(±)-Methamidophos

Basic Info

Common Name(±)-Methamidophos(F05102)
2D Structure
Description

Methamidophos is a highly active, systemic, residual organophosphate insecticide/acaricide/avicide with contact and stomach action. Its mode of action in insects and mammals is through inhibition of acetylcholinesterase. This enzyme is essential in the normal transmission of nerve impulses. Methamidophos is a potent acetylcholinesterase inhibitor. It is particularly effective against chewing and sucking insects and is used to control aphids, flea beetles, worms, whiteflies, thrips, cabbage loopers, Colorado potato beetles, potato tubeworms, armyworms, mites, leafhoppers, and many others. Crop uses include broccoli, Brussel sprouts, cauliflower, grapes, celery, sugar beets, cotton, tobacco, and potatoes. It is used abroad for many vegetables, hops, corn, peaches, and other crops Due to its toxicity, the use of pesticides that contain methamidophos is currently being phased out in Brazil. Methamidophos is highly toxic via oral, dermal and inhalation routes of exposure. Methamidophos was found in dumplings (gyoza) manufactured in China for the Japanese market after a number of consumers became sick.

FRCD IDF05102
CAS Number115182-35-9
PubChem CID4096
FormulaC2H8NO2PS
IUPAC Name

[amino(methylsulfanyl)phosphoryl]oxymethane

InChI Key

NNKVPIKMPCQWCG-UHFFFAOYSA-N

InChI

InChI=1S/C2H8NO2PS/c1-5-6(3,4)7-2/h1-2H3,(H2,3,4)

Canonical SMILES

COP(=O)(N)SC

Isomeric SMILES

COP(=O)(N)SC

Synonyms
        
            Hamidop
        
            methamidophos
        
            Metamidophos
        
            Tamaron
        
            Pillaron
        
            Tahmabon
        
            Amidor
        
            Filitox
        
            Patrole
        
            Tamanox
Classifies
                

                  
                    Pollutant
                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganophosphorus compounds
ClassOrganothiophosphorus compounds
SubclassPhosphoramidothioic-acid-O,S-diesters
Intermediate Tree NodesNot available
Direct ParentPhosphoramidothioic-acid-O,S-diesters
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsPhosphoramidothioic-acid-o,s-diester - Sulfenyl compound - Organic nitrogen compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organosulfur compound - Organooxygen compound - Aliphatic acyclic compound
DescriptionThis compound belongs to the class of organic compounds known as phosphoramidothioic-acid-o,s-diesters. These are organooxygen compounds containing a O,S-diester derivative of phosphoroamidothioic acid. They have the general structure RSP(=O)(OR')(NH2), where R,R' are organyl groups.

