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VR (nerve agent)

VR (nerve agent) 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 VR (nerve agent) rather than just read about it. In short: VR (Russian VX, VXr, Soviet V-gas, GOSNIIOKhT substance No. 33, Agent "November") is a "V-series" unitary nerve agent closely related (it is an isomer) to the better-known VX nerve agent. It became a prototype for the series of Novichok agents.

VR (nerve agent) — main illustration
VR (nerve agent) — illustration

Key takeaways

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

Reference excerpt

VR (Russian VX, VXr, Soviet V-gas, GOSNIIOKhT substance No. 33, Agent "November") is a "V-series" unitary nerve agent closely related (it is an isomer) to the better-known VX nerve agent. It became a prototype for the series of Novichok agents. According to chemical weapons expert Jonathan Tucker, the first binary formulation developed under the Soviet Foliant program was used to make Substance 33, differing from VX only in the alkyl substituents on its nitrogen and oxygen atoms. "This weapon was given the code name Novichok."

History The development of VR started in 1957, after the Soviet Union obtained information about detection of high level of toxicity in phos­phoryl­thio­cholines (the same year Lars-Erik Tammelin published his first articles on fluoro­phos­phoryl­cholines and phos­phoryl­thio­cholines in Acta Chemica Scandinavica) by a team from the Soviet Union's Scientific Research Institute No. 42 (NII-42). Sergei Zotovich Ivin, Leonid Soborovsky, and Iya Danilovna Shilakova jointly developed this analogue of VX. They completed their work in 1963 and were later awarded the Lenin Prize for their achievement. A binary weapon comprising two less toxic precursors which mixed during flight to form Substance 33 was later developed by a team led by Nikolai Kuznetsov. In 1972 the Soviets opened Cheboksary Khimprom, a manufacturing plant for VR in Novocheboksarsk. All facilities in USSR produced 15,557 tons of VR according to their declaration to the Organisation for the Prohibition of Chemical Weapons (OPCW), although most if not all of this has now been destroyed under disarmament treaties.

Comparison to VX VR has similar lethal dose levels to VX (10 – 50 mg), as well as being similar in appearance. However, due to usage of diethyl­amino radicals instead of diiso­propyl­amino it is more prone to decomposition. The former are worse at sterically protecting the nitrogen atom from attacking either phosphorus or the α-carbon atom adjacent to sulfur than the latter. According to UK Defence Science and Technology Laboratory Detection Department scientists Robin M. Black and John M. Harrison, chemical stability was an important factor why of all the similarly toxic phos­phoryl­thio­cholines, ethyl N-2-diiso­propyl­amino­ethyl methyl­phos­phono­thiolate in particular (now known as VX), was weaponized in the West. According to Russian CW developer Vil Mirzayanov, in the late 1980s a group of GosNIIOKhT chemists led by Georgiy Drozd prepared a scientific report that Substance 33 had much lower shelf life than VX. The report, writes Mirzayanov, caused 'panic' in the institute top management and the military representative office, and later was met with administrative resistance. This finding was independently verified by another chemist Igor Revelskiy but his report was not approved either. Following the poisoning of Sergei and Yulia Skripal, former head of the GosNIIOKhT security department Nikolay Volodin said in an interview to Novaya Gazeta that Substance 33 was decomposing too quickly in combat conditions, and implied that this fact may have influenced the decision to continue research on the Novichok program.

Toxicity Both agents have similar symptoms and method of action to other nerve agents that act on cholin­esterase, and treatment remains the same. However, the window for effectively treating second generation V series seizures is shorter, as they rapidly denature the acetyl­cholin­esterase protein in a similar manner to soman, making treatment with the standard nerve gas antidote pralidoxime ineffective unless it is given very soon after exposure. Pre-treatment with pyrido­stigmine prior to exposure, and treatment with other drugs such as atropine and diazepam after exposure, will reduce symptoms of nerve agent toxicity but may not be sufficient to prevent death if a large dose of nerve agent has been absorbed. In addition to the standard seizures, some of the second generation V series agents are known to cause comas.

See also A-234 (nerve agent) Novichok agent

References

Illustrations

VR (nerve agent): Skeletal formula of VR
Skeletal formula of VR
VR (nerve agent): Ball-and-stick model of VR
Ball-and-stick model of VR

Worked examples

Example 1 — a first encounter with VR (nerve agent)

Start with the simplest possible case. Write down what VR (nerve agent) 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 VR (nerve agent) 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 VR (nerve agent) 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 VR (nerve agent)

In research
VR (nerve agent) 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 VR (nerve agent) 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
VR (nerve agent) is common in secondary-school and first-year university syllabi. It links to neighbouring topics Acetylcholinesterase inhibitors, Chemical weapons, Cold War weapons of the Soviet Union, so understanding it makes those chapters shorter.
In everyday life
Look for VR (nerve agent) 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.
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How to study VR (nerve agent) in 20 minutes

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

Frequently asked questions

What is VR (nerve agent) in simple terms?

VR (Russian VX, VXr, Soviet V-gas, GOSNIIOKhT substance No. 33, Agent "November") is a "V-series" unitary nerve agent closely related (it is an isomer) to the better-known VX nerve agent. It became a prototype for the series of Novichok agents.

Why does VR (nerve agent) 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 VR (nerve agent)?

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 VR (nerve agent).

Tags

  • Acetylcholinesterase inhibitors
  • Chemical weapons
  • Cold War weapons of the Soviet Union
  • Diethylamino compounds
  • Isobutyl esters
  • Phosphonothioates
  • Science and technology in the Soviet Union
  • Soviet chemical weapons program
  • Soviet inventions
  • V-series nerve agents

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