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GV (nerve agent)

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GV
Ball-and-stick model of GV
Ball-and-stick model of GV
Skeletal formula of GV
Skeletal formula of GV
Names
IUPAC name
2-(Dimethylamino)ethyl N,N-dimethylphosphoramidofluoridate
Other names
EA-5365; Deanylfluorotabun; G-agent P
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C6H16FN2OP/c1-8(2)5-6-11(7,10)9(3)4/h5-6H2,1-4H3 checkY
    Key: JJHAGEZAXYOCMC-UHFFFAOYSA-N checkY
  • InChI=1/C6H16FN2OP/c1-8(2)5-6-11(7,10)9(3)4/h5-6H2,1-4H3
    Key: JJHAGEZAXYOCMC-UHFFFAOYAS
  • FP(=O)(N(C)C)CCN(C)C
Properties
C6H16FN2O2P
Molar mass 198.176 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
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GV (IUPAC name: 2-(Dimethylamino)ethyl N,N-dimethylphosphoramidofluoridate), also known as EA-5365 and GP (USACC cryptonym), is an organophosphate nerve agent. GV is a part of a series of nerve agents with properties similar to the "G-series" and "V-series".[1][2]

Physical structure

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GV is an organophosphate derived from fluorotabun. It does not have a plane of symmetry and is therefore chiral. It has a melting point of -110 degrees Celsius, the lowest among all 5 GV agents.[3]

Manufacture

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GV is synthesized by various routes.[3] It is synthesized on an industrial scale in a similar manner to tabun and sarin.

A solution of dimethylamine, hydrofluoric acid and deanol in a molar ratio of 4:1:1 is added dropwise to a phosphoryl chloride solution under agitation. The product is filtered from the cake and then distilled under reduced pressure.

4 (H3C)2NH + Cl3P(O) + (CH3)2N(CH2)2OH + F− + H+ → (H3C)2NP(O)FO(CH2)2N(CH3)2 + 3 Cl− + 3 (H3C)2NH+2

GV can be synthesized in a similar manner to sarin, from a reaction between an equimolar mixture of dichlor and difluor.

(H3C)2NCl2P(O) + (H3C)2NF2P(O) + 2 (CH3)2N(CH2)2OH → 2 (H3C)2NP(O)FO(CH2)2N(CH3)2 + 2 Cl− + 2 H+

Toxicity

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It is a potent acetylcholinesterase inhibitor with properties similar to other nerve agents. GV is structurally a derivative of the nerve agent tabun, being closely structurally related to fluorotabun, differing from the latter by the replacement of a proton on the alpha carbon of the alkoxide group by a dimethylamino group and presenting a toxicity only lower than that of VX.[4] GV appears to be the most toxic agent in the GV series.[5]

It has an LCT50 of 40 mg m-3 - 2.5 times less than sarin, and 250 times less than chlorine gas.[6]

Treatment for poisoning with GV involves drugs such as atropine, benactyzine, obidoxime, and HI-6.[7][8]

GV being a derivative of the agent fluorotabun, four other derivatives of phosphoric acid are more toxic than the latter.[9]

History

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The GV agent was independently developed in the United States at the Edgewood Arsenal, under the code EA-5365, during the 1970s and in Czechoslovakia in 1983.[10][11][12]

In Czechoslovakia, it was given the internal cryptonym GV. The cryptonym 'GV' also encompasses a number of similar compounds, sharing the typical structure - probably candidates for the cryptonym.[13][3][14][15] In the United States, the compound is denoted by the cryptonym GP, belonging to the series of the same cryptonym.[13]

The GV compounds investigated at edgewood arsenal have a more diverse structure.[16][17] The purpose of developing the GV agent in the United States is not known for certain, but it may be related to the development program for a binary intermediate volatility agent (IVA).[18][19][20][21][22][23][24] The production of binary agents is satisfactory for G agents of the second generation of nerve agents, but is not efficient for organophosphates with a deanyl group and their larger homologues - with a possible exception to the compounds EA 5400 and EA 5410, candidates for the cryptonym GX -, since the formation of the ammonium ion increases the instability of the agent by several tens of times to hydrolysis.[25][26]

Due to its tendency to polymerize and high water instability, the GV agent did not meet the requirements for an IVA agent and was replaced by a binary mixture of sarin and EA-1356.[22][27][28]

As GV-2, two substances are mentioned together, EA-5615 and EA-5636 - probably the dichloro and difluoro compounds -, with RA probably going to deanol or deanol plus base.[21][26]

Agent GV belongs to the series of fourth generation chemical warfare agents, developed approximately in the same decade that novichok agents.[5]

Agent GJ

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A crucial element of Operation Shocker was the deliberate transmission of information about a nerve agent known as "GJ" to the Soviets. By 1964, Joseph Edward Cassidy had gained enough trust to steer Soviet research toward this agent. The US believed that GJ could not be made stable or weaponizable.[29][30]

The probable structure of the chemical agent under the cryptonym “GJ”, in addition to the structure of the GV agent.

