Mipafox

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 InfoCard 100.006.130 Edit 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 mass 182.179 g·mol−1
Density 1.2
Melting point 65 °C (149 °F; 338 K)
Boiling point 125 °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 their standard state (at 25 °C [77 °F], 100 kPa).

Mipafox is a highly toxic organophosphate insecticide that is an irreversible acetylcholinesterase inhibitor and is resistant to cholinesterase reactivators.[1] It was developed in the 1950s and is now believed to be no longer in use.[2]

Toxicity

There are case reports of delayed neurotoxicity and paralysis due to acute exposure to mipafox.[3]

Synthesis

Phosphoryl chloride is first reacted with isopropylamine. The resulting product is then reacted with potassium fluoride or ammonium fluoride to produce mipafox.[4]

See also

References

  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. 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".


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