Difference between revisions of "Tetrahydrocannabivarin"
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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. | 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. | ||
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| + | [[File:tetrahydrocannabivarin.png|200px|thumb|right|]] | ||
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| + | == Chemistry == | ||
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| + | Similarly to [[THC]], THCV has 7 double bond isomers and 30 stereoisomers (see: Tetrahydrocannabinol#Isomerism). | ||
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| + | == Description == | ||
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| + | 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. | ||
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| + | 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 (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 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 enzyme THCV synthase. At that point, THCVA can be decarboxylated with heat or UV light to create THCV. | ||
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| + | == Medical Useage == | ||
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| + | THCv is a strong anorectic, meaning it suppresses appetite and can be very useful in the treatment of obesity [http://www.ncbi.nlm.nih.gov/pubmed/25542687]. Among other properties, THC also may have an anti-psychotic effect, thereby counteracting the euphoriant agents in cannabis [http://www.ncbi.nlm.nih.gov/pubmed/25363799]. It also has the potential to modulate insulin sensitivity and ameliorate cases of diabetes or obesity [http://www.ncbi.nlm.nih.gov/pubmed/23712280]. Moreover, its anti-inflammatory effect can prove therapeutic in other immune disorders [http://www.ncbi.nlm.nih.gov/pubmed/21470208]. | ||
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| + | == Legal status == | ||
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| + | It is not scheduled by Convention on Psychotropic Substances. | ||
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| + | '''United States''' | ||
| + | THCV is not scheduled at the federal level in the United States, 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. | ||
Latest revision as of 10:42, 6 May 2015
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.
Chemistry
Similarly to THC, THCV has 7 double bond isomers and 30 stereoisomers (see: Tetrahydrocannabinol#Isomerism).
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.
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 (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 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 enzyme THCV synthase. At that point, THCVA can be decarboxylated with heat or UV light to create THCV.
Medical Useage
THCv is a strong anorectic, meaning it suppresses appetite and can be very useful in the treatment of obesity [1]. Among other properties, THC also may have an anti-psychotic effect, thereby counteracting the euphoriant agents in cannabis [2]. It also has the potential to modulate insulin sensitivity and ameliorate cases of diabetes or obesity [3]. Moreover, its anti-inflammatory effect can prove therapeutic in other immune disorders [4].
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, 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.
