Paraquat

Paraquat
Names
Preferred IUPAC name
1,1′-Dimethyl[4,4′-bipyridine]-1,1′-diium dichloride
Other names
Paraquat dichloride; Methyl viologen dichloride; MVCl2; Crisquat; Dexuron; Esgram; Gramuron; Ortho Paraquat CL; Para-col; Pillarxone; Tota-col; Toxer Total; PP148; Cyclone; Gramixel; Gramoxone; Pathclear; AH 501; Bai Cao Ku.
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.016.015
PubChem CID
UNII
InChI
  • InChI=1S/C12H14N2.2ClH/c1-13-7-3-11(4-8-13)12-5-9-14(2)10-6-12;;/h3-10H,1-2H3;2*1H/q+2;;/p-2 Y
    Key: FIKAKWIAUPDISJ-UHFFFAOYSA-L Y
  • InChI=1/C12H14N2.2ClH/c1-13-7-3-11(4-8-13)12-5-9-14(2)10-6-12;;/h3-10H,1-2H3;2*1H/q+2;;/p-2/fC12H14N2.2Cl/h;2*1h/qm;2*-1
  • InChI=1/C12H14N2.2ClH/c1-13-7-3-11(4-8-13)12-5-9-14(2)10-6-12;;/h3-10H,1-2H3;2*1H/q+2;;/p-2
    Key: FIKAKWIAUPDISJ-NUQVWONBAF
SMILES
  • C[n+]1ccc(cc1)c2cc[n+](cc2)C.[Cl-].[Cl-]
Properties
Chemical formula
 C12H14Cl2N2
Molar mass 257.16 g·mol−1
Appearance Yellow solid[1]
Odor faint, ammonia-like[1]
Density 1.25 g/cm3
Melting point 175 to 180 °C (347 to 356 °F; 448 to 453 K)[2]
Boiling point > 300 °C (572 °F; 573 K)[2]
Solubility in water
 High
Vapor pressure <0.0000001 mmHg (20 °C)[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic, environmental hazard
GHS labelling:
Pictograms
Hazard statements
 H301, H311, H315, H319, H330, H335, H372, H410[3]
Precautionary statements
 P260, P273, P280, P284, P301+P310, P305+P351+P338
Lethal dose or concentration (LD, LC):
57 mg/kg (rat, oral)
120 mg/kg (mouse, oral)
25 mg/kg (dog, oral)
22 mg/kg (guinea pig, oral)[4]
3 mg/m3 (mouse, 30 min respirable dust)
3 mg/m3 (guinea pig, 30 min respirable dust)[4]
1 mg/m3 (rat, respirable dust, 6 h)
6400 mg/m3 (rat, nonrespirable dust, 4 h)[4]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 0.5 mg/m3 (resp) [skin][1]
REL (Recommended)
 TWA 0.1 mg/m3 (resp) [skin][1]
IDLH (Immediate danger)
 1 mg/m3[1]
Safety data sheet (SDS) Aldrich MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Paraquat (trivial name; /ˈpærəkwɒt/), or N,N′-dimethyl-4,4′-bipyridinium dichloride (systematic name), also known as methyl viologen, is a toxic organic compound with the chemical formula [(C6H7N)2]Cl2. It is classified as a viologen, a family of redox-active heterocycles of similar structure.[5] It is one of the most widely used herbicides worldwide.[6] It is quick-acting and non-selective, killing green plant tissue on contact.

Paraquat is highly toxic to humans and other animals. The toxicity and lethality depends on the dose and how the herbicide is absorbed by the body. In humans, paraquat damages the mouth, stomach, and intestines if it is ingested orally.[7] Once absorbed in the body, paraquat causes particular damage to the lungs, kidneys, and liver.[7] Paraquat's lethality is attributed to its enhancing production of superoxide anions and human lung cells can accumulate paraquat. Paraquat exposure has been strongly linked to the development of Parkinson's disease.[8]

Paraquat may be in the form of salt with chloride or other anions; quantities of the substance are sometimes expressed by cation mass alone (paraquat cation, paraquat ion). The name is derived from the para positions of the quaternary nitrogens.

  1. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0478". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ a b "Paraquat dichloride". International Programme on Chemical Safety. October 2001. Archived from the original on 2010-12-19. Retrieved 2007-09-06.
  3. ^ Sigma-Aldrich Co., 1,1′-Dimethyl-4,4′-bipyridinium dichloride hydrate. Retrieved on 2015-03-29.
  4. ^ a b c "Paraquat". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  5. ^ In 1932, the German-American chemist Leonor Michaelis (1875–1949) named paraquat "methyl viologen" and used it as an indicator in redox reactions. See:
    • Michaelis, L. (1932). "Ein Reduktions-Indikator im Potentialbereich der Wasserstoffüberspannung" [A reduction indicator in the voltage range of hydrogen overpotential]. Biochemische Zeitschrift (in German). 250: 564–567.
    • See also: Michaelis, L.; Hill, Edgar S. (1933). "The viologen indicators" (PDF). The Journal of General Physiology. 16 (6): 859–873. doi:10.1085/jgp.16.6.859. PMC 2141252. PMID 19872744. Archived (PDF) from the original on 2019-08-16. Retrieved 2019-08-16.
  6. ^ "CDC | Facts about Paraquat". emergency.cdc.gov. 2019-05-16. Retrieved 2024-10-28.
  7. ^ a b "CDC | Facts about Paraquat". emergency.cdc.gov. 2019-05-16. Retrieved 2024-11-18.
  8. ^ Kamel, F. (2013). "Paths from Pesticides to Parkinson's". Science. 341 (6147): 722–723. Bibcode:2013Sci...341..722K. doi:10.1126/science.1243619. PMID 23950519. S2CID 11119082. Archived from the original on 2018-11-27. Retrieved 2018-09-13.
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