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Tetrahydrocannabutol

Chemical compound

Summary

Chemical compound

Field	Value
Verifiedfields	changed
Watchedfields	changed
verifiedrevid	448003399
IUPAC_name	(−)-(6aR,10aR)-6,6,9-trimethyl-3-butyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol
image	Tetrahydrocannabinol-c4.svg
image_class	skin-invert-image
image2	THCB 3D BS.png
image_class2	bg-transparent
drug_name	Δ9-Tetrahydrocannabinol-C4
CAS_number_Ref
CAS_number	60008-00-6
UNII_Ref
UNII	LIC9QAS59U
ATC_prefix	none
PubChem	6453891
ChemSpiderID_Ref
ChemSpiderID	4956237
ChEMBL	4437290
C	20	H=28	O=2
smiles	CCCCC1=CC2=C([C@@H]3C=C(CC[C@H]3C(O2)(C)C)C)C(=C1)O
StdInChI_Ref
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
StdInChIKey_Ref
StdInChIKey	QHCQSGYWGBDSIY-HZPDHXFCSA-N

| elimination_half-life =

Δ9-Tetrahydrocannabutol (Δ9-THCB, THC-B, tetrahydrocannabinol-C4, THC-C4, (C4)-Δ9-THC, or butyl-THC) is a phytocannabinoid found in cannabis that is a homologue of tetrahydrocannabinol (THC), the main active component of Cannabis. 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

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. The formalin test in vivo was performed on Δ9-THCB in order to reveal possible analgesic and anti-inflammatory properties. The tetrad test in mice showed a partial agonistic activity of Δ9-THCB toward the CB1 receptor. THCB has rarely been isolated from cannabis samples, but appears to be less commonly present than THC or THCV. It is metabolized in a similar manner to THC.

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).

Chemistry

Similarly to THC, it has 7 double bond isomers and 30 stereoisomers. The Δ8 isomer is known as a synthetic cannabinoid under the code name JWH-130, and the ring-opened analogue cannibidibutol (CBDB) is also known. THC-Butyl can be synthesized from 4-butylresorcinol.

Cannabidibutol (CBDB), 60113-11-3 [https://pubchem.ncbi.nlm.nih.gov/compound/59444413]]]{{clear left}}

JWH-130 (Δ<sup>8</sup>-THCB), 51768-59-3 [https://pubchem.ncbi.nlm.nih.gov/compound/6452496]]]{{clear left}}

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.

References

(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.
(1942). "Tetrahydrocannabinol Homologs and Analogs with Marihuana Activity. XIII¹". Journal of the American Chemical Society.
(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.
(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.
(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.
"Verschil THC Olie, CBD olie, wietolie, hennepolie en cannabisolie?".
(2016). "The Structure-Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation". Perspectives in Medicinal Chemistry.
(November 2016). "Phytocannabinoids: a unified critical inventory". Natural Product Reports.

Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

terpeno-phenolic-compounds cannabinoids diterpenes benzochromenes tetrahydrocannabinol

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