The MPTP Story: Mao Activates Tetrahydropyridine Derivatives to Toxins Causing Parkinsonism

References

• Tretiakoff C. 1919, Contribution à lètude de ľanatomie pathologique du locus niger de Soemmering avec quelques déductions relatives à la pathogénie des troubles du tonus musculaire et de la maladie de Parkinson, Thèse de Paris
   Google Scholar
• Hassler R. “Zur Pathologie der Paralysis Agitans und des postenzephalitischen Parkinsonismus”. J. Psychol. Neurol 1938; 48: 387–476
   Google Scholar
• Greenfield J. G., Bosanquet F. D. “The brain-stem lesions in parkinsonism”. J. Neurol. Neurosurgery Psychiatry 1953; 16: 213–226
   PubMed Web of Science ®Google Scholar
• Ehringer H., Hornykiewicz O. “Verteilung von Noradrenalin und Dopamin (3-Hydroxytyramin) im Gehirn des Menschen und ihr Verhalten bei Erkrankungen des extrapyramidalen System”. Klinische Wochenschrift 1960; 38: 1238–1239
   Google Scholar
• Bernheimer H., Birkmayer W., Hornykiewicz O. “Zur Biochemie des Parkinsonsyndroms des Menschen”. Klinische Wochenschrift 1963; 41: 564–569
   Google Scholar
• Bernheimer H., Hornykiewicz O. “Herabgesetzte Konzentration der Homovanillinsäure im Gehirn von Parkinsonkranken Menschen als Ausdruck der Storung des Zentralen Dopaminstoffwechsel”. Klinische Wochenschrift 1965; 43: 711–715
   PubMedGoogle Scholar
• Jenner P. Clues to the mechanism underlying dopamine cell death in Parkinson's disease. J. Neurol. Neurosurgery Psychiatry 1989; 22–28, Special Suppl.
   PubMed Web of Science ®Google Scholar
• Jenner P. MPTP-induced parkinsonism: the relevance to idiopathic Parkinson's disease. Disorders of movement, N. Quinn, P. Jenner. Academic Press, London 1989; 157–175
   Google Scholar
• Duvoisin R. C. The cause of Parkinson's disease. Neurology 2, Movement Disorders, C. D. Marsden, S. Fahn. Butterworth Scientific, London 1981; 8–24
   Google Scholar
• Calne D. B., Langston J. W. Aetiology of Parkinson's disease. Lancet 1983; ii: 1457–1459
   Google Scholar
• Duvoisin R. C., Eldridge R., Williams A., Nutt J., Calne D. Twin study of Parkinson disease. Neurology 1981; 31: 77–80
   PubMed Web of Science ®Google Scholar
• Tanner C. M. “The role of environmental toxins in the aetiology of Parkinson's disease”. Trends Neurol. Sci. 1989; 12: 49–54
   PubMed Web of Science ®Google Scholar
• Barbeau A., Cloutier T., Roy M., Plasse L., Paris S., Poirier J. Ecogenetics of Parkinson's disease: 4-hydroxylation of debrisoquine. Lancet 1985; ii: 1213–1216
   Google Scholar
• Poirier J., Roy M., Campanella G., Cloutier T., Paris S. Debrisoquine metabolism in parkinsonian patients treated with antihistamine drugs. Lancet 1987; i: 386
   Google Scholar
• Cornelia C. L., Tanner C. M., Goetz C. G., Gans S., Rapp D., Fischer J. Debrisoquine metabolism in Parkinson's disease. Neurol. 1987; 37: 261–262, Suppl. 1
   Google Scholar
• Makino Y., Ohta S., Tachikawa O., Hirobe M. “Presence of tetrahydroisoquinoline and 1-methyl-tetrahydro-isoquinoline in foods: compounds related to Parkinson's disease”. Life Sci. 1988; 43: 373–378
   PubMed Web of Science ®Google Scholar
• Waring R. H., Steventon G. B., Sturman S. G., Heafield M. T. E., Smith M. C. G., Williams A. C. S-methylation in motorneuron disease and Parkinson's disease. Lancet 1989; i: 356–357
   Google Scholar
• Steventon G. B., Heafield M. T. E., Waring R. H., Williams A. C. Xenobiotic metabolism in Parkinson's disease. Neurology 1989; 39: 883–887
   PubMed Web of Science ®Google Scholar
• Nefzeger M. D., Quadfasel F. A., Karl A. A retrospective study of smoking in Parkinson's disease. Am. J. Epidemiol 1968; 88: 149–158
   PubMed Web of Science ®Google Scholar
• Kessler I. I., Diamond K. L. “Epidemiological studies of Parkinson's disease: I. Smoking and Parkinson's disease”. Am. J. Epidemiol. 1971; 94: 16–25
   PubMed Web of Science ®Google Scholar
• Bauman R. J., Jameson H. D., Weisberg L. H., McKean H. E., Haack D. G. Cigarette smoking and Parkinson's disease. Neurology 1980; 30: 839–843
   PubMed Web of Science ®Google Scholar
• Perry T. L., Godin D. V., Hansen S. Parkinson's disease: A disorder due to nigral glutathione deficiency?. Neurosci. Lett. 1982; 33: 305–310
   PubMed Web of Science ®Google Scholar
• Perry T. L., Yong V. W. Idiopathic Parkinson's disease, progressive supranuclear palsy and glutathione metabolism in the substantia nigra of patients. Neurosci. Lett. 1986; 67: 269–274
   PubMed Web of Science ®Google Scholar
• Bannon M. J., Goedert M., Williams B. The possible relation of glutathione, melanin and l-methyl-4-phenyl-1,2,5,6-tetrahydropyridine (MPTP) to Parkinson's disease. Biochem. Pharmacol 1984; 33: 2697–2698
   PubMed Web of Science ®Google Scholar
• Graham D. G. “Oxidative pathways for catecholamine in the genesis of neuromelanin and cytotoxic quinones”. Mol Pharmacol 1978; 14: 633–643
