Methylfluorophosphonylcholine
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| Names | |
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| Preferred IUPAC name
N,N,N-Trimethyl-2-[(methylphosphonofluoridoyl)oxy]ethan-1-aminium | |
| Other names
Methylfluorophosphorylcholine, MFPCh
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C6H16FNO2P | |
| Molar mass | 184.171 g·mol−1 |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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Extremely toxic |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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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).
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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] 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]- ^ "ChemIDplus".
- ^ 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. Bibcode:2004ArTox..78..212W. doi:10.1007/s00204-003-0533-0. PMID 14647978. S2CID 21857766.
- ^ 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
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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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