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199915

Sigma-Aldrich

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

97%

Synonym(s):

MPTP

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About This Item

Empirical Formula (Hill Notation):
C12H15N
CAS Number:
28289-54-5
Molecular Weight:
173.25
MDL number:
MFCD00006120
UNSPSC Code:
12352200
PubChem Substance ID:
329751964

assay

97%

form

solid

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

Skull and crossbonesHealth hazard
GHS06,GHS08

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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Gejuan Zhang et al.
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Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 40(1-2), 18-26 (2016-11-15)
Development of effective therapeutic drugs for Parkinson's disease is in great need. During the progression of Parkinson's disease, Rho-associated protein kinase 2 (ROCK2) is activated to promote neurodegeneration. Hydrogen sulfide (H2S) has a neuroprotective effect during the neural injury of
David I Finkelstein et al.
Acta neuropathologica communications, 5(1), 53-53 (2017-07-01)
Elevated iron in the SNpc may play a key role in Parkinson's disease (PD) neurodegeneration since drug candidates with high iron affinity rescue PD animal models, and one candidate, deferirpone, has shown efficacy recently in a phase two clinical trial.
Adjia Hamadjida et al.
Journal of neural transmission (Vienna, Austria : 1996), 125(9), 1355-1360 (2017-12-17)
Trazodone is a clinically available anti-depressant that exhibits affinity for serotonin 1A and 2A receptors, as well as for alpha-adrenoceptors, suggesting that it may be useful to treat L-3,4-dihydroxyphenylalanine (L-DOPA)-induced dyskinesia and psychosis that are encountered in advanced Parkinson's disease
Yan Liu et al.
Aging, 11(14), 5008-5034 (2019-07-18)
Parkinson's disease (PD) is a common neurodegenerative disease, featured by motor deficits and non-motor symptoms such as cognitive impairment, and malfunction of gamma-aminobutyric acid (GABA) mediated inhibitory transmission plays an important role in PD pathogenesis. The ginsenoside Rb1 molecule, a
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