VX (nerve agent)
IUPAC name	O-ethyl S-(2-diisopropylaminoethyl) methylphosphonothiolate IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ...
Identifiers
CAS number	[50782-69-9]
SMILES	O=P(C)(OCC)SCCN(C(C)C)C(C)C
Properties
Molecular formula	C11H26NO2PS
Density	1.00083 g/mL
Melting point	-50 °C, 223 K, -58 °F CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... This article is about the Latin alphabet letter. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Density (disambiguation). ... The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. ...
Boiling point	298 °C, 571 K, 568 °F Italic text This article is about the boiling point of liquids. ...
Vapor pressure	0.0007 mm Hg (0.0933256 Pa) at 25 °C
Hazards
NFPA 704	1 4 1
Flash point	159 °C[1]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

VX (O-ethyl-S-[2(diisopropylamino)ethyl] methylphosphonothiolate) is an extremely toxic substance whose sole application is as a nerve agent. As a chemical weapon, it is classified as a weapon of mass destruction by the United Nations in UN Resolution 687. Production and stockpiling of VX was outlawed by the Chemical Weapons Convention of 1993. Vapor pressure is the pressure of a vapor in equilibrium with its non-vapor phases. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links NFPA_704. ... For other uses, see Flash point (disambiguation). ... The plimsoll symbol as used in shipping In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals exactly). ... This article is about the chemical. ... For the Xzibit album, see Weapons of Mass Destruction (album). ... UN and U.N. redirect here. ... United Nations Security Council Resolution 687 was adopted at the 2981st meeting on April 3, 1991, to welcome the restoration of the independence of Kuwait. ... Chemical Weapons Convention Opened for signature January 13, 1993 in Paris Entered into force April 29, 1997 Conditions for entry into force Ratification by 50 states and the convening of a Preparatory Commission Parties 181 (as of Oct. ...

The VX nerve agent is the most well-known of the V-series of nerve agents and is considered an area denial weapon due to its physical properties. This article is about the chemical. ... This article is about the chemical. ... Area denial weapons are used to prevent an adversary from occupying or traversing an area of land. ...

Discovery

Dr. Jacob Matthews, a chemist at the Plant Protection Laboratories of Imperial Chemical Industries was investigating a class of organophosphate compounds (organophosphate esters of substituted aminoethanethiols). Like the earlier investigator of organophosphates, Dr. Schrader, Dr. Ghosh found that they were quite effective pesticides. In 1954, ICI put one of them on the market under the trade name Amiton. It was subsequently withdrawn, as it was too toxic for safe use. The toxicity did not go unnoticed - samples of it had been sent to the British Armed Forces research facility at Porton Down for evaluation. After the evaluation was complete, several members of this class of compounds would become a new group of nerve agents, the V agents. The best known of these is probably VX, with the Russian V-gas coming a close second (Amiton is largely forgotten as VG). This class of compounds is also sometimes known as Tammelin's esters, after Lars-Erik Tammelin of the Swedish Institute of Defense Research. Dr. Tammelin was also conducting research on this class of compounds in 1952, but for obvious reasons he did not publicize his work widely. This article does not cite any references or sources. ... An organophosphate (sometimes abbreviated OP) is the general name for esters of phosphoric acid and is one of the organophosphorus compounds. ... A cropduster spreading pesticide. ... Skeletal formula of VG Ball-and-stick model of VG VG (O,O-Diethyl-S-[2-(diethylamino)ethyl] phosphorothioate) (also called Amiton or Tetram) is a V-series nerve agent chemically similar to the better-known VX nerve agent. ... Defence Science and Technology Laboratory, Porton Down, or often known more simply as Porton Down, is a United Kingdom government facility for military research, including CBRN defence. ...

