Structure via PubChem · Public domain (PubChem)
cyperquat
Sign in to saveAlso known as 1-methyl-4-phenylpyridinium, N-Methyl-4-phenylpyridine, N-Methyl-4-phenylpyridinium ion, MPP+
MPP+ (1-methyl-4-phenylpyridinium) or cyperquat 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.
Chemical data
- Formula
- C12H12N+
- Molecular weight
- 170.23 g/mol
- IUPAC name
- 1-methyl-4-phenylpyridin-1-ium
- SMILES
- C[N+]1=CC=C(C=C1)C2=CC=CC=C2
- InChIKey
- FMGYKKMPNATWHP-UHFFFAOYSA-N
- XLogP
- 2.7
- Polar surface area
- 3.9 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 1
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
2,946 papers- Parkinson's disease.Lancet (London, England) · 1990
- Effects of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), cyperquat (MPP+) and paraquat on isolated mitochondria from rat striatum, cortex and liver.Life sciences · 1988
- Structural basis of drug recognition by human MATE1 transporter.Nature communications · 2025
- 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), its metabolite cyperquat (MPP+) and energy transduction in mitochondria from rat striatum and liver.Progress in neuro-psychopharmacology & biological psychiatry · 1988
- [Neurotoxicity Mechanism of Environmental Chemicals and Its Evaluation System].Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan · 2018
via PubMed
Wikidata facts
Show 3 more facts
- canonical SMILES
- C[N+]1=CC=C(C=C1)C2=CC=CC=C2
- Commons category
- MPP+
- chemical formula
- C₁₂H₁₂N⁺
Sources (2)
via Wikidata · CC0
~9 min read
Encyclopedic overview
11 sectionsContents
- History
- Synthesis
- Laboratory
- Biological
- Mechanism of toxicity
- Uses
- In scientific research
- As a [[pesticide]]
- Safety
- References
- External links
MPP+ (1-methyl-4-phenylpyridinium) or cyperquat 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.
Excerpted from Wikipedia’s “cyperquat” article, available under the CC BY-SA 4.0 licence.