Article · Wikipedia archive · Last revised Jul 29, 2026

Mipafox

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

Last revised
Jul 29, 2026
Read time
≈ 1 min
Length
320 w
Citations
4
Source
Wikipedia ↗
Mipafox
source ↗
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
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

See also

References

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. 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".