Diisopropylfluorophosphate

Image:Diisopropylfluorophosphate.png Diisopropylfluorophosphate (DFP, diisopropyl fluorophosphate) is an organophosphateinsecticide. It is an oily, colorless or faint yellow liquid with melting point -82 °C and boiling point 46 °C. Its chemical formula is C{{{else{{{test|}}}|{{{test{{{test|}}}|{{{then|}}}}}}}}}}|then=_{{{1}}}}}₆H{{{else{{{test|}}}|{{{test{{{test|}}}|{{{then|}}}}}}}}}}|then=_{{{1}}}}}₁₄FO{{{else{{{test|}}}|{{{test{{{test|}}}|{{{then|}}}}}}}}}}|then=_{{{1}}}|}}₃P. It is stable, and it undergoes hydrolysis when subjected to moisture, producing hydrofluoric acid. It is a structural analog of sarin.

Its CAS numberis 55-91-4[1]and its SMILESstructure is FP(OC(C)C) (OC(C)C)=O.

It is known also under names Demecarium, Difluorophate, Diflupyl, Diflurphate, Dyflos, Dyphlos, Echothiophate, Fluoropropyl, Fluropryl, Fluostigmine, Humorsol, isofluorophate, isofluorphate, Neoglaucit, PF-3, PF3, T-1703, TL 466, and others.

Diisopropylfluorophosphate has been used in ophthalmologyas a mioticagent in treatment of chronic glaucoma, as a mioticin veterinary medicine, and as an experimental agent in neuroscience because of its acetylcholinesteraseinhibitoryproperties and ability to induce delayed peripheral neuropathy. It is known as fluostigmine and Dyflos in such uses.

Diisopropylfluorophosphate was discovered by British scientist Bernard Saundersas a chemical warfare agentand labeled PF-3. It was much less deadly than tabun or sarin, however it could be mixed with mustard gas, forming a more potent mixture with significantly lower melting point, resulting in an agent suitable for use in cold weather. In military research, due to its physical and chemical similarities and comparatively low toxicity, it is used as a simulant of G-agents(GA, GB, GD, GF).

Diisopropylfluorophosphate is a very potent neurotoxin. Its LD50for rats is 1.3 mg/kg. It combines with the amino acidserine(contains the ?SH group) at the active site of the enzyme acetylcholinesterase. The enzyme deactivates the neurotransmitteracetylcholine. Neurotransmitters are needed to continue the passage of nerve impulsesfrom one neuronto another across the synapse. Once the impulse has been transmitted, acetylcholinesterase functions to deactivate the acetycholine almost immediately by breaking it down. If the enzyme is inhibited, acetylcholine accumulates and nerve impulses cannot be stopped, causing prolonged muscle contraction. Paralysisoccurs and deathmay result since the respiratory musclesare affected.

Sources

• Brenner, G. M. (2000). Pharmacology. Philadelphia, PA: W.B. Saunders Company. ISBN 0-7216-7757-6

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