chemistry

Tetrahydrocannabivarin

Tetrahydrocannabivarin is a chemistry topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand Tetrahydrocannabivarin rather than just read about it. In short: Tetrahydrocannabivarin (THCV, THV, O-4394, GWP42004) is a homologue of tetrahydrocannabinol (THC) having a propyl (3-carbon) side chain instead of pentyl (5-carbon), making it non-psychoactive in lower doses. It has been shown to exhibit neuroprotective activity, appetite suppression, glycemic control and reduced side effects compared to THC, making it a potential treatment for management of obesity and diabetes.

Key takeaways

Tetrahydrocannabivarin belongs to chemistry; place it in that map before memorising details.
Learn the definition first, then one example that makes the definition concrete.
Connect Tetrahydrocannabivarin to a quantity you can measure, compute or draw — that is where exam questions come from.
Reproduce the core statement of Tetrahydrocannabivarin from memory before moving on to harder problems.

Reference excerpt

Tetrahydrocannabivarin (THCV, THV, O-4394, GWP42004) is a homologue of tetrahydrocannabinol (THC) having a propyl (3-carbon) side chain instead of pentyl (5-carbon), making it non-psychoactive in lower doses. It has been shown to exhibit neuroprotective activity, appetite suppression, glycemic control and reduced side effects compared to THC, making it a potential treatment for management of obesity and diabetes. THCV was studied by Roger Adams as early as 1942. THCV is prevalent in certain central Asian and southern African strains of Cannabis.

Pharmacology

Mechanism of action THCV is a cannabinoid receptor type 1 antagonist or, at higher doses, a CB1 receptor agonist 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. THCV is an antagonist of CB1 receptors and lessens the psychoactive effects of THC. THCV also acts as an agonist of GPR55 and l-α-lysophosphatidylinositol (LPI), and beyond the endocannabinoid system, THCV also activate 5-HT1A receptors to produce an antipsychotic effect, that has shown therapeutic potential for ameliorating some of the negative, cognitive and positive symptoms of schizophrenia. THCV furthermore interacts with different transient receptor potential (TRP) channels including TRPV2, which may contribute to the analgesic, anti-inflammatory and anti-cancer effects of cannabinoids and Cannabis extracts. It has also shown anti-epileptiform and anticonvulsant properties, that suggest possible therapeutic application in the treatment of pathophysiologic hyperexcitability states such as untreatable epilepsy. THCV is found to inhibit the activity of both fatty acid amide hydrolase (FAAH) and monoacyl glycerol lipase (MGL), even at micromolar concentrations, and thereby able to inhibit the hydrolysis of the endocannabinoids anandamide (AEA: C22H37NO2; 20:4, ω-6) besides other N-acylethanolamines and 2-Arachidonoylglycerol (2-AG: C23H38O4; 20:4, ω-6), respectively, therefore, it can also act as an indirect agonist at the cannabinoid receptors, by enhancing the activity of the endocannabinoid system (ECS).

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, but it is not known to have been isolated from Cannabis plant material.

Synthesis 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.

Natural occurrence 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 20% of total cannabinoids have been reported.[2]

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.

Energy and motivation A 2:1 ratio of naturally derived THCV to THC extract has been demonstrated to show energizing and motivating effects in a double blind placebo clinical study which relied on a self-reported user survey for results.

Society and culture

Legal status It is not scheduled by Convention on Psychotropic Substances.

United States THCV is not scheduled at the federal level so long as it is not derived from cannabis varieties that produce more than .3% THC on a dry weight basis in the United States. The 2018 United States farm bill legalized the production and sale of THCV if it is derived from hemp compliant with the farm bill.

See also Cannabinoid Cannabis Cannabivarin (CBV) Cannabidivarin (CBDV) Federal Analogue Act Hexahydrocannabivarin Medical cannabis Parahexyl Rimonabant (synthetic CB1 antagonist) Tetrahydrocannabiorcol (Δ9-THCC, (C1)-Δ9-THC) Tetrahydrocannabutol (Δ9-THCB, (C4)-Δ9-THC) Tetrahydrocannabihexol (Δ9-THCH, (C6)-Δ9-THC) Tetrahydrocannabiphorol (Δ9-THCP, (C7)-Δ9-THC)

References

External links Erowid Compounds found in Cannabis sativa

Illustrations

Worked examples

Example 1 — a first encounter with Tetrahydrocannabivarin

Start with the simplest possible case. Write down what Tetrahydrocannabivarin claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In chemistry, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to Tetrahydrocannabivarin before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about Tetrahydrocannabivarin ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of Tetrahydrocannabivarin

In research: Tetrahydrocannabivarin appears in chemistry research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry: Engineering practice reuses Tetrahydrocannabivarin in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom: Tetrahydrocannabivarin is common in secondary-school and first-year university syllabi. It links to neighbouring topics Benzochromenes, CB1 receptor antagonists, Drugs not assigned an ATC code, so understanding it makes those chapters shorter.
In everyday life: Look for Tetrahydrocannabivarin outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.

Ask Teacher Smith questions about this articleOpens your AI tutor with a question about “Tetrahydrocannabivarin” →

Affiliate

Preply — study more efficiently by working with a personal tutor. 50% off.

How to study Tetrahydrocannabivarin in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Tetrahydrocannabivarin means in your own words.
Compare your version with the excerpt and mark what you missed.
Work through the three examples above with pen and paper.
Explain Tetrahydrocannabivarin out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Tetrahydrocannabivarin in simple terms?

Why does Tetrahydrocannabivarin matter?

Because it connects several chemistry ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study Tetrahydrocannabivarin?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on Tetrahydrocannabivarin.