Paraoxon

Paraoxon

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 Y
PubChem CID	9395
ChemSpider	9026 Y
UNII	Q9CX8P80JW
KEGG	D10529 N
ChEBI	CHEBI:27827 N
ChEMBL	ChEMBL23838 Y
CompTox Dashboard (EPA)	DTXSID6024046
ECHA InfoCard	100.005.657
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 Y Key:WYMSBXTXOHUIGT-UHFFFAOYSA-N Y
NY (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.^[1][2] 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.^[3]

EA-1370 is a phosphonate analogue, isopropyl para-nitrophenyl methylphosphonate, the junction of the nerve agent sarin with the leaving group of paraoxon.^[4] Contact with the fluoride ion in a polar-aprotic solvent regenerates it to sarin.^[5][6]

1. ^ Deshpande LS, Carter DS, Phillips KF, Blair RE, DeLorenzo RJ (September 2014). "Development of status epilepticus, sustained calcium elevations and neuronal injury in a rat survival model of lethal paraoxon intoxication". Neurotoxicology. 44: 17–26. Bibcode:2014NeuTx..44...17D. doi:10.1016/j.neuro.2014.04.006. PMC 4176600. PMID 24785379.
2. ^ Deshpande LS, Phillips K, Huang B, DeLorenzo RJ (September 2014). "Chronic behavioral and cognitive deficits in a rat survival model of paraoxon toxicity". Neurotoxicology. 44: 352–7. Bibcode:2014NeuTx..44..352D. doi:10.1016/j.neuro.2014.08.008. PMC 4175062. PMID 25172410.
3. ^ "Paraoxon". NTI Country Overviews: South Africa: Chemical Capabilities. Washington, DC: Nuclear Threat Initiative. March 2004. Archived from the original on 2008-07-08.
4. ^ Higuchi T (24 March 1964). Molecular Catalysis and Interactions in Aqueous Solutions (PDF) (Report). Contract No. DA 18-108-AMC-88A - Final Report.
5. ^ Davis GT, Demek MM, Sowa JR, Epstein J (1971-08-01). "Solvent effects on displacement of fluoride ion from isopropyl methylphosphonofluoridate". Journal of the American Chemical Society. 93 (17): 4093–4103. Bibcode:1971JAChS..93.4093D. doi:10.1021/ja00746a001. ISSN 0002-7863.
6. ^ Camp HB, Fukuto TR, Metcalf RL (March 1969). "Toxicity of isopropyl parathion. Effect of structure on toxicity and anticholinesterase activity". Journal of Agricultural and Food Chemistry. 17 (2): 243–248. Bibcode:1969JAFC...17..243C. doi:10.1021/jf60162a038.

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