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Details

Stereochemistry ACHIRAL
Molecular Formula C6H11N2O4PS3
Molecular Weight 302.331
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHIDATHION

SMILES

COC1=NN(CSP(=S)(OC)OC)C(=O)S1

InChI

InChIKey=MEBQXILRKZHVCX-UHFFFAOYSA-N
InChI=1S/C6H11N2O4PS3/c1-10-5-7-8(6(9)16-5)4-15-13(14,11-2)12-3/h4H2,1-3H3

HIDE SMILES / InChI
Molecular Formula C6H11N2O4PS3
Molecular Weight 302.331
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Methidathion is an organophosphate insecticide and acaricide (U.S. EPA, 1988). Methidathion and its oxygen analog produce their toxic reaction primarily through their inhibition of cholinesterase (ChE) enzymes, including acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). Methidathion is used to control a variety of insects and mites in many crops such as fruits, vegetables, tobacco, alfalfa and sunflowers. Methidathion is also used in greenhouses and on rose cultures. It is especially useful against scale insects.

CNS Activity

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 460.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
A concentration addition model to assess activation of the pregnane X receptor (PXR) by pesticide mixtures found in the French diet.
2014-09
Activity profiles of 309 ToxCast™ chemicals evaluated across 292 biochemical targets.
2011-03-28
Coacervative microextraction ultrasound-assisted back-extraction technique for determination of organophosphates pesticides in honey samples by gas chromatography-mass spectrometry.
2010-10-08
An investigation on lung tissue damage and morphological changes in newborns of pregnant rats exposed to methidathion. Protective effects of caffeic acid phenethyl ester.
2010-10
Capillary electrophoresis with immobilized quantum dot fluorescence detection for rapid determination of organophosphorus pesticides in vegetables.
2010-09
Analysis of phosphorothionate pesticides using a chloroperoxidase pretreatment and acetylcholinesterase biosensor detection.
2010-08-11
Effects of glyphosate and methidathion on the expression of the Dhb, Vtg, Arnt, CYP4 and CYP314 in Daphnia magna.
2010-03
A disposable organophosphorus pesticides enzyme biosensor based on magnetic composite nano-particles modified screen printed carbon electrode.
2010
Selectivity of pesticides used in integrated apple production to the lacewing, Chrysoperla externa.
2010
Pesticide inputs from the sewage treatment plant of Agrinio to River Acheloos, western Greece: occurrence and removal.
2010
Factors for determining survival in acute organophosphate poisoning.
2009-12
Simultaneous determination of pesticides at trace levels in water using multiwalled carbon nanotubes as solid-phase extractant and multivariate calibration.
2009-09-30
Homicidal poisoning by injection of methidathion: the first ever report.
2009-08
Dissipation of insecticides in a Mediterranean soil in the presence of wastewater and surfactant solutions. A kinetic model approach.
2009-05
Multiwalled carbon nanotubes as matrix solid-phase dispersion extraction absorbents to determine 31 pesticides in agriculture samples by gas chromatography-mass spectrometry.
2009-04-22
Longitudinal trends in organophosphate incidents reported to the National Pesticide Information Center, 1995-2007.
2009-04-20
Impact of pesticides use in agriculture: their benefits and hazards.
2009-03
Degradation of a four-pesticide mixture by combined photo-Fenton and biological oxidation.
2009-02
Oxidation of selected organophosphate pesticides during chlorination of simulated drinking water.
2009-02
Spontaneous, bilateral, quadriceps tendon rupture caused by local exposure to methidathion.
2009
Dialkylphosphates (DAPs) in fruits and vegetables may confound biomonitoring in organophosphorus insecticide exposure and risk assessment.
2008-11-26
Caenorhabditis elegans: an emerging model in biomedical and environmental toxicology.
2008-11
