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| Other names | Isofluorophate, Isofluorphate, DFP, DIFP, DIPF, Diisopropyl phosphorofluoridate, EA-1152, PF-3, T-1703, TL-466 |
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| ECHA InfoCard | 100.000.225 |
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| Formula | C6H14FO3P |
| Molar mass | 184.147 g·mol−1 |
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| Melting point | −82 °C (−116 °F) |
| Boiling point | 183 °C (361 °F) 1013 mbar |
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Diisopropyl fluorophosphate (DFP) orIsoflurophate is an oily, colorless liquid with the chemical formula C6H14FO3P. It is used in medicine[1] and as anorganophosphorusinsecticide.[2] It is stable, but undergoes hydrolysis when subjected to moisture.
Diisopropyl fluorophosphate is aparasympathomimetic drugirreversible anti-cholinesterase and has been used inophthalmology as amiotic agent in treatment of chronicglaucoma, as a miotic in veterinary medicine, and as an experimental agent in neuroscience because of itsacetylcholinesteraseinhibitory properties and ability to inducedelayed peripheral neuropathy.[1]
The marked toxicity of esters ofmonofluorophosphoric acid was discovered in 1932, whenWilly Lange and his PhD student Gerda von Krueger prepared the methyl, ethyl, n-propyl, and n-butyl esters and incidentally experienced their toxic effects. Another homologue of this series of esters, Diisopropyl fluorophosphate, was developed by British scientistBernard Charles Saunders. On his search for compounds to be used aschemical warfare agents, Saunders was inspired by the report by Lange and Krueger and decided to prepare the new homologue which he labeled PF-3. It was much less effective as a chemical weapon than the G series agents. It was often mixed withmustard gas, forming a more effective mixture with significantly lower melting point, resulting in an agent suitable for use in cold weather.
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In military research, due to its physical and chemical similarities and comparatively low toxicity, it is used as a simulant ofG-agents (GA,GB,GD, andGF). Diisopropyl fluorophosphate is used in civilian laboratories to mimic lethal nerve gas exposure or organophosphate toxicities.[3][4][5] It has also been used to develop a rodent model ofGulf War Syndrome.[6]
Diisopropyl fluorophosphate is a very potentneurotoxin. ItsLD50 in rats is 6 mg/kg (oral). It combines with theamino acidserine at the active site of the enzymeacetylcholinesterase,[7] an enzyme that deactivates theneurotransmitteracetylcholine. Neurotransmitters are needed to continue the passage ofnerve impulses from oneneuron to another across thesynapse. Once the impulse has been transmitted, acetylcholinesterase functions to deactivate the acetylcholine almost immediately by breaking it down. If the enzyme is inhibited, acetylcholine accumulates and nerve impulses cannot be stopped, causing prolonged muscle contraction.Paralysis occurs anddeath may result since therespiratory muscles are affected.
DFP also inhibits someproteases. It is a useful additive for protein or cell isolation procedure.
Diisopropyl fluorophosphate (DFP) was a nerve gas developed by the German during theSecond World War. DFP irreversibly binds with the enzymes containing serine at the active site, e g. Serine proteases, acetylcholine esterase.
Isoflurophate, the diisopropyl ester of fluorophosphoric acid, is made by reactingisopropyl alcohol withphosphorus trichloride, forming diisopropylphosphite, which is chlorinated and further reacted withsodium fluoride to replace the chlorine atom with fluorine, thus giving diisopropyl fluorophosphate.[8]
DFP is a diagnostic test for the presence of the active site Ser in serine proteases, as well as a serine protease inhibitor.PMSF andAEBSF are less toxic alternatives that work well for most serine proteases. However, only DFP potently inhibits a subclass of serine proteases collectively known as neutrophil serine proteases (namely, neutrophil elastase, cathepsin G, and proteinase 3). DFP and other analogous organophosphate neurotoxins are inactivated by the enzymeparaoxonase, which is present in widely varying levels in humans.
It is marketed under many brand names including Difluorophate, Diflupyl, Diflurphate, Dyflos, Dyphlos, Fluropryl, Fluostigmine, Neoglaucit.[citation needed]
