Tetrahydrocannabutol
- none
- (−)-(6aR,10aR)-6,6,9-trimethyl-3-butyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol
- 60008-00-6 Y
- 6453891
- 4956237 Y
- LIC9QAS59U
- ChEMBL4437290
- DTXSID10208712
- Interactive image
- CCCCC1=CC2=C([C@@H]3C=C(CC[C@H]3C(O2)(C)C)C)C(=C1)O
- InChI=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 N
- Key:QHCQSGYWGBDSIY-HZPDHXFCSA-N N
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. THCB was studied by Roger Adams as early as 1942 [2]
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][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 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).[5]
Chemistry
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 name JWH-130,[7] and the ring-opened analogue cannibidibutol (CBDB) is also known.[8] THC-Butyl can be synthesized from 4-butylresorcinol.[citation needed]
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
- Cannabis
- Cannabinoid
- Hexahydrocannabutol
- Parahexyl
- Perrottetinene
- Tetrahydrocannabihexol
- Tetrahydrocannabiphorol
References
- ^ a b c d e Linciano P, Citti C, Luongo L, Belardo C, Maione S, Vandelli MA, et al. (January 2020). "Isolation of a High-Affinity Cannabinoid for the Human CB1 Receptor from a Medicinal Cannabis sativa Variety: Δ9-Tetrahydrocannabutol, the Butyl Homologue of Δ9-Tetrahydrocannabinol". Journal of Natural Products. 83 (1): 88–98. doi:10.1021/acs.jnatprod.9b00876. PMID 31891265. S2CID 209519659.
- ^ Adams R, Loewe S, Smith CM, McPhee WD (1942). "Tetrahydrocannabinol Homologs and Analogs with Marihuana Activity. XIII1". Journal of the American Chemical Society. 64 (3): 694–697. doi:10.1021/ja01255a061.
- ^ 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): 280–285. 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): 417–427. doi:10.3109/00498258809041678. PMID 2840781.
- ^ Liu C, Puopolo T, Li H, Cai A, Seeram NP, Ma H (September 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. PMC 9502466. 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.
- v
- t
- e
(comparison)
Cannabibutols |
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Cannabichromenes | |
Cannabicyclols |
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Cannabidiols | |
Cannabielsoins |
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Cannabigerols | |
Cannabiphorols |
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Cannabinols | |
Cannabitriols |
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Cannabivarins |
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Delta-8-tetrahydrocannabinols |
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Delta-9-tetrahydrocannabinols | |
Delta-10-Tetrahydrocannabinols | |
Miscellaneous cannabinoids |
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Active metabolites |
- Arachidonoyl ethanolamide (AEA; anandamide)
- 2-Arachidonoylglycerol (2-AG)
- 2-Arachidonyl glyceryl ether (2-AGE; noladin ether)
- 2-Oleoylglycerol (2-OG)
- N-Arachidonoyl dopamine (NADA)
- N-Arachidonylglycine (NAGly)
- 2-Arachidonoyl lysophosphatidylinositol (2-ALPI)
- N-Arachidonoyl serotonin (AA-5-HT)
- Docosatetraenoylethanolamide (DEA)
- Lysophosphatidylinositol (LPI)
- Oleamide
- Oleoylethanolamide (OEA)
- Palmitoylethanolamide (PEA)
- RVD-Hpα
- Stearoylethanolamide (SEA)
- O-Arachidonoyl ethanolamine (O-AEA; virodhamine)
cannabinoid
receptor
agonists /
neocannabinoids
enhancers
(inactivation inhibitors)
- 4-Nonylphenylboronic acid
- AM-404
- Arachidonoyl serotonin
- Arvanil
- BIA 10-2474
- Biochanin A
- CAY-10401
- CAY-10429
- Genistein
- Guineesine
- IDFP
- JNJ 1661010
- JNJ-42165279
- JZL184
- JZL195
- Kaempferol
- LY-2183240
- MK-4409
- O-1624
- O-2093
- Oleoylethanolamide (OEA)
- Olvanil
- Palmitoylethanolamide (PEA)
- PF-04457845
- PF-622
- PF-750
- PF-3845
- PHOP
- URB-447
- URB-597
- URB-602
- URB-754
- VDM-11
(antagonists/inverse
agonists/antibodies)
- AM-251
- AM-281
- AM-630
- AM-1387
- AM-4113
- AM-6527
- AM-6545
- BML-190
- Brizantin (Бризантин)
- CAY-10508
- CB-25
- CB-52
- CB-86
- Dietressa (Диетресса)
- Drinabant (AVE1625)
- Hemopressin
- Ibipinabant (SLV319)
- JTE-907
- LH-21
- LY-320,135
- MDA-77
- MJ-15
- MK-9470
- NESS-0327
- NIDA-41020
- O-606
- O-1184
- O-1248
- O-1918
- O-2050
- O-2654
- Otenabant (CP-945,598)
- PF-514273
- PipISB
- PSB-SB-487
- Rimonabant (SR141716)
- Rosonabant (E-6776)
- SR-144,528
- Surinabant (SR147778)
- Taranabant (MK-0364)
- TM-38837
- VCHSR
- See also: Cannabinoid receptor modulators (cannabinoids by pharmacology)
- List of: AM cannabinoids
- JWH cannabinoids
- Designer drugs § Synthetic cannabimimetics