   PubMed Web of Science ®Google Scholar
• Pawelek J. M., Lerner A. B. 5,6-Dihydroxyindole is a melanin precursor showing potent cytotoxicity. Nature 1978; 276: 627–628
   Web of Science ®Google Scholar
• Marsden C. D. “Neuromelanin and Parkinson's disease”. J. Neural. Trans., Suppl 1983; 19: 121–141
   PubMedGoogle Scholar
• Blin J., Bonnet A.-M., Agid Y. Does levodopa aggravate Parkinson's disease?. Neurology 1988; 38: 1410–1416
   PubMed Web of Science ®Google Scholar
• Davis G. C., Williams A. C., Markey S. P., Ebert M. H., Caine E. D., Reichert C. M., Kopin I. J. “Chronic Parkinsonism secondary to intravenous injection of meperidine analogues”. Psychiatry Res. 1979; 1: 249–254
   PubMed Web of Science ®Google Scholar
• Langston J. W., Ballard P., Tetrud J. W., Irwin I. “Chronic Parkinsonism in humans due to a product of meperidine-analog synthesis”. Science 1983; 219: 979–980
   PubMed Web of Science ®Google Scholar
• Ballard P. A., Langston J. W., Tetrud J., Burns R. S. Chemically induced chronic parkinsonism in young adults: clinical and neuropharmacologic aspects. Neurology 1983; 33: 90, Suppl. 2
   PubMedGoogle Scholar
• Langston J. W., Ballard P. Parkinsonism induced by l-methyl-4- phenyl-1,2,3,6-tetrahydropyridine (MPTP): Implications for treatment and the pathogenesis of Parkinson's disease. Canad. J. Neurol. Sci. 1984; 11: 160–165
   PubMed Web of Science ®Google Scholar
• Burns R. S., Chiueh C. C., Markey S. P., Ebert M. H., Jacobowitz D. M., Kopin I. J. A primate model of parkinsonism: selective destruction of dopaminergic neurons in the pars compacta of the substantia nigra by N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine. Proc. Natl. Acad. Sci. USA 1983; 80: 4546–4550
   PubMed Web of Science ®Google Scholar
• Kolata G. Monkey model of Parkinson's disease. Science 1983; 220: 705
   PubMed Web of Science ®Google Scholar
• Langston J. W., Forno L. S., Rebert C. S., Irwin I. Selective nigral toxicity after systematic administration of l-methyl-4-phenyl-1,2,5,6- tetrahydropyridine (MPTP) in the squirrel monkey. Brain Res. 1984; 292: 390–394
   PubMed Web of Science ®Google Scholar
• Forno L. S., Langston J. W., DeLanney L. E., Irwin I., Ricaurte G. A. “Locus ceruleus lesions and eosinophilic inclusions in MPTP-treated monkeys”. Ann. Neurol 1986; 20: 449–455
   PubMed Web of Science ®Google Scholar
• Forno L. S., Langston J. W., DeLanney L. E., Irwin I. “An electron microscopic study of MPTP-induced inclusion bodies in an old monkey”. Brain Res. 1988; 448: 150–157
   PubMed Web of Science ®Google Scholar
• Miyoshi R., Kito S., Ishida H., Katayama S. Alterations of the central noradrenergic system in MPTP-induced monkey parkinsonism. Res. Commun. Chem. Pathol. Pharmacol. 1988; 62: 93–102
   PubMedGoogle Scholar
• Pifl C., Schingnitz G., Homykiewicz O. “The neurotoxin MPTP does not reproduce in the rhesus monkey the interregional pattern of striatal dopamine loss typical of human idiopathic Parkinson's disease”. Neurosci. Lett. 1988; 92: 228–233
   PubMed Web of Science ®Google Scholar
• Markey S. P., Johannessen J. N., Chiueh C. C., Burns R. S., Herkenham M. A. “Intraneuronal generation of a pyridinium metabolite may cause drug-induced parkinsonism”. Nature 1984; 311: 464–467
   PubMed Web of Science ®Google Scholar
• Langston J. W., Irwin I., Langston E. B., Forno L. S. 1-Methyl-4-phenylpyridinium ion (MPP+): Identification of a metabolite of MPTP, a toxin selective to the substantia nigra. Neurosci. Lett. 1984; 48: 87–92
   PubMed Web of Science ®Google Scholar
• Heikkila R. E., Manzino L., Cabbat F. S., Duvoisin R. C. Protection against the dopaminergic neurotoxicity of l-methyl-4-phenyl-1,2,5,6-tetrahydropyridine by monoamine oxidase inhibitors. Nature 1984; 311: 467–469
   PubMed Web of Science ®Google Scholar
• Chiba K., Trevor A, Castagnoli N., Jr. Metabolism of the neurotoxic tertiary amine, MPTP, by brain monoamine oxidase. Biochem. Biophys. Res. Commun. 1984; 120: 574–578
   PubMed Web of Science ®Google Scholar
• Chiba K., Peterson L. A., Castagnoli K. P., Trevor A. J., Castagnoli N., Jr. Studies on the molecular mechanism of bioactivation of the selective nigrostriatal toxin l-methyl-4-phenyl-1,2,3,6-tetrahydro-pyridine. Drug. Metab. Dispos. 1985; 13: 342–347
   PubMed Web of Science ®Google Scholar
• Kindt M. V., Youngster S. K., Sonsalla P. K., Duvoisin R. C., Heikkila R. E. Role for monoamine oxidase-A (MAO-A) in the bioactivation and nigrostriatal dopaminergic neurotoxicity of the MPTP analog, 2′-Me-MPTP. Eur. J. Pharmacol 1988; 146: 313–318
   PubMed Web of Science ®Google Scholar
• Heikkila R. E., Kindt M. V., Sonsalla P. K., Giovanni A., Youngster S. K., McKeown K. A., Singer T. P. Importance of monoamine oxidase A in the bioactivation of neurotoxic analogs of l-methyl-4-phenyl-1,2,3,6-tetrahydropyridine. Proc. Natl. Acad. Sci. USA 1988; 85: 6172–6176
   PubMed Web of Science ®Google Scholar
• Javitch J. A., d'Amato R. J., Strittmatter S. M., Snyder S. H. Parkinsonism-inducing neurotoxin, N-methyl-4-phenyl-1,2,3,6-tetra-hydropyridine: uptake of the metabolite N-methyl-4-phenylpyridine by dopamine neurons explains selective toxicity. Proc. Natl. Acad. Sci. USA 1985; 82: 2173–2177
   PubMed Web of Science ®Google Scholar
• Chiba K., Trevor A. J., Castagnoli N., Jr. Active uptake of MPP+, a metabolite of MPTP, by brain synaptosomes. Biochem. Biophys. Res. Commun. 1985; 128: 1228–1232
   PubMed Web of Science ®Google Scholar
• Naoi M., Suzuki H., Kiuchi K., Takahashi T., Nagatsu T. Effect of N-methyl-4-phenylpyridinium ion on monoamine oxidase in a clonal rat pheochromocytoma cell line, PC12h. J. Neurochem. 1987; 48: 1912–1916
   PubMed Web of Science ®Google Scholar
• Takahashi T., Naoi M., Nagatsu T. Uptake of N-methyl-4-phenylpyridinium ion (MPP+) into PC12h pheochromocytoma cells. Neurochem. Int. 1987; 11: 89–93
   PubMed Web of Science ®Google Scholar
• d'Amato R. J., Lipman Z. P., Snyder S. H. Selectivity of the parkinsonian neurotoxin MPTP: toxic metabolite MPP+ binds to neuromelanin. Science 1986; 231: 987–989
   PubMed Web of Science ®Google Scholar
• d'Amato R. J., Benham D. F., Snyder S. H. Characterization of the binding of N-methyl-4-phenylpyridine, the toxic metabolite of the parkinsonian neurotoxin AT-methyl-4-phenyl-1,2,3,6-tetrahydropyri-dine, to neuromelanin. J. Neurochem. 1987; 48: 653–658
   PubMed Web of Science ®Google Scholar
• Mayer R. A., Kindt M. V., Heikkila R. E. Prevention of the nigrostriatal toxicity of l-methyl-4-phenyl-1,2,3,6-tetrahydropyridine by inhibitors of 3,4-dihydroxyphenylethylamine transport. J. Neurochem. 1986; 47: 1073–1079
   PubMed Web of Science ®Google Scholar
• Barnes N. J. G., Costall B., Naylor R. J. Is the dopamine uptake system required for MPTP to induce neurotoxicity in the primate brain?. Br. J. Pharmacol 1987; 90: 241P
   Google Scholar
• Schultz W., Scarnati E., Sundström E., Tsutsumi T., Jonsson G. “The catecholamine uptake blocker nomifensine protects against MPTP-induced parkinsonism in monkeys”. Exp. Brain Res. 1986; 63: 216–220
   PubMed Web of Science ®Google Scholar
• Ramsay R. R., Singer T. P. Energy-dependent uptake of N-methyl-4-phenylpyridinium, the neurotoxic metabolite of l-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, by mitochondria. J. Biol. Chem. 1986; 261: 7585–7587
   PubMed Web of Science ®Google Scholar
• Ramsay R. R., Dadgar J., Trevor A., Singer T. P. Energy-driven uptake of N-methyl-4-phenylpyridine by brain mitochondria mediates the neurotoxicity of MPTP. Life Sci. 1986; 39: 581–588
   PubMed Web of Science ®Google Scholar
• Ramsay R. R., Salach J. I., Singer T. P. Uptake of the neurotoxin 1-methyl-4-phenylpyridine (MPP+) by mitochondria and its relation to the inhibition of the mitochondrial oxidation of NADMinked substrates by MPP+. Biochem. Biophys. Res. Commun. 1986; 134: 743–748
   PubMed Web of Science ®Google Scholar
• Nicklas W. J., Vyas I., Heikkila R. E. Inhibition of NADH-linked oxidation in brain mitochondria by l-methyl-4-phenylpyridine, a metabolite of the neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropy-ridine. Life Sci. 1985; 36: 2503–2508
   PubMed Web of Science ®Google Scholar
• Vyas I., Heikkila R. E., Nicklas W. J. Studies on the neurotoxicity of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine: Inhibition of NAD-linked substrate oxidation by its metabolite, 1-methyl-4-phenylpyri-dinium. J. Neurochem. 1986; 46: 1501–1507
   PubMed Web of Science ®Google Scholar
• Singer T. P., Castagnoli N., Jr., Ramsay R. R., Trevor A. J. Biochemical events in the development of parkinsonism induced by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine,7. Neurochem. 1987; 49: 1–8
   PubMed Web of Science ®Google Scholar
• Poirier J., Barbeau A. 1-Methyl-4-phenyl-pyridinium-induced inhibition of nicotinamide adenosine dinucleotide cytochrome c reductase. Neurosci. Lett. 1985; 62: 7–11
   PubMed Web of Science ®Google Scholar
• Ramsay R. R., Salach J. I., Dadgar J., Singer T. P. “Inhibition of mitochondrial NADH dehydrogenase by pyridine derivatives and its possible relation to experimental idiopathic parkinsonism”. Biochem. Biophys. Res. Commun. 1986; 135: 269–275
   PubMed Web of Science ®Google Scholar
• Ramsay R. R., McKeown K. A., Johnson E. A., Booth R. G., Singer T. P. “Inhibition of NADH oxidation by pyridine derivatives”. Biochem. Biophys. Res. Commun. 1987; 146: 53–60
   PubMed Web of Science ®Google Scholar