Properties

Property NameProperty Value
Molecular Weight141.125
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Complexity95.7
Monoisotopic Mass141.001
Exact Mass141.001
XLogP-0.9
Formal Charge0
Heavy Atom Count7
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9758
Human Intestinal AbsorptionHIA+0.9871
Caco-2 PermeabilityCaco2-0.5366
P-glycoprotein SubstrateNon-substrate0.9299
P-glycoprotein InhibitorNon-inhibitor0.9451
Non-inhibitor0.9964
Renal Organic Cation TransporterNon-inhibitor0.9602
Distribution
Subcellular localizationMitochondria0.5301
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8688
CYP450 2D6 SubstrateNon-substrate0.8275
CYP450 3A4 SubstrateNon-substrate0.6486
CYP450 1A2 InhibitorNon-inhibitor0.6215
CYP450 2C9 InhibitorNon-inhibitor0.7524
CYP450 2D6 InhibitorNon-inhibitor0.9241
CYP450 2C19 InhibitorNon-inhibitor0.6971
CYP450 3A4 InhibitorNon-inhibitor0.9674
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8877
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9671
Non-inhibitor0.9409
AMES ToxicityNon AMES toxic0.8293
CarcinogensNon-carcinogens0.5209
Fish ToxicityHigh FHMT0.5000
Tetrahymena Pyriformis ToxicityLow TPT0.8898
Honey Bee ToxicityHigh HBT0.9062
BiodegradationReady biodegradable0.5600
Acute Oral ToxicityI0.7843
Carcinogenicity (Three-class)Non-required0.4831
Model Value Unit
Absorption
Aqueous solubility-0.8874LogS
Caco-2 Permeability0.8581LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.6448LD50, mol/kg
Fish Toxicity2.1890pLC50, mg/L
Tetrahymena Pyriformis Toxicity-1.2057pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Pine nut kernels (Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels ...0120090European Union0.02*26/04/2013
Wine grapes (Amur river grapes, Muscadine grapes,)0151020European Union0.01*26/04/2013
Dewberries (Boysenberries, Loganberries, Olallieberries, Salmonberries, Tayberries, Thimbleberries, Youngberries, Other species and hybrids of genus Rubus, not elsewhere mentioned,)0153020European Union0.01*26/04/2013
Blueberries (Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Bearberries, Bilberries/E...0154010European Union0.01*26/04/2013
Soursops/guanabanas0163110European Union0.01*26/04/2013
Cassava roots/manioc (Blue taros/blue tannias, Canna, Chayotes/christophines roots, Dasheen taros, Eddoe taros, Konjac roots, Tannias/arrowleaf elephant ears/tajer,)0212010European Union0.01*26/04/2013
Brussels sprouts (Flower sprouts,)0242010European Union0.01*26/04/2013
Chinese cabbages/pe-tsai (Chinese flat cabbages/tatsoi/tai goo choi, Indian mustards/mustard greens, Komatsuna/mustard spinaches, Mizuna (4), Pak-choi/paksoi, Turnip greens/turnip tops (5), Seakale,)0243010European Union0.01*26/04/2013
Cresses and other sprouts and shoots (Alfalfa/lucerne sprouts, Chinese chives/oriental garlic/garlic chives sprouts, Broccoli sprouts, Daikon/Japanese radish sprouts, Ginger shoots, Mung bean sprou...0251040European Union0.01*26/04/2013
Beans (with pods) (Azuki beans, Black eyed peas/cowpeas, Broad beans/fava beans/horse beans/tic beans, Borlotti beans/cannelini beans/common beans/flageolets/French beans/slicing beans/snap beans, ...0260010European Union0.01*26/04/2013
Cultivated fungi (Common mushrooms/button mushrooms/champignons mushrooms, Corn smuts/ Mexican truffles, Enokitake/winter mushrooms, Fusarium venenatum, Horse mushrooms, Jew's ears/hirneola, Nameko...0280010European Union0.01*26/04/2013
Kapok0402040European Union0.02*26/04/2013
Buckwheat and other pseudocereals (Amaranth/kiwicha, Amaranth/kiwicha, Amaranth/kiwicha, Kaniwa/canihua, Quinoa, Chia seeds,)0500020European Union0.01*26/04/2013
Rose (Almond, Bee balm, Bitter orange/sour orange, Black locust, Cat’s foot, Chrysanthemum, Cinnamon, Clary sage, Cornflower, Cowslip/primrose, Daisy, Dyer’s broom, Elder, Field poppy, Great mullei...0631030European Union0.05*26/04/2013
Strawberry (Absinth/common wormwood, Agrimony, Alfalfa/lucerne, Aloe (leaf gel), Alpine ladies mantle, Bearberry, Bilberry/European blueberry/whortleberry, Birch, Bitter orange/sour orange, Blackbe...0632010European Union0.05*26/04/2013
Fennel (Bitter fennel, Sweet fennel,)0810070European Union0.1*26/04/2013
Peppercorn (black, green and white) (Brazilian pepper, Cubeb/tailed pepper, Grain of paradise, Long pepper/pipali, Pink pepper, Sumac, West African pepper,)0820060European Union0.1*26/04/2013
Edible offals (other than liver and kidney)1015050European Union0.01*26/04/2013
(f) poultry (Bobwhite quail, Chicken (including silkie chicken), Collared Dove, Duck, Geese, Green peafowl, Guinea fowl, Japanese quail, Muskovy duck, Mute swan, Partridge, Peafowl, Pheasant, Pigeo...1016000European Union0.01*26/04/2013
KaleBritain0.01mg/kg

