuseppe; Laganà, Aldo; Montone, Carmela Maria; Cannazza, Giuseppe (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". Journal of Natural Products. 83 (1): 88–98. doi:10.1021/acs.jnatprod.9b00876. ISSN 0163-3864. PMID 31891265. S2CID 209519659.
- ^ Harvey DJ (April 1976). "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. doi:10.1111/j.2042-7158.1976.tb04153.x. PMID 6715. S2CID 32734030.
- ^ Brown NK, Harvey DJ (April 1988). "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. doi:10.3109/00498258809041678. PMID 2840781.
- ^ Liu, Chang; Puopolo, Tess; Li, Huifang; Cai, Ang; Seeram, Navindra P.; Ma, Hang (2022). "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. 27 (18): 6127. doi:10.3390/molecules27186127. PMID 36144858.
- ^ "Verschil THC Olie, CBD olie, wietolie, hennepolie en cannabisolie?". Dutch-Headshop.com. Retrieved 19 November 2016.
- ^ Bow EW, Rimoldi JM (2016). "The Structure-Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation". Perspectives in Medicinal Chemistry. 8: 17–39. doi:10.4137/PMC.S32171. PMC 4927043. PMID 27398024.
- ^ Hanuš LO, Meyer SM, Muñoz E, Taglialatela-Scafati O, Appendino G (November 2016). "Phytocannabinoids: a unified critical inventory". Natural Product Reports. 33 (12): 1357–1392. doi:10.1039/c6np00074f. PMID 27722705.