Suitability of microwave-assisted extraction coupled with solid-phase extraction for organophosphorus pesticide determination in olive oil.
2008-10-17
[Simulating methidathion transport in soil chromatographic column].
2008-09
Analysis of currently used pesticides in fine airborne particulate matter (PM 2.5) by pressurized liquid extraction and liquid chromatography-tandem mass spectrometry.
2008-07-25
Comparative evaluation of some flavonoids and tocopherol acetate against the systemic toxicity induced by sulphur mustard.
2008-06
Effectiveness of pressurized liquid extraction and solvent extraction for the simultaneous quantification of 14 pesticide residues in green tea using GC.
2008-06
Synthesis of three haptens for the class-specific immunoassay of O,O-dimethyl organophosphorus pesticides and effect of hapten heterology on immunoassay sensitivity.
2008-05-19
Fast gas chromatography for pesticide residues analysis using analyte protectants.
2008-04-04
Household vacuum cleaners vs. the high-volume surface sampler for collection of carpet dust samples in epidemiologic studies of children.
2008-02-21
Critical evaluation and comparison of enrichment efficiency of multi-walled carbon nanotubes, C18 silica and activated carbon towards some pesticides from environmental waters.
2008-02-15
Combined photo-Fenton and biological oxidation for pesticide degradation: effect of photo-treated intermediates on biodegradation kinetics.
2008-02
Pesticide adsorption on a calcareous soil modified with sewage sludge and quaternary alkyl-ammonium cationic surfactants.
2008-01
Modification and re-validation of the ethyl acetate-based multi-residue method for pesticides in produce.
2007-11
Multi-residue determination of pesticides in water using multi-walled carbon nanotubes solid-phase extraction and gas chromatography-mass spectrometry.
2007-09-21
Effect of oxidation and dimensions of multi-walled carbon nanotubes on solid phase extraction and enrichment of some pesticides from environmental waters prior to their simultaneous determination by high performance liquid chromatography.
2007-09-14
Detoxification and/or increase of the biodegradability of aqueous solutions of dimethoate by means of solar photocatalysis.
2007-07-31
Ovarian toxicity in rats caused by methidathion and ameliorating effect of vitamins E and C.
2007-06
Increased biodegradability of Ultracid in aqueous solutions with solar TiO2 photocatalysis.
2007-06
Determination of several pesticides in water by solid-phase extraction, liquid chromatography and electrospray tandem mass spectrometry.
2007-05-25
Rapid simultaneous determination for organophosphorus pesticides in human serum by LC-MS.
2007-05-09
[Determination of organic phosphorus pesticide residues in scallion by gas chromatography coupled with microwave clean-up].
2007-05
Recoveries of four representative organophosphorus pesticides from 18 plant products belonging to different botanical categories: implications for matrix effects.
2007-04
Electrometric measurement of plasma, erythrocyte, and whole blood cholinesterase activities in healthy human volunteers.
2007-03
[Toxicity of pesticides recommended in the integrated apple production (IAP) to populations of Chrysoperla externa (Hagen) (Neuroptera: Chrysopidae)].
2006-11-18
Survey of carbamate and organophosphorous pesticide export from a south Florida (U.S.A.) agricultural watershed: implications of sampling frequency on ecological risk estimation.
2006-11
Organophosphorus pesticides residues in Italian raw milk.
2006-08
Screening method for organophosphorus insecticides and their metabolites in olive oil samples based on headspace solid-phase microextraction coupled with gas chromatography.
2006-07-28
The effects of subchronic methidathion toxicity on rat liver: role of antioxidant vitamins C and E.
2006-05
Monooxygenase activity in methidathion resistant and susceptible populations of Amblyseius womersleyi (Acari: Phytoseiidae).
2006
Patents

