Structural Formula Vector Image
Title: MPTP
CAS Registry Number: 28289-54-5
CAS Name: 1,2,3,6-Tetrahydro-1-methyl-4-phenylpyridine
Additional Names: 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
Molecular Formula: C12H15N
Molecular Weight: 173.25
Percent Composition: C 83.19%, H 8.73%, N 8.08%
Literature References: Piperidine derivative which causes irreversible symptoms of parkinsonism in humans, monkeys. Prepn as hydrochloride by Grignard reaction: A. Ziering et al., J. Org. Chem. 12, 894 (1947). Alternative prepn: C. J. Schmidle, R. C. Mansfield, J. Am. Chem. Soc. 78, 425 (1956). Identification as impurity in "synthetic heroin" and effect on drug users: J. W. Langston et al., Science 219, 979 (1983). Selective destruction of dopaminergic neurons in primates: R. S. Burns et al., Proc. Natl. Acad. Sci. USA 80, 4546 (1983). In vitro metabolism by rat brain monoamine oxidase to 1-methyl-4-phenylpyridinium ion (MPP+): K. Chiba et al., Biochem. Biophys. Res. Commun. 120, 574 (1984). Studies on mechanism of neurotoxicity: J. W. Langston et al., Science 225, 1480 (1984); S. P. Markey et al., Nature 311, 464 (1984). Binding studies in rat brain: C. M. Wieczorek et al., Eur. J. Pharmacol. 98, 453 (1984); B. Parsons, T. C. Rainbow, ibid. 102, 375 (1984); in rat, human brain: J. A. Javitch et al., Proc. Natl. Acad. Sci. USA 81, 4591 (1984). Comparison of idiopathic and MPTP-induced parkinsonism in humans: R. S. Burns et al., N. Engl. J. Med. 312, 1418 (1985). Review: T. P. Singer et al., Trends Biochem. Sci. 12, 266-270 (1987); L. M. Sayre, Toxicol. Lett. 48, 121-149 (1989).
Properties: Crystals from heptane, mp 40-42°. bp0.8 85-90°.
Melting point: mp 40-42°
Boiling point: bp0.8 85-90°

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