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Mipafox

From Wikipedia, the free encyclopedia
Mipafox
Names
Preferred IUPAC name
N,N′-Di(propan-2-yl)phosphorodiamidic fluoride
Other names
Bis(isopropylamino)fluorophosphine oxide; Isopestox
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard100.006.130Edit this at Wikidata
EC Number
  • 206-742-3
KEGG
UNII
  • InChI=1S/C6H16FN2OP/c1-5(2)8-11(7,10)9-6(3)4/h5-6H,1-4H3,(H2,8,9,10)
    Key: UOSHUBFBCPGQAY-UHFFFAOYSA-N
  • CC(C)NP(=O)(NC(C)C)F
Properties
C6H16FN2OP
Molar mass182.179 g·mol−1
Density1.2
Melting point65 °C (149 °F; 338 K)
Boiling point125 °C (257 °F; 398 K)
80 g/L
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Highly toxic
GHS labelling:
GHS06: ToxicGHS07: Exclamation mark
Danger
H301,H370
P260,P264,P270,P301+P310,P307+P311,P321,P330,P405,P501
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Mipafox is a highly toxicorganophosphateinsecticide that is an irreversibleacetylcholinesterase inhibitor and is resistant tocholinesterase reactivators.[1] It was developed in the 1950s and is now believed to be no longer in use.[2]

Toxicity

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There arecase reports of delayedneurotoxicity andparalysis due to acute exposure to mipafox.[3]

Synthesis

[edit]

Phosphoryl chloride is first reacted withisopropylamine. The resulting product is then reacted withpotassium fluoride orammonium fluoride to produce mipafox.[4]

See also

[edit]

References

[edit]
  1. ^Mangas, I; Taylor, P; Vilanova, E; Estévez, J; França, TC; Komives, E; Radić, Z (March 2016)."Resolving pathways of interaction of mipafox and a sarin analog with human acetylcholinesterase by kinetics, mass spectrometry and molecular modeling approaches".Archives of Toxicology.90 (3):603–16.Bibcode:2016ArTox..90..603M.doi:10.1007/s00204-015-1481-1.PMC 4833118.PMID 25743373.
  2. ^"The WHO Recommended Classification of Pesticides by Hazard and Guidelines to Classification 2019"(PDF). World Health Organization.
  3. ^BIDSTRUP, PL; BONNELL, JA; BECKETT, AG (16 May 1953)."Paralysis following poisoning by a new organic phosphorus insecticide (mipafox); report on two cases".British Medical Journal.1 (4819):1068–72.doi:10.1136/bmj.1.4819.1068.PMC 2016450.PMID 13042137.
  4. ^"Process for the preparation of bisisopropyl-amino-fluoro-phosphine oxide".
Enzyme
(modulators)
ChATTooltip Choline acetyltransferase
AChETooltip Acetylcholinesterase
BChETooltip Butyrylcholinesterase
Transporter
(modulators)
CHTTooltip Choline transporter
VAChTTooltip Vesicular acetylcholine transporter
Release
(modulators)
Inhibitors
Enhancers
Carbamates
Inorganic compounds
Insect growth regulators
Neonicotinoids
Organochlorides
Organophosphorus
Pyrethroids
Diamides
Other chemicals
Metabolites
Biopesticides
Animal toxins
Bacterial
Cyanotoxins
Plant toxins
Mycotoxins
Pesticides
Nerve agents
Bicyclic phosphates
Cholinergic neurotoxins
Psychoactive drugs
Other


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