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{{Short description|Chemical compound}} |
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{{Drugbox |
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{{cs1 config|name-list-style=vanc|display-authors=6}} |
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| verifiedrevid = 354916523 |
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{{Infobox drug |
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| verifiedrevid = 448003399 |
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| IUPAC_name = (−)-(6a''R'',10a''R'')-6,6,9-trimethyl-3-butyl-6a,7,8,10a-tetrahydro-6''H''-benzochromen-1-ol |
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| IUPAC_name = (−)-(6a''R'',10a''R'')-6,6,9-trimethyl-3-butyl-6a,7,8,10a-tetrahydro-6''H''-benzochromen-1-ol |
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| image = Tetrahydrocannabinol-c4.svg |
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| image = Delta-9-tetrahydrocannabinol-C4.png |
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| image2 = THCB 3D BS.png |
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| drug_name = Δ<sup>9</sup>-Tetrahydrocannabinol-C4 |
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| drug_name = Δ<sup>9</sup>-Tetrahydrocannabinol-C4 |
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| tradename = |
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| legal_status = ? |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| metabolism = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|CAS}} |
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| CAS_number = |
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| CAS_number = 60008-00-6 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = LIC9QAS59U |
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| ATC_prefix = none |
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| ATC_prefix = none |
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| ATC_suffix = |
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| PubChem = |
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| PubChem = 6453891 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 4956237 |
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| ChEMBL = 4437290 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=20 | H=28 | O=2 |
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| C=20 | H=28 | O=2 |
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| smiles = CCCCC1=CC2=C(3C=C(CC3C(O2)(C)C)C)C(=C1)O |
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| molecular_weight = 300.43 g/mol |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C20H28O2/c1-5-6-7-14-11-17(21)19-15-10-13(2)8-9-16(15)20(3,4)22-18(19)12-14/h10-12,15-16,21H,5-9H2,1-4H3/t15-,16-/m1/s1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = QHCQSGYWGBDSIY-HZPDHXFCSA-N |
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'''Δ<sup>9</sup>-Tetrahydrocannabutol''' ('''tetrahydrocannabinol-C4''', '''THC-C4''', '''Δ<sup>9</sup>-THCB''', '''(C4)-Δ<sup>9</sup>-THC''', '''butyl-THC''') is a ] found in ] that is a ] of ] (THC), the main active component of Cannabis.<ref name=":0">{{cite journal | vauthors = Linciano P, Citti C, Luongo L, Belardo C, Maione S, Vandelli MA, Forni F, Gigli G, Laganà A, Montone CM, Cannazza G | title = Isolation of a High-Affinity Cannabinoid for the Human CB1 Receptor from a Medicinal ''Cannabis sativa'' Variety: Δ<sup>9</sup>-Tetrahydrocannabutol, the Butyl Homologue of Δ<sup>9</sup>-Tetrahydrocannabinol | journal = Journal of Natural Products | volume = 83 | issue = 1 | pages = 88–98 | date = January 2020 | pmid = 31891265 | doi = 10.1021/acs.jnatprod.9b00876 | s2cid = 209519659 }}</ref> Structurally, they are only different by the ] ] being replaced by a ] side chain. THCB was studied by ] as early as 1942 <ref>{{cite journal | url=https://pubs.acs.org/doi/abs/10.1021/ja01255a061 | doi=10.1021/ja01255a061 | title=Tetrahydrocannabinol Homologs and Analogs with Marihuana Activity. XIII<sup>1</sup> | date=1942 | vauthors = Adams R, Loewe S, Smith CM, McPhee WD | journal=Journal of the American Chemical Society | volume=64 | issue=3 | pages=694–697 }}</ref> |
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'''Tetrahydrocannabinol-C4''', also known as '''THC-C4''' and '''butyl-THC''', is a ] of ] (THC), the active component of '']''. They are only different by the ] ] being replaced by a ] sidechain. It is unknown whether THC-C4 is an ], ], or ] at the ]s. The ] anolog, ] is a known antagonist while ] itself is an agonist. |
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== Pharmacology == |
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Δ<sup>9</sup>-THCB, showed an affinity for the human CB<sub>1</sub> (''K''i = 15 nM) and CB<sub>2</sub> receptors (''K''i = 51 nM) comparable to that of Δ<sup>9</sup>-THC.<ref name=":0" /> The formalin test in vivo was performed on Δ<sup>9</sup>-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 Δ<sup>9</sup>-THCB toward the CB<sub>1</sub> 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 = 280–285 | 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 = 417–427 | date = April 1988 | pmid = 2840781 | doi = 10.3109/00498258809041678 }}</ref> |
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In an analysis by the ] on ] it was found that THC-Butyl had the highest ] inhibitor activity against ] out of all the phytocannabinoids tested within that study but not as high as the ] ] (81% THCB vs. 100% GC376).<ref>{{cite journal | vauthors = Liu C, Puopolo T, Li H, Cai A, Seeram NP, Ma H | 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 | journal = Molecules | volume = 27 | issue = 18 | page = 6127 | date = September 2022 | pmid = 36144858 | doi = 10.3390/molecules27186127 | pmc = 9502466 | doi-access = free }}</ref> |
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== Chemistry == |
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Similarly to THC, it has 7 double bond isomers and 30 stereoisomers.<ref>{{cite web |title=Verschil THC Olie, CBD olie, wietolie, hennepolie en cannabisolie? |url=http://www.dutch-headshop.com/nl/verschil-thc-olie-cannabisolie-cbd-olie-wietolie-hennepolie-a-176.html |website=Dutch-Headshop.com |access-date=19 November 2016 }}</ref> The Δ<sup>8</sup> isomer is known as a synthetic cannabinoid under the code name '''JWH-130''',<ref name="pmid27398024">{{cite journal | vauthors = Bow EW, Rimoldi JM | title = The Structure-Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation | journal = Perspectives in Medicinal Chemistry | volume = 8 | pages = 17–39 | date = 2016 | pmid = 27398024 | pmc = 4927043 | doi = 10.4137/PMC.S32171 }}</ref> and the ring-opened analogue '''cannibidibutol''' ('''CBDB''') is also known.<ref name="pmid27722705">{{cite journal | vauthors = Hanuš LO, Meyer SM, Muñoz E, Taglialatela-Scafati O, Appendino G | title = Phytocannabinoids: a unified critical inventory | journal = Natural Product Reports | volume = 33 | issue = 12 | pages = 1357–1392 | date = November 2016 | pmid = 27722705 | doi = 10.1039/c6np00074f | doi-access = free }}</ref> THC-Butyl can be synthesized from ].{{cn|date=March 2024}} |
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==Legality== |
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THCB is not scheduled internationally under the ], but may be controlled under analogue law in some individual jurisdictions as a homologue of THC. |
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== See also == |
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== See also == |
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* ] |
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* '']'' |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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== References == |
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{{reflist}} |
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{{Cannabinoids}} |
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{{Cannabinoids}} |
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{{cannabinoid-stub}} |
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] |
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