Methidathion (CHEM002840)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (15)XML
Record Information
Version1.0
Creation Date2013-04-25 07:56:53 UTC
Update Date2016-11-09 01:08:59 UTC
Accession NumberCHEM002840
Identification
Common NameMethidathion
ClassSmall Molecule
DescriptionMethidathion is an organophosphate insecticide; its use is banned in the European Community.
Contaminant Sources
  • Clean Air Act Chemicals
  • EPA Endocrine Screening
  • HPV EPA Chemicals
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ester
  • Ether
  • Insecticide
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Phosphorodithioic acid, S-[(5-methoxy-2-oxo-1,3,4-thiadiazol-3(2H)-yl)methyl] O,O-dimethyl esterChEBI
S-(2,3-Dihydro-5-methoxy-2-oxo-1,3,4-thiadiazol-3-methyl) dimethyl phosphorothiolothionateChEBI
S-[(5-Methoxy-2-oxo-1,3,4-thiadiazol-3(2H)-yl)methyl] O,O-dimethyl dithiophosphateChEBI
SupracideChEBI
Phosphorodithioate, S-[(5-methoxy-2-oxo-1,3,4-thiadiazol-3(2H)-yl)methyl] O,O-dimethyl esterGenerator
S-(2,3-Dihydro-5-methoxy-2-oxo-1,3,4-thiadiazol-3-methyl) dimethyl phosphorothiolothionic acidGenerator
S-[(5-Methoxy-2-oxo-1,3,4-thiadiazol-3(2H)-yl)methyl] O,O-dimethyl dithiophosphoric acidGenerator
O,O-Dimethyl S-(2-methoxy-1,3,4-thiadiazole-5)-(4H)-onyl-(4)-methylphosphorodithioateMeSH
S-2,3-dihydro-5-Methoxy-2-oxo-1,3,4-thiadiazol-3-ylmethyl O,O-dimethyl phosphorodithioateMeSH
S-(5-Methoxy-2-oxo-1,3,4-thiadiazol-3-(2H)-yl) O,O-dimethylphosphorodithioateMeSH
MetidathionMeSH
Chemical FormulaC6H11N2O4PS3
Average Molecular Mass302.331 g/mol
Monoisotopic Mass301.962 g/mol
CAS Registry Number950-37-8
IUPAC NameO,O-dimethyl {[(5-methoxy-2-oxo-2,3-dihydro-1,3,4-thiadiazol-3-yl)methyl]sulfanyl}phosphonothioate
Traditional NameO,O-dimethyl [(5-methoxy-2-oxo-1,3,4-thiadiazol-3-yl)methyl]sulfanylphosphonothioate
SMILESCOC1=NN(CSP(=S)(OC)OC)C(=O)S1
InChI IdentifierInChI=1S/C6H11N2O4PS3/c1-10-5-7-8(6(9)16-5)4-15-13(14,11-2)12-3/h4H2,1-3H3
InChI KeyMEBQXILRKZHVCX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,3,4-thiadiazol-3-yl-organothiophosphates. These are aromatic heterocyclic compounds containing a 1,3,4-thiadiazole ring, which is substituted at the 2-position with an organothiophosphate group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassThiadiazoles
Direct Parent1,3,4-thiadiazol-3-yl-organothiophosphates
Alternative Parents
Substituents
  • 1,3,4-thiadiazol-3-yl-organothiophosphate
  • Alkyl aryl ether
  • Dithiophosphate s-ester
  • Dithiophosphate o-ester
  • Heteroaromatic compound
  • Organic dithiophosphate
  • Azacycle
  • Sulfenyl compound
  • Organothiophosphorus compound
  • Ether
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.04 g/LALOGPS
logP1.18ALOGPS
logP2.29ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)-9.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area60.36 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity70.01 m³·mol⁻¹ChemAxon
Polarizability26.97 ųChemAxon
Number of Rings1ChemAxon
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, Positivesplash10-0229-9650000000-90b86210e49548eefd28Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0a4i-9000000000-65a78dd3d363cf20902aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0abi-9000000000-afbf99f53ac04c355e2bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-059i-9000000000-a25f5e4e21a4a79e5ed9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-0079-9100000000-d08ecb728b3e5637fa89Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0002-2900000000-abce1a72497794da1539Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-007a-9500000000-cbfe306a168d0eee91deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ufr-0669000000-4c08c979983bd7c9d7a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-3519000000-c37f9b32d5943c863283Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0900000000-065add8950330d0fc0e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-4279000000-fea55d07d8b4df13a920Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-6250bc1397d71de7f6c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-5da9ff2c3db6b25a255bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f6t-0906000000-bd6e03ff86b320d35167Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-82ead2f9508545c8fe36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-5900000000-3699972d20ee29ae1f54Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uk9-0609000000-0c4f0554b3910a4e954eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0901000000-55914153d26da6a92b69Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-4900000000-abaad0569a52715d1c43Spectrum
MSMass Spectrum (Electron Ionization)splash10-000b-9600000000-e57a196ea91d0a871b8bSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityMethidathion 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/SourcesThis is a man-made compound that is used as a pesticide.
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.
SymptomsSymptoms of low dose exposure include excessive salivation and eye-watering. Acute dose symptoms include 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. Hypertension, hypoglycemia, anxiety, headache, tremor and ataxia may also result.
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 LinkMethidathion
Chemspider IDNot Available
ChEBI ID34837
PubChem Compound ID13709
Kegg Compound IDC14431
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available