VX (nerve agent)

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
CAS Number	50782-69-9 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:136185 ;
ChEMBL	ChEMBL483105 ;
ChemSpider	36386 ;
MeSH	VX
PubChem CID	39793;
UNII	9A4381183B ;
CompTox Dashboard (EPA)	DTXSID80866161 ;
	InChI 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 Key: JJIUCEJQJXNMHV-UHFFFAOYSA-N ; 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;
	SMILES CCOP(C)(=O)SCCN(C(C)C)C(C)C; O=P(OCC)(SCCN(C(C)C)C(C)C)C;
Properties
Chemical formula	C11H26NO2PS
Molar mass	267.37 g·mol−1
Appearance	amber liquid
Odor	odorless
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)	4 1 1
Flash point	159 °C (318 °F; 432 K)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	7 μg/kg (intravenous, rat)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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. VX has been allegedly used in warfare and has been used in several assassinations. 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 February 13, 2017, by two women. He died while 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. It 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.^[9]

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.^[10] 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,^[11] 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".^[12]

^ Cite error: The named reference Thiermann15 was invoked but never defined (see the help page).
^ ^a ^b Chambers, Michael. "Substance Name: VX". ChemIDplus. U.S. National Library of Medicine, National Institutes of Health. Retrieved February 24, 2017.
^ "Material Safety Data Sheet: Nerve Agent (VX)". ilpi.com. Interactive Learning Paradigms Incorporated. December 22, 2000 [1998]. Retrieved October 25, 2007.
^ "CDC | Facts About VX". emergency.cdc.gov. Centers for Disease Control and Prevention. Archived from the original on March 7, 2018. Retrieved March 20, 2018.
^ Cite error: The named reference FoAS was invoked but never defined (see the help page).
^ "Nerve Agent VX | U.S. Army Chemical Materials Activity". Retrieved November 4, 2023.
^ Bethany Halford (September 26, 2016). "Detoxifying VX". Chemical & Engineering News. 94 (38): 10–11. doi:10.1021/cen-09438-scicon001.
^ 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.
^ Sidell, Frederick R. (1997). "Chapter 5: Nerve Agents" (PDF). Medical Aspects of Chemical and Biological Warfare. p. 142ff.
^ 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
^ "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.
^ 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 August 26, 2016.

[Thiermann15-1] Cite error: The named reference Thiermann15 was invoked but never defined (see the help page).

[Substance_Name:_VX-2] Chambers, Michael. "Substance Name: VX". ChemIDplus. U.S. National Library of Medicine, National Institutes of Health. Retrieved February 24, 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 March 7, 2018. Retrieved March 20, 2018.

[FoAS-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 November 4, 2023.

[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.

[ke.army.mil-9] Sidell, Frederick R. (1997). "Chapter 5: Nerve Agents" (PDF). Medical Aspects of Chemical and Biological Warfare. p. 142ff.

[10] 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

[11] "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.

[12] 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 August 26, 2016.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]

VX (nerve agent)

From Wikipedia, the free encyclopedia · View on Wikipedia