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Paraoxon

Summary

Paraoxon is a parasympathomimetic 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]

Paraoxon
Clinical data
ATC code
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • 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
CompTox Dashboard (EPA)
  • DTXSID6024046 Edit this at Wikidata
ECHA InfoCard100.005.657 Edit this at Wikidata
Chemical and physical data
FormulaC10H14NO6P
Molar mass275.197 g·mol−1
3D model (JSmol)
  • Interactive image
  • [O-][N+](=O)c1ccc(OP(=O)(OCC)OCC)cc1
  • 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)

See also edit

References edit

  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. 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. doi:10.1016/j.neuro.2014.08.008. PMC 4175062. PMID 25172410.
  3. ^ NTI Country Overviews:South Africa:Chemical Capabilities:Paraoxon Archived 2008-07-08 at the Wayback Machine