• Ramsay R. R., Kowal A. T., Johnson M. K., Salach J. I., Singer T. P. The inhibition site of MPP+, the neurotoxic bioactivation product of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine is near the Q-binding site of NADH dehydrogenase. Arch. Biochem. Biophys. 1987; 259: 645–649
   PubMed Web of Science ®Google Scholar
• Rollema H., Kuhr W. G., Kranenborg G., de Vries J., van den Berg C. MPP+ -induced efflux of dopamine and lactate from rat striatum have similar time courses as shown by in vivo brain dialysis. J. Pharmacol. Exp. Ther. 1988; 245: 858–866
   PubMed Web of Science ®Google Scholar
• Mizuno Y., Saitoh T., Sone N. “Inhibition of mitochondrial NADH-ubiquinone oxidoreductase activity by 1-methyl-4-phenylpy-ridinium ion”. Biochem. Biophys. Res. Commun. 1987; 143: 294–299
   PubMed Web of Science ®Google Scholar
• Mizuno Y., Suzuki K., Sone N., Saitoh T. Inhibition of ATP synthesis by 1-methyl-4-phenylpyridinium ion (MPP+) in isolated mitochondria from mouse brains. Neurosci. Lett. 1987; 81: 204–208
   PubMed Web of Science ®Google Scholar
• Sanchez-Ramos J. R., Hollinden G. E., Stick T. J., Rosenthal M. 1-Methyl-4-phenylpyridinium (MPP+) increases oxidation of cytochrome-*) in rat striatal slices. Brain Res. 1988; 443: 183–189
   PubMed Web of Science ®Google Scholar
• Singer T. P., Ramsay R. R., McKeown K., Trevor A., Castagnoli N. E., Jr. Mechanism of the neurotoxicity of l-methyl-4-phenylpyridinium (MPP+), the toxic bioactivation product of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP). Toxicology 1988; 49: 17–23
   PubMed Web of Science ®Google Scholar
• DiMonte D., Jewell S. A., Ekstrom G., Sandy M. S., Smith M. T. 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) and 1-methyl-4-phenyl-pyridine (MPP+) cause rapid ATP depletion in isolated hepatocytes. Biochem. Biophys. Res. Commun. 1986; 137: 310–315
   PubMed Web of Science ®Google Scholar
• DiMonte D., Sandy M. S., Smith M. T. Increase efflux rather than oxidation is the mechanism of glutathione depletion by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP). Biochem. Biophys. Res. Commun. 1987; 148: 153–160
   PubMed Web of Science ®Google Scholar
• Kass G. E. N., Wright J. W., Nicotera P., Orrenius S. The mechanism of 1-mefhyl-4-phenyl-1,2,3,6-tetrahydropyridine toxicity: role of intracellular calcium. Arch. Biochem. Biophys. 1988; 260: 789–797
   PubMed Web of Science ®Google Scholar
• Rossetti Z. L., Sotgiu A., Sharp D. E., Hadjiconstantinou M., Neff N. H. 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) and free radicals in vitro. Biochem. Pharmacol. 1988; 37: 4573–4574
   PubMed Web of Science ®Google Scholar
• DiMonte D., Sandy M. S., Ekstrom G., Smith M. T. Comparatives studies on the mechanisms of paraquat and 1-methyl-4-phenyl-pyridine (MPP+) cytotoxicity. Biochem. Biophys. Res. Commun. 1986; 137: 303–309
   PubMed Web of Science ®Google Scholar
• Frank D. M., Arora P. K., Blumer J. L., Sayre L. M. Model study on the bioreduction of paraquat, MPP+, and analogs. Evidence against a “redox cycling” mechanism in MPTP neurotoxicity. Biochem. Biophys. Res. Commun. 1987; 147: 1095–1104
   PubMed Web of Science ®Google Scholar
• Sayre L. M., Arora P. K., Feke S. C., Urbach F. L. Mechanism of induction of Parkinson's disease by 1-methyl-4-phenyl-1,2,3,6-tetra-hydropyridine (MPTP). Chemical and electrochemical characterization of a geminal-dimethyl-blocked analogue of a postulated toxic metabolite. J. Am. Chem. Soc 1986; 108: 2464–2466
   PubMed Web of Science ®Google Scholar
• Linkous C. A., Schaich K. M., Forman A., Borg D. C. An electrochemical study of the neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine and its oxidation products. Bioelectrochemistry and Bioenergetics 1988; 19: 477–490, (a section of J. Electroanal. Chem. 253)
   Web of Science ®Google Scholar
• Castagnoli N., Jr., Chiba K., Trevor A. J. Potential bioactivation pathways for the neurotoxin 1-mefhyl-4-phenyl-1,2,3,6-tetrahydropy-ridine (MPTP). Life ScL 1985; 36: 225–230
   PubMed Web of Science ®Google Scholar
• Peterson L. A., Caldera P. S., Trevor A., Chiba K., Castagnoli N., Jr. Studies on the 1-methyl-4-phenyl-2,3-dihydropyridinium species 2,3-MPDP+, the monoamine oxidase catalyzed oxidation product of the nigrostriatal toxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP). J. Med. Chem. 1985; 28: 1432–1436
   PubMed Web of Science ®Google Scholar
• Trevor A. J., Castagnoli N., Jr., Caldera P., Ramsay R. R., Singer T. P. “Bioactivation of MPTP: Reactive metabolites and possible biochemical sequelae”. Life Sci. 1987; 40: 713–719
   PubMed Web of Science ®Google Scholar
• Chacón J. N., Chedekel M. R., Land E. J., Truscott T. G. Chemically induced Parkinson's disease II: Intermediates in the oxidation and reduction reactions of the 1-methyl-4-phenyl-2,3-dihydropyridinium ion and its deprotonated form. Biochem. Biophys. Res. Commun. 1989; 158: 63–71
