Methylfluorophosphonylcholine
Names
Preferred IUPAC name
N,N,N-Trimethyl-2-[(methylphosphonofluoridoyl)oxy]ethan-1-aminium
Other names
Methylfluorophosphorylcholine, MFPCh
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C6H16FNO2P/c1-8(2,3)5-6-10-11(4,7)9/h5-6H2,1-4H3/q+1
    Key: OKNSDXKIPFDADW-UHFFFAOYSA-N
  • C[N+](C)(C)CCOP(=O)(C)F
Properties
C6H16FNO2P
Molar mass 184.171 g·mol−1
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Extremely toxic
Lethal dose or concentration (LD, LC):
100 μg/kg (mice, intraperitoneal)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Methylfluorophosphonylcholine (MFPCh) is an extremely toxic chemical compound related to the G-series nerve agents. It is an extremely potent acetylcholinesterase inhibitor which is around 100 times more potent than sarin at inhibiting acetylcholinesterase in vitro,[2] and around 10 times more potent in vivo, depending on route of administration and animal species tested.[3] MFPCh is resistant to oxime reactivators, meaning the acetylcholinesterase inhibited by MFPCh can't be reactivated by cholinesterase reactivators.[2][4][5] MFPCh also acts directly on the acetylcholine receptors.[6] However, despite its high toxicity, methylfluorophosphonylcholine is a relatively unstable compound and degrades rapidly in storage, so it was not deemed suitable to be weaponised for military use.[7]

See also

References

  1. ^ "ChemIDplus".
  2. ^ a b Szinicz, L.; Worek, F.; Thiermann, H. (1 April 2004). "Reactivation and aging kinetics of human acetylcholinesterase inhibited by organophosphonylcholines". Archives of Toxicology. 78 (4): 212–217. doi:10.1007/s00204-003-0533-0. PMID 14647978. S2CID 21857766.
  3. ^ Black RM, Harrison JM. The chemistry of organophosphorus chemical warfare agents. Chapter 10 of The chemistry of organophosphorus compounds. Volume 4, Ter- and quinque-valent phosphorus acids and their derivatives. (1996) ISBN 0-471-95706-2
  4. ^ Enander, Inger; Villadsen, John V.; Sillén, Lars Gunnar; Sillén, Lars Gunnar; Zaar, B.; Diczfalusy, E. (1958). "Experiments with Methyl-fluoro-phosphorylcholine-inhibited Cholinesterase". Acta Chemica Scandinavica. 12: 780–781. doi:10.3891/acta.chem.scand.12-0780.
  5. ^ Fredriksson, T.; Tibbling, G. (May 1959). "Reversal of effects on the rat nerve-diaphragm preparation produced by methylfluorophosphorylcholines". Biochemical Pharmacology. 2 (1): 63–64. doi:10.1016/0006-2952(59)90058-9.
  6. ^ Fredriksson, T.; Tibbling, G. (November 1959). "Demonstration of direct cholinergic receptor effects of methylfluorophosphorylcholines". Biochemical Pharmacology. 2 (4): 286–289. doi:10.1016/0006-2952(59)90042-5.
  7. ^ Black RM, Harrison JM. The chemistry of organophosphorus chemical warfare agents. Chapter 10 of The chemistry of organophosphorus compounds. Volume 4, Ter- and quinque-valent phosphorus acids and their derivatives. (1996) ISBN 0-471-95706-2
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