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M0896

Sigma-Aldrich

MPTP Hydrochloride

≥98% (AgNO3), powder, dopaminergic neurotoxin

Synonym(s):

MPTP HCl, Pyridine, 1,2,3,6-tetrahydro-1-methyl-4-phenyl-, hydrochloride, MPTP hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C12H15N · HCl
CAS Number:
23007-85-4
Molecular Weight:
209.72
Beilstein:
3707312
MDL number:
MFCD00012790
UNSPSC Code:
12352200
PubChem Substance ID:
24896578
NACRES:
NA.77

product name

1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride, powder

form

powder

Quality Level

200

drug control

kontrollierte Droge in Deutschland

color

white to off-white

SMILES string

Cl[H].CN1CCC(=CC1)c2ccccc2

InChI

1S/C12H15N.ClH/c1-13-9-7-12(8-10-13)11-5-3-2-4-6-11;/h2-7H,8-10H2,1H3;1H

InChI key

KOWJANGMTAZWDT-UHFFFAOYSA-N

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General description

MPTP shows its effects by causing inflammation, excitotoxicity, mitochondrial apoptosis, formation of inclusion bodies, and oxidative stress that leads to dopaminergic neuronal damage in the striatum and substantia nigra. In dopaminergic neurons, MPTP blocks the mitochondrial complex I which leads to mitochondrial dysfunction.

Application

1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride has been used to induce Parkinson′s disease (PD) in animal models:
  • to study the effect of docosahexaenoic acid on the apelin distribution of the nervous system
  • to study the behavioral impairments correlated to neurochemical deficits
  • to study the effects of treadmill exercise on neuroprotection and neuroinflammation

MPTP has been used to study its effects on microglial innate immune memory. It has also been used to study the protective effects of phenylpropionamides in Pakinson’s diseased mice models.

Biochem/physiol Actions

1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) is a piperidine derivative and dopaminergic neurotoxin, useful in neurological research. MPTP is metabolized to 1-methyl-4-phenylpyridine (MPP+), which in turn can cause free radical production in vivo and lead to oxidative stress. Thus MPP+ is generally acknowledged as the active metabolite of MPTP. MPTP is widely used in in vivo research studies as a model for Parkinsonism. A review describes the application of MPTP in studies related to programmed cell death in neurogenerative diseases.
Dopaminergic neurotoxin.

Warning

Reportedly causes a severe and irreversible Parkinsonian condition in humans and monkeys.

Other Notes

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

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H370

Hazard Classifications

Acute Tox. 3 Oral - STOT SE 1

Target Organs

Nervous system

WGK

WGK 3

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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Yi-Kai Jiang et al.
Fitoterapia, 175, 105883-105883 (2024-03-09)
Parkinson's disease (PD) is the second most common neurodegenerative disease in the world. As one of the major degradation pathways, autophagy plays a pivotal role in maintaining the effective turnover of proteins and damaged organelles in cells. Lewy bodies composed
Musa Mustapha et al.
Bosnian journal of basic medical sciences, 21(4), 422-433 (2020-12-29)
Among the popular animal models of Parkinson's disease (PD) commonly used in research are those that employ neurotoxins, especially 1-methyl- 4-phenyl-1, 2, 3, 6-tetrahydropyridine (MPTP). This neurotoxin exerts it neurotoxicity by causing a barrage of insults, such as oxidative stress
Hypoxia inducible factor-1? regulates microglial innate immune memory and the pathology of Parkinson?s disease
Dong, et al.
Journal of Neuroinflammation (2024)
Ibrahim Kaya et al.
NPJ Parkinson's disease, 9(1), 118-118 (2023-07-27)
Metabolism of MPTP (1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine) to the neurotoxin MPP+ in the brain causes permanent Parkinson's disease-like symptoms by destroying dopaminergic neurons in the pars compacta of the substantia nigra in humans and non-human primates. However, the complete molecular pathology underlying MPTP-induced
Isoquinuclidines: a review of chemical and pharmacological properties
Khan MOF, et al.
Studies in Natural Products Chemistry, 34, 753-787 (2008)
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