   PubMed Web of Science ®Google Scholar
• Snyder S. H., d'Amato R. J. “Predicting Parkinson's disease”. Nature 1985; 317: 198–199
   PubMedGoogle Scholar
• Snyder S. H., d'Amato R. J. “MPTP: A neurotoxin relevant to the pathophysiology of Parkinson's disease”. Neurology 1986; 36: 250–258
   PubMed Web of Science ®Google Scholar
• Arai Y., Kinemuchi H., Hamamichi N., Satoh N., Tadano T., Kisara K. Inhibition of rat brain monoamine oxidase by some analogues of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine and l-methyl-4-phenylpyridinium ion. Neurosci. Lett. 1986; 66: 43–48
   PubMed Web of Science ®Google Scholar
• Irwin I., Langston J. W., DeLanney L. E. 4-Phenylpyridine (4PP) and MPTP: The relationship between striatal MPP+ concentrations and neurotoxicity. Life Sci. 1987; 40: 731–740
   PubMed Web of Science ®Google Scholar
• Ansher S. S., Cadet J. L., Jakoby W. B., Baker J. K. Role of N-methyltransferases in the neurotoxicity associated with the metabolites of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) and other 4-substituted pyridines present in the environment. Biochem. Pharmacol. 1986; 35: 3359–3363
   PubMed Web of Science ®Google Scholar
• Godin C. S., Crooks P. A. N-methylation as toxication route for xenobiotics. II. In vivo formation of NN′-dimethyl-4,4′-bipyridyl ion (Paraquat) from 4,4′-bipyridyl in the guinea pig. Drug Metab. Dispos. 1989; 17: 180–185
   PubMed Web of Science ®Google Scholar
• Perry T. L., Jones K., Hansen S., Wall R. A. 2-Phenylpyridine and 3-phenylpyridine, constituents of tea, are unlikely to cause idiopathic Parkinson's disease. J. Neurol. Sci. 1988; 85: 309–317
   PubMed Web of Science ®Google Scholar
• Perry T. L., Jones K., Hansen S., Wall R. A. 4-Phenylpyridine and three other analogues of l-methyl-4-phenyl-1,2,3,6-tetrahydropyridine lack dopaminergic nigrostriatal neurotoxicity in mice and marmosets. Neurosci. Lett. 1987; 75: 65–70
   PubMed Web of Science ®Google Scholar
• Suzuki K., Mizuno Y., Yoshida M. “Selective inhibition of complex I of the brain electron transport system by tetrahydroisoquinoline”. Biochem. Biophys. Res. Commun. 1989; 162: 1541–1545
   PubMed Web of Science ®Google Scholar
• Fuller R. W., Hemrick-Luecke S. K. Persistent depletion of striatal dopamine in mice by m-hydroxy-MPTP. Res. Commun. Chem. Pathol. Pharmacol. 1986; 53: 167–172
   PubMedGoogle Scholar
• Zimmerman D. M., Cantrell B. E., Reel J. K., Hemrick-Luecke S. K., Fuller R. W. Characterization of the neurotoxic potential of m-methoxy-MPTP and the use of its N-ethyl analogue as a means of avoiding exposure to a possible parkinsonism-causing agent. J. Med. Chem. 1986; 29: 1517–1520
   PubMed Web of Science ®Google Scholar
• Fuller R. W., Hemrick-Luecke S. K. Persistent depletion of striatal dopamine and its metabolites in mice by TMMP, an analogue of MPTP. J. Pharm. Phamacol 1987; 39: 667–669
   PubMed Web of Science ®Google Scholar
• Fuller R. W., Hemrick-Luecke S. K. Depletion of heart norepinephrine in mice by some analogs of MPTP (1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine). Res. Commun. Chem. Pathol. Pharmacol 1987; 56: 147–156
   PubMedGoogle Scholar
• Fuller R. W., Hemrick-Luecke S. K., Robertson D. W. Comparison of l-methyl-4-(p-chlorophenyl)-1,2,3,6-tetrahydropyridine, 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) and p-chloroampheta-mine as monoamine depletors. Res. Commun. Chem. Pathol. Pharmacol. 1985; 50: 57–65
   PubMedGoogle Scholar
• Fuller R. W., Robertson D. W., Hemrick-Luecke S. K. Comparison of the effects of two 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine analogs, 1-methyl-4-(2-thienyl)-1,2,3,6-tetrahydropyridine and 1-methyl-4-(3-thienyl)-1,2,3,6-tetrahydropyridine, on monoamine oxidase in vitro and on dopamine in mouse brain. J. Pharmacol. Exp. Ther. 1987; 240: 415–420
   PubMed Web of Science ®Google Scholar
• Markey S. P., Schmuff N. R. The pharmacology of the parkinsonian syndrome producing neurotoxin MPTP (1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine) and structurally related compounds. Med. Res. Rev. 1986; 6: 389–429
   PubMed Web of Science ®Google Scholar
• Gessner W., Brossi A., Shen R.-S., Abell C. W. Synthesis and dihydropteridine reductase inhibitory effects of potential metabolites of the neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine. J. Med. Chem. 1985; 25: 311–317
   Google Scholar
• Hoppel C. L., Greenblatt D., Kwok H.-C., Arora P. K., Singh M. P., Sayre L. M. Inhibition of mitochondrial respiration by analogs of 4-phenylpyridine and 1-methyl-4-phenylpyridinium cation (MPP+), the neurotoxic metabolite of MPTP. Biochem. Biophys. Res. Commun. 1987; 148: 684–693
