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M1021

Sigma-Aldrich

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

Synonym(s):

MPTP

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About This Item

Empirical Formula (Hill Notation):
C12H15N
CAS Number:
28289-54-5
Molecular Weight:
173.25
EC Number:
248-939-7
MDL number:
MFCD00006120
UNSPSC Code:
12352100

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

bp

128-132 °C/12 mmHg (lit.)

SMILES string

CN1CCC(=CC1)c2ccccc2

InChI

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

InChI key

PLRACCBDVIHHLZ-UHFFFAOYSA-N

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Biochem/physiol Actions

Dopaminergic neurotoxin.

Warning

Reportedly causes a severe and irreversible Parkinsonism condition in humans and monkeys. New Engl. J. Med. 1983, 309, 310. Science 1983, 219, 979. ibid. 1984, 224, 1083, 1451. ibid. 1984, 225, 529. J. Med. Chem. 1985, 28, 997.

pictograms

Health hazardSkull and crossbones
GHS08,GHS06

signalword

Danger

hcodes

H301,H370

Hazard Classifications

Acute Tox. 3 Oral - STOT SE 1

Storage Class

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

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

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Cécile Moro et al.
BMC neuroscience, 14, 40-40 (2013-03-28)
We have shown previously that near-infrared light (NIr) treatment or photobiomodulation neuroprotects dopaminergic cells in substantia nigra pars compacta (SNc) from degeneration induced by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) in Balb/c albino mice, a well-known model for Parkinson's disease. The present study explores
Some features of the nigrostriatal dopaminergic neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) in the mouse.
R E Heikkila et al.
Molecular and chemical neuropathology, 10(3), 171-183 (1989-06-01)
Sang-Bing Ong et al.
Thrombosis and haemostasis, 113(3), 513-521 (2014-09-26)
The mechanism through which the protein kinase Akt (also called PKB), protects the heart against acute ischaemia-reperfusion injury (IRI) is not clear. Here, we investigate whether Akt mediates its cardioprotective effect by modulating mitochondrial morphology. Transfection of HL-1 cardiac cells
The pharmacology of the parkinsonian syndrome producing neurotoxin MPTP (1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine) and structurally related compounds.
S P Markey et al.
Medicinal research reviews, 6(4), 389-429 (1986-10-01)
Rui D S Prediger et al.
Current pharmaceutical design, 17(5), 489-507 (2011-03-08)
Parkinson's disease (PD) is the second most common neurodegenerative disorder affecting approximately 1% of the population older than 60 years. Classically, PD is considered to be a motor system disease and its diagnosis is based on the presence of a
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