Chemical characteristics

With its high viscosity and low volatility, VX has the texture and feel of high-grade motor oil. This makes it especially dangerous, as it has a high persistence in the environment. It is odourless and tasteless, and can be distributed as a liquid or, through evaporation, into small amounts of vapor. It works as a nerve agent by blocking the function of the enzyme acetylcholinesterase. Normally, an electric nerve pulse would cause the release of acetylcholine over a synapse that would stimulate muscle contraction. The acetylcholine is then broken down to non-reactive substances (acetic acid and choline) by the acetylcholinesterase enzyme. If more muscle tension is needed the nerve must release more acetylcholine. VX blocks the action of acetylcholinesterase, thus resulting in sustained contractions of all the muscles in the body. Sustained contraction of the diaphragm muscle causes death by asphyxiation. For other uses, see Viscosity (disambiguation). ... The ability of a liquid to evaporate quickly and at relatively low temperatures. ... Ribbon diagram of the enzyme TIM, surrounded by the space-filling model of the protein. ... In biochemistry, cholinesterase is a term which refers to one of the two enzymes (EC 3. ... The chemical compound acetylcholine, often abbreviated as ACh, was the first neurotransmitter to be identified. ... Illustration of the major elements in a prototypical synapse. ... R-phrases , S-phrases , , , Flash point 43 °C Related Compounds Related carboxylic; acids Formic acid; Propionic acid; Butyric acid Related compounds acetamide; ethyl acetate; acetyl chloride; acetic anhydride; acetonitrile; acetaldehyde; ethanol; thioacetic acid; acetylcholine; acetylcholinesterase Supplementary data page Structure and properties n, εr, etc. ... Choline is an organic compound, classified as an essential nutrient and usually grouped within the Vitamin B complex. ...

Synthesis

VX is produced via the "Transester Process". This entails a complex chemical transition whereby phosphorus trichloride is methylated to produce methyl phosphonous dichloride. The resulting material is reacted with ethanol to form a diester. This is then transesterified to produce the immediate precursor of VX. Finally, the immediate precursor is reacted with sulfur to form VX. Phosphorus trichloride (formula PCl3) is the most important of the three phosphorus chlorides. ... In organic chemistry, transesterification is the process of exchanging the alkoxy group of an ester compound by another alcohol. ...

VX can also be delivered in binary chemical weapons which mix in-flight to form the agent prior to release. Binary VX is referred to as VX2, and is created by mixing O-(2-diisopropylaminoethyl) O'-ethyl methylphosphonite (Agent QL) with elemental sulfur (Agent NE) as is done in the BIGEye aerial chemical bomb. It may also be produced by mixing with sulfur compounds, as with the liquid dimethyl polysulfide mixture (Agent NM) in the cancelled XM-768 8-inch binary projectile program.

Solvolysis

Like other organophosphorus nerve agents, VX may be destroyed by reaction with strong nucleophiles such as pralidoxime. The reaction of VX with concentrated aqueous sodium hydroxide results in competing cleavage of the P-O and P-S esters, with P-S cleavage dominating. This is somewhat problematic, since the product of P-O bond cleavage (named EA 2192) remains toxic. In contrast, reaction with the anion of hydrogen peroxide (hydroperoxidolysis) leads to exclusive cleavage of the P-S bond.^[2] Organophosphorus compounds are chemical compounds containing carbon-phosphorus bonds. ... Structure of the molecule pralidoxime Pralidoxime belongs to a family of compounds, called oximes that bind to organophosphate inactivated acetylcholinesterase. ...

P-O cleavage ...or it can cleave VX's P-O bond, forming ethanol and EA 2192 (shown in red), which has similar toxicity to VX itself

Biological effects

Further information: Nerve agent biological effects and treatment

VX is one of the most toxic nerve agents ever synthesized.^[3] The median lethal dose (LD₅₀) for humans is estimated to be about 10 milligrams through skin contact and the LCt₅₀ for inhalation is estimated to be 30-50 mg•min/m³.^[4] This article is about the chemical. ... This article is about the toxicological term. ... The milligram (symbol mg) is an SI unit of mass. ...

Early symptoms of percutaneous exposure (skin contact) may be local muscular twitching or sweating at the area of exposure followed by nausea or vomiting. Some of the early symptoms of a VX vapor exposure to nerve agent may be rhinorrhea (runny nose) and/or tightness in the chest with shortness of breath (bronchial constriction). Miosis (pinpointing of the pupils) may be an early sign of agent exposure but is not usually used as the only indicator of exposure.^[5] Miosis should not be confused with meiosis, the cellular division process involved in sexual reproduction. ...

Treatment

Primary consideration should be given to removal of the liquid agent from the skin before removal of the individual to an uncontaminated area or atmosphere. After removal from the contaminated area, the casualty will be decontaminated by washing the contaminated areas with household bleach and flushing with clean water. After decontamination, the contaminated clothing is removed and skin contamination washed away. If possible, decontamination is completed before the casualty is taken for further medical treatment.