   PubMed Web of Science ®Google Scholar
• Finnegan K. T., Irwin I., DeLanney L. E., Ricaurte G. A., Langston J. W. 1,2,3,6-Tetrahydro-1-methyl-4-(methylpyrrol-2-yl)pyridine: Studies on the mechanism of action of 1-methyl-4-phenyl-1,2,3,6- tetrahydropyridine. J. Pharmacol. Exp. Ther. 1987; 242: 1144–1151
   PubMed Web of Science ®Google Scholar
• Heikkila R. E., Manzino L., Cabbat F. S., Duvoisin R. C. Effects of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) and several of its analogues on the dopaminergic nigrostriatal pathway in mice. Neurosci. Lett. 1985; 58: 133–137
   PubMed Web of Science ®Google Scholar
• Youngster S. K., Duvoisin R. C., Hess A., Sonsalla P. K., Kindt M. V., Heikkila R. E. 1-Methyl-4-(2′-methylphenyl)-1,2,3,6-tetrahydropyridine (2′-CH3-MPTP) is a more potent dopaminergic neurotoxin than MPTP in mice. Eur. J. Pharmacol. 1986; 122: 283–287
   PubMed Web of Science ®Google Scholar
• Sonsalla P. K., Youngster S. K., Kindt M. V., Heikkila R. E. Characteristics of 1 -methyl-4-(2′-methylpheny 1)-1,2,3,6-tetrahydropy-ridine-induced neurotoxicity in the mouse. J. Pharmacol. Exp. Then 1987; 242: 850–857
   PubMed Web of Science ®Google Scholar
• Youngster S. K., Saari W. S., Heikkila R. E. 1-Methyl-4-cyclohexyl-1,2,3,6-tetrahydropyridine (MCTP): An alicyclic MPTP like neurotoxin. Neurosci. Lett. 1987; 79: 151–156
   PubMed Web of Science ®Google Scholar
• Fries D. S., de Vries J., Hazelhoff B., Horn A. S. Synthesis and toxicity towards nigrostriatal dopamine neurons of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) analogues. J. Med. Chem. 1986; 29: 424–427
   PubMed Web of Science ®Google Scholar
• Johannessen J. N., Savitt J. M., Markey C. J., Bacon J. P., Weisz A., Hanselman D. S., Markey S. P. “the development of amine substituted analogues of MPTP as unique tools for the study of MPTP toxicity and Parkinson's disease”. Life Sci. 1987; 40: 697–704
   PubMed Web of Science ®Google Scholar
• Riachi N. J., Arora P. K., Sayre L. M., Harik S. I. Potent neurotoxic fluorinated 1 -methyl-4-plienyl-1,2,3,6-tetrahydropyridine analogs as potential probes in models of Parkinson's disease. J. Neurochem. 1988; 50: 1319–1321
   PubMed Web of Science ®Google Scholar
• Testa B., Naylor R., Costall B., Jenner P., Marsden C. D. Does an endogenous methylpyridinium analogue cause Parkinson's disease?. J. Pharm. Pharmacol. 1985; 37: 679–680
   PubMed Web of Science ®Google Scholar
• Nagatsu T., Hirata Y. Inhibition of the tyrosine hydroxylase system by MPTP, 1-methyl-4-phenylpyridinium ion (MPP+) and the structurally related compounds in vitro and in vivo. Eur. J. Neurol. 1987; 26(Suppl. 1)11–15
   Google Scholar
• Nagatsu T., Yoshida M. An endogenous substance of the brain, tetrahydroisoquinoline, produces parkinsonism in primates with decreased dopamine, tyrosine hydroxylase and biopterin in the nigrostriatal regions. Neurosci. Lett. 1988; 87: 178–182
   PubMed Web of Science ®Google Scholar
• Sandler Carter M., Bonham S., Hunter K. R., Stern G. M. Tetrahydroisoquinoline alkaloids: in vivo metabolites of L-dopa in man. Nature 1973; 241: 439–443
   PubMed Web of Science ®Google Scholar
• Collins M. A., Neafsey E. J. β-Carboline analogues of N-methyl-4-phenyl-1,2,5,6-tetrahydropyridine (MPTP): Endogenous factors underlying idiopathic Parkinsonism?. Neurosci. Lett. 1985; 55: 179–184
   PubMed Web of Science ®Google Scholar
• Ramsden D. B., Williams A. C. Production in nature of compounds resembling methylphenyltetrahydropyridine, a possible cause of Parkinson's disease. Lancet 1985; i: 215–216
   Google Scholar
• Fellman J. H., Nutt J. N. MPTP-like molecules and Parkinson's disease. Lancet 1985; i: 924
   Google Scholar
• Ohkubo S., Hirano T., Oka K. Methyltetrahydro-β-carbolines and Parkinson's disease. Lancet 1985; i: 1272–1273
   Google Scholar
• Youngster S. K., Sonsalla P. K., Sieber B.-A., Heikkila R. E. Structure-activity study of the mechanism of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced neurotoxicity. I. Evaluation of the biological activity of MPTP analogs. J. Pharmacol. Exp. Ther. 1989; 249: 820–828
   PubMed Web of Science ®Google Scholar
• Youngster S. K., Sonsalla P. K., Heikkila R. E. Evaluation of the biological activity of several analogs of the dopaminergic neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine. J. Neurochem. 1987; 48: 929–934
   PubMed Web of Science ®Google Scholar
• Nicklas W. J., Youngster S. K., Kindt M. V., Heikkila R. E. MPTP, MPP+, and mitochondrial function. Life Sci. 1987; 40: 721–729
   PubMed Web of Science ®Google Scholar
• Brossi A. “Further explorations of unnatural alkaloids”. J. Natural Products 1985; 48: 878–893
   PubMed Web of Science ®Google Scholar
