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M103

Sigma-Aldrich

1-Methyl-4-(2′-methylphenyl)-1,2,3,6-tetrahydropyridine hydrochloride

solid

Synonym(s):

2′-Methyl-MPTP hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C13H17N · HCl
CAS Number:
127382-79-0
Molecular Weight:
223.74
MDL number:
MFCD00055222
UNSPSC Code:
12352200
PubChem Substance ID:
329817848
NACRES:
NA.77

form

solid

Quality Level

100

color

white

solubility

H2O: soluble
ethanol: soluble

SMILES string

Cl[H].CN1CCC(=CC1)c2ccccc2C

InChI

1S/C13H17N.ClH/c1-11-5-3-4-6-13(11)12-7-9-14(2)10-8-12;/h3-7H,8-10H2,1-2H3;1H

InChI key

QLIQCKBPYIWPTE-UHFFFAOYSA-N

Application

1-Methyl-4-(2′-methylphenyl)-1,2,3,6-tetrahydropyridine hydrochloride has been used to study its effect on core temperature in C57BL/6J mice.

Biochem/physiol Actions

1-Methyl-4-(2′-methylphenyl)-1,2,3,6-tetrahydropyridine hydrochloride (MPTP) is a tertiary amine. It is widely used to induce experimental parkinsonism in mice.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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E Sundström et al.
Pharmacology & toxicology, 81(5), 226-231 (1997-12-13)
Three steps in 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) neurotoxicity were compared with the neurodegenerative effects of the toxin in mice and rats. Firstly, we compared the neurotoxicity of MPTP, mediated by monoamine oxidase (MAO)-B, to that of 1-methyl-4-(2'-methylphenyl)-1,2,3,6-tetrahydropyridine (2'-CH3-MPTP), an analogue oxidized by
M Mizobuchi et al.
Brain research, 612(1-2), 319-321 (1993-05-28)
Neuroendocrine abnormality of the hypothalamic-pituitary-adrenal axis was investigated in 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-treated dogs as a model of Parkinson's disease. Blood samples were collected every 4 h for 3-4 days before MPTP treatment, around 2 and 4 weeks after the treatment of
M Del Zompo et al.
British journal of pharmacology, 109(2), 411-414 (1993-06-01)
1. In the present study we provide evidence for a saturable, Mg2+/ATP- and temperature-dependent, tetrabenazine-, dopamine-, and amphetamine-sensitive uptake of 1-methyl-4-phenylpyridinium ion (MPP+) in synaptic vesicles from mouse striatum. 2. Similarity in the properties of the vesicular uptake suggests that
S K Youngster et al.
European journal of pharmacology, 122(2), 283-287 (1986-03-18)
The administration to mice of 1-methyl-4-(2'-methylphenyl)-1,2,3, 6-tetrahydropyridine (2'-CH3-MPTP), a substituted analog of the dopaminergic neurotoxin MPTP caused even more dopaminergic toxicity than MPTP itself. Under conditions in which MPTP was relatively ineffective (i.e. two injections per day of 0.113 mmol/kg
N Lermontova et al.
Molecular and chemical neuropathology, 25(2-3), 135-141 (1995-06-01)
The neurotoxic actions of MPTP and its 4-(O-tolyl) analog (2'-Me-MPTP) on two breeds of rabbits were investigated. MPTP, but not 2'-Me-MPTP, causes a reduction (about 40%) in striatal dopamine content in rabbits of the "little silver-black" breed. The dopamine content
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