A-242

Last updated
A-242
Novichok A242 (Mirzayanov 2009).svg
Names
IUPAC name
methyl-(bis(diethylamino)methylene)phosphonamidofluoridate
Systematic IUPAC name
1,1,3,3-tetraethyl-2-[fluoro(methyl)phosphoryl]guanidine
Identifiers
  • 2387496-14-0 X mark.svgN
3D model (JSmol)
PubChem CID
  • InChI=1S/C10H23FN3OP/c1-6-13(7-2)10(12-16(5,11)15)14(8-3)9-4/h6-9H2,1-5H3
    Key: WJDIQLITBJEMBA-UHFFFAOYSA-N
  • CCN(CC)C(=N[P](C)(F)=O)N(CC)CC
Properties
C10H23FN3OP
Molar mass 251.286 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

A-242 is an organophosphate nerve agent. It was developed in the Soviet Union under the FOLIANT program and is one of the group of compounds referred to as Novichok agents that were revealed by Vil Mirzayanov. Mirzayanov gives little specific information about A-242, stating that it is highly toxic but no figures are given to compare it to other related agents. It is reportedly a solid rather than a volatile liquid as with most nerve agents, and in order to weaponise it successfully, it had to be milled into a fine powder form that could be dispersed as a dust. [1]

Contents

A-242 has been added to Schedule 1 of the Annex on Chemicals of the Chemical Weapons Convention as of June 2020, and it has been explicitly named as an example compound for schedule 1.A.15. [2] [3] For chemicals listed in Schedule 1, the most stringent declaration and verification measures are in place combined with far-reaching limits and bans on production and use.

See also

Related Research Articles

Organisation for the Prohibition of Chemical Weapons Intergovernmental organisation and the implementing body for the Chemical Weapons Convention

The Organisation for the Prohibition of Chemical Weapons (OPCW) is an intergovernmental organisation and the implementing body for the Chemical Weapons Convention, which entered into force on 29 April 1997. The OPCW, with its 193 member states, has its seat in The Hague, Netherlands, and oversees the global endeavour for the permanent and verifiable elimination of chemical weapons.

Chemical warfare Using poison gas or other toxins in war

Chemical warfare (CW) involves using the toxic properties of chemical substances as weapons. This type of warfare is distinct from nuclear warfare, biological warfare and radiological warfare, which together make up CBRN, the military acronym for nuclear, biological, and chemical, all of which are considered "weapons of mass destruction" (WMDs). None of these fall under the term conventional weapons which are primarily effective due to their destructive potential. In theory, with proper protective equipment, training, and decontamination measures, the primary effects of chemical weapons can be overcome. In practice, they continue to cause much suffering, as most victims are defenseless. Many nations possess vast stockpiles of weaponized agents in preparation for wartime use. The threat and the perceived threat have become strategic tools in planning both measures and counter-measures.

Chemical Weapons Convention 1997 treaty that outlaws producing, stockpiling, and using chemical weapons

The Chemical Weapons Convention (CWC), officially the Convention on the Prohibition of the Development, Production, Stockpiling and Use of Chemical Weapons and on their Destruction, is an arms control treaty administered by the Organisation for the Prohibition of Chemical Weapons (OPCW), an intergovernmental organization based in The Hague, The Netherlands. The treaty entered into force on 29 April 1997, and prohibits the large-scale use, development, production, stockpiling and transfer of chemical weapons and their precursors, except for very limited purposes. The main obligation of member states under the convention is to effect this prohibition, as well as the destruction of all current chemical weapons. All destruction activities must take place under OPCW verification.

Sarin Highly toxic chemical compound

Sarin is an extremely toxic synthetic organophosphorus compound. A colourless, odourless liquid, it is used as a chemical weapon due to its extreme potency as a nerve agent. Exposure is lethal even at very low concentrations, where death can occur within one to ten minutes after direct inhalation of a lethal dose, due to suffocation from respiratory paralysis, unless antidotes are quickly administered. People who absorb a non-lethal dose, but do not receive immediate medical treatment, may suffer permanent neurological damage.

Soman Chemical compound (nerve agent)

Soman is an extremely toxic chemical substance. It is a nerve agent, interfering with normal functioning of the mammalian nervous system by inhibiting the enzyme cholinesterase. It is an inhibitor of both acetylcholinesterase and butyrylcholinesterase. As a chemical weapon, it is classified as a weapon of mass destruction by the United Nations according to UN Resolution 687. Its production is strictly controlled, and stockpiling is outlawed by the Chemical Weapons Convention of 1993 where it is classified as a Schedule 1 substance. Soman was the third of the so-called G-series nerve agents to be discovered along with GA (tabun), GB (sarin), and GF (cyclosarin).

VX (nerve agent) Chemical compound and chemical warfare nerve agent

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 recent years, VX was found to be the agent used in the assassination of Kim Jong-nam. In its pure form, VX is an oily, relatively non-volatile, liquid that is amber-like in color. Because of its low volatility, VX persists in environments where it is dispersed.

Chlorosarin Chemical compound

Chlorosarin is a chemical precursor used in the final step of one method for the production of the nerve agent sarin. Also known as O-isopropyl methylphosphonochloridate and isopropyl methylphosphonic chloride, it has a molecular weight of 156.55 g/mol and a molecular formula of C4H10ClO2P.

