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
Stimulation of the regrowth of MPP+-damaged dopaminergic fibers by the treatment of mesencephalic cultures with basigin.	2001	11725815
Glutamate is not involved in the MPP+-induced dopamine overflow in the striatum of freely moving C57BL/6 mice.	2001	11685630
Dependence of excitotoxic neurodegeneration on mitochondrial aconitase inactivation.	2001 Aug	11520895
Nitric oxide enhances MPP(+) inhibition of complex I.	2001 Aug 24	11522295
MPP(+) downregulates mitochondrially encoded gene transcripts and their activities in dopaminergic neuronal cells: protective role of Bcl-2.	2001 Aug 24	11511111
Substantial loss of substrate by diffusion during uptake in HEK-293 cells expressing neurotransmitter transporters.	2001 Aug 31	11514069
Regulation of human extraneuronal monoamine transporter (hEMT) expressed in HEK293 cells by intracellular second messenger systems.	2001 Dec	11770002
Eldepryl prevents 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced nigral neuronal apoptosis in mice.	2001 Mar	11780305
EGb761 blocks MPP+-induced lipid peroxidation in mouse corpus striatum.	2001 Nov	11874207
Caspase-3 activation induced by inhibition of mitochondrial complex I is facilitated by glycogen synthase kinase-3beta and attenuated by lithium.	2001 Nov 16	11689167
[Human GDNF cDNA-engineered SH-SY5Y cells' neurotrophic and protective effect on primary dopaminergic neurons of rat].	2001 Nov 25	11930634
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 Nov 30	11731015
1-Methyl-4-phenyl-pyridinium increases S-adenosyl-L-methionine dependent phospholipid methylation.	2001 Sep	11566147
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
Capillary electrophoretic determination of apoptosis of rat cerebellar granule cells induced by 1-methyl-4-phenyl pyridium ion.	2002 Apr	11981859
Semicarbazide-sensitive amine oxidase (SSAO) in the brain.	2002 Apr	11958526
Amino acids involved in differences in the pharmacological profiles of the rat and human noradrenaline transporters.	2002 Apr	11919656
Differential effect of catecholamines and MPP(+) on membrane permeability in brain mitochondria and cell viability in PC12 cells.	2002 Apr	11792467
Role of mitochondrial oxidant generation in endothelial cell responses to hypoxia.	2002 Apr 1	11950692
Caspase inhibitors attenuate 1-methyl-4-phenylpyridinium toxicity in primary cultures of mesencephalic dopaminergic neurons.	2002 Apr 1	11923429
Uptake of (3)H-1-methyl-4-phenylpyridinium ((3)H-MPP(+)) by human intestinal Caco-2 cells is regulated by phosphorylation/dephosphorylation mechanisms.	2002 Apr 15	11996899
Protection of dopaminergic neurons in primary culture by lisuride.	2002 Feb	12075855
Differential expression of Bcl-2 and APP immunoreactivity after intrastriatal injection of MPP+ in the rat.	2002 Feb	11738483
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 Feb 15	11835316
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 Jan	11902121
Neuroprotection by adenosine A2A receptor blockade in experimental models of Parkinson's disease.	2002 Jan	11902116
Nitric oxide and depolarization induce hydroxyl radical generation.	2002 Jan	11855667
Intrastriatal injection of sonic hedgehog reduces behavioral impairment in a rat model of Parkinson's disease.	2002 Jan	11771942
Environmental risk factors and Parkinson's disease: selective degeneration of nigral dopaminergic neurons caused by the herbicide paraquat.	2002 Jul	12127150
Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3.	2002 Jul	12110607
1-Methyl-4-phenylpyridinium ion, a toxin that can cause parkinsonism, alters branched structures of DNA.	2002 Jul	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 Jul	12089365
Inhibition of the mitochondrial permeability transition by the nonimmunosuppressive cyclosporin derivative NIM811.	2002 Jul	12065751
Phenylethanolamine N-methyltransferase has beta-carboline 2N-methyltransferase activity: hypothetical relevance to Parkinson's disease.	2002 Jun	11900856
Role of hydroxyl radical formation in neurotoxicity as revealed by in vivo free radical trapping.	2002 Jun 14	12044541
Specific up-regulation of GADD153/CHOP in 1-methyl-4-phenyl-pyridinium-treated SH-SY5Y cells.	2002 Jun 15	12111836
Progressive alteration of neuronal dopamine transporter activity in a rat injured by an intranigral injection of MPP+.	2002 Jun 21	12031549
The human organic cation transporter (hOCT2) recognizes the degree of substrate ionization.	2002 Jun 21	11953440
Pharmacological properties of the naturally occurring Ala(457)Pro variant of the human norepinephrine transporter.	2002 Mar	11875370
Protective effect of serotonin on 6-hydroxydopamine- and dopamine-induced oxidative damage of brain mitochondria and synaptosomes and PC12 cells.	2002 Mar	11741005
Thioredoxin suppresses 1-methyl-4-phenylpyridinium-induced neurotoxicity in rat PC12 cells.	2002 Mar 15	11872262
Synthetic neuromelanin is toxic to dopaminergic cell cultures.	2002 May	12111457
Pergolide protects dopaminergic neurons in primary culture under stress conditions.	2002 May	12111455
Inhibition of the neuronal isoform of nitric oxide synthase significantly attenuates 1-methyl-4-phenylpyridinium (MPP(+)) toxicity in vitro.	2002 May	12111451
Contradictory effects of sodium nitroprusside and S-nitroso-N-acetylpenicillamine on oxidative stress in brain dopamine neurons in vivo.	2002 May	12076963
Inhibitors of mitochondrial complex I attenuate the accumulation of hypoxia-inducible factor-1 during hypoxia in Hep3B cells.	2002 May	12062197
Regulation of [(3)H]MPP(+) transport by phosphorylation/dephosphorylation pathways in RBE4 cells: role of ecto-alkaline phosphatase.	2002 May	12012020
Melatonin attenuates MPP+-induced neurodegeneration and glutathione impairment in the nigrostriatal dopaminergic pathway.	2002 May	11982797
MPP+ increases alpha-synuclein expression and ERK/MAP-kinase phosphorylation in human neuroblastoma SH-SY5Y cells.	2002 May 10	12062470

Patents

Substance Class	Chemical Created by `admin` on `Thu Jul 06 01:01:47 UTC 2023` Edited by `admin` on `Thu Jul 06 01:01:47 UTC 2023`
Record UNII	R865A5OY8J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CYPERQUAT

Common Name

English

MPP+

Common Name

English

CYPERQUAT ION

Common Name

English

N-METHYL-4-PHENYLPYRIDINIUM ION

Common Name

English

CYPERQUAT CATION

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