Paraoxon

Paraoxon

File:Paraoxon structure.svg
File:Paraoxon-3D-balls.png
Clinical data
ATC code	S01EB10 (WHO)
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name Diethyl 4-nitrophenyl phosphate
CAS Number	311-45-5 checkY
PubChem CID	9395
ChemSpider	9026 checkY
UNII	Q9CX8P80JW
KEGG	D10529 ☒N
ChEBI	CHEBI:27827 ☒N
ChEMBL	ChEMBL23838 checkY
E number	{{#property:P628}}
CompTox Dashboard (EPA)	{{#property:P3117}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C10H14NO6P
Molar mass	275.197 g·mol−1
3D model (JSmol)	Interactive image
SMILES [O-][N+](=O)c1ccc(OP(=O)(OCC)OCC)cc1
InChI InChI=1S/C10H14NO6P/c1-3-15-18(14,16-4-2)17-10-7-5-9(6-8-10)11(12)13/h5-8H,3-4H2,1-2H3 checkY Key:WYMSBXTXOHUIGT-UHFFFAOYSA-N checkY
☒NcheckY (what is this?)  (verify)

Paraoxon is a parasympathomimetic drug which acts as an cholinesterase inhibitor. It is an organophosphate oxon, and the active metabolite of the insecticide parathion. It is also used as an ophthalmological drug against glaucoma. Paraoxon is one of the most potent acetylcholinesterase-inhibiting insecticides available, around 70% as potent as the nerve agent sarin, and so is now rarely used as an insecticide due to the risk of poisoning to humans and other animals. Paraoxon has been used by scientists to study acute and chronic effects of organophosphate intoxication. It is easily absorbed through skin, and was allegedly used as an assassination weapon by the apartheid-era South African chemical weapons program Project Coast.

EA-1370 is a phosphonate analogue, isopropyl para-nitrophenyl methylphosphonate, the junction of the nerve agent sarin with the leaving group of paraoxon. Contact with the fluoride ion in a polar-aprotic solvent regenerates it to sarin.

See also

• Armine (chemical)
• O-isobutylarmine
• O-neopentyl p-nitrophenyl methylphosphonate