Tetrahydrocannabivarin

From Wikipedia, the free encyclopedia

Tetrahydrocannabivarin
IUPAC name 6,6,9-trimethyl-3-propyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
Identifiers
CAS number [28172-17-0]
PubChem 34180
SMILES CCCC1=CC2=C(C3C=C(CCC3C(O2)(C)C)C)C(=C1)O
Properties
Molecular formula C19H26O2
Molar mass 286.41
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Tetrahydrocannabivarin, also known as tetrahydrocannabivarol, THCV, or THV, is a psychoactive cannabinoid found in the hemp plant Cannabis sativa. It is an analog of tetrahydrocannabinol (THC) with the sidechain shortened by two CH2 groups. THCV can be used as a marker compound to differentiate between the consumption of hemp products and synthetic THC (Dronabinol, Marinol).

Contents

[edit] Natural occurrence

THCV is found in largest quantities from Indica strains. Some varieties that produce propyl cannabinoids in significant amounts, over five percent of total cannabinoids, have been found in plants from South Africa, Nigeria, Afghanistan, India, Pakistan and Nepal with THCV as high as 53.69% of total cannabinoids.[1] They usually have moderate to high levels of both THC and CBD and hence have a complex cannabinoid chemistry representing some of the world's most exotic cannabis varieties.[2]

[edit] Pharmaceutical properties

It has been shown to be a CB1 antagonist, i.e. blocks the effects of THC.[3] In 2007 GW Pharmaceuticals announced that THCV is safe in humans in a clinical trial and it will continue to develop THCV as a potential cannabinoid treatment for type 2 diabetes and related metabolic disorders, similar to the CB1-antagonist rimonabant.[4]

[edit] See also

[edit] Notes

  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. ^ Deluxe Marijuana Grower's Guide, by Mel Frank [revised edition 1997] pg.37
  3. ^ Pertwee RG, Thomas A, Stevenson LA, et al (2007). "The psychoactive plant cannabinoid, Delta9-tetrahydrocannabinol, is antagonized by Delta8- and Delta9-tetrahydrocannabivarin in mice in vivo". Br. J. Pharmacol. 150 (5): 586–94. doi:10.1038/sj.bjp.0707124. PMID 17245367. 
  4. ^ Press Release by GW Pharmaceuticals[1]

[edit] External links

v • d • e
Cannabinoids
Plant cannabinoids
CBD • CBDV • CBN • CBG • CBV • CBL • THC • THC-C4 • THCV
Cannabinoid metabolites
Endogenous cannabinoids
Arachidonoyl ethanolamide (Anandamide or AEA) • 2-Arachidonoylglycerol (2-AG) • 2-Arachidonyl glyceryl ether (noladin ether) • Virodhamine • N-arachidonoyl-dopamine (NADA)
Synthetic cannabinoid agonists
Classical cannabinoids (Dibenzopyrans)

A-41988 • Ajulemic acid • AM-087 • AM-411 • AM-855 • AM-905 • AM-906 • AM-919 • AM-938 • AM-4030 • AMG-1 • AMG-3 • AMG-36 • AMG-41 • Dexanabinol (HU-211) • DMHP • Dronabinol • HU-210 • JWH-051 • JWH-133 • JWH-139 • L-759,633 • L-759,656 • Levonantradol • Nabilone • Nabitan • O-806 • O-823 • O-1057 • O-1125 • O-1238 • O-2545 • O-2694 • Parahexyl • THC-O-acetate • THC-O-phosphate
Nonclassical cannabinoids
Aminoalkylindoles

AM-630 • AM-1241 • JWH-015 • JWH-018 • JWH-073 • JWH-081 • JWH-200 • L-768,242 • Pravadoline • WIN 55,212-2
Aminoalkylpyrroles

JWH-030 • JWH-147 • JWH-307
Eicosanoids

AM-883 • Arachidonyl-2'-chloroethylamide • Arachidonylcyclopropylamide • Methanandamide • O-585 • O-689 • O-1812 • O-1860 • O-1861
Others

BAY 38-7271 • BAY 59-3074 • JWH-171 • O-2220
Endocannabinoid activity enhancers

AM-404 • N-arachidonoyl-serotonin • O-1624 • URB-597 • URB-754
Cannabinoid antagonists and inverse agonists

AM-251 • AM-281 • AM-630 • BML-190 • JTE-907 • LY-320,135 • NESS-0327 • O-1184 • O-2050 • O-2654 • Rimonabant • SLV-319 • SR-144,528 • Surinabant • Taranabant • VCHSR
Tablets  This pharmacology-related article is a stub. You can help Wikipedia by expanding it.