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Paraoxon

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Paraoxon
Clinical data
ATC code
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • Diethyl 4-nitrophenyl phosphate
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.005.657Edit this at Wikidata
Chemical and physical data
FormulaC10H14NO6P
Molar mass275.197 g·mol−1
3D model (JSmol)
  • [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)

Paraoxon is aparasympathomimetic drug which acts as ancholinesterase inhibitor. It is anorganophosphateoxon, and the activemetabolite of the insecticideparathion. It is also used as anophthalmological drug againstglaucoma. Paraoxon is one of the most potent acetylcholinesterase-inhibitinginsecticides available, around 70% as potent as the nerve agentsarin, and so is now rarely used as an insecticide due to the risk ofpoisoning 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 anassassination weapon by the apartheid-eraSouth Africanchemical weapons programProject 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]

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.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 fromthe 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.
Drugs used forglaucoma preparations andmiosis (S01E)
Sympathomimetics
Parasympathomimetics
muscarinic
muscarinic/nicotinic
acetylcholinesterase inhibitors
Carbonic anhydrase inhibitors/
(sulfonamides)
Beta blocking agents
Prostaglandin analogues (F)
Other agents
Carbamates
Inorganic compounds
Insect growth regulators
Neonicotinoids
Organochlorides
Organophosphorus
Pyrethroids
Diamides
Other chemicals
Metabolites
Biopesticides
Enzyme
(modulators)
ChATTooltip Choline acetyltransferase
AChETooltip Acetylcholinesterase
BChETooltip Butyrylcholinesterase
Transporter
(modulators)
CHTTooltip Choline transporter
VAChTTooltip Vesicular acetylcholine transporter
Release
(modulators)
Inhibitors
Enhancers
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