An individual who has received a known nerve-agent exposure or who exhibits definite signs or symptoms of nerve-agent exposure should immediately have the nerve agent antidote drugs atropine, pralidoxime (2-PAM), and diazepam injected. In several nations the nerve agent anti-dotes are issued for military personnel in the form of an autoinjector such as the United States military Mark I NAAK.^[5] Atropine is a tropane alkaloid extracted from the deadly nightshade (Atropa belladonna) and other plants of the family Solanaceae. ... Structure of the molecule pralidoxime Pralidoxime belongs to a family of compounds, called oximes that bind to organophosphate inactivated acetylcholinesterase. ... Diazepam (IPA: ), first marketed as Valium by Hoffmann-La Roche) is a benzodiazepine derivative drug. ... This article or section does not adequately cite its references or sources. ... The Mark I NAAK, or MARK I Kit, is United States military nomenclature for the Nerve Agent Antidote Kit. It is a dual-chamber auto-injector: Two anti-nerve agent drugs -- atropine sulfate and pralidoxime chloride -- each in injectible form, constitute the kit. ...

Atropine works by binding and blocking a subset of acetylcholine receptors (known as muscarinic acetylcholine receptor, mAchR), so that the build up of acetylcholine produced by loss of the acetylcholinesterase function can no longer affect their target. The injection of pralidoxime regenerates bound acetylcholinesterase. Amanita muscaria from which muscarine was isolated Acetylcholine - natural agonist of muscarinic and nicotinic receptors. ...

History

The following is the specific history of VX, which is closely linked to the history of similar nerve agents also discovered in Germany during or soon after World War II. That broader history is detailed in Nerve Agent: History. This article is about the chemical. ...

The chemists Ranajit Ghosh and J.F. Newman discovered the V-series nerve agents at ICI in 1952, patenting diethyl S-2-diethylaminoethyl phosphor-othiolate (VG) in November, 1952. Further commercial research on similar compounds ceased in 1955 when its lethality to humans was discovered. Information on the substance was passed to Porton Down in 1954 and research there led to VX within a year. This was traded to the United States as the British passed over VX in favour of continuing with sarin as the UK chemical weapon of choice, the reasoning behind the decision is unclear, although the recent completion of a sarin production facility at Nancekuke may have played a part. This article does not cite any references or sources. ... Year 1952 (MCMLII) was a leap year starting on Tuesday (link will display full calendar) of the Gregorian calendar. ... VG may stand for: VG Airlines (defunct belgian airline) VLM Airlines (IATA code) Norways largest circulation newspaper, Verdens Gang Volume group British Virgin Islands: ISO country code An abbreviation of very good. ... Defence Science and Technology Laboratory, Porton Down, or often known more simply as Porton Down, is a United Kingdom government facility for military research, including CBRN defence. ... For other uses, see Sarin (disambiguation). ...

Despite creating the agent, the United Kingdom unilaterally renounced chemical and biological weapons in 1956.^{[citation needed]} In 1958 the British government traded their research on VX technology with the United States of America in exchange for information on thermonuclear weapons.^{[citation needed]} The US then went into production of large amounts of VX in 1961 at Newport Chemical Depot. The mushroom cloud of the atomic bombing of Nagasaki, Japan, in 1945 lifted nuclear fallout some 18 km (60,000 feet) above the epicenter. ... Year 1961 (MCMLXI) was a common year starting on Sunday (link will display full calendar) of the Gregorian calendar. ... The Newport Chemical Depot is a bulk chemical storage and destruction facility in west central Indiana, thirty miles north of Terre Haute. ...

Iraq under Saddam Hussein admitted to UNSCOM that it had researched VX, but had failed to weaponize the agent due to production failure. After U.S. and allied forces had invaded Iraq, no proof of weaponized VX was found. [1] Subsequent investigation after the 2003 Invasion of Iraq indicates that Iraq had indeed weaponized VX in 1988, and had dropped three VX-filled bombs on Iran. [2] Saddam Hussein Abd al-Majid al-Tikriti (28 April 1937 – 30 December 2006) was the fifth President of Iraq and Chairman of the Iraqi Revolutionary Command Council from 1979 until his overthrow by US forces in 2003. ... United Nations Special Commission (UNSCOM) was a United Nations organisation performing arms inspections in Iraq after the Gulf War. ... This article is about the 2003 invasion of Iraq. ...

The only countries known to possess VX are the United States and Russia.^[3] However, under Saddam Hussein's regime, Iraq was suspected of buying VX;^[3] a Sudanese pharmaceutical facility was bombed by the U.S. in 1998 following allegations that it in some way used VX and that the origin of the agent was associated with both Iraq and Al Qaeda.^[6] Saddam Hussein Abd al-Majid al-Tikriti (28 April 1937 – 30 December 2006) was the fifth President of Iraq and Chairman of the Iraqi Revolutionary Command Council from 1979 until his overthrow by US forces in 2003. ... This article or section is not written in the formal tone expected of an encyclopedia article. ... Map of major attacks attributed to al-Qaeda Al-Qaeda (also al-Qaida or al-Qaida or al-Qaidah) (Arabic: ‎ , translation: The Base) is an international alliance of terrorist organizations founded in 1988[4] by Osama bin Laden and other veteran Afghan Arabs after the Soviet War in...

VX Stockpile elimination

In the late 1960s, the US cancelled its chemical weapons programs and began the destruction of its stockpiles of agents by a variety of methods. Early disposal included the US Army's CHASE (Cut Holes And Sink 'Em) program, in which old ships were filled with chemical weapons stockpiles and then scuttled. CHASE 8 was conducted on June 15, 1967, in which the S.S. Cpl. Eric G. Gibson was filled with 7,380 VX rockets and scuttled in 7,200 feet of water, off the coast of Atlantic City, New Jersey. Later incineration was used at Johnston Island in the North Pacific starting in 1990 (with the stockpile there eliminated in 2000). Newport Chemical Depot began stockpile elimination using chemical neutralization in 2005. The VX is hydrolyzed to much less toxic byproducts by using concentrated caustic solution. The resulting waste is then shipped off-site for further processing. Technical and political issues regarding this secondary byproduct resulted in some delays but most of Newport's stockpile was eliminated in 2007. Operation CHASE (Cut Holes and Sink Em) was a United States Army program which involved the disposal of unwanted munitions into the Atlantic Ocean during the late 1960s and early 1970s. ... German battlecruiser Derfflinger scuttled at Scapa Flow. ... is the 166th day of the year (167th in leap years) in the Gregorian calendar. ... Year 1967 (MCMLXVII) was a common year starting on Sunday (link will display full calendar) of the 1967 Gregorian calendar. ... Atlantic City redirects here. ... For other forms of waste plant that produce energy see waste-to-energy. ... Johnston Atoll is a 2. ...

Worldwide, VX disposal continues, since 1997 under the mandate of the Chemical Weapons Convention. The US is destroying chemical weapons stockpiles containing VX in several locations and providing support for Russian destruction activities. Chemical Weapons Convention Opened for signature January 13, 1993 in Paris Entered into force April 29, 1997 Conditions for entry into force Ratification by 50 states and the convening of a Preparatory Commission Parties 181 (as of Oct. ...

See also

• Nerve agents in popular culture

This article is about the chemical. ...

References

1. ^ MSDS: Nerve Agent (VX). Edgewood Chemical Biological Center (ECBC), Department of the Army (22 December 2000). Retrieved on 2007-10-25.
2. ^ Yang, Yu-Chu. "Chemical Detoxification of Nerve Agent VX", Acc. Chem. Res., 1999, p. 109-115.. 
3. ^ ^{a b c} VX. Council on Foreign Relations (2006-01). Retrieved on 2007-03-27.
4. ^ Federation of American Scientists :: Types of Chemical Weapons
5. ^ ^{a b} US Army Toxic Chemical Agent Safety Standards. DA PAM 385-61. Section 7-8 Self/Buddy Aid Procedures. US Army. Retrieved on 2007-12-15.
6. ^ Chomsky, Noam (Oct. 2001). 9-11. Open Media. 

Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ... is the 298th day of the year (299th in leap years) in the Gregorian calendar. ... The Council on Foreign Relations (CFR) is an influential and independent, nonpartisan foreign policy membership organization founded in 1921 and based at 58 East 68th Street (corner Park Avenue) in New York City, with an additional office in Washington, D.C. Through its membership, meetings, and studies, it has been... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ... is the 86th day of the year (87th in leap years) in the Gregorian calendar. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ... is the 349th day of the year (350th in leap years) in the Gregorian calendar. ...

External links

Wikinews has related news:

United States begins testing equipment for demolition of a major VX nerve gas stockpile

• Oxford website on Nerve Agents
• Questions and Answers for VX
• CDC Facts About VX
• U.S. Army's Chemical Materials Agency (CMA)
• CBW Info
• National Academies: Health effects of VX
• DA PAM 385-61 US Army Toxic Chemical Agent Safety Standards
• Decommissioning Surplus VX - Article from NYTimes.com