Mipafox

{{Chembox

| Name = Mipafox

| ImageFile = Mipafox.svg

| ImageSize = 180px

| PIN = N,N′-Di(propan-2-yl)phosphorodiamidic fluoride

| OtherNames = Bis(isopropylamino)fluorophosphine oxide; Isopestox

| Section1 = {{Chembox Identifiers

| CASNo = 371-86-8

| ChemSpiderID = 9355

| PubChem = 9738

| EC_number = 206-742-3

| ChEBI = 82142

| KEGG = C19008

| UNII = 24MJP5H3YN

| SMILES = CC(C)NP(=O)(NC(C)C)F

| StdInChI = InChI=1S/C6H16FN2OP/c1-5(2)8-11(7,10)9-6(3)4/h5-6H,1-4H3,(H2,8,9,10)

| StdInChIKey = UOSHUBFBCPGQAY-UHFFFAOYSA-N

}}

| Section2 = {{Chembox Properties

| C=6|H=16|F=1|N=2|O=1|P=1

| Density = 1.2

| Solubility = 80 g/L

| MeltingPtC = 65

| BoilingPtC = 125

}}

| Section3 = {{Chembox Hazards

| MainHazards = Highly toxic

| GHSPictograms = {{GHS06}}{{GHS07}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|301|370}}

| PPhrases = {{P-phrases|260|264|270|301+310|307+311|321|330|405|501}}

}}

}}

Mipafox is a highly toxic organophosphate insecticide that is an irreversible acetylcholinesterase inhibitor and is resistant to cholinesterase reactivators.{{cite journal |last1=Mangas |first1=I |last2=Taylor |first2=P |last3=Vilanova |first3=E |last4=Estévez |first4=J |last5=França |first5=TC |last6=Komives |first6=E |last7=Radić |first7=Z |title=Resolving pathways of interaction of mipafox and a sarin analog with human acetylcholinesterase by kinetics, mass spectrometry and molecular modeling approaches. |journal=Archives of Toxicology |date=March 2016 |volume=90 |issue=3 |pages=603–16 |doi=10.1007/s00204-015-1481-1 |pmid=25743373 |pmc=4833118}} It was developed in the 1950s and is now believed to be no longer in use.{{Cite web | url = https://apps.who.int/iris/bitstream/handle/10665/332193/9789240005662-eng.pdf | title = The WHO Recommended Classification of Pesticides by Hazard and Guidelines to Classification 2019| publisher = World Health Organization }}

Toxicity

There are case reports of delayed neurotoxicity and paralysis due to acute exposure to mipafox.{{cite journal |last1=BIDSTRUP |first1=PL |last2=BONNELL |first2=JA |last3=BECKETT |first3=AG |title=Paralysis following poisoning by a new organic phosphorus insecticide (mipafox); report on two cases. |journal=British Medical Journal |date=16 May 1953 |volume=1 |issue=4819 |pages=1068–72 |pmid=13042137 |pmc=2016450 |doi=10.1136/bmj.1.4819.1068}}

Synthesis

Phosphoryl chloride is first reacted with isopropylamine. The resulting product is then reacted with potassium fluoride or ammonium fluoride to produce mipafox.{{cite web |title=Process for the preparation of bisisopropyl-amino-fluoro-phosphine oxide |url=https://patents.google.com/patent/US2678334A}}

See also

References

{{Reflist}}

{{Acetylcholine metabolism and transport modulators}}

{{Insecticides}}

{{Neurotoxins}}

Category:Acetylcholinesterase inhibitors

Category:Organophosphate insecticides

Category:Fluorine compounds

Category:Isopropylamino compounds

{{Organic-compound-stub}}