• Gibb C., Willoughby J., Glover V., Sandler M., Testa B., Jenner P., Marsden C. D. Analogues of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine as monoamine oxidase substrates: a second ring is not necessary. Neurosci. Lett 1987; 76: 316–322
   PubMed Web of Science ®Google Scholar
• Sandler M., personal communication
   Google Scholar
• Naoi M., Matsuura S., Parvez H., Takahashi T., Hirata Y., Minami M., Nagatsu T. Oxidation of N-methyl-1,2,3,4-tetrahydroisoquinoline into the N-methylisoquinolinium ion by monoamine oxidase. J. Neurochem. 1989; 52: 653–655
   PubMed Web of Science ®Google Scholar
• Langston J. W., Irwin I., Langston E. B., Forno L. S. “The importance of the 4′-5′ double bond for neurotoxicity in primates of the pyridine derivative MPTP”. Neurosci. Lett. 1984; 50: 289–294
   PubMed Web of Science ®Google Scholar
• Bradbury A. J., Costall B., Domeney A. M., Testa B., Jenner P. G., Marsden C. D., Naylor R. J. The toxic actions of MPTP and its metabolite MPP+ are not mimicked by analogues of MPTP lacking an M-methyl moiety. Neurosci. Lett. 1985; 61: 121–126
   PubMed Web of Science ®Google Scholar
• Riachi N. J., Harik S. I., Kalaria R. N., Sayre L. M. On the mechanisms underlying 1 -methyl-4-pheny 1–1,2,3,6-tetrahydropyridine neurotoxicity. II. Susceptibity among mammalian species correlates with the toxin's metabolic patterns in brain microvessels and liver. J. Pharmacol. Exp. Ther. 1988; 244: 443–448
   PubMed Web of Science ®Google Scholar
• Arora P. K., Riachi N. J., Harik S. I., Sayre L. M. Chemical oxidation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) and its in vivo metabolism in rat brain and liver. Biochem. Biophys. Res. Commun. 1988; 152: 1339–1347
   PubMed Web of Science ®Google Scholar
• Chiba K., Kubota E., Miyakawa T., Kato Y., Ishizaki T. Characterization of hepatic microsomal metabolism as in vivo detoxication pathway of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine in mice. J. Pharmacol. Exp. Ther. 1988; 246: 1108–1115
   PubMed Web of Science ®Google Scholar
• Di Monte D., Shinka T., Sandy M. S., Castagnoli N., Jr., Smith M. T. Quantitative analysis of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine metabolism in isolated rat hepatocytes. Drug Metab. Dispos. 1988; 16: 250–255
   PubMed Web of Science ®Google Scholar
• Wu E., Shinka T., Caldera-Munoz P., Yoshizumi H., Trevor A., Castagnoli N., Jr. Metabolic studies on the nigrostriatal toxin MPTP and its MAO-B generated dihydropyridinium metabolite MPDP+. Chem. Res. Toxicol. 1988; 1: 186–194
   PubMed Web of Science ®Google Scholar
• Fonne-Pfister R., Bargetzi M. J., Meyer U. A. MPTP, the neurotoxin inducing Parkinson's disease, is a potent competitive inhibitor of human and rat cytochrome P450 isozymes (P450bufl, P450dbl) catalyzing debrisoquine 4-hydroxylation. Biochem. Biophys. Res. Commun. 1987; 148: 1144–1150
   PubMed Web of Science ®Google Scholar
• Shahi G. S., Moochlala S. M., Das N. P. Depression of the hepatic cytochrome P-450 monooxygenase system by the neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP). Pharmacol. Toxicol. 1989; 64: 107–110
   PubMedGoogle Scholar
• Sahgal A., Andrews J. S., Biggins J. A., Candy J. M., Edwardson J. A., Keith A. B., Turner J. D., Wright C. N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) affects locomotor activity without producing a nigrostriatal lesion in the rat. Neurosci. Lett. 1984; 48: 179–184
   PubMed Web of Science ®Google Scholar
• Boyce S., Kelly E., Reavill C., Jenner P., Marsden C. D. Repeated administration of N-methyM-phenyl-1,2,3,6-tetrahydropyridine to rats is not toxic to striatal dopamine neurons. Biochem. Pharmacol. 1984; 33: 1747–1752
   PubMed Web of Science ®Google Scholar
• Heikkila R. E., Hess A., Duvoisin R. C. Dopaminergic neurotoxicity of 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine in mice. Science 1984; 224: 1451–1453
   PubMed Web of Science ®Google Scholar
• Wallace R. A., Boldry R., Schmittgen T., Miller D., Uretski N. Effect of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) on monoamine neurotransmitters in mouse brain and heart. Life Sci. 1984; 35: 285–291
   PubMed Web of Science ®Google Scholar
• Schneider J. S., Yuwiler A., Markham C. H. Production of a parkinson-like syndrome in the cat with N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP): Behavior, histology, and biochemistry. Exp. Neurol 1986; 91: 293–307
   PubMed Web of Science ®Google Scholar
• Johannessen J. N., Chiueh C. C., Bacon J. P., Garrick N. A., Burns R. S., Weise V. K., Kopin I. J., Parisi J. E., Markey S. P. Effects of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine in the dog: Effect of pargyline pretreatment. J. Neurochem. 1989; 53: 582–589
   PubMed Web of Science ®Google Scholar
