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A-234 (nerve agent)

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A-234 (according to Mirzayanov)
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Names
IUPAC nameExpression error: Unexpected > operator.
ethyl N-[(1E)-1-(diethylamino)ethylidene]-phosphoramidofluoridate
Other names
N-2-diethylaminomethylacetamidido-ethoxyphosphonofluoridate
Identifiers
ChemSpider 64808787 YesY
Jmol 3D model Interactive image
PubChem 132472361
Properties
Chemical formula
 C8H18FN2O2P
Molar mass 224.22 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-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.[1][2][3][4] 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.[5] 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.[6]

According to a classified (secret) report by the US Army National Ground Intelligence Center in Military Intelligence Digest dated 24 January 1997,[7] the agent designated as A-232 and its ethyl analog A-234, developed under the Foliant program, "are as toxic as VX, as resistant to treatment as soman, and more difficult to detect and easier to manufacture than VX". Of the agent's binary versions, one is reportedly formed by acetonitrile and an organic phosphate "that can be disguised as a pesticide precursor," while for another, Bill Gertz wrote, "soldiers need only add alcohol".

No certain data on toxicity exist but it is estimated that the median lethal concentration of A-234 is 7 mg/m3. This means that half of 70 kg men, under slight physical activity (15 l of air per minute), would die after 2 minutes of exposure. This equates to median lethal dose of 0.2 mg via respiration.[8]

Alternative structure[]

A-234 (according to Hoenig)
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Names
IUPAC nameExpression error: Unexpected > operator.
([(2-chloro-1-methylpropoxy)fluorohydroxyphosphinyl]oxy)carbonimidic chloride fluoride[citation needed]
Identifiers
CAS Number
 26102-99-8 N
Jmol 3D model Interactive image
Properties
Chemical formula
 C5H8Cl2F2NO3P
Molar mass 269.99 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

An alternative structure for A-234 and the related Novichok agents has been put forward by Western chemical weapons experts such as Steven Hoenig and D. Hank Ellison.[9][10] These structures are supported by Soviet literature of the time and were tested as acetylcholinesterase inhibitors,[11][12][13] however Mirzayanov claims that a number of weaker agents developed as part of the Foliant program were published in the open literature as organophosphate pesticides, in order to disguise the secret nerve agent program as legitimate pesticide research.

See also[]

References[]

  1. ↑ Mirzayanov, Vil S. (2008). State Secrets: An Insider's Chronicle of the Russian Chemical Weapons Program. Outskirts Press. ISBN 978-1-4327-2566-2. 
  2. ↑ Vásárhelyi, Györgyi; Földi, László (2007). "History of Russia's chemical weapons". pp. 135–146. http://archiv.uni-nke.hu/downloads/aarms/docs/Volume6/Issue1/pdf/15vasa.pdf. [dead link]
  3. ↑ Halámek, E.; Kobliha, Z. (2011). "Potenciální Bojové Chemické Látky". pp. 323–333. https://www.researchgate.net/publication/288702130. 
  4. ↑ Peplow, Mark (19 March 2018). "Nerve agent attack on spy used 'Novichok' poison". p. 3. https://cen.acs.org/articles/96/i12/Nerve-agent-attack-on-spy-used-Novichok-poison.html. Retrieved 16 March 2018. 
  5. ↑ Russian spy: What are Novichok agents and what do they do? BBC News, 19 March 2018
  6. ↑ Novichok inventor on Amesbury poisoning: ‘I completely understand panic of those living in Salisbury’. The Independent, 6 July 2018
  7. ↑ Bill Gertz. Russia dodges chemical arms ban. The Washington Times, 4 February 1997
  8. ↑ Franca, Tanos C. C.; Kitagawa, Daniel A. S.; Cavalcante, Samir F. de A.; da Silva, Jorge A. V.; Nepovimova, Eugenie; Kuca, Kamil (January 2019). "Novichoks: The Dangerous Fourth Generation of Chemical Weapons" (in en). pp. 1222. Digital object identifier:10.3390/ijms20051222. https://www.mdpi.com/1422-0067/20/5/1222. 
  9. ↑ Hoenig, Steven L. (2007), Compendium of Chemical Warfare Agents, Springer, ISBN 978-0-387-34626-7
  10. ↑ Ellison, D. Hank (2008), Handbook of Chemical and Biological Warfare Agents (Second ed.), CRC Press, ISBN 978-0-849-31434-6
  11. ↑ Kruglyak, Yu. L.; Malekin, S. I.; Martynov, I. V. (1972). "Phosphorylated oximes. XII. Reactions of 2-halophospholanes with dichlorofluoronitrosomethane". pp. 811–14. 
  12. ↑ Raevskii, O. A.; Chapysheva, N. V.; Ivanov, A. N.; Sokolov, V. B.; Martynov, I. V. (1987). "Effect of Alkyl Substituents in Phosphorylated Oximes". pp. 2720–2723. 
  13. ↑ Raevskii, O. A.; Grigor'ev, V. Yu.; Solov'ev, V. P.; Ivanov, A. N.; Sokolov, V. B.; Martynov, I. V. (1987). "Electron-Donor Functions of Ethyl Methylchloroformimino Methylphosphonate". pp. 2073–2078. 
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