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.

Biosynthesis[edit]

Unlike THC, cannabidiol (CBD), and cannabichromene (CBC), THCV doesn’t begin as cannabigerolic acid (CBGA). Instead of combining with olivetolic acid to create CBGA, the geranyl phosphate joins forces with divarinolic acid, which has 2 less carbon molecules. The result is cannabigerovarin acid (CBGVA). Once CBGVA is created, the process continues exactly same as it would for THC. CBGVA is broken down to tetrahydrocannabivarin carboxylic acid (THCVA) by the THCV synthase. At that point, THCVA can be decarboxylated with heat or UV light to create THCV.[5]

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.
  5. ^ MedicalJane. "What is Tetrahydrocannabivarin?". 

External links[edit]