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Tetrahydrocannabivarin

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Title: Tetrahydrocannabivarin  
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Subject: Cannabis (drug), Cannabinoid, Parahexyl, Cannabidiol, Effects of cannabis
Collection: Benzochromenes, Cannabinoids, Cb1 Receptor Antagonists, Terpeno-Phenolic Compounds
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Tetrahydrocannabivarin

Tetrahydrocannabivarin
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 of
administration
Oral, Smoked, Inhaled
Identifiers
CAS Registry Number  N
ATC code None
PubChem CID:
IUPHAR/BPS
ChemSpider  N
Chemical data
Formula C19H26O2
Molecular mass 286.41 g/mol
 N   

Tetrahydrocannabivarin (THCV, THV) is a homologue of tetrahydrocannabinol (THC) having a propyl (3-carbon) side chain instead of a pentyl (5-carbon) group on the molecule, which makes it produce very different effects from THC.[1] 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.

Contents

  • Chemistry 1
  • Description 2
  • Biosynthesis 3
  • Research 4
  • Legal status 5
    • United States 5.1
  • See also 6
  • References 7
  • External links 8

Chemistry

Similarly to THC, THCV has 7 double bond isomers and 30 stereoisomers (see: Tetrahydrocannabinol#Isomerism). Its melting point is < 220 degrees Celsius, < 428 degrees Fahrenheit.[2]

Description

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. [3] [4]

THCV is a cannabinoid receptor type 1 antagonist and cannabinoid receptor type 2 partial agonist.[5] Δ8-THCV has also been shown to be a CB1 antagonist.[6] Both papers describing the antagonistic properties of THCV were demonstrated in murine models.

Biosynthesis

Unlike THC, cannabidiol (CBD), and cannabichromene (CBC), THCV doesn’t begin as cannabigerolic acid (CBGA). Instead of combining with olivetolic acid to create CBGA, geranyl pyrophosphate joins with divarinolic acid, which has 2 less carbon atoms. 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 enzyme THCV synthase. At that point, THCVA can be decarboxylated with heat or UV light to create THCV.[7]

Research

GW Pharmaceuticals is studying plant-derived tetrahydrocannabivarin (as GWP42004) for type 2 diabetes in addition to metformin.[8] The phase 2b trial will follow 200 patients for 12 weeks and completion is expected in 2015.

Legal status

It is not scheduled by Convention on Psychotropic Substances.

United States

THCV is not scheduled at the federal level in the United States,[9] but it is possible that THCV could legally be considered an analog of THC, in which case purchase, sale, or possession could be prosecuted under the Federal Analog Act.

See also

References

  1. ^ SC Labs, Cannabinoids
  2. ^ Skunk Pharma Search, Cannabinoid and Terpene info
  3. ^ 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
  4. ^ 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.
  5. ^ 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.  
  6. ^ 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.
  7. ^ MedicalJane. "What is Tetrahydrocannabivarin?". 
  8. ^ plc, GW Pharmaceuticals. "GW Pharmaceuticals Provides Update on Cannabinoid Pipeline". Retrieved 2015-09-19. 
  9. ^ §1308.11 Schedule I.

External links

  • Erowid Compounds found in Cannabis sativa


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