N-methyl-4-phenylpyridinium (CHEBI:641)

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ChEBI Name	N-methyl-4-phenylpyridinium

ChEBI ID	CHEBI:641

ChEBI ASCII Name	N-methyl-4-phenylpyridinium

Definition	A pyridinium ion that is N-methylpyridinium having a phenyl substituent at the 4-position.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ZINC000000967769

Download	Molfile XML SDF

Wikipedia	License
MPP+ (1-methyl-4-phenylpyridinium) is a positively charged organic molecule with the chemical formula C12H12N+. It is a monoaminergic neurotoxin that acts by interfering with oxidative phosphorylation in mitochondria by inhibiting complex I, leading to the depletion of ATP and eventual cell death. MPP+ arises in the body as the toxic metabolite of the closely related compound MPTP. MPTP is converted in the brain into MPP+ by the enzyme MAO-B, ultimately causing parkinsonism in primates by killing certain dopamine-producing neurons in the substantia nigra. The ability for MPP+ to induce Parkinson's disease has made it an important compound in Parkinson's research since this property was discovered in 1983. The chloride salt of MPP+ found use in the 1970s as an herbicide under the trade name cyperquat. Though no longer in use as an herbicide, cyperquat's closely related structural analog paraquat still finds widespread usage, raising some safety concerns.
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Formula

C12H12N

Net Charge

Average Mass

170.23040

Monoisotopic Mass

170.09643

InChI

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

InChIKey

FMGYKKMPNATWHP-UHFFFAOYSA-N

SMILES

C[n+]1ccc(cc1)-c1ccccc1

Roles Classification
Biological Role(s):	human xenobiotic metabolite Any human metabolite produced by metabolism of a xenobiotic compound in humans. apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms. neurotoxin A poison that interferes with the functions of the nervous system.

Application(s):	herbicide A substance used to destroy plant pests.

ChEBI Ontology
Outgoing	N-methyl-4-phenylpyridinium (CHEBI:641) has role apoptosis inducer (CHEBI:68495) N-methyl-4-phenylpyridinium (CHEBI:641) has role herbicide (CHEBI:24527) N-methyl-4-phenylpyridinium (CHEBI:641) has role human xenobiotic metabolite (CHEBI:76967) N-methyl-4-phenylpyridinium (CHEBI:641) has role neurotoxin (CHEBI:50910) N-methyl-4-phenylpyridinium (CHEBI:641) is a pyridinium ion (CHEBI:50334)

IUPAC Name

1-methyl-4-phenylpyridinium

Synonyms	Sources
1-Methyl-4-phenylpyridinium	KEGG COMPOUND
Cyperquat	KEGG COMPOUND
MPP+	ChEBI
N-Methyl-4-phenylpyridine	KEGG COMPOUND
N-methyl-4-phenylpyridine	UniProt
N-Methyl-4-phenylpyridinium ion	ChemIDplus

Citations

Last Modified

16 February 2016