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Malaoxon

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Malaoxon
Skeletal formula
Ball-and-stick model
Names
IUPAC name
diethyl 2-(dimethoxyphosphorylsulfanyl)butanedioate
Other names
2-(dimethoxyphosphorylthio) butanedioic acid diethyl ester
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard100.162.859Edit this at Wikidata
EC Number
  • 204-497-7
KEGG
UNII
  • InChI=1S/C10H19O7PS/c1-5-16-9(11)7-8(10(12)17-6-2)19-18(13,14-3)15-4/h8H,5-7H2,1-4H3 ☒N
    Key: WSORODGWGUUOBO-UHFFFAOYSA-N ☒N
  • InChI=1/C10H19O7PS/c1-5-16-9(11)7-8(10(12)17-6-2)19-18(13,14-3)15-4/h8H,5-7H2,1-4H3
    Key: WSORODGWGUUOBO-UHFFFAOYAC
  • CCOC(=O)CC(C(=O)OCC)SP(=O)(OC)OC
Properties
C10H19O7PS
Molar mass314.292421
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound

Malaoxon (Liromat, Malation oxon, Malthon oxon) is achemical compound with theformula C10H19O7PS. More specifically, it is aphosphorothioate. It is a breakdown product of, and more toxic than,malathion.

Air and water

[edit]

This chemical may be sensitive to prolonged exposure to air.[1] Slightly water-soluble.

Fire hazard

[edit]

This chemical is combustible.[1]

Health hazard

[edit]

Symptoms of exposure to this type of compound include cholinesterase inhibition,miosis, frontal headache, increased bronchial secretion, nausea, vomiting, sweating, abdominal cramps, diarrhea,lacrimation, increased salivation,bradycardia,cyanosis and muscular twitching of the eyelids, tongue, face and neck, possibly progressing to convulsions. Other symptoms includehyperemia of the conjunctiva, dimness of vision,rhinorrhea,bronchoconstriction, cough,fasciculation,anorexia, incontinence, eye changes, weakness,dyspnea,bronchospasm,hypotension orhypertension due toasphyxia, restlessness, anxiety, dizziness, drowsiness, tremor,ataxia, depression, confusion,neuropathy (rare), coma and death from depression of respiratory or cardiovascular systems. Exposure to this type of compound may result in giddiness, nervousness, blurred vision, discomfort (tightness) in chest,papilledema, muscular weakness, loss of reflexes, loss of sphincter control,cardiac arrhythmias, various degrees of heart block and cardiac arrest. It may also result in spasm of accommodation, aching pain in and about the eye,nystagmus, delayed distalaxonopathy andparesthesias and paralysis of limbs. A decrease in blood pressure may occur.Respiratory failure may also occur.

Acute/chronic hazards

[edit]

This compound is toxic by ingestion. It is acholinesterase inhibitor. When heated to decomposition, it emits toxic fumes of sulfur oxides and phosphorus oxides.[1]

Reactivity profile

[edit]

A thioorganophosphate,ester.Organophosphates are susceptible to formation of highly toxic and flammablephosphine gas in the presence of strongreducing agents such ashydrides. Partial oxidation byoxidizing agents may result in the release of toxicphosphorus oxides. Esters react with acids to liberate heat along with alcohols and acids. Strongoxidizing acids may cause a vigorous reaction that is sufficientlyexothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters withalkali metals and hydrides.

References

[edit]
  1. ^abcNational Toxicology Program, 1992
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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