DIQUAT

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H12N2
Molecular Weight	184.2371
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	2

SHOW SMILES / InChI

Structure Search

SMILES

C1C[N+]2=C(C=CC=C2)C3=CC=CC=[N+]13

InChI

InChIKey=SYJFEGQWDCRVNX-UHFFFAOYSA-N

InChI=1S/C12H12N2/c1-3-7-13-9-10-14-8-4-2-6-12(14)11(13)5-1/h1-8H,9-10H2/q+2

HIDE SMILES / InChI

Molecular Formula	C12H12N2
Molecular Weight	184.2371
Charge	2
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Diquat causes caspase-independent cell death in SH-SY5Y cells by production of ROS independently of mitochondria.	2015-10	25693864
A high-throughput screen for teratogens using human pluripotent stem cells.	2014-01	24154490
Evaluation of aggregating brain cell cultures for the detection of acute organ-specific toxicity.	2013-06	22954530
Pyrosequencing-based transcriptomic resources in the pond snail Lymnaea stagnalis, with a focus on genes involved in molecular response to diquat-induced stress.	2012-11	22814884
Nrf2 protects against diquat-induced liver and lung injury.	2012-10	22762311
Responses of growth performance and tryptophan metabolism to oxidative stress induced by diquat in weaned pigs.	2012-06	22558963
Implementation of a high-throughput screen for identifying small molecules to activate the Keap1-Nrf2-ARE pathway.	2012	23056183
Effect of diquat-induced oxidative stress on iron metabolism in male Fischer-344 rats.	2011-12	21698372
Redox cycling and increased oxygen utilization contribute to diquat-induced oxidative stress and cytotoxicity in Chinese hamster ovary cells overexpressing NADPH-cytochrome P450 reductase.	2011-04-01	21215309
Identification and dissection of the Nrf2 mediated oxidative stress pathway in human renal proximal tubule toxicity.	2011-04	21172416
Hepatic response to oxidative injury in long-lived Ames dwarf mice.	2011-01	20826540
Does reduced IGF-1R signaling in Igf1r+/- mice alter aging?	2011	22132081
A high-throughput method for assessing chemical toxicity using a Caenorhabditis elegans reproduction assay.	2010-06-01	20206647
Impact of environmental chemicals on key transcription regulators and correlation to toxicity end points within EPA's ToxCast program.	2010-03-15	20143881
Evaluation of transcriptional activity of caspase-3 gene as a marker of acute neurotoxicity in rat cerebellar granular cells.	2010-03	19815060
Short form glutathione peroxidase 4 is the essential isoform required for survival and somatic mitochondrial functions.	2009-11-06	19744930
Long-lived ames dwarf mice are resistant to chemical stressors.	2009-08	19414510
Evaluation of diquat against an acute experimental infection of Flavobacterium columnare in channel catfish, Ictalurus punctatus (Rafinesque).	2009-05	19392680
The in vivo gene expression signature of oxidative stress.	2008-06-12	18445702
Thioredoxin 2 haploinsufficiency in mice results in impaired mitochondrial function and increased oxidative stress.	2008-03-01	18164269
Targeted disruption of the glutaredoxin 1 gene does not sensitize adult mice to tissue injury induced by ischemia/reperfusion and hyperoxia.	2007-11-01	17893043
Protective effects of wheat bran against diquat toxicity in male Fischer-344 rats.	2007-07	17617720
Nrf2 regulates an adaptive response protecting against oxidative damage following diquat-mediated formation of superoxide anion.	2006-10-01	16962985
Gene expression patterns in rainbow trout, Oncorhynchus mykiss, exposed to a suite of model toxicants.	2006-05-25	16488489
Transgenic mice overexpressing glutathione peroxidase 4 are protected against oxidative stress-induced apoptosis.	2004-12-31	15496407
Multiple deficiencies in antioxidant enzymes in mice result in a compound increase in sensitivity to oxidative stress.	2004-06-15	15182862
Compartmental inhibition of hepatic glutathione reductase activities by 1,3-bis(2-chloroethyl)-N-nitrosourea (BCNU) in Sprague-Dawley and Fischer-344 rats.	2004-03-07	15104113
Role of capsaicin-sensitive afferent nerves in different models of gastric inflammation in rats.	2004-02-27	15046732
Tetracyanometalates of Ni, Pd, and Pt with cyclic diquaternary cations of 2,2'-bipyridine and 1,10-phenanthroline. A vibrational, crystallographic, and theoretical study of intermolecular weak interactions.	2002-08-26	12184756
Comparative impacts of glutathione peroxidase-1 gene knockout on oxidative stress induced by reactive oxygen and nitrogen species in mouse hepatocytes.	2001-11-01	11672444
Lipopolysaccharide and interferon-gamma-induced nitric oxide production and protein oxidation in mouse peritoneal macrophages are affected by glutathione peroxidase-1 gene knockout.	2001-08-15	11498278
Glutathione peroxidase-1 gene knockout on body antioxidant defense in mice.	2001	11568445
Knockout of cellular glutathione peroxidase gene renders mice susceptible to diquat-induced oxidative stress.	1999-09	10490281
Upregulation of glucose-6-phosphate dehydrogenase in response to hepatocellular oxidative stress: studies with diquat.	1995-12	8934631
The effects of diquat and ciprofibrate on mRNA expression and catalytic activities of hepatic xenobiotic metabolizing and antioxidant enzymes in rat liver.	1995-09	7676460
Effects of oxidative stress caused by hyperoxia and diquat. A study in isolated hepatocytes.	1986	3505239
Acute diquat intoxication. Interest of its repeated determination in urine and the evaluation of renal proximal tubule integrity.	1984	6527399
Assessment of the mutagenic properties of diquat and paraquat in the murine dominant lethal test.	1974-06	4850670

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:51:14 GMT 2025` Edited by `admin` on `Mon Mar 31 17:51:14 GMT 2025`
Record UNII	A9A615U4MP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

9,10-DIHYDRO-8A,10A-DIAZONIAPHENANTHRENE

Preferred Name

English

DIQUAT

Common Name

English

6,7-DIHYDRODIPYRIDO(1,2-A:2',1'-C)PYRAZINEDIIUM

Systematic Name

English

DIQUAT [ISO]

Common Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

32202