1-methyl-4-phenylpyridinium

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WordNet

1. the univalent radical CH3- derived from methane (同)methyl_group, methyl radical

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/07/12 22:58:32」(JST)

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Not to be confused with MPTP or MPPP.

MPP+

Names
IUPAC name 1-Methyl-4-phenylpyridin-1-ium
Other names Cyperquat; 1-Methyl-4-phenylpyridinium; N-Methyl-4-phenylpyridine
Identifiers
CAS Number	39794-99-5 N
ChEBI	CHEBI:641 Y
ChEMBL	ChEMBL311617 Y
ChemSpider	36101 Y
EC Number	248-939-7
IUPHAR/BPS	4568
Jmol 3D model	Interactive image
MeSH	1-Methyl-4-phenylpyridinium
PubChem	39484
InChI InChI=1S/C12H12N/c1-13-9-7-12(8-10-13)11-5-3-2-4-6-11/h2-10H,1H3/q+1 Y Key: FMGYKKMPNATWHP-UHFFFAOYSA-N Y
SMILES C[n+]1=cc=c(c=c1)c2=cc=cc=c2
Properties
Chemical formula	C12H12N+
Molar mass	170.25 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

MPP+ (1-methyl-4-phenylpyridinium) is a positively charged molecule with chemical formula C₁₂H₁₂N⁺. It is toxic and acts by interfering with oxidative phosphorylation in mitochondria by inhibiting complex I, leading to the depletion of ATP and cell death. Mitochondria in cells treated with MPP+ also display a phenotype indicative of apoptosis: small, round, and fewer in number. It also inhibits the synthesis of catecholamines, reduces levels of dopamine and cardiac norepinephrine, and inactivates tyrosine hydroxylase.

The neurotoxin MPTP is converted in the brain into MPP+ by the enzyme MAO-B, causing parkinsonism in primates by killing certain dopamine-producing neurons in the substantia nigra. MPP+-induced neurodegeneration is specific to dopamine neurons and can be prevented by drug treatment or by limiting the function of the dopamine transporter.

The chloride salt of MPP+ has been used as a herbicide under the trade name cyperquat and is structurally similar to the herbicide paraquat.

In a rat model of Parkinson's disease, nobiletin, a flavonoid found in citrus, can rescue dopaminergic neurons from degeneration caused by treatment with MPP+.

References

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English Journal

• Effects of Agmatine on Depressive-Like Behavior Induced by Intracerebroventricular Administration of 1-Methyl-4-phenylpyridinium (MPP+).

• Moretti M1, Neis VB, Matheus FC, Cunha MP, Rosa PB, Ribeiro CM, Rodrigues AL, Prediger RD.
• Neurotoxicity research.Neurotox Res.2015 Jul 9. [Epub ahead of print]
• Considering that depression is a common non-motor comorbidity of Parkinson's disease and that agmatine is an endogenous neuromodulator that emerges as a potential agent to manage diverse central nervous system disorders, this study investigated the antidepressant-like effect of agmatine in mice intr
• PMID 26156429

• Functional characterization of the organic cation transporters (OCTs) in human airway pulmonary epithelial cells.

• Ingoglia F1, Visigalli R1, Rotoli BM1, Barilli A1, Riccardi B2, Puccini P2, Dall'Asta V3.
• Biochimica et biophysica acta.Biochim Biophys Acta.2015 Jul;1848(7):1563-72. doi: 10.1016/j.bbamem.2015.04.001. Epub 2015 Apr 13.
• Organic cation transporters (OCT1-3) mediate the transport of organic cations including inhaled drugs across the cell membrane, although their role in lung epithelium hasn't been well understood yet. We address here the expression and functional activity of OCT1-3 in human airway epithelial cells A5
• PMID 25883089

• Neuroprotective effects of ginkgetin against neuroinjury in Parkinson's disease model induced by MPTP via chelating iron.

• Wang YQ1, Wang MY, Fu XR, Peng-Yu, Gao GF, Fan YM, Duan XL, Zhao BL, Chang YZ, Shi ZH.
• Free radical research.Free Radic Res.2015 Jul 1:1-12. [Epub ahead of print]
• Disruption of neuronal iron homeostasis and oxidative stress are closely related to the pathogenesis of Parkinson's disease (PD). Ginkgetin, a natural biflavonoid isolated from leaves of Ginkgo biloba L, has many known effects, including anti-inflammatory, anti-influenza virus, and anti-fungal activ
• PMID 25968939

Japanese Journal

• Neuroprotective effect of Buddleja cordata methanolic extract in the 1-methyl-4-phenylpyridinium Parkinson's disease rat model

• Journal of natural medicines 69(1), 86-93, 2015
• NAID 40020305682

• Methylmercury can induce Parkinson's-like neurotoxicity similar to 1-methyl-4- phenylpyridinium: a genomic and proteomic analysis on MN9D dopaminergic neuron cells

• The Journal of Toxicological Sciences 40(6), 817-828, 2015
• NAID 130005108860

• Therapeutic Effects of Multifunctional Tetramethylpyrazine Nitrone on Models of Parkinson's Disease <i>in Vitro</i> and <i>in Vivo</i>

• Biological and Pharmaceutical Bulletin 37(2), 274-285, 2014
• NAID 130003382123

Related Pictures

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★リンクテーブル★

リンク元	「1-メチル-4-フェニルピリジニウム」「メチルフェニルピリジニウム」「MPP+」
関連記事	「phenylpyridinium」

「1-メチル-4-フェニルピリジニウム」

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英

1-methyl-4-phenylpyridinium、MPP+

関

メチルフェニルピリジニウム

「メチルフェニルピリジニウム」

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英

1-methyl-4-phenylpyridinium

関

1-メチル-4-フェニルピリジニウム

「MPP+」

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1メチル4フェニルピリジニウム

関

1-methyl-4-phenylpyridinium

「phenylpyridinium」

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フェニルピリジニウム