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词条 VR (nerve agent)
释义

  1. History

  2. Comparison to VX

  3. Toxicity

  4. See also

  5. References

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 428728291
| Name = VR (nerve agent)
| ImageFile = VR nerve agent.svg
| ImageName = Skeletal formula of VR
| ImageFile1 = VR-3D-balls.png
| ImageName1 = Ball-and-stick model of VR
| IUPACName = N,N-diethyl-2-(methyl-(2-methylpropoxy)phosphoryl)sulfanylethanamine
| Section1 = {{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 159939-87-4
| SMILES = CCN(CC)CCSP(=O)(C)OCC(C)C
| PubChem = 178033
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 154981
| ChEBI = 140422
| InChI = 1/C11H26NO2PS/c1-6-12(7-2)8-9-16-15(5,13)14-10-11(3)4/h11H,6-10H2,1-5H3
| InChIKey = MNLAVFKVRUQAKW-UHFFFAOYAF
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C11H26NO2PS/c1-6-12(7-2)8-9-16-15(5,13)14-10-11(3)4/h11H,6-10H2,1-5H3
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = MNLAVFKVRUQAKW-UHFFFAOYSA-N
| Section2 = {{Chembox Properties
| Formula = C11H26NO2PS
| MolarMass = 267.368 g/mol
| Density =
| MeltingPt =
| BoilingPt =
}}VR (Russian VX, Soviet V-gas, Substance 33, R-33, Agent "November") is a "V-series" unitarynerve agent closely related (isomer) to the better-known VX nerve agent.[1] 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."[2]

History

The development of VR started in 1957, after the Soviet Union obtained information about detection of high level of toxicity in phosphorylthiocholines[3] (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.[4] 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, for which they were awarded the 1990 Lenin Prize.[5]

In 1972 the Soviets opened Cheboksary Khimprom, a manufacturing plant for VR in Novocheboksarsk.[6] All facilities in USSR produced 15,557 tons of VR according to their declaration to the Organisation for the Prohibition of Chemical Weapons (OPCW),[7] although most if not all of this has now been destroyed under disarmament treaties.[8]

Comparison to VX

VR has similar lethal dose levels to VX (between 10–50 mg), as well as being similar in appearance.[9] 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 sulphur 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.[10]

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 wasn't approved either.[11]

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.[12]

Toxicity

Both agents has 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.{{citation needed|date=March 2018}} 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

1. ^Fedorov L. A. Undeclared Chemical War in Russia. Moscow, 1995 (Russian)
2. ^{{cite journal |url=https://cen.acs.org/articles/96/i12/Nerve-agent-attack-on-spy-used-Novichok-poison.html |title=Nerve agent attack on spy used 'Novichok' poison |date=19 March 2018 |volume=96 |issue= 12 |page=3 |journal=Chemical & Engineering News |first=Mark |last=Peplow |publisher=American Chemical Society |access-date=28 March 2018}}
3. ^Major General Antonov, Nikolai S. Khimicheskoe Oruzhiye na Rubezhe Dvukh Stoletii 'Chemical Weapons at the Turn of the Century', p. 22 (Moscow: Progress: 1994) {{ISBN|01-004462-5}}
4. ^Tucker, J. B.; War of Nerves; Anchor Books; New York; 2006; pp 181-182.
5. ^Vil S. Mirzayanov. State Secrets. An Insider's Chronicle of the Russian Chemical Weapons Program. (2009) pp166-168. {{ISBN|978-1-4327-2566-2}}
6. ^Tucker, J. B.; War of Nerves; Anchor Books; New York; 2006; pp 230–231.
7. ^Factsheets on Chemical and Biological Warfare Agents
8. ^Federation of American Scientists. Chemical Weapons - Russian/Soviet Nuclear Forces
9. ^https://www.acs.org/content/acs/en/molecule-of-the-week/archive/v/vr.html
10. ^Black R.M., Harrison J.M. The chemistry of organophosphorus chemical warfare agents. Chapter 10 of The chemistry of organophosphorus compounds. Volume 4, Ter- and quinque-valent phosphorus acids and their derivatives. (1996) {{Cite journal|doi=10.1002/9780470682531.pat0070|ISBN=0-471-95706-2}}
11. ^https://books.google.com/books?id=ldpNPgAACAAJ
12. ^https://www.novayagazeta.ru/articles/2018/03/23/75908-demonstrativnoe-ubiystvo-mozhno-bylo-organizovat-prosche
{{Chemical warfare}}{{Neurotoxins}}{{Acetylcholine metabolism and transport modulators}}

9 : Acetylcholinesterase inhibitors|V-series nerve agents|Phosphonothioates|Chemical weapons|Cold War weapons of the Soviet Union|Soviet inventions|Science and technology in the Soviet Union|Amines|Soviet chemical weapons program

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