• Johannessen J. N., Chiueh C. C., Burns R. S., Markey S. P. “Differences in the metabolism of MPTP in the rodent and primate parallel differences in sensitivity to its neurotoxic effects”. Life ScL 1985; 36: 219–224
   PubMed Web of Science ®Google Scholar
• Kalaria R. N., Mitchell M. J., Harik S. I. Correlation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine neurotoxicity with blood-brain barrier monoamine oxidase activity. Proc. Natl. Acad. Sci. USA 1987; 84: 3521–3525
   PubMed Web of Science ®Google Scholar
• Irwin I., DeLanney L. E., Di Monte D., Langston J. W. The biodisposition of MPP+ in mouse brain. Neurosci. Lett. 1989; 101: 83–88
   PubMed Web of Science ®Google Scholar
• Sershen H., Mason M. F., Hashim A., Lajtha A. Effect of N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) on age-related changes in dopamine turnover and transporter function in the mouse striatum. Eur. J. Pharmacol. 1985; 113: 135–136
   PubMed Web of Science ®Google Scholar
• Gupta M., Gupta B. K., Thomas R., Bruemmer V., Sladek J. R., Jr., Felten D. L. Aged mice are more sensitive to 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine treatment than young adults. Neurosci. Lett. 1986; 70: 326–331
   PubMed Web of Science ®Google Scholar
• Ricaurte G. A., DeLanney L. E., Irwin I., Langston J. W. “Older dopaminergic neurons do not recover from the effects of MPTP”. Neuropharmacology 1987; 26: 97–99
   PubMed Web of Science ®Google Scholar
• Saitoh T., Nijima K., Mizuno Y. Long term effect of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) on striatal dopamine content in young and mature mice. J. Neurol. Sci. 1987; 77: 229–235
   PubMed Web of Science ®Google Scholar
• Jossan S. S., Sakurai E., Oreland L. MPTP toxicity in relation to age, dopamine uptake and MAO-B activity in two rodent species. Pharmacol. Toxicol. 1989; 64: 314–318
   PubMedGoogle Scholar
• Ricaurte G. A., Irwin I., Forno L. S., DeLanney L. E., Langston E., Langston J. W. Aging and 1-methyl-4-phenyl-1,2,3,6-tetrahydropyri-dine-induced degeneration of dopaminergic neurons in the substantia nigra. Brain Res. 1987; 403: 43–51
   PubMed Web of Science ®Google Scholar
• Mitchell I. J., Cross A. J., Sambrook M. A., Crossman A. R. Sites of the neurotoxic action of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine in the macaque monkey include the ventral tegmental area and the locus coeruleus. Neurosci. Lett. 1985; 61: 195–200
   PubMed Web of Science ®Google Scholar
• Reinhard J. F., Jr., Diliberto E. J., Jr., Viveros O. H., Daniels A. J. “Subcellular compartmentalization of 1-methyl-4-phenylpyridinium with catecholamines in adrenal medullary chromaffin vesicules may explain the lack of toxicity to adrenal chromaffin cells”. Proc. Natl. Acad. Sci. USA 1987; 84: 8160–8164
   PubMed Web of Science ®Google Scholar
• Reinhard J. F., Jr., Diliberto E. J., Jr., Daniels A. J. Characterization of cellular transport, subcellular distribution, and secretion of the neurotoxicant 1-methyl-4-phenyIpyridinium in bovine adrenomedullary cell cultures. J. Neurochem. 1989; 52: 1253–1259
   PubMed Web of Science ®Google Scholar
• Cramer R. D., III, Patterson D. E., Bunce J. D. “Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins”. J. Am. Chem. Soc 1988; 110: 5959–5967
   PubMed Web of Science ®Google Scholar
• Maret G., El N., Tayar P., Carrupt A., Testa B., Jenner P., Baird M. Toxication of MPTP (1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine) and analogs by monoamine oxidase: A structure-reactivity relationship study. Biochem. Pharmacol, in press
   PubMed Web of Science ®Google Scholar
• Dostert P. L., Strolin Benedetti M., Tipton K. F. “Interactions of monoamine oxidase with substrates and inhibitors”. Med. Res. Rev. 1989; 9: 45–89
   PubMed Web of Science ®Google Scholar
• Smith T. E., Weissbach H., Udenfriend S. Studies on the mechanism of action of monoamine oxidase: metabolism of N,N-dimethyitryptamine and N1N-dimethyltryptamine-N-oxide. Biochemistry 1962; 1: 137–143
   PubMed Web of Science ®Google Scholar
• Silverman R. B., Hoffman S. J., Catus W. B., III. “A mechanism for mitochondrial monoamine oxidase catalyzed amine oxidation”. J. Am. Chem. Soc 1980; 102: 7126–7128
   Web of Science ®Google Scholar
• Simpson J. T., Krantz A., Lewis F. D., Kokel B. “Photochemical and photophysical studies of amines with excited flavins. Relevance to the mechanism of action of the flavin-dependent monoamine oxidase”. J. Am. Chem. Soc 1982; 104: 7155–7161
   Web of Science ®Google Scholar
• Yelekci K., Lu X., Silverman R. B. “Electron spin resonance studies of monoamine oxidase B. First direct evidence for a substrate radical intermediate”. J. Am. Chem. Soc 1989; 111: 1138–1140
   Web of Science ®Google Scholar
• Barker S. A., Harrison R. E. W., Monti J. A., Brown