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D048

Sigma-Aldrich

MPP+ iodide

≥98% (HPLC), powder

Synonym(s):

1-Methyl-4-phenylpyridinium iodide

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About This Item

Empirical Formula (Hill Notation):
C12H12IN
CAS Number:
36913-39-0
Molecular Weight:
297.13
MDL number:
MFCD00055096
UNSPSC Code:
12352200
PubChem Substance ID:
24893235
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: 10 mg/mL, clear

SMILES string

[I-].C[n+]1ccc(cc1)-c2ccccc2

InChI

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

InChI key

RFDFRDXIIKROAI-UHFFFAOYSA-M

General description

1-Methyl-4-phenylpyridinium (MPP+) acts as a selective ERα antagonist.induces neurotoxicity by inhibiting mitochondrial redox functions in the striatal synaptosomes. It is a potential neurotoxin and induces Parkinson′s disease in animal models. It mediates apoptosis by the generation of reactive oxygen species in cerebellar granule neurons and neuroblastoma cells. MPP+ modulates the distribution of dopamine. It elicits neurotoxicity by activating neuronal nitric oxide synthase (nNOS), resulting in excess nitric oxide.

Application

MPP+ iodide has been used:
  • to induce oxidative stress in zebrafish embryos
  • for the inhibition of glutamate uptake in mitochondria of astrocytes
  • in testing cell viability using MTT (3 (4,5-dimethylthiazol)-2-yl-2,5-diphenyltetrazolium bromide) in microglia (BV2) cells

Biochem/physiol Actions

MPP+ iodide is an active metabolite of dopaminergic neurotoxin MPTP.

Caution

Photosensitive.

Preparation Note

Solutions should be freshly prepared.

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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1-Methyl-4-phenylpyridinium (MPP+)-induced apoptosis and mitochondrial oxidant generation: role of transferrin-receptor-dependent iron and hydrogen peroxide
Kalivendi SV, et al.
The Biochemical Journal, 371(1), 151-164 (2003)
The MPTP story
Langston, J William
Journal of Parkinson's Disease, 7(s1), S11-S19 (2017)
Bart de Nijs et al.
Nature communications, 8(1), 994-994 (2017-10-24)
Nanoparticles attached just above a flat metallic surface can trap optical fields in the nanoscale gap. This enables local spectroscopy of a few molecules within each coupled plasmonic hotspot, with near thousand-fold enhancement of the incident fields. As a result
1-Methyl-4-phenylpyridinium (MPP+) decreases mitochondrial oxidation-reduction (REDOX) activity and membrane potential (DeltaPsim) in rat striatum
Nakai M, et al.
Experimental Neurology, 179(1), 103-110 (2003)
Hai-Bing Zhou et al.
Bioorganic & medicinal chemistry letters, 19(1), 108-110 (2008-11-19)
Methyl-piperidino-pyrazole (MPP), an estrogen receptor alpha (ERalpha)-selective antagonist we developed, has a basic side chain (BSC) attached to an ERalpha-selective agonist ligand, methyl-pyrazole-triol (MPT) through an ether linkage. To remove the possibility that metabolic cleavage of the BSC in MPP
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