Back في إكس (غاز أعصاب) Arabic وی‌ایکس (عامل اعصاب) AZB VX (химическо оръжие) Bulgarian ভিএক্স (নার্ভ এজেন্ট) Bengali/Bangla VX (agent nerviós) Catalan ڤی ئێکس (گازی دەماری) CKB VX Czech VX German VX Spanish VX (nerbio-gasa) Basque

VX (nerve agent)

Not to be confused with V-sub x.

VX[1]
Stereo structural formula VX ((S)-phosphinate)
SP-(−)-VX enantiomer
Ball and stick model of VX ((R)-phosphinate)
Names
Preferred IUPAC name
S-{2-[Di(propan-2-yl)amino]ethyl} O-ethyl methylphosphonothioate
Other names
[2-(Diisopropylamino)ethyl]-O-ethyl methylphosphonothioate
Ethyl {[2-(diisopropylamino)ethyl]sulfanyl}(methyl)phosphinate
Ethyl N-2-diisopropylaminoethyl methylphosphonothiolate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
MeSH VX
UNII
  • InChI=1S/C11H26NO2PS/c1-7-14-15(6,13)16-9-8-12(10(2)3)11(4)5/h10-11H,7-9H2,1-6H3 checkY
    Key: JJIUCEJQJXNMHV-UHFFFAOYSA-N checkY
  • InChI=1/C11H26NO2PS/c1-7-14-15(6,13)16-9-8-12(10(2)3)11(4)5/h10-11H,7-9H2,1-6H3
    Key: JJIUCEJQJXNMHV-UHFFFAOYAV
  • CCOP(C)(=O)SCCN(C(C)C)C(C)C
  • O=P(OCC)(SCCN(C(C)C)C(C)C)C
Properties
C11H26NO2PS
Molar mass 267.37 g·mol−1
Appearance amber liquid
Odor odourless
Density 1.0083 g cm−3
Melting point −51 °C (−60 °F; 222 K)
Boiling point 300 °C (572 °F; 573 K)
log P 2.047
Vapor pressure 0.09 Pa
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
4
1
1
Flash point 159 °C (318 °F; 432 K)[3]
Lethal dose or concentration (LD, LC):
7 μg/kg (intravenous, rat)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
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VX is an extremely toxic synthetic chemical compound in the organophosphorus class, specifically, a thiophosphonate. In the class of nerve agents, it was developed for military use in chemical warfare after translation of earlier discoveries of organophosphate toxicity in pesticide research. In its pure form, VX is an oily, relatively non-volatile liquid that is amber-like in colour.[4] Because of its low volatility, VX persists in environments where it is dispersed.[5][6]

VX, short for "venomous agent X",[7] is one of the best known of the V nerve agents and originated from pesticide development work at Imperial Chemical Industries (ICI). It was developed further at Porton Down in England during the early 1950s,[8] based on research first done by Gerhard Schrader, a chemist working for IG Farben in Germany during the 1930s.[citation needed] It is now one of a broader V-series of agents which are classified as nerve agents. To date (2024), VX has not been used in combat,[9] though claims as to its use as a weapon in assassinations have some credibility. [10] The brother of North Korean leader Kim Jong Un, Kim Jong Nam, had the substance thrown in his face in Kuala Lumpur International Airport on the 13th February 2017 by two women. He died being rushed to hospital approximately 15 minutes later.

The substance is extremely deadly; VX fatalities occur with exposure to tens of milligram quantities via inhalation or absorption through skin; VX is more potent than sarin, another nerve agent with a similar mechanism of action. On such exposure, these agents severely disrupt the body's signaling between the nervous and muscular systems, leading to a prolonged neuromuscular blockade, flaccid paralysis of all the muscles in the body including the diaphragm, and death by asphyxiation.[11]

The danger of VX, in particular, lies in direct exposure to the chemical agent persisting where it was dispersed, and not through its evaporating and being distributed as a vapor; it is not considered a vapor hazard due to its relative non-volatility. VX is considered an area denial weapon due to these physical and biochemical characteristics.[12] As a chemical weapon, it is categorized as a weapon of mass destruction by the United Nations and is banned by the Chemical Weapons Convention of 1993,[13] where production and stockpiling of VX exceeding 100 grams (3.53 oz) per year is outlawed. The only exception is for "research, medical or pharmaceutical purposes outside a single small-scale facility in aggregate quantities not exceeding 10 kg (22 lb) per year per facility".[14]

  1. ^ Cite error: The named reference Thiermann15 was invoked but never defined (see the help page).
  2. ^ a b Chambers, Michael. "Substance Name: VX". ChemIDplus. U.S. National Library of Medicine, National Institutes of Health. Retrieved 24 February 2017.
  3. ^ "Material Safety Data Sheet: Nerve Agent (VX)". ilpi.com. Interactive Learning Paradigms Incorporated. December 22, 2000 [1998]. Retrieved October 25, 2007.
  4. ^ "CDC | Facts About VX". emergency.cdc.gov. Centers for Disease Control and Prevention. Archived from the original on 2018-03-07. Retrieved 2018-03-20.
  5. ^ Cite error: The named reference FoAS was invoked but never defined (see the help page).
  6. ^ "Nerve Agent VX | U.S. Army Chemical Materials Activity". Retrieved 2023-11-04.
  7. ^ Bethany Halford (September 26, 2016). "Detoxifying VX". Chemical & Engineering News. 94 (38): 10–11. doi:10.1021/cen-09438-scicon001.
  8. ^ Worek, Franz; Thiermann, Horst; Wille, Timo (2020). "Organophosphorus compounds and oximes: a critical review". Archives of Toxicology. 94 (7): 2275–2292. doi:10.1007/s00204-020-02797-0. ISSN 0340-5761. PMC 7367912. PMID 32506210.
  9. ^ Doyle, Gerry (2017-02-24). "What Is VX Nerve Agent? A Deadly Weapon, Rarely Seen". The New York Times. ISSN 0362-4331. Retrieved 2023-11-04.
  10. ^ Paddock, Richard C.; Sang-Hun, Choe (2017-02-24). "Kim Jong-nam Was Killed by VX Nerve Agent, Malaysians Say". The New York Times. ISSN 0362-4331. Retrieved 2023-11-04.
  11. ^ Sidell, Frederick R. (1997). "Chapter 5: Nerve Agents" (PDF). Medical Aspects of Chemical and Biological Warfare. p. 142ff.
  12. ^ Takafuji, Ernest T.; Kok, Allart B. (1997). "Chapter 4: The Chemical Warfare Threat and the Military Healthcare Provider" (PDF). Medical Aspects of Chemical and Biological Warfare. p. 123. Given favorable weather conditions, the use of persistent agents such as mustard and VX may pose a threat for many days. Such agents can deny or interfere with enemy occupation of terrain or use of equipment
  13. ^ "Convention on the Prohibition of the Development, Production, Stockpiling and Use of Chemical Weapons and on their Destruction. Annex on Chemicals". United Nations Organisation for the Prohibition of Chemical Weapons.
  14. ^ OPCW (2005). "Convention on the Prohibition of the Development, Production, Stockpiling and Use of Chemical Weapons and on their Destruction" (PDF). OPCW.org. Organization for the Prohibition of Chemical Weapons (OPCW). p. 122. Retrieved 26 August 2016.

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