References

TitleJournalDatePubmed ID
Estimated assessment of cumulative dietary exposure to organophosphorus residues from tea infusion in China.Environ Health Prev Med2018 Feb 1429444637
Distribution and risk assessment of banned and other current-use pesticides insurface and groundwaters consumed in an agricultural catchment dominated by cocoacrops in the Ankobra Basin, Ghana.Sci Total Environ2018 Aug 1529597160
Probabilistic acute risk assessment of cumulative exposure to organophosphorusand carbamate pesticides from dietary vegetables and fruits in Shanghaipopulations.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2017May28077027
Pesticide residues in leafy vegetables and human health risk assessment in North Central agricultural areas of Chile.Food Addit Contam Part B Surveill2017 Jun28090975
Pesticide incidence in poisoned baits: A 10-year report.Sci Total Environ2017 Dec 128564626
Prioritization of pesticides based on daily dietary exposure potential asdetermined from the SHEDS model.Food Chem Toxicol2016 Oct27497764
Multiresidue method for simultaneous analysis of aflatoxin M1, avermectins, organophosphate pesticides and milbemycin in milk by ultra-performance liquid chromatography coupled to tandem mass spectrometry.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2016 Jun27144891
Children's diets, pesticide uptake, and implications for risk assessment: AnIsraeli case study.Food Chem Toxicol2016 Jan26585921
The Measurement of Stable Carbon Isotope Ratios of Eight Methamidophos Samples.J Forensic Sci2015 Sep26120050
Estimation of human health risk associated with the consumption ofpesticide-contaminated vegetables from Kumasi, Ghana.Environ Monit Assess2015 May25864079
Enantioselective Dissipation of Acephate and Its Metabolite, Methamidophos, during Tea Cultivation, Manufacturing, and Infusion.J Agric Food Chem2015 Feb 425582130
Thin-layer chromatography/direct analysis in real time time-of-flight massspectrometry and isotope dilution to analyze organophosphorus insecticides infatty foods.J Chromatogr A2014 Nov 2825454149
[Ocuurence of organophosphorus pesticides in animal foods and their diet exposureassessment].Zhonghua Yu Fang Yi Xue Za Zhi2014 May24985383
Effect of new and old pesticides on Orius armatus (Gross) - an Australian predator of western flower thrips, Frankliniella occidentalis (Pergande).Pest Manag Sci2014 Mar23616278
Enantioselective interaction of acid α-naphthyl acetate esterase with chiral organophosphorus insecticides.J Agric Food Chem2014 Feb 1924475784
Simultaneous determination of ten organophosphate pesticide residues in fruits bygas chromatography coupled with magnetic separation.J Sep Sci2014 Apr24470377
Multiresidue analysis of pesticides in vegetables and fruits by supercriticalfluid extraction and liquid chromatography-tandem mass spectrometry.Shokuhin Eiseigaku Zasshi201424990761
Multiresidue pesticide analysis of botanical dietary supplements using salt-outacetonitrile extraction, solid-phase extraction cleanup column, and gaschromatography-triple quadrupole mass spectrometry.Anal Chem2013 May 723534560
Total diet study on pesticide residues in France: levels in food as consumed and chronic dietary risk to consumers.Environ Int2012 Sep 1522595191
Chromogenic platform based on recombinant Drosophila melanogasteracetylcholinesterase for visible unidirectional assay of organophosphate andcarbamate insecticide residues.Anal Chim Acta2012 Mar 3022365130

Targets

Target Details

Cholinesterase

General Function:
Identical protein binding
Specific Function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular Weight:
68417.575 Da
References
  1. Tacal O, Lockridge O: Methamidophos, dichlorvos, O-methoate and diazinon pesticides used in Turkey make a covalent bond with butyrylcholinesterase detected by mass spectrometry. J Appl Toxicol. 2010 Jul;30(5):469-75. doi: 10.1002/jat.1518. [20229498 ]
Target Details

Urokinase plasminogen activator surface receptor

General Function:
Urokinase plasminogen activator receptor activity
Specific Function:
Acts as a receptor for urokinase plasminogen activator. Plays a role in localizing and promoting plasmin formation. Mediates the proteolysis-independent signal transduction activation effects of U-PA. It is subject to negative-feedback regulation by U-PA which cleaves it into an inactive form.
Gene Name:
PLAUR
Uniprot ID:
Q03405
Molecular Weight:
36977.62 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]