Tetrahydrocannabivarin

Tetrahydrocannabivarin
Clinical data
Routes of
administration		Oral, Smoked, Inhaled
ATC code
  • none
Legal status
Legal status
  • Legal in US, UK, Canada and Netherlands
Identifiers
IUPAC name
  • 6,6,9-Trimethyl-3-propyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H26O2
Molar mass286.415 g·mol−1
3D model (JSmol)
SMILES
  • CCCC1=CC2=C(C3C=C(CCC3C(O2)(C)C)C)C(=C1)O
InChI
  • InChI=1S/C19H26O2/c1-5-6-13-10-16(20)18-14-9-12(2)7-8-15(14)19(3,4)21-17(18)11-13/h9-11,14-15,20H,5-8H2,1-4H3/t14-,15-/m1/s1 checkY
  • Key:ZROLHBHDLIHEMS-HUUCEWRRSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Tetrahydrocannabivarin (THCV, THV, O-4394, GWP42004) 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]

Natural occurrence

THCV is prevalent in certain central Asian and southern African strains of Cannabis.[2][3]

Chemistry

Similar to THC, THCV has 7 possible double bond isomers and 30 stereoisomers (see: Tetrahydrocannabinol#Isomerism). The alternative isomer Δ8-THCV is known as a synthetic compound with a code number of O-4395,[4] but it is not known to have been isolated from Cannabis plant material.

O-4395 (Δ8-THCV), 31262-38-1

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.[5][6]

THCV is a cannabinoid receptor type 1 antagonist and cannabinoid receptor type 2 partial agonist.[7] Δ8-THCV has also been shown to be a CB1 antagonist.[8] Both papers describing the antagonistic properties of THCV were demonstrated in murine models. THCV is an antagonist of THC at CB1 receptors and lessens the psychoactive effects of THC.[9]

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 two fewer carbon atoms. The result is cannabigerovarin acid (CBGVA). Once CBGVA is created, the process continues exactly the 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.

Research

Reducing blood sugar

THCV is a new potential treatment against obesity-associated glucose intolerance with pharmacology different from that of CB1 inverse agonists/antagonists.[10] GW Pharmaceuticals is studying plant-derived tetrahydrocannabivarin (as GWP42004) for type 2 diabetes in addition to metformin.

Appetite control

THC increases appetite (aka "the munchies") by acting as a CB1 agonist. As a CB1 antagonist, THCV has been shown to reduce appetite in murine models.[11]

It is not scheduled by Convention on Psychotropic Substances. In the United States, THCV is not specifically listed as a Schedule I drug, but "Marijuana Extract" is.[12] THCV could be considered an analog of THC, in which case, sales or possession intended for human consumption could be prosecuted under the Federal Analog Act.

United States

THCV is not scheduled at the federal level so long as it is not derived from the cannabis plant in the United States.[13]

The 2018 United States farm bill legalized the production and sale of THCV if it is derived from hemp compliant with the farm bill.[14]

See also

References

  1. ↑ SC Labs, Cannabinoids
  2. ↑ Baker PB, Gough TA, Taylor BJ (1980). "Illicitly imported Cannabis products: some physical and chemical features indicative of their origin". Bulletin on Narcotics. 32 (2): 31–40. PMID 6907024.
  3. ↑ Hillig KW, Mahlberg PG (June 2004). "A chemotaxonomic analysis of cannabinoid variation in Cannabis (Cannabaceae)". American Journal of Botany. 91 (6): 966–75. doi:10.3732/ajb.91.6.966. PMID 21653452.
  4. ↑ Brown NK, Harvey DJ (April 1988). "In vivo metabolism of the n-propyl homologues of delta-8- and delta-9-tetrahydrocannabinol in the mouse". Biomedical & Environmental Mass Spectrometry. 15 (7): 403–10. doi:10.1002/bms.1200150708. PMID 2839261.
  5. ↑ Turner CE, Hadley K, Fetterman PS (October 1973). "Constituents of Cannabis sativa L. VI. Propyl homologs in samples of known geographical origin". Journal of Pharmaceutical Sciences. 62 (10): 1739–41. doi:10.1002/jps.2600621045. PMID 4752132.
  6. ↑ Hillig KW, Mahlberg PG (June 2004). "A chemotaxonomic analysis of cannabinoid variation in Cannabis (Cannabaceae)". American Journal of Botany. 91 (6): 966–75. doi:10.3732/ajb.91.6.966. PMID 21653452. S2CID 32469533.
  7. ↑ Pertwee RG (January 2008). "The diverse CB1 and CB2 receptor pharmacology of three plant cannabinoids: delta9-tetrahydrocannabinol, cannabidiol and delta9-tetrahydrocannabivarin". British Journal of Pharmacology. 153 (2): 199–215. doi:10.1038/sj.bjp.0707442. PMC 2219532. PMID 17828291.
  8. ↑ Pertwee RG, Thomas A, Stevenson LA, Ross RA, Varvel SA, Lichtman AH, et al. (March 2007). "The psychoactive plant cannabinoid, Delta9-tetrahydrocannabinol, is antagonized by Delta8- and Delta9-tetrahydrocannabivarin in mice in vivo". British Journal of Pharmacology. 150 (5): 586–94. doi:10.1038/sj.bjp.0707124. PMC 2189766. PMID 17245367.
  9. ↑ 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.
  10. ↑ Wargent ET, Zaibi MS, Silvestri C, Hislop DC, Stocker CJ, Stott CG, et al. (May 2013). "The cannabinoid Δ(9)-tetrahydrocannabivarin (THCV) ameliorates insulin sensitivity in two mouse models of obesity". Nutrition & Diabetes. 3 (5): e68. doi:10.1038/nutd.2013.9. PMC 3671751. PMID 23712280.
  11. ↑ Riedel G, Fadda P, McKillop-Smith S, Pertwee RG, Platt B, Robinson L (2009). "Synthetic and plant-derived cannabinoid receptor antagonists show hypophagic properties in fasted and non-fasted mice". British Journal of Pharmacology. 156 (7): 1154–1166. doi:10.1111/j.1476-5381.2008.00107.x. PMC 2697695. PMID 19378378.
  12. ↑ Federal Register, Vol. 81, No. 240, December 14, 2016]
  13. ↑ §1308.11 Schedule I. section (d) Hallucinogenic substances part (33)
  14. ↑ "Summary of H.R. 2 (115th): Agriculture Improvement Act of 2018".
  • Erowid Compounds found in Cannabis sativa
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