Ethion (CHEM000088)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (10)XML
Record Information
Version1.0
Creation Date2009-03-06 18:58:04 UTC
Update Date2016-11-09 01:08:09 UTC
Accession NumberCHEM000088
Identification
Common NameEthion
ClassSmall Molecule
DescriptionEthion is an organophosphate pesticide. It does not occur naturally in the environment. Ethion is used in agriculture, mainly to control insects on citrus trees, but also on cotton, fruit and nut trees, and some vegetables. It may also be used on lawns and turf grasses, but it is not used in the home for pest control. Ethion affects the nervous systems by inhibiting acetylcholineserases. (1)
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ester
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organophosphate
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Bis(S-(diethoxyphosphinothioyl)mercapto)methaneChEBI
O,O,O',o'-tetraethyl S,s'-methanediyl bis(dithiophosphate)ChEBI
O,O,O',o'-tetraethyl S,s'-methylenebis(phosphorodithioate)ChEBI
S,S'-methylene bis(O,O-diethyl phosphorodithioate)ChEBI
O,O,O',o'-tetraethyl S,s'-methanediyl bis(dithiophosphoric acid)Generator
O,O,O',o'-tetraethyl S,s'-methylenebis(phosphorodithioic acid)Generator
S,S'-methylene bis(O,O-diethyl phosphorodithioic acid)Generator
NialateMeSH
EthopazMeSH
Niagara 1240MeSH
DiethionMeSH
Chemical FormulaC9H22O4P2S4
Average Molecular Mass384.476 g/mol
Monoisotopic Mass383.988 g/mol
CAS Registry Number563-12-2
IUPAC NameO,O-diethyl [({[diethoxy(sulfanylidene)-λ⁵-phosphanyl]sulfanyl}methyl)sulfanyl]phosphonothioate
Traditional NameO,O-diethyl ({[diethoxy(sulfanylidene)-λ⁵-phosphanyl]sulfanyl}methyl)sulfanylphosphonothioate
SMILESCCOP(=S)(OCC)SCSP(=S)(OCC)OCC
InChI IdentifierInChI=1S/C9H22O4P2S4/c1-5-10-14(16,11-6-2)18-9-19-15(17,12-7-3)13-8-4/h5-9H2,1-4H3
InChI KeyRIZMRRKBZQXFOY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dithiophosphate o-esters. These are o-ester derivatives of dithiophosphates, with the general structure RSP(O)(O)=S (R = organyl group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic dithiophosphoric acids and derivatives
Sub ClassDithiophosphate O-esters
Direct ParentDithiophosphate O-esters
Alternative Parents
Substituents
  • Dithiophosphate o-ester
  • Dithiophosphate s-ester
  • Sulfenyl compound
  • Organothiophosphorus compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateLiquid
AppearancePure ethion is a clear to yellowish liquid with an unpleasant sulfur-like smell.
Experimental Properties
PropertyValue
Melting Point-13°C
Boiling Point165 °C at 0.3 mm Hg
Solubility0.002 mg/mL at 25 °C [SHIU,WY et al.(1990)]
Predicted Properties
PropertyValueSource
Water Solubility0.0021 g/LALOGPS
logP4.74ALOGPS
logP3.93ChemAxon
logS-5.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area36.92 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity97.25 m³·mol⁻¹ChemAxon
Polarizability38.11 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00b9-1629000000-c869d0f0d28ea74ceebcSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-014j-0950000000-e19ab87f70cf70354b7eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0006-0900000000-ce96156c313ab16101c9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-01ox-0900000000-8c26a1eef2be50869a50Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-03dl-0900000000-f3a2645d7b1872791175Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-0900000000-1dc17037d52590bd0397Spectrum
LC-MS/MSLC-MS/MS Spectrum - 55V, Positivesplash10-014j-0691000000-5db8ef20942945e5520eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-01vn-0900000000-558d731e3575ad23df7aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0006-0900000000-aeaa41357cc31df300c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0910000000-fb4239c007f1287fd8edSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00dm-0900000000-fc666c84ff17b492cf6cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-03di-0900000000-749b13fd0ffb2e5a4048Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-03di-0900000000-ddf9be86cb7c4a4d0987Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-03di-0900000000-a452eb2661cba68befa1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 55V, Positivesplash10-01ow-5900000000-51d281c1df6e870f62efSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-014j-0691000000-abb20671de495da52a58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-1894000000-47c6391b2b69dca9754dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fmj-0911000000-57efcef02f9a486a21c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fc1-7910000000-3a107354a7516b2494a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f89-0409000000-650678c2715999d47b1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f89-0579000000-6f45f71aff73fce1fc62Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0btc-0159000000-5c5a03c8f28eda995617Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0902000000-a8b921aa95b39659582bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00e9-0903000000-843d1fd4c451af4e2f7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9300000000-ecafc78c964ef11868f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-20b61d6e6c76f39927d0Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-7971000000-2c3388c23fc41590f253Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral (1) ; inhalation (1) ; dermal (1)
Mechanism of ToxicityEthion is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.
MetabolismMetabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesEthion enters the air, water, and soil during its manufacture and use. It is not known if ethion levels can build up in plants or fish. Chemical plant workers, transport workers, and pesticide applicators are the major occupational groups that might be exposed to ethion. The general population may be exposed to very small amounts of ethion by eating or drinking. People living near hazardous waste sites containing ethion or near its manufacturing, processing, or storage facilities could potentially be exposed. (1)
Minimum Risk LevelNot Available
Health EffectsAcute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.
SymptomsExposure to high levels of ethion can cause nausea, sweating, diarrhea, loss of bladder control, blurring or dimness of vision, muscle tremors, and labored breathing. Severe poisoning may result in coma, inability to breathe, and death. (1)
TreatmentIf the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEthion
Chemspider IDNot Available
ChEBI ID38663
PubChem Compound ID3286
Kegg Compound IDC18725
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21366965
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21560835
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23127602
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24398360
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24401442