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Details

Stereochemistry ACHIRAL
Molecular Formula C12H12N.Cl
Molecular Weight 205.683
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYPERQUAT CHLORIDE

SMILES

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

InChI

InChIKey=LMGBDZJLZIPJPZ-UHFFFAOYSA-M
InChI=1S/C12H12N.ClH/c1-13-9-7-12(8-10-13)11-5-3-2-4-6-11;/h2-10H,1H3;1H/q+1;/p-1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

PubMed

TitleDatePubMed
Environmental risk factors and Parkinson's disease: selective degeneration of nigral dopaminergic neurons caused by the herbicide paraquat.
2002-07
Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3.
2002-07
1-Methyl-4-phenylpyridinium ion, a toxin that can cause parkinsonism, alters branched structures of DNA.
2002-07
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
Inhibition of the mitochondrial permeability transition by the nonimmunosuppressive cyclosporin derivative NIM811.
2002-07
Progressive alteration of neuronal dopamine transporter activity in a rat injured by an intranigral injection of MPP+.
2002-06-21
The human organic cation transporter (hOCT2) recognizes the degree of substrate ionization.
2002-06-21
Specific up-regulation of GADD153/CHOP in 1-methyl-4-phenyl-pyridinium-treated SH-SY5Y cells.
2002-06-15
Role of hydroxyl radical formation in neurotoxicity as revealed by in vivo free radical trapping.
2002-06-14
Phenylethanolamine N-methyltransferase has beta-carboline 2N-methyltransferase activity: hypothetical relevance to Parkinson's disease.
2002-06
MPP+ increases alpha-synuclein expression and ERK/MAP-kinase phosphorylation in human neuroblastoma SH-SY5Y cells.
2002-05-10
Synthetic neuromelanin is toxic to dopaminergic cell cultures.
2002-05
Pergolide protects dopaminergic neurons in primary culture under stress conditions.
2002-05
Inhibition of the neuronal isoform of nitric oxide synthase significantly attenuates 1-methyl-4-phenylpyridinium (MPP(+)) toxicity in vitro.
2002-05
Contradictory effects of sodium nitroprusside and S-nitroso-N-acetylpenicillamine on oxidative stress in brain dopamine neurons in vivo.
2002-05
Inhibitors of mitochondrial complex I attenuate the accumulation of hypoxia-inducible factor-1 during hypoxia in Hep3B cells.
2002-05
Regulation of [(3)H]MPP(+) transport by phosphorylation/dephosphorylation pathways in RBE4 cells: role of ecto-alkaline phosphatase.
2002-05
Melatonin attenuates MPP+-induced neurodegeneration and glutathione impairment in the nigrostriatal dopaminergic pathway.
2002-05
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
Role of mitochondrial oxidant generation in endothelial cell responses to hypoxia.
2002-04-01
Caspase inhibitors attenuate 1-methyl-4-phenylpyridinium toxicity in primary cultures of mesencephalic dopaminergic neurons.
2002-04-01
Capillary electrophoretic determination of apoptosis of rat cerebellar granule cells induced by 1-methyl-4-phenyl pyridium ion.
2002-04
Semicarbazide-sensitive amine oxidase (SSAO) in the brain.
2002-04
Amino acids involved in differences in the pharmacological profiles of the rat and human noradrenaline transporters.
2002-04
Differential effect of catecholamines and MPP(+) on membrane permeability in brain mitochondria and cell viability in PC12 cells.
2002-04
The roles of thioredoxin in protection against oxidative stress-induced apoptosis in SH-SY5Y cells.
2002-03-22
Thioredoxin suppresses 1-methyl-4-phenylpyridinium-induced neurotoxicity in rat PC12 cells.
2002-03-15
Pharmacological properties of the naturally occurring Ala(457)Pro variant of the human norepinephrine transporter.
2002-03
Protective effect of serotonin on 6-hydroxydopamine- and dopamine-induced oxidative damage of brain mitochondria and synaptosomes and PC12 cells.
2002-03
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
Protection of dopaminergic neurons in primary culture by lisuride.
2002-02
Differential expression of Bcl-2 and APP immunoreactivity after intrastriatal injection of MPP+ in the rat.
2002-02
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
Neuroprotection by adenosine A2A receptor blockade in experimental models of Parkinson's disease.
2002-01
Nitric oxide and depolarization induce hydroxyl radical generation.
2002-01
Intrastriatal injection of sonic hedgehog reduces behavioral impairment in a rat model of Parkinson's disease.
2002-01
Comparative study of the neuroprotective effect of dehydroepiandrosterone and 17beta-estradiol against 1-methyl-4-phenylpyridium toxicity on rat striatum.
2002
Stimulation of non-alpha7 nicotinic receptors partially protects dopaminergic neurons from 1-methyl-4-phenylpyridinium-induced toxicity in culture.
2002
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
Regulation of human extraneuronal monoamine transporter (hEMT) expressed in HEK293 cells by intracellular second messenger systems.
2001-12
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
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
[Human GDNF cDNA-engineered SH-SY5Y cells' neurotrophic and protective effect on primary dopaminergic neurons of rat].
2001-11-25
Caspase-3 activation induced by inhibition of mitochondrial complex I is facilitated by glycogen synthase kinase-3beta and attenuated by lithium.
2001-11-16
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
EGb761 blocks MPP+-induced lipid peroxidation in mouse corpus striatum.
2001-11
Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules.
2001-11
Mechanisms of MPP(+) incorporation into cerebellar granule cells.
2001-09-15
Eldepryl prevents 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced nigral neuronal apoptosis in mice.
2001-03
Stimulation of the regrowth of MPP+-damaged dopaminergic fibers by the treatment of mesencephalic cultures with basigin.
2001
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 20:11:17 GMT 2025
Edited
by admin
on Mon Mar 31 20:11:17 GMT 2025
Record UNII
MRP3DNB9K9
Record Status Validated (UNII)
Record Version
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Name Type Language
CYPERQUAT CHLORIDE
ISO  
Common Name English
S-21634
Preferred Name English
CYPERQUAT CHLORIDE [ISO]
Common Name English
PYRIDINIUM, 1-METHYL-4-PHENYL-, CHLORIDE
Systematic Name English
N-METHYL-4-PHENYLPYRIDINIUM CHLORIDE
Systematic Name English
1-METHYL-4-PHENYLPYRIDINIUM CHLORIDE
Systematic Name English
PYRIDINIUM, 1-METHYL-4-PHENYL-, CHLORIDE (1:1)
Systematic Name English
Code System Code Type Description
PUBCHEM
94497
Created by admin on Mon Mar 31 20:11:17 GMT 2025 , Edited by admin on Mon Mar 31 20:11:17 GMT 2025
PRIMARY
EPA CompTox
DTXSID8041826
Created by admin on Mon Mar 31 20:11:17 GMT 2025 , Edited by admin on Mon Mar 31 20:11:17 GMT 2025
PRIMARY
ALANWOOD
cyperquat chloride
Created by admin on Mon Mar 31 20:11:17 GMT 2025 , Edited by admin on Mon Mar 31 20:11:17 GMT 2025
PRIMARY
CAS
39794-99-5
Created by admin on Mon Mar 31 20:11:17 GMT 2025 , Edited by admin on Mon Mar 31 20:11:17 GMT 2025
PRIMARY
FDA UNII
MRP3DNB9K9
Created by admin on Mon Mar 31 20:11:17 GMT 2025 , Edited by admin on Mon Mar 31 20:11:17 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE