Tetrahydrocannabivarin (THCV, THV, O-4394, GWP42004) is a homologue of

tetrahydrocannabinol Tetrahydrocannabinol (THC) is the principal psychoactive constituent of cannabis and one of at least 113 total cannabinoids identified on the plant. Although the chemical formula for THC (C21H30O2) describes multiple isomers, the term ''THC' ...

(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.

Natural occurrence

THCV is prevalent in certain central Asian and southern African strains of ''Cannabis''.

Chemistry

Similar to THC, THCV has 7 possible double bond

isomers In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of 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, but it is not known to have been isolated from ''

Cannabis ''Cannabis'' () is a genus of flowering plants in the family Cannabaceae. The number of species within the genus is disputed. Three species may be recognized: '' Cannabis sativa'', '' C. indica'', and '' C. ruderalis''. Alternative ...

'' plant material. D8THCV_structure

]

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 India, officially the Republic of India (Hindi: ), is a country in South Asia. It is the List of countries and dependencies by area, seventh-largest country by area, the List of countries and dependencies by population, second-most populous ...

Nepal Nepal (; ne, नेपाल ), formerly the Federal Democratic Republic of Nepal ( ne, सङ्घीय लोकतान्त्रिक गणतन्त्र नेपाल ), is a landlocked country in South Asia. It is ma ...

, Thailand,

Afghanistan Afghanistan, officially the Islamic Emirate of Afghanistan,; prs, امارت اسلامی افغانستان is a landlocked country located at the crossroads of Central Asia and South Asia. Referred to as the Heart of Asia, it is borde ...

, and

Pakistan Pakistan ( ur, ), officially the Islamic Republic of Pakistan ( ur, , label=none), is a country in South Asia. It is the world's List of countries and dependencies by population, fifth-most populous country, with a population of almost 24 ...

, 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 or, at higher doses, a CB₁ receptor agonist and cannabinoid receptor type 2

partial agonist In pharmacology, partial agonists are drugs that bind to and activate a given receptor, but have only partial efficacy at the receptor relative to a full agonist. They may also be considered ligands which display both agonistic and antagonis ...

. Δ⁸-THCV has also been shown to be a CB₁ antagonist. Both papers describing the antagonistic properties of THCV were demonstrated in

murine The Old World rats and mice, part of the subfamily Murinae in the family Muridae, comprise at least 519 species. Members of this subfamily are called murines. In terms of species richness, this subfamily is larger than all mammal families ex ...

models. THCV is an antagonist of THC at CB₁ receptors and lessens the psychoactive effects of THC.

Biosynthesis

Unlike THC, cannabidiol (CBD), and

cannabichromene Cannabichromene (CBC), also called cannabichrome, cannanbichromene, pentylcannabichromene or cannabinochromene, is an anti-inflammatory which may contribute to the pain-killing effect of cannabis. It is one of the hundreds of cannabinoids found i ...

(CBC), THCV doesn't begin as cannabigerolic acid (CBGA). Instead of combining with

olivetolic acid Olivetolic acid is an organic compound that is an intermediate in the biosynthetic pathway of the cannabinoids in ''Cannabis sativa''. The ester dimer of olivetolic acid, anziaic acid, is found in lichen A lichen ( , ) is a composite or ...

to create CBGA, geranyl pyrophosphate joins with divarinolic acid, which has two fewer carbon atoms. The result is

cannabigerovarin acid Cannabigerovarin (CBGV), the propyl homolog of cannabigerol (CBG), is a cannabinoid present in ''Cannabis''. There is no observation related to the psychoactive or psychotropic effects of CBGV when consumed or inhaled. The possible benefits of c ...

(CBGVA). Once CBGVA is created, the process continues exactly the same as it would for THC. CBGVA is broken down to

tetrahydrocannabivarin carboxylic acid 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. ...

(THCVA) by the enzyme

THCV synthase 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. ...

. At that point, THCVA can be

decarboxylated Decarboxylation is a chemical reaction that removes a carboxyl group and releases carbon dioxide (CO2). Usually, decarboxylation refers to a reaction of carboxylic acids, removing a carbon atom from a carbon chain. The reverse process, which is ...

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. GW Pharmaceuticals is studying plant-derived tetrahydrocannabivarin (as GWP42004) for type 2 diabetes in addition to metformin.

Appetite control

THC increases appetite, which is sometimes referred to as "the munchies." THC acts as a CB1 agonist. As a CB1 antagonist, THCV has been shown to reduce appetite in murine models.

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 The Controlled Substances Act (CSA) is the statute establishing federal government of the United States, federal drug policy of the United States, U.S. drug policy under which the manufacture, importation, possession, use, and distribution of ...

, 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 cannabis plant in the United States.§1308.11 Schedule I.
section (d) Hallucinogenic substances part (33) The

2018 United States farm bill The 2018 farm bill or Agriculture Improvement Act of 2018 is an enacted United States farm bill that reauthorized $867 billion for many expenditures approved in the prior farm bill (the Agricultural Act of 2014). The bill was passed by the Sena ...

legalized the production and sale of THCV if it is derived from hemp compliant with the farm bill.

References

External links

Erowid
Compounds found in ''Cannabis sativa'' {{Cannabinoidergics Phytocannabinoids CB1 receptor antagonists Terpeno-phenolic compounds Benzochromenes