Tetrahydrocannabivarin


Tetrahydrocannabivarin is a homologue of tetrahydrocannabinol having a propyl side chain instead of a pentyl group on the molecule, which makes it produce very different effects from THC.

Chemistry

Similar to THC, THCV has 7 double bond isomers and 30 stereoisomers.

Description

Plants with elevated levels of propyl cannabinoids have been found in populations of Cannabis sativa L. ssp. indica 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.
THCV is a cannabinoid receptor type 1 antagonist and cannabinoid receptor type 2 partial agonist. Δ8-THCV has also been shown to be a CB1 antagonist. Both papers describing the antagonistic properties of THCV were demonstrated in murine models.

Biosynthesis

Unlike THC, cannabidiol, and cannabichromene, THCV doesn’t begin as cannabigerolic acid. 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. Once CBGVA is created, the process continues exactly the same as it would for THC. CBGVA is broken down to tetrahydrocannabivarin carboxylic acid by the enzyme THCV synthase. At that point, THCVA can be decarboxylated with heat or UV light to create THCV.

Research

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

Legal status

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. 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 plant in the United States.