Cassidy provided the Soviets with over 4,500 documents, mixing real and invented research on the compound GJ - Edgewood Arsenal attempted to develop a GJ agent and failed, with the files passed on being partially falsified -, with the intent to mislead and waste Soviet resources on a chemical weapon program that was, in essence, a dead end.[30][27]

It is likely that this counterintelligence tactic was responsible for the Soviet Union's development of Novichok agents.[27][30]

The nerve agent description is very similar to the GV agent, although GV has been developed during the 1970s, has intermediate volatility, and the unitary agent has a recent EA number identifier.[29] In the 1950s, attention was given to methylphosphonates G agents, with Tammelin esters with very high toxicity and instability, with the latter being very similar to the GV - except to present ammonium ion.[5][31]

See also

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References

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  1. ^ Ellison, D. Hank (2008). Handbook of chemical and biological warfare agents (2nd ed.). Boca Raton: CRC Press. ISBN 978-1-4200-0329-1.
  2. ^ Journal of NBC protection corps. Volume 3, No. 2, April-June 2019 [1]
  3. ^ a b c Ivan MAŠEK; Otakar Jiří MIKA; Zdeněk ŠAFAŘÍK. INTERESTING GROUP OF HIGH-TOXIC ORGANOPHOSPHORUS COMPOUNDS. THE SCIENCE FOR POPULATION PROTECTION 2/2015
  4. ^ Holmstedt, Bo (1963), Koelle, George B. (ed.), "Structure-Activity Relationships of the Organophosphorus Anticholinesterase Agents", Cholinesterases and Anticholinesterase Agents, Handbook of Experimental Pharmacology, vol. 15, Berlin, Heidelberg: Springer Berlin Heidelberg, pp. 428–485, doi:10.1007/978-3-642-99875-1_9, ISBN 978-3-642-99877-5, retrieved 2025-03-11 {{citation}}: ISBN / Date incompatibility (help)
  5. ^ a b c INVISIBLE WEAPONS - History Of The Development And Use Of Non-Lethal Chemical Weapons. Nerve Agents: Intermediate Volatility Agent (IVA).[2]
  6. ^ Defending the U.S. Air Transportation System Against Chemical and Biological Threats. Washington, D.C.: National Academies Press. 2006-01-10. doi:10.17226/11556. ISBN 978-0-309-10074-8.
  7. ^ Fusek J, Bajgar J (1994). "Treatment of intoxication with GV compound in laboratory rats". Sb Ved Pr Lek Fak Karlovy Univerzity Hradci Kralove. 37 (2): 57–62. PMID 7784799.
  8. ^ Kassa J, Bajgar J (1996). "Therapeutic efficacy of obidoxime or HI-6 with atropine against intoxication with some nerve agents in mice". Acta Medica (Hradec Kralove). 39 (1): 27–30. PMID 9106387.
  9. ^ Holmstedt, Bo (1963), Koelle, George B. (ed.), "Structure-Activity Relationships of the Organophosphorus Anticholinesterase Agents", Cholinesterases and Anticholinesterase Agents, Handbook of Experimental Pharmacology, vol. 15, Berlin, Heidelberg: Springer Berlin Heidelberg, pp. 428–485, doi:10.1007/978-3-642-99875-1_9, ISBN 978-3-642-99877-5, retrieved 2025-05-19 {{citation}}: ISBN / Date incompatibility (help)
  10. ^ Jiri Matousek; Ivan Masek. ON THE NEW GROUP OF POTENTIAL SUPER TOXIC LETHAL ORGANOPHOSPHORUS CHEMICAL WARFARE AGENTS WITH INTERMEDIARY VOLATILITY. FacuIty of Chemistry, Technical University Brno
  11. ^ Jiri Bajgar, Josef Fusek and Frantisek Skopec. INTOXICATION WITH NERVE AGENT GV (2-DIMETHYLAMINOETHYL DIMETHYLAMlDO-PHOSPHONOFLUORlDATE) AND ITS TREATMENT. Department Toxicology, Military Medical Academy.
