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Methylfluorophosphonylcholine

From Wikipedia, the free encyclopedia
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 mass184.171 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 theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Methylfluorophosphonylcholine (MFPCh) is an extremely toxicchemical compound related to the G-seriesnerve agents. It is an extremely potentacetylcholinesterase inhibitor which is around 100 times more potent thansarin at inhibiting acetylcholinesterasein vitro,[2] and around 10 times more potentin vivo, depending onroute of administration and animal species tested.[3] MFPCh is resistant to oxime reactivators, meaning theacetylcholinesterase inhibited by MFPCh can't be reactivated bycholinesterase reactivators.[2][4][5] MFPCh also acts directly on theacetylcholine receptors.[6] MFPCh is a relatively unstable compound and degrades rapidly in storage, so despite its enhanced toxicity it was not deemed suitable to be weaponised for military use.[7]

See also

[edit]

References

[edit]
  1. ^"ChemIDplus".
  2. ^abSzinicz, 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.Bibcode:2004ArTox..78..212W.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.PMID 13824695.
  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
Enzyme
(modulators)
ChATTooltip Choline acetyltransferase
AChETooltip Acetylcholinesterase
BChETooltip Butyrylcholinesterase
Transporter
(modulators)
CHTTooltip Choline transporter
VAChTTooltip Vesicular acetylcholine transporter
Release
(modulators)
Inhibitors
Enhancers
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