VG (nerve agent) Chemical compound

VG is a "V-series" nerve agent chemically similar to the better-known VX nerve agent. Tetram is the common Russian name for the substance. Amiton was the trade name for the substance when it was marketed as an insecticide by ICI in the mid-1950s.

Chemical weapon proliferation Prevalence and spread of chemical weapons

Many nations continue to research and/or stockpile chemical weapon agents despite numerous efforts to reduce or eliminate them. Most states have joined the Chemical Weapons Convention (CWC), which required the destruction of all chemical weapons by 2012. Twelve nations have declared chemical weapons production facilities and six nations have declared stockpiles of chemical weapons. All of the declared production facilities have been destroyed or converted to civilian use after the treaty went into force. According to the United States government, at least 17 nations currently have active chemical weapons programs.

A Novichok agent is a group of nerve agents, some of which are binary chemical weapons. The agents were developed at the GosNIIOKhT state chemical research institute by the Soviet Union and Russia between 1971 and 1993. Some Novichok agents at STP are solids while others are liquids. It is thought that dispersal for the solids is possible by ultrafine powder.

Methylphosphonyl difluoride (DF), also known as EA-1251 or difluoro, is a chemical weapon precursor. Its chemical formula is CH3POF2. It is a Schedule 1 substance in the sense of the Chemical Weapons Convention. It is used for production of sarin and soman as a component of binary chemical weapons; an example is the M687 artillery shell, where it is used together with a mixture of isopropyl alcohol and isopropyl amine, producing sarin.

VR (nerve agent) Chemical compound

VR is a "V-series" unitary nerve agent closely related to the better-known VX nerve agent. 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."

EA-3148 Chemical compound

EA-3148 is a "V-series" nerve agent related to the better-known compounds VX and VR. It was studied by both the US and Soviet chemical weapons programmes during the Cold War, and is notable as the only V-series organophosphate nerve agent specifically identified in public domain sources as having a higher absolute potency as an acetylcholinesterase inhibitor than VX. However, both the US and Soviet investigations of the compound concluded that despite its high potency, the physicochemical properties of the substance made it unsuitable for weaponisation, and further research was not conducted. The chemical structure of EA-3148 falls within the scope of compounds designated "Toxic chemicals" under Schedule 1 of the Chemical Weapons Convention and so it is illegal throughout the world under international law and may only be used for certain types of scientific and medical research.

Vil Sultanovich Mirzayanov is a Russian chemist of ethnic Tatar origin who now lives in the United States, best known for revealing secret chemical weapons experimentation in Russia.

A-232 Chemical compound

A-232 is an organophosphate nerve agent. It was developed in the Soviet Union under the FOLIANT program and is one of the group of compounds referred to as Novichok agents that were revealed by Vil Mirzayanov. A-232 is reportedly slightly less potent as a nerve agent compared to some of the other compounds in the series such as A-230 and A-234, having similar potency to the older nerve agent VR. However it proved to be the most versatile agent as it was chemically stable and remained a volatile liquid over a wide temperature range, making it able to be used in standard chemical munitions without requiring special delivery mechanisms to be developed.

A-234 (nerve agent) Chemical compound

A-234 is an organophosphate nerve agent. It was developed in the Soviet Union under the FOLIANT program and is one of the group of compounds referred to as Novichok agents that were revealed by Vil Mirzayanov. In March 2018 the Russian ambassador to the UK, Alexander Yakovenko, claimed to have been informed by British authorities that A-234 had been identified as the agent used in the poisoning of Sergei and Yulia Skripal. Vladimir Uglev, one of the inventors of the Novichok series of compounds, said he was "99 per cent sure that it was A-234" in relation to the 2018 Amesbury poisonings, noting its unusually high persistence in the environment.

Chemical weapons have been a part of warfare in most societies, although their use has been particularly controversial since the 20th century.

A-230 Chemical compound

A-230 is an organophosphate nerve agent. It was developed in the Soviet Union under the FOLIANT program and is one of the group of compounds referred to as Novichok agents that were revealed by Vil Mirzayanov. A-230 is possibly the most potent nerve agent for which specific toxicity figures have been published, with a human lethal dose estimated to be less than 0.1mg. However it was felt to be less suitable for weaponisation than other agents such as A-232 and A-234, due to issues with the liquid agent exhibiting low volatility and solidifying at low temperatures, as well as poor stability in the presence of water.

A-262 Chemical compound

A-262 is an organophosphate nerve agent. It was developed in the Soviet Union under the FOLIANT program and is one of the group of compounds referred to as Novichok agents that were revealed by Vil Mirzayanov. Mirzayanov gives little specific information about A-262, stating that it is highly toxic but no figures are given to compare it to other related agents. It is reportedly a solid rather than a volatile liquid as with most nerve agents, and in order to weaponise it successfully, it had to be milled into a fine powder form that could be dispersed as a dust.

References

  1. Mirzayanov VS (2008). State Secrets: An Insider's Chronicle of the Russian Chemical Weapons Program. Outskirts Press. ISBN   978-1-4327-2566-2.
  2. "S/1821/2019/Rev.1 Note by the Technical Secretariat Guidance for States Parties on Article VI Declaration Obligations and Inspections Following Entry Into Force of Changes to Schedule 1 of the Annex on Chemicals to the Chemical Weapons Convention" (PDF). 14 January 2020.
  3. "Schedule 1". Organisation for the Prohibition of Chemical Weapons (OPCW). Retrieved 2020-07-26.