  12. ^ Maciej, Boczkowski; Stanisław, Popiel; Jakub, Nawała; Hubert, Suska (January 2025). "History of Organophosphorus Compounds in the Context of Their Use as Chemical Warfare Agents". Molecules. 30 (7). doi:10.3390/molecule (inactive 17 May 2025). ISSN 1420-3049. Archived from the original on 2025-05-09.{{cite journal}}: CS1 maint: DOI inactive as of May 2025 (link)
  13. ^ a b Jiri Matousek. NEW TOXIC AGENTS AND THE CONVENTION: New supertoxic lethal chemicals, their binary components and Schedule 1.
  14. ^ Jiří BAJGAR; Josef FUSEK; František SKOPEC. FARMAKOLOGICKÁ A BIOCHIÇMICKÁ CNARAKTEMSTHŠA NĚKTERÝCH ÚČINKÚ VYSOCE TOXICKE NERVOVE PARALYTICKÉ LATKY GV. Vojenská lékařská akademie J. E. Purkyně, Hradec Králové
  15. ^ Jiří CABAL. Srovnáni' Vlastností Esterů Dialkylamidofluoryosforečné Kyseliny S Ostatními Fluororganofosfaty. Vojenská lékařská akademie JEP, Hradec Králové
  16. ^ James Y. King; H. Arthur Brown, Jr. ASPECTS OF PARTITION COEPFICIENT ESTIMATION IN AGENT RESEARCH.
  17. ^ Samuel, John B.; Penski, Elwin C.; Callahan, John J. "Physical Properties of Standard Agents, Candidate Agents, and Related Compounds at Several Temperatures". apps.dtic.mil. Archived from the original on 2025-02-02. Retrieved 2025-03-09.{{cite web}}: CS1 maint: multiple names: authors list (link)
  18. ^ Joseph Scott Murphey. District. ARCHITECTURAL RECORDATION OF THE INTEGRATED BINARY PRODUCTION FACILITY, PINE BLUFF ARSENAL, ARKANSAS. U.S. Army Corps of Engineers, Fort Worth District, CESWF-PER-EC, 2004
  19. ^ Rotblat, Joseph; Hellman, Sven, eds. (1985). "Nuclear Strategy and World Security". SpringerLink. doi:10.1007/978-1-349-17878-0. ISBN 978-0-333-39668-1.
  20. ^ Marine mammals. Hearings, Ninety-second Congress--first session. Washington: U.S. Govt. Print. Off. 1971. p. 304. doi:10.5962/bhl.title.45688.
  21. ^ a b DEPARTMENT OF THE ARMY ANNUAL REPORT ON CHEMICAL WARFARE AND BIOLOGICAL RESEARCH PROGRAM. GPO-CRECB-1978-pt6-4-1. p 7482.[3]
  22. ^ a b Nikolai Antonov. Chemical Weapons at the Turn of the Century. 31 jan 1996.
  23. ^ DEPARTMENT OF THE ARMY ANNUAL REPORT ON CHEMICAL WARFARE AND BIOLOGICAL RESEARCH PROGRAM. GPO-CRECB. GPO-CRECB-1973-pt27-10.[4]
  24. ^ Zlatko BINENFELD. KEMIJSKA ORUŽJA I RAZORUŽANJE; 1976-195 p 123-129 [5]
  25. ^ O'Brien, Richard D. (1960). Toxic Phosphorus Esters: Chemistry, Metabolism, and Biological Effects. Academic Press.
  26. ^ a b INVISIBLE WEAPONS - History Of The Development And Use Of Non-Lethal Chemical Weapons. Nerve Agents: Notes on Binary Chemical Weapons.[6]
  27. ^ a b c Tucker, Jonathan (2007-12-18). War of Nerves: Chemical Warfare from World War I to Al-Qaeda. Knopf Doubleday Publishing Group. p. 247. ISBN 978-0-307-43010-6.
  28. ^ Reid Kirby. Nerve gas - America's fifteen-year struggle for modern chemical weapons. CML Army Chemical Review 2004.[7]
  29. ^ a b booknotes.c-span.org https://booknotes.c-span.org/FullPage.aspx?SID=156370-1. Retrieved 2025-05-17. {{cite web}}: Missing or empty |title= (help)
  30. ^ a b c Wise, David (2000). Cassidy's Run: The Secret Spy War Over Nerve Gas. G.K. Hall. ISBN 978-0-7838-9144-6.
  31. ^ Benschop, H. P.; van den Berg, G. R.; Kraay, G. W. (1970). "Organophosphorus compounds. Part IX: Decomposition of ω-dimethylaminoalkyl methylphosphonofluoridates and isomerization of 2-dipropylaminoethyl methylphosphonofluoridothionate". Recueil des Travaux Chimiques des Pays-Bas. 89 (10): 1025–1037. doi:10.1002/recl.19700891004. ISSN 0165-0513.
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