Diisopropyl fluorophosphate 3207188 198466668 2008-03-15T19:38:34Z Benjah-bmm27 126395 3D [[ball-and-stick model]] added {{drugbox | IUPAC_name = 2-(fluoro-(1-methylethoxy)phosphoryl)oxypropane | image = Diisopropylfluorophosphate.svg | image2 = Diisopropyl-fluorophosphate-3D-balls.png | CAS_number = 55-91-4 | ATC_prefix = S01 | ATC_suffix = EB07 | ATC_supplemental = | PubChem = 5936 | DrugBank = APRD00763 | C=6 | H=14 | F=1 | O=3 | P=1 | molecular_weight = 184.146 g/mol | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | pregnancy_category = | legal_status = | routes_of_administration = | smiles = FP(OC(C)C)(OC(C)C)=O | melting_point = -82 | boiling_point = 46 | boiling_notes = 5 mmHg }} '''Diisopropyl fluorophosphate''' ('''DFP''', '''diisopropyl phosphorofluoridate''') is an oily, colorless or faint yellow liquid with the chemical formula C<sub>6</sub>H<sub>14</sub>FO<sub>3</sub>P. It is used in medicine and as an [[organophosphate]] [[insecticide]]. It is stable, but undergoes hydrolysis when subjected to moisture, producing [[hydrofluoric acid]]. It is a structural analog of [[sarin]]. It is known also under names '''Demecarium''', '''Difluorophate''', '''Diflupyl''', '''Diflurphate''', '''Dyflos''', '''Dyphlos''', '''Fluoropropyl''', '''Fluropryl''', '''Fluostigmine''', '''Humorsol''', '''isofluorophate''', '''isofluorphate''', '''Neoglaucit''', '''PF-3''', '''PF3''', '''T-1703''', '''TL 466''', and others. ==Uses in medicine== Diisopropyl fluorophosphate (closely related to [[demecarium bromide]]) has been used in [[ophthalmology]] as a [[miotic]] agent in treatment of chronic [[glaucoma]], as a miotic in veterinary medicine, and as an experimental agent in neuroscience because of its [[acetylcholinesterase]] [[Enzyme inhibitor|inhibitor]]y properties and ability to induce [[Organophosphate-induced delayed neuropathy|delayed peripheral neuropathy]]. It is known as '''fluostigmine''' and '''Dyflos''' in such uses. ==Uses as toxin== The marked toxicity of esters of monofluorophosphoric acid was discovered in 1932, when [[Willy 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 scientist [[Bernard Charles Saunders]]. On his search for compounds to be used as [[chemical warfare]] agents, Saunders was inspired by the report by Lange und Krueger and decided to prepare the new homologue which he 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-agent]]s ([[tabun (nerve agent)|GA]], [[sarin|GB]], [[soman|GD]], [[cyclosarin|GF]]). Diisopropyl fluorophosphate is a very potent [[neurotoxin]]. Its [[LD50]] for rats is 1.3 mg/kg. It combines with the [[amino acid]] [[serine]] at the active site of the enzyme [[acetylcholinesterase]], an enzyme that deactivates the [[neurotransmitter]] [[acetylcholine]]. Neurotransmitters are needed to continue the passage of [[nerve impulse]]s from one [[neuron]] to another across the [[synapse]]. 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 and [[death]] may result since the [[diaphragm (anatomy)|respiratory muscle]]s are affected. ==Sources== *Brenner, G. M. (2000): ''Pharmacology.'' Philadelphia, PA: W.B. Saunders Company. ISBN 0-7216-7757-6 * Meiers, P. (2006): [http://www.fluoride-history.de/p-mfp.htm History of the fluorophosphates] ==External links== {{Antiglaucoma preparations and miotics}} [[Category:Organophosphate insecticides]] [[Category:Anticholinesterases]] [[Category:Organophosphates]] [[Category:Ophthalmology]] [[Category:Neurotoxins]] [[de:Diisopropylfluorophosphat]] [[pl:DFP_(chemia)]]