GV (nerve agent)

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GV
Ball-and-stick model of GV GV-3D-balls-by-AHRLS.png
Ball-and-stick model of GV
Skeletal formula of GV GV-2D-skeletal.png
Skeletal formula of GV
Names
IUPAC name
2-(Dimethylamino)ethyl N,N-dimethylphosphoramidofluoridate
Other names
EA-5365
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C6H16FN2OP/c1-8(2)5-6-11(7,10)9(3)4/h5-6H2,1-4H3 Yes check.svgY
    Key: JJHAGEZAXYOCMC-UHFFFAOYSA-N Yes check.svgY
  • 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).
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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". 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.

Contents

Treatment for poisoning with GV involves drugs such as atropine, benactyzine, obidoxime, and HI-6. [1] [2]

History

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. [3] [4]

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. [5] [6] [7] [8] In the United States, the compound is denoted by the cryptonym GP, belonging to the series of the same cryptonym. [5]

The GV compounds investigated at edgewood arsenal have a more diverse structure. [9] [10] 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 an binary intermediate volatility agent (IVA). [11] [12] [13] [14] 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. [15] [16]

As GV-2, two substances are mentioned together, EA-5615 and EA-5636, with RA probably going to deanol or deanol plus base. [14]

See also

References

  1. ↑ 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.
  2. ↑ 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.
  3. ↑ 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
  4. ↑ Jiri Bajgar, Josef Fusek and Frantisek Skopec. INTOXICATION WITH NERVE AGENT GV (2-DIMETHYLAMINOETHYL DIMETHYLAMlDO-PHOSPHONOFLUORlDATE) AND ITS TREATMENT. Department Toxicology, Military Medical Academy.
  5. 1 2 Jiri Matousek. NEW TOXIC AGENTS AND THE CONVENTION: New supertoxic lethal chemicals, their binary components and Schedule 1.
  6. ↑ Ivan MAŠEK; Otakar Jiří MIKA; Zdeněk ŠAFAŘÍK. INTERESTING GROUP OF HIGH-TOXIC ORGANOPHOSPHORUS COMPOUNDS. THE SCIENCE FOR POPULATION PROTECTION 2/2015
  7. ↑ 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
  8. ↑ Jiří CABAL. Srovnáni' Vlastností Esterů Dialkylamidofluoryosforečné Kyseliny S Ostatními Fluororganofosfaty. Vojenská lékařská akademie JEP, Hradec Králové
  9. ↑ James Y. King; H. Arthur Brown, Jr. ASPECTS OF PARTITION COEPFICIENT ESTIMATION IN AGENT RESEARCH.
  10. ↑ 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)
  11. ↑ 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
  12. ↑ Rotblat, Joseph; Hellman, Sven, eds. (1985). "Nuclear Strategy and World Security". SpringerLink. doi:10.1007/978-1-349-17878-0.
  13. ↑ Marine mammals. Hearings, Ninety-second Congress--first session. Washington: U.S. Govt. Print. Off. 1971. p. 304.
  14. 1 2 DEPARTMENT OF THE ARMY ANNUAL REPORT ON CHEMICAL WARFARE AND BIOLOGICAL RESEARCH PROGRAM. GPO-CRECB-1978-pt6-4-1. p 7482.
  15. ↑ Nikolai Antonov. Chemical Weapons at the Turn of the Century. 31 jan 1996. p 82.
  16. ↑ 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.
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