Patents

JP4673837B2
32

Sample Use Guides

In Vivo Use Guide
Methidathion is highly toxic via the oral route, with reported acute oral LD50 values of 25 to 54 mg/kg in the rat, and 18 to 25 mg/kg in the mouse
Route of Administration: Oral
In Vitro Use Guide
The concentration at which methidathion inhibited 50% of the free AChE activity in electric eel and bovine red blood cells (RBCs) was reported to be 2.3 x 10-4 M and 4.6 x 10-4 M, respectively.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:49:02 GMT 2025
Edited
by admin
on Mon Mar 31 17:49:02 GMT 2025
Record UNII
Y2P145U7KK
Record Status Validated (UNII)
Record Version
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Name Type Language
GS-13005
Preferred Name English
METHIDATHION
HSDB   ISO   MI  
Common Name English
DITHIOPHOSPHORIC ACID O,O'-DIMETHYL-S-((5-METHOXY-1,3,4-THIADIAZOL-2(3H)-ONE-3-YL)METHYL) ESTER
Common Name English
O,O'-DIMETHYL-S-((2-METHOXY-1,3,4-THIADIAZOLE-5(4H)-ONE-4-YL)METHYL) DITHIOPHOSPHATE
Common Name English
METHIDATHION [ISO]
Common Name English
S-((5-METHOXY-2-OXO-1,3,4-THIADIAZOL-3(2H)-YL)METHYL) O,O-DIMETHYL PHOSPHORODITHIOATE
Systematic Name English
PHOSPHORODITHIOIC ACID S-((5-METHOXY-2-OXO-1,3,4-THIADIAZOL-3(2H)-YL)METHYL)O,O-DIMETHYL ESTER
Common Name English
S-2,3-DIHYDRO-5-METHOXY-2-OXO-1,3,4-THIADIAZOL-3-YLMETHYL O,O-DIMETHYL PHOSPHORODITHIOATE
Common Name English
DITHIOPHOSPHORIC ACID O,O'-DIMETHYL-S-((2-METHOXY-1,3,4-THIADIAZOL-5(4H)-ON-4-YL)METHYL) ESTER
Common Name English
DMTP
Common Name English
SUPRACIDE
Common Name English
ULTRACIDE
Common Name English
SUPRATHIM
Common Name English
METHIDATHION [MI]
Common Name English
METHIDATHION [HSDB]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 100301
Created by admin on Mon Mar 31 17:49:02 GMT 2025 , Edited by admin on Mon Mar 31 17:49:02 GMT 2025
Code System Code Type Description
PUBCHEM
13709
Created by admin on Mon Mar 31 17:49:02 GMT 2025 , Edited by admin on Mon Mar 31 17:49:02 GMT 2025
PRIMARY
EPA CompTox
DTXSID5020819
Created by admin on Mon Mar 31 17:49:02 GMT 2025 , Edited by admin on Mon Mar 31 17:49:02 GMT 2025
PRIMARY
MERCK INDEX
m7312
Created by admin on Mon Mar 31 17:49:02 GMT 2025 , Edited by admin on Mon Mar 31 17:49:02 GMT 2025
PRIMARY Merck Index
MESH
C005828
Created by admin on Mon Mar 31 17:49:02 GMT 2025 , Edited by admin on Mon Mar 31 17:49:02 GMT 2025
PRIMARY
CHEBI
73436
Created by admin on Mon Mar 31 17:49:02 GMT 2025 , Edited by admin on Mon Mar 31 17:49:02 GMT 2025
PRIMARY
FDA UNII
Y2P145U7KK
Created by admin on Mon Mar 31 17:49:02 GMT 2025 , Edited by admin on Mon Mar 31 17:49:02 GMT 2025
PRIMARY
CHEBI
34837
Created by admin on Mon Mar 31 17:49:02 GMT 2025 , Edited by admin on Mon Mar 31 17:49:02 GMT 2025
PRIMARY
WIKIPEDIA
METHIDATHION
Created by admin on Mon Mar 31 17:49:02 GMT 2025 , Edited by admin on Mon Mar 31 17:49:02 GMT 2025
PRIMARY
HSDB
1594
Created by admin on Mon Mar 31 17:49:02 GMT 2025 , Edited by admin on Mon Mar 31 17:49:02 GMT 2025
PRIMARY
ALANWOOD
methidathion
Created by admin on Mon Mar 31 17:49:02 GMT 2025 , Edited by admin on Mon Mar 31 17:49:02 GMT 2025
PRIMARY
NCI_THESAURUS
C163672
Created by admin on Mon Mar 31 17:49:02 GMT 2025 , Edited by admin on Mon Mar 31 17:49:02 GMT 2025
PRIMARY
ECHA (EC/EINECS)
213-449-4
Created by admin on Mon Mar 31 17:49:02 GMT 2025 , Edited by admin on Mon Mar 31 17:49:02 GMT 2025
PRIMARY
CAS
950-37-8
Created by admin on Mon Mar 31 17:49:02 GMT 2025 , Edited by admin on Mon Mar 31 17:49:02 GMT 2025
PRIMARY
NIH
NCATS
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