Paraquat

Basic Info

Common NameParaquat(F06220)
2D Structure
FRCD IDF06220
CAS Number4685-14-7
PubChem CID15939
FormulaC12H14N2+2
IUPAC Name

1-methyl-4-(1-methylpyridin-1-ium-4-yl)pyridin-1-ium

InChI Key

INFDPOAKFNIJBF-UHFFFAOYSA-N

InChI

InChI=1S/C12H14N2/c1-13-7-3-11(4-8-13)12-5-9-14(2)10-6-12/h3-10H,1-2H3/q+2

Canonical SMILES

C[N+]1=CC=C(C=C1)C2=CC=[N+](C=C2)C

Isomeric SMILES

C[N+]1=CC=C(C=C1)C2=CC=[N+](C=C2)C

Synonyms
        
            4,4'-Bipyridinium, 1,1'-dimethyl-
        
            PARAQUAT
        
            1,1'-Dimethyl-4,4'-bipyridinium
        
            4685-14-7
        
            Paraquat ion
        
            Dimethyl viologen
        
            Paraquat dication
        
            Starfire
        
            Weedol
        
            Spraytop-graze
Classifies
                

                  
                    Pollutant
                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassPyridines and derivatives
SubclassBipyridines and oligopyridines
Intermediate Tree NodesNot available
Direct ParentBipyridines and oligopyridines
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsBipyridine - 4,4p-bipyridinium - N-methylpyridinium - Pyridinium - Heteroaromatic compound - Azacycle - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Organic cation - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as bipyridines and oligopyridines. These are organic compounds containing two pyridine rings linked to each other.

Properties

Property NameProperty Value
Molecular Weight186.258
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count0
Rotatable Bond Count1
Complexity145
Monoisotopic Mass186.116
Exact Mass186.116
XLogP1.7
Formal Charge2
Heavy Atom Count14
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Table grapes (Kiwiberries/dwarf kiwi (2), Schisandra berries,)0151010European Union0.02*28/05/2011
Dewberries (Boysenberries, Loganberries, Olallieberries, Salmonberries, Tayberries, Thimbleberries, Youngberries, Other species and hybrids of genus Rubus, not elsewhere mentioned,)0153020European Union0.02*28/05/2011
Soursops/guanabanas0163110European Union0.02*28/05/2011
(b) head brassica0242000European Union0.02*28/05/2011
Head cabbages (Pointed head cabbages, Red cabbages, Savoy cabbages, White cabbage,)0242020European Union0.02*28/05/2011
Kales (Borecoles/collards greens/curly kales, Cow cabbages/stem kales, Cow cabbages/Jersey kales, Kohlrabies leaves (6), Rape kales/Siberian kales, Portuguese kales/tronchuda kales/Portuguese cabba...0243020European Union0.02*28/05/2011
Legume vegetables0260000European Union0.02*28/05/2011
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 Union0.02*28/05/2011
Oil fruits0402000European Union0.02*28/05/2011
Olives for oil production0402010European Union0.02*28/05/2011
Common millet/proso millet (Black fonio, Canary grass, Finger millet/African millet/koracan, Foxtail millet, Job's tears, Little millet, Pearl millet, Teff/tef, White fonio,)0500040European Union0.02*28/05/2011
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*28/05/2011
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*28/05/2011
Black caraway/black cumin (Nigella,)0810020European Union0.05*28/05/2011
Peppercorn (black, green and white) (Brazilian pepper, Cubeb/tailed pepper, Grain of paradise, Long pepper/pipali, Pink pepper, Sumac, West African pepper,)0820060European Union0.05*28/05/2011
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*28/05/2011
Horseradishes (Dandelion roots, Gentiana roots, East Indian galangal/aromatic ginger/sand galangal, Fingerroot, Galangal roots, Galangal roots, Galangal roots, Galangal roots, Ginger roots, Greater...0213040European Union0.02*28/05/2011
Other Leafy BrassicasBritain0.02mg/kg
ShallotsBritain0.02mg/kg
Other Root And Tuber VegetablesBritain0.02mg/kg

References

TitleJournalDatePubmed ID
Neuroprotective effects of Cassia tora against paraquat-inducedneurodegeneration: relevance for Parkinson's disease.Nat Prod Res2018 Jun28714346
PBPK/PD assessment for Parkinson's disease risk posed by airborne pesticideparaquat exposure.Environ Sci Pollut Res Int2018 Feb29209972
Rapid and sensitive surface-enhanced Raman spectroscopy (SERS) method combinedwith gold nanoparticles for determination of paraquat in apple juice.J Sci Food Agric2018 Aug29364504
Simultaneous Voltammetric Detection of Carbaryl and Paraquat Pesticides onGraphene-Modified Boron-Doped Diamond Electrode.Sensors (Basel)2017 Sep 628878151
Fast analysis of quaternary ammonium pesticides in food and beverages usingcation-exchange chromatography coupled with isotope-dilution high-resolution massspectrometry.J Sep Sci2017 Oct28779575
Paraquat exposure-induced Parkinson's disease-like symptoms and oxidative stress in Drosophila melanogaster: Neuroprotective effect of Bougainvillea glabraChoisy.Biomed Pharmacother2017 Nov28843913
Correlation Between Nasal Epithelial Injury and In Vitro Cytotoxicity Using a Series of Small Molecule Protein Tyrosine Phosphatase 1B Inhibitors Investigated for Reversal of Leptin Resistance in Obesity.Int J Toxicol2017 Jul/Aug28592157
Xenobiotic transporters and kidney injury.Adv Drug Deliv Rev2017 Jul 128111348
Utilization of Red-Light-Emitting CdTe Nanoparticles for the Trace-LevelDetection of Harmful Herbicides in Adulterated Food and Agricultural Crops.Chem Asian J2017 Jan 327925415
Protection by extra virgin olive oil against oxidative stress in vitro and invivo. Chemical and biological studies on the health benefits due to a majorcomponent of the Mediterranean diet.PLoS One2017 Dec 2829283995
Propolis supplementation attenuates the negative effects of oxidative stressinduced by paraquat injection on productive performance and immune function inturkey poults.Poult Sci2017 Dec 129053856
Oral Exposure to Paraquat Triggers Earlier Expression of Phosphorylatedα-Synuclein in the Enteric Nervous System of A53T Mutant Human α-SynucleinTransgenic Mice.J Neuropathol Exp Neurol2017 Dec 129040593
Foliar Desiccators Glyphosate, Carfentrazone, and Paraquat Affect theTechnological and Chemical Properties of Cowpea Grains.J Agric Food Chem2017 Aug 1628731694
Clinical screening of paraquat in plasma samples using capillary electrophoresis with contactless conductivity detection: Towards rapid diagnosis and therapeutic treatment of acute paraquat poisoning in Vietnam.J Chromatogr B Analyt Technol Biomed Life Sci2017 Aug 1528609698
The toxic influence of paraquat on hippocampal neurogenesis in adult mice.Food Chem Toxicol2017 Aug28576469
Difference in oxidative stress tolerance between rice cultivars estimated withchlorophyll fluorescence analysis.BMC Res Notes2017 Apr 2628446247
Paraquat and maneb co-exposure induces noradrenergic locus coeruleusneurodegeneration through NADPH oxidase-mediated microglial activation.Toxicology2017 Apr 128202386
Tualang Honey Protects the Rat Midbrain and Lung against Repeated Paraquat Exposure.Oxid Med Cell Longev201728127418
Protective action of Omega-3 on paraquat intoxication in Drosophila melanogaster.J Toxicol Environ Health A201728849990
Determination of polar pesticides in olive oil and olives by hydrophilicinteraction liquid chromatography coupled to tandem mass spectrometry and highresolution mass spectrometry.Talanta2016 Sep 127343599