EA-1356

EA-1356
Names
Preferred IUPAC name
2-Methylcyclohexyl methylphosphonofluoridate
Other names
Methyl cyclosarin[1]
Identifiers
CAS Number
  • 85473-32-1
3D model (JSmol)
  • Interactive image
ChemSpider
  • 162952
PubChem CID
  • 187443
CompTox Dashboard (EPA)
  • DTXSID301006016 Edit this at Wikidata
InChI
  • InChI=1S/C8H16FO2P/c1-7-5-3-4-6-8(7)11-12(2,9)10/h7-8H,3-6H2,1-2H3
    Key: YBZCCTLVJWWETH-UHFFFAOYSA-N
  • CC1CCCCC1OP(=O)(C)F
Properties
Chemical formula
C8H16FO2P
Molar mass 194.186 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
Chemical compound

EA-1356 is an organophosphate nerve agent of the G-series.[2][3] It is highly resistant to enzymatic degradation in the body. [4] The nerve agent was tested at Edgewood Arsenal in Maryland (the "EA" in "EA-1356") among many other chemicals tested on humans. A novel enzyme was patented by the US Army in 2018 to break down EA-1356. It is a schedule 1 substance by the Chemical Weapons Convention standards. It is under the category of munitions of ML7.b.1.a.

References

  1. ^ Noga, M.; Michalska, A.; Jurowski, K. (2024). "The estimation of acute oral toxicity (LD(50)) of G-series organophosphorus-based chemical warfare agents using quantitative and qualitative toxicology in silico methods". Archives of Toxicology. doi:10.1007/s00204-024-03714-5. PMID 38493428.
  2. ^ Söderström MT, Ketola RA, Kostiainen O (1995). "Identification of some nerve agent homologues and dialkyl methylphosphonates by gas chromatography/Fourier transform infrared spectrometry". Fresenius' Journal of Analytical Chemistry. 352 (6): 550–556. doi:10.1007/BF00323072. S2CID 100910978.
  3. ^ Ellison DH (2008). Handbook of Chemical and Biological Warfare Agents (Second ed.). CRC Press. ISBN 978-0-849-31434-6.
  4. ^ US 10124043, Harvey SP, Guelta MA, McMahon LR, "Mutant OPAA enzymes with increased catalytic efficiency on organophosphorus compound EA1356", issued 13 November 2018, assigned to U.S. Army Edgewood Chemical Biological Center 
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Enzyme
(modulators)
ChATTooltip Choline acetyltransferase
  • Inhibitors: 1-(-Benzoylethyl)pyridinium
  • 2-(α-Naphthoyl)ethyltrimethylammonium
  • 3-Chloro-4-stillbazole
  • 4-(1-Naphthylvinyl)pyridine
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  • CM-54,903
  • N,N-Dimethylaminoethylacrylate
  • N,N-Dimethylaminoethylchloroacetate
AChETooltip Acetylcholinesterase
BChETooltip Butyrylcholinesterase
Transporter
(modulators)
CHTTooltip Choline transporter
VAChTTooltip Vesicular acetylcholine transporter
Release
(modulators)
Inhibitors
  • SNAP-25Tooltip Synaptosomal-associated protein 25 inactivators: Botulinum toxin (A, C, E)
  • VAMPTooltip Vesicle-associated membrane protein inactivators: Botulinum toxin (B, D, F, G)
Enhancers
See also
Receptor/signaling modulators
Muscarinic acetylcholine receptor modulators
Nicotinic acetylcholine receptor modulators
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