Tetrahydrocannabinol-C4

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Δ9-Tetrahydrocannabinol-C4
Tetrahydrocannabinol-c4.svg
Clinical data
ATC code
  • none
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H28O2
Molar mass300.442 g·mol−1
3D model (JSmol)
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Tetrahydrocannabinol-C4 (Δ9-THCB, (C4)-Δ9-THC, butyl-THC), is a homologue of tetrahydrocannabinol (THC), the active component of cannabis. They are only different by the pentyl side chain being replaced by a butyl side chain. It is unknown whether THCB is an agonist, partial agonist, or antagonist at the cannabinoid receptors. The propyl analog, THCV, is a cannabinoid receptor type 1 and cannabinoid receptor type 2 antagonist,[1] while THC is a CB1 agonist. THCB has rarely been isolated from cannabis samples,[2] but appears to be less commonly present than THC or THCV. It is metabolised in a similar manner to THC.[3] Similarly to THC, it has 7 double bond isomers and 30 stereoisomers.[4]

Legality[edit]

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[edit]

References[edit]

  1. ^ Thomas A, Stevenson LA, Wease KN, Price MR, Baillie G, Ross RA, Pertwee RG (December 2005). "Evidence that the plant cannabinoid Delta9-tetrahydrocannabivarin is a cannabinoid CB1 and CB2 receptor antagonist". British Journal of Pharmacology. 146 (7): 917–26. doi:10.1038/sj.bjp.0706414. PMC 1751228. PMID 16205722.
  2. ^ 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.
  3. ^ 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.
  4. ^ "Verschil THC Olie, CBD olie, wietolie, hennepolie en cannabisolie?". Dutch-Headshop.com. Retrieved 19 November 2016.