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MPP+

MPP+
MPP+.svg
Names
IUPAC name
1-Methyl-4-phenylpyridin-1-ium
Other names
Cyperquat; 1-Methyl-4-phenylpyridinium; N-Methyl-4-phenylpyridine
Identifiers
39794-99-5 
ChEBI CHEBI:641 Yes
ChEMBL ChEMBL311617 Yes
ChemSpider 36101 Yes
EC number 248-939-7
Jmol-3D images Image
MeSH 1-Methyl-4-phenylpyridinium
PubChem 39484
Properties
C12H12N+
Molar mass 170.25 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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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.[1] It also inhibits the synthesis of catecholamines, reduces levels of dopamine and cardiac norepinephrine, and inactivates tyrosine hydroxylase.[1]

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.[2]

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

References

  1. ^ a b PubChem Compound entry on MPP+
  2. ^ Wiemerslage L, Schultz BJ, Ganguly A, Lee D (2013). "Selective degeneration of dopaminergic neurons by MPP(+) and its rescue by D2 autoreceptors in Drosophila primary culture.". J Neurochem 126 (4): 529–40. doi:10.1111/jnc.12228. PMID 23452092.