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	1910-42-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28786 ;
ChEMBL	ChEMBL458019 ;
ChemSpider	15146 ;
ECHA InfoCard	100.016.015
IUPHAR/BPS	4552;
PubChem CID	15938;
UNII	2KZ83GSS73 ;
CompTox Dashboard (EPA)	DTXSID7024243 ;
	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;21H/q+2;;/p-2 Key: FIKAKWIAUPDISJ-UHFFFAOYSA-L ; InChI=1/C12H14N2.2ClH/c1-13-7-3-11(4-8-13)12-5-9-14(2)10-6-12;;/h3-10H,1-2H3;21H/q+2;;/p-2/fC12H14N2.2Cl/h;21h/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
Odor	faint, ammonia-like
Density	1.25 g/cm3
Melting point	175 to 180 °C (347 to 356 °F; 448 to 453 K)
Boiling point	> 300 °C (572 °F; 573 K)
Solubility in water	High
Vapor pressure	<0.0000001 mmHg (20 °C)
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
Precautionary statements	P260, P273, P280, P284, P301+P310, P305+P351+P338
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	57 mg/kg (rat, oral); 120 mg/kg (mouse, oral); 25 mg/kg (dog, oral); 22 mg/kg (guinea pig, oral)
LC50 (median concentration)	3 mg/m3 (mouse, 30 min respirable dust); 3 mg/m3 (guinea pig, 30 min respirable dust)
LCLo (lowest published)	1 mg/m3 (rat, respirable dust, 6 h); 6400 mg/m3 (rat, nonrespirable dust, 4 h)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 0.5 mg/m3 (resp) [skin]
REL (Recommended)	TWA 0.1 mg/m3 (resp) [skin]
IDLH (Immediate danger)	1 mg/m3
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] This salt is one of the most widely used herbicides worldwide.^[6] It is quick-acting and non-selective, killing green plant tissue on contact. It is also toxic (lethal) to human beings and animals. Its lethality is attributed to its enhancing production of superoxide anions. It has been linked to the development of Parkinson's disease.^[7]

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.

^ ^a ^b ^c ^d ^e ^f NIOSH Pocket Guide to Chemical Hazards. "#0478". National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b "Paraquat dichloride". International Programme on Chemical Safety. October 2001. Archived from the original on 2010-12-19. Retrieved 2007-09-06.
^ Sigma-Aldrich Co., 1,1′-Dimethyl-4,4′-bipyridinium dichloride hydrate. Retrieved on 2015-03-29.
^ ^a ^b ^c "Paraquat". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^
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.
^ "CDC | Facts about Paraquat". emergency.cdc.gov. 2019-05-16. Retrieved 2024-10-28.
^ 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.

[PGCH-1] ^ ^a ^b ^c ^d ^e ^f NIOSH Pocket Guide to Chemical Hazards. "#0478". National Institute for Occupational Safety and Health (NIOSH).

[ipcs-2] "Paraquat dichloride". International Programme on Chemical Safety. October 2001. Archived from the original on 2010-12-19. Retrieved 2007-09-06.

[sigma-3] Sigma-Aldrich Co., 1,1′-Dimethyl-4,4′-bipyridinium dichloride hydrate. Retrieved on 2015-03-29.

[IDLH-4] "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] 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.

[7] 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.

[Kamel2013-7] 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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