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VX (nerve agent)

VX
Stereo structural formula VX ((S)-phosphinate)
Ball and stick model of VX ((R)-phosphinate)
VX-S-enantiomer-3D-vdW.png
Names
IUPAC name
Ethyl ({2-[bis(propan-2-yl)amino]ethyl}sulfanyl)(methyl)phosphinate
Systematic IUPAC name
Ethyl ({2-[bis(propan-2-yl)amino]ethyl}sulfanyl)(methyl)phosphinate
Other names
[2-(Diisopropylamino)ethyl]-O-ethyl methylphosphonothioate
Ethyl {[2-(diisopropylamino)ethyl]sulfanyl}(methyl)phosphinate
Ethyl N-2-diisopropylaminoethyl methylphosphonothiolate
Identifiers
50782-69-9 YesY
51848-47-6 YesY
53800-40-1 YesY
65143-05-7 N
3D model (Jmol) Interactive image
Interactive image
ChEBI CHEBI:609247 N
ChEMBL ChEMBL483105 YesY
ChemSpider 36386 YesY
MeSH VX
PubChem 39793
Properties
C11H26NO2PS
Molar mass 267.37 g·mol−1
Density 1.0083 g cm−3
Melting point −3.90 °C (24.98 °F; 269.25 K)
Boiling point 300 °C (572 °F; 573 K)
log P 2.047
Vapor pressure 0.09 Pa
Hazards
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 4: Very short exposure could cause death or major residual injury. E.g., VX gas Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
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).
N  (what is YesYN ?)
Infobox references

VX is an extremely toxic organophosphate. A tasteless and odorless liquid with an amber-like color, it severely disrupts the body's nervous system and is used as a nerve agent in chemical warfare. Ten milligrams (0.00035 oz) is sufficient for it to be fatal through skin contact, and the median lethal dose for inhalation is estimated to be 30–50 mg·min/m3. As a chemical weapon, this weapon of mass destruction is banned by the Chemical Weapons Convention of 1993, and 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".

The VX nerve agent is the best-known of the V-series of nerve agents and is considered an area denial weapon due to its physical properties. It is more potent than sarin, another well-known nerve agent toxin, but works in a similar way.

With its high viscosity and low volatility, VX has the texture and feel of motor oil. This makes it especially dangerous, as it has a high persistence in the environment. It is odorless and tasteless, and can be distributed as a liquid, either pure or as a mixture with a clay or talc in the form of thickened agent, or as an aerosol.

VX is an acetylcholinesterase inhibitor, i.e., it works by blocking the function of the enzyme acetylcholinesterase. Normally, when a motor neuron is stimulated, it releases the neurotransmitter acetylcholine into the space between the neuron and an adjacent muscle cell. When this acetylcholine is taken up by the muscle cell, it stimulates muscle contraction. To avoid a state of constant muscle contraction, the acetylcholine is then broken down to non-reactive substances (acetic acid and choline) by the enzyme acetylcholinesterase. VX blocks the action of acetylcholinesterase, resulting in an accumulation of acetylcholine in the space between the neuron and muscle cell, leading to uncontrolled muscle contraction. This results in initial violent contractions, followed by sustained supercontraction restricted to the subjunctional endplate sarcoplasm and prolonged depolarizing neuromuscular blockade, the latter resulting in flaccid paralysis of all the muscles in the body. Sustained paralysis of the diaphragm muscle causes death by asphyxiation.


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