Methyl fluorophosphonate

Chemical name Ethyl dimethylamido cyanophosphate Isopropyl methyl pho.sphonofl uoridate Pinacolyl methyl phosphonoflooridate U-cy clohcx yl methyl fluorophosphonate 5-(2-diisopropyl-aminoeth>i) 0-ethyl methyl phosphonothiolate... 

Isopropyl methylphos-phonofluoridate O-isopropyl methyl-phosphonofluoridate phosphonofluoridic acid, methyl-, 1-meth-ylethyl ester phosphonofluoridic acid, methyl-, isopropyl ester isopropoxymeth-ylphosphoryl fluoride isopropyl methyl-fluorophosphonate isopropyl methylphos-phonofluoridate meth-ylfluorophosphoric acid isopropyl ester... 

It was obviously of interest to determine whether other esters of fluoroacetic acid would prove to be more or less toxic than the methyl ester. In the phosphorofluoridate series, for example, we found that esters of secondary alcohols were far more potent than those of primary alcohols for instance, di-isopropyl fluorophosphonate (I) was a compound of considerable activity. Accordingly ethyl, ra-propyl and isopropyl fluoroacetates were prepared by heating the corresponding esters of chloroacetic acid in the rotating autoclave with potassium fluoride. The toxicity figures of these esters were very similar to those of methyl fluoroacetate. 

YC Lio, LJ Reynolds, J Balsinde, EA Dennis. Irreversible inhibition of Ca(2 + )-independent phospholipase A2 by methyl arachidonyl fluorophosphonate. Biochim... 

Little is yet known in regard to factors that might cause individual variation in acetylcholinesterase activity. The activity is greatly reduced in erythrocytes of persons with paroxysmal nocturnal hemoglobinuria, but this condition is rare (42). It has been reported that extended inhibition by organophosphates does not appear to affect adversely the survival of erythrocytes in the circulation as evidenced by observations (28,60,92) with DFP (diisopropyl fluorophosphonate), OMPA (octa-methyl pyrophosphoramide), and malathion (O,O-dimethyl dithiophos-phate of diethyl mercaptosuccinate). 

Synonyms Cyclosarin Cyclohexyl methylphos-phonofluoridate CMPF Cyclosin Methyl-phosphonofluoridic acid cyclohexyl ester Methyl cyclohexylfluorophosphonate Cyclohexyl ester of methylphosphonofluoridic acid Cyclo-hexylmethyl-fluorophosphonate Methylfluoro-cyclohexylphosphonate Nerve gas Nerve agent Chemical/Pharmaceutical/Other Class GF is a colorless, liquid, organophosphate human-made nerve agent with intermediate persistence. The evaporation rate is l/20th that of water. It has a... 

PA-PLAi was inhibited by methyl arachidonyl fluorophosphonate (MAFP), an inhibitor of certain PLA2S, but not by DFP [39], which is a potent inhibitor of mPA-PLAi. The activity of PA-PLAi was Ca -independent at neutral pH but Ca -dependent at alkaline pH [39]. 

Deutsch DG, Omeir R, Arreaza G, Salehani D, Prestwich GD, Huang Z, Howlett A (1997b) Methyl arachidonyl fluorophosphonate a potent irreversible inhibitor of anandamide amidase. Biochem Pharmacol 53 255-260... 

Fernando SR, Pertwee RG (1997) Evidence that methyl arachidonyl fluorophosphonate is an irreversible cannabinoid receptor antagonist. Br J Pharmacol 121 1716-1720... 

Two confomers of the compound (also known as cyclohexylsarin) were detected in the microwave spectrum. The fluorophosphonate group is placed at the equatorial or axial position of the cyclohexyl ring. For both conformers the rotational transitions are split due to the internal rotation of the methyl group. 

The fluorophosphonates GB and GD hydrolyze first through the loss of fluorine and second, more slowly, through the loss of the alkoxy group (Kingery and Allen 1995 MacNaughton and Brewer 1994). Under acidic conditions, the products of GB hydrolysis are isopropyl methylphosphonic acid and fluoride the former slowly hydrolyzes to methyl phosphonic acid with the loss of isopropanol (Fig. 5). According to Clark (1989), alkaline hydrolysis results in isopro-... 

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