Tetrahydrocannabinol-C4

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Δ9-Tetrahydrocannabinol-C4
Tetrahydrocannabinol-c4.svg
Systematic (IUPAC) name
(−)-(6aR,10aR)-6,6,9-trimethyl-3-butyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol
Clinical data
Legal status
  •  ?
Identifiers
CAS Registry Number 60008-00-6 N
ATC code None
PubChem CID: 6453891
Chemical data
Formula C20H28O2
Molecular mass 300.43 g/mol
 N (what is this?)  (verify)

Tetrahydrocannabinol-C4, also known as THC-C4 and 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 THC-C4 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. THC-C4 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.

It is not scheduled by Convention on Psychotropic Substances.

See also[edit]

References[edit]

  1. ^ Thomas, Adèle; Stevenson, Lesley A; Wease, Kerrie N; Price, Martin R; Baillie, Gemma; Ross, Ruth A; Pertwee, Roger G (December 2005). "Evidence that the plant cannabinoid Δ9-tetrahydrocannabivarin is a cannabinoid CB1 and CB2 receptor antagonist". British Journal of Pharmacology 146 (7): 917–926. doi:10.1038/sj.bjp.0706414. PMC 1751228. PMID 16205722. 
  2. ^ Harvey, DJ (Apr 1976). "Characterization of the butyl homologues of delta1-tetrahydrocannabinol, cannabinol and cannabidiol in samples of cannabis by combined gas chromatography and mass spectrometry". Journal of Pharmacy and Pharmacology 28 (4): 280–5. doi:10.1111/j.2042-7158.1976.tb04153.x. PMID 6715. 
  3. ^ Brown, NK; Harvey, DJ (Apr 1988). "In vivo metabolism of the n-butyl-homologues of delta 9-tetrahydrocannabinol and delta 8-tetrahydrocannabinol by the mouse". Xenobiotica 18 (4): 417–27. doi:10.3109/00498258809041678. PMID 2840781.