CYPERQUAT

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H12N
Molecular Weight	170.2304
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=FMGYKKMPNATWHP-UHFFFAOYSA-N

InChI=1S/C12H12N/c1-13-9-7-12(8-10-13)11-5-3-2-4-6-11/h2-10H,1H3/q+1

HIDE SMILES / InChI

Molecular Formula	C12H12N
Molecular Weight	170.2304
Charge	1
Count

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

Approval Year

PubMed

Title	Date	PubMed
Environmental risk factors and Parkinson's disease: selective degeneration of nigral dopaminergic neurons caused by the herbicide paraquat.	2002-07	12127150
Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3.	2002-07	12110607
1-Methyl-4-phenylpyridinium ion, a toxin that can cause parkinsonism, alters branched structures of DNA.	2002-07	12091462
cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney.	2002-07	12089365
Inhibition of the mitochondrial permeability transition by the nonimmunosuppressive cyclosporin derivative NIM811.	2002-07	12065751
Progressive alteration of neuronal dopamine transporter activity in a rat injured by an intranigral injection of MPP+.	2002-06-21	12031549
The human organic cation transporter (hOCT2) recognizes the degree of substrate ionization.	2002-06-21	11953440
Specific up-regulation of GADD153/CHOP in 1-methyl-4-phenyl-pyridinium-treated SH-SY5Y cells.	2002-06-15	12111836
Role of hydroxyl radical formation in neurotoxicity as revealed by in vivo free radical trapping.	2002-06-14	12044541
Phenylethanolamine N-methyltransferase has beta-carboline 2N-methyltransferase activity: hypothetical relevance to Parkinson's disease.	2002-06	11900856
MPP+ increases alpha-synuclein expression and ERK/MAP-kinase phosphorylation in human neuroblastoma SH-SY5Y cells.	2002-05-10	12062470
Synthetic neuromelanin is toxic to dopaminergic cell cultures.	2002-05	12111457
Pergolide protects dopaminergic neurons in primary culture under stress conditions.	2002-05	12111455
Inhibition of the neuronal isoform of nitric oxide synthase significantly attenuates 1-methyl-4-phenylpyridinium (MPP(+)) toxicity in vitro.	2002-05	12111451
Contradictory effects of sodium nitroprusside and S-nitroso-N-acetylpenicillamine on oxidative stress in brain dopamine neurons in vivo.	2002-05	12076963
Inhibitors of mitochondrial complex I attenuate the accumulation of hypoxia-inducible factor-1 during hypoxia in Hep3B cells.	2002-05	12062197
Regulation of [(3)H]MPP(+) transport by phosphorylation/dephosphorylation pathways in RBE4 cells: role of ecto-alkaline phosphatase.	2002-05	12012020
Melatonin attenuates MPP+-induced neurodegeneration and glutathione impairment in the nigrostriatal dopaminergic pathway.	2002-05	11982797
Uptake of (3)H-1-methyl-4-phenylpyridinium ((3)H-MPP(+)) by human intestinal Caco-2 cells is regulated by phosphorylation/dephosphorylation mechanisms.	2002-04-15	11996899
Role of mitochondrial oxidant generation in endothelial cell responses to hypoxia.	2002-04-01	11950692
Caspase inhibitors attenuate 1-methyl-4-phenylpyridinium toxicity in primary cultures of mesencephalic dopaminergic neurons.	2002-04-01	11923429
Capillary electrophoretic determination of apoptosis of rat cerebellar granule cells induced by 1-methyl-4-phenyl pyridium ion.	2002-04	11981859
Semicarbazide-sensitive amine oxidase (SSAO) in the brain.	2002-04	11958526
Amino acids involved in differences in the pharmacological profiles of the rat and human noradrenaline transporters.	2002-04	11919656
Differential effect of catecholamines and MPP(+) on membrane permeability in brain mitochondria and cell viability in PC12 cells.	2002-04	11792467
The roles of thioredoxin in protection against oxidative stress-induced apoptosis in SH-SY5Y cells.	2002-03-22	11751890
Thioredoxin suppresses 1-methyl-4-phenylpyridinium-induced neurotoxicity in rat PC12 cells.	2002-03-15	11872262
Pharmacological properties of the naturally occurring Ala(457)Pro variant of the human norepinephrine transporter.	2002-03	11875370
Protective effect of serotonin on 6-hydroxydopamine- and dopamine-induced oxidative damage of brain mitochondria and synaptosomes and PC12 cells.	2002-03	11741005
Inhibition by R(+) or S(-) pramipexole of caspase activation and cell death induced by methylpyridinium ion or beta amyloid peptide in SH-SY5Y neuroblastoma.	2002-02-15	11835316
Protection of dopaminergic neurons in primary culture by lisuride.	2002-02	12075855
Differential expression of Bcl-2 and APP immunoreactivity after intrastriatal injection of MPP+ in the rat.	2002-02	11738483
Evaluation of the protective effect of oestradiol against toxicity induced by 6-hydroxydopamine and 1-methyl-4-phenylpyridinium ion (Mpp+) towards dopaminergic mesencephalic neurones in primary culture.	2002-01	11902121
Neuroprotection by adenosine A2A receptor blockade in experimental models of Parkinson's disease.	2002-01	11902116
Nitric oxide and depolarization induce hydroxyl radical generation.	2002-01	11855667
Intrastriatal injection of sonic hedgehog reduces behavioral impairment in a rat model of Parkinson's disease.	2002-01	11771942
Comparative study of the neuroprotective effect of dehydroepiandrosterone and 17beta-estradiol against 1-methyl-4-phenylpyridium toxicity on rat striatum.	2002	11823067
Stimulation of non-alpha7 nicotinic receptors partially protects dopaminergic neurons from 1-methyl-4-phenylpyridinium-induced toxicity in culture.	2002	11801364
Protective effect of histidine on para-nonylphenol-enhanced hydroxyl free radical generation induced by 1-methyl-4-phenylpyridinium ion (MPP+) in rat striatum.	2001-12-05	11750765
Regulation of human extraneuronal monoamine transporter (hEMT) expressed in HEK293 cells by intracellular second messenger systems.	2001-12	11770002
Protective effect and mechanism of Ginkgo biloba leaf extracts for Parkinson disease induced by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine.	2001-12	11749805
Lactoferrin is synthesized by activated microglia in the human substantia nigra and its synthesis by the human microglial CHME cell line is upregulated by tumor necrosis factor alpha or 1-methyl-4-phenylpyridinium treatment.	2001-11-30	11731015
[Human GDNF cDNA-engineered SH-SY5Y cells' neurotrophic and protective effect on primary dopaminergic neurons of rat].	2001-11-25	11930634
Caspase-3 activation induced by inhibition of mitochondrial complex I is facilitated by glycogen synthase kinase-3beta and attenuated by lithium.	2001-11-16	11689167
Impairment of the neuronal dopamine transporter activity in MPP(+)-treated rat was not prevented by treatments with nitric oxide synthase or poly(ADP-ribose) polymerase inhibitors.	2001-11-13	11698152
EGb761 blocks MPP+-induced lipid peroxidation in mouse corpus striatum.	2001-11	11874207
Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules.	2001-11	11758759
Mechanisms of MPP(+) incorporation into cerebellar granule cells.	2001-09-15	11704348
Eldepryl prevents 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced nigral neuronal apoptosis in mice.	2001-03	11780305
Stimulation of the regrowth of MPP+-damaged dopaminergic fibers by the treatment of mesencephalic cultures with basigin.	2001	11725815

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:51:06 GMT 2025` Edited by `admin` on `Mon Mar 31 18:51:06 GMT 2025`
Record UNII	R865A5OY8J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CYPERQUAT

Common Name

English

CYPERQUAT CATION

Preferred Name

English

MPP+

Common Name

English

CYPERQUAT ION

Common Name

English

N-METHYL-4-PHENYLPYRIDINIUM ION

Common Name

English

1-METHYL-4-PHENYLPYRIDINIUM ION

Common Name

English

CYPERQUAT [ISO]

Common Name

English

N-METHYL-4-PHENYLPYRIDINE

Systematic Name

English

N-METHYL-4-PHENYLPYRIDINIUM

Systematic Name

English

PYRIDINIUM, 1-METHYL-4-PHENYL-

Systematic Name

English

1-METHYL-4-PHENYLPYRIDINIUM

Systematic Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

271700