Tetrahydrocannabivarin

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Tetrahydrocannabivarin
Thcv.svg
Tetrahydrocannabivarin-3D-balls.png
Systematic (IUPAC) name
6,6,9-trimethyl-3-propyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol
Clinical data
Legal status ?
Routes Oral, Smoked, Inhaled
Identifiers
CAS number 28172-17-0 N
ATC code None
PubChem CID 34180
ChemSpider 31500 N
Chemical data
Formula C19H26O2 
Mol. mass 286.41 g/mol
 N (what is this?)  (verify)

Tetrahydrocannabivarin (THCV, THV) is a homologue of tetrahydrocannabinol (THC) having a propyl (3-carbon) side chain. This terpeno-phenolic compound is found naturally in Cannabis, sometimes in significant amounts. The psychoactive effects of THCV in Cannabis preparations are not well characterized.

Similarly to THC, it has 7 double bond isomers and 30 stereoisomers (see: Tetrahydrocannabinol#Isomerism). It is not scheduled by Convention on Psychotropic Substances.

Description[edit]

Plants with elevated levels of propyl cannabinoids (including THCV) have been found in populations of Cannabis sativa L. ssp. indica (= Cannabis indica Lam.) from China, India, Nepal, Thailand, Afghanistan, and Pakistan, as well as southern and western Africa. THCV levels up to 53.7% of total cannabinoids have been reported. [1] [2]

THCV is a Cannabinoid receptor type 1 antagonist and Cannabinoid receptor type 2 partial agonist.[3] Δ8-THCV has also been shown to be a CB1 antagonist.[4] Both papers describing the antagonistic properties of THCV were demonstrated in murine models.

See also[edit]

References[edit]

  1. ^ Turner, C.E., Hadley, K.W., and Fetterman, P. 1973. Constituents of Cannabis Sativa L., VI: Propyl Homologues in Samples of Known Geographical Origin. J. Pharm. Sci. 62(10):1739-1741
  2. ^ Hillig, Karl W. and Paul G. Mahlberg. 2004. A chemotaxonomic analysis of cannabinoid variation in Cannabis (Cannabaceae). American Journal of Botany 91(6): 966-975.
  3. ^ Pertwee, Roger G (September 2007). "The diverse CB1 and CB2 receptor pharmacology of three plant cannabinoids: Δ9-tetrahydrocannabinol, cannabidiol and Δ9-tetrahydrocannabivarin". British Journal of Pharmacology 153 (2): 199–215. doi:10.1038/sj.bjp.0707617. 
  4. ^ Pertwee RG, Thomas A, Stevenson LA, et al. 2007. The psychoactive plant cannabinoid, Δ9-tetrahydrocannabinol, is antagonized by Δ8- and Δ9-tetrahydrocannabivarin in mice in vivo. Br. J. Pharmacol. 150(5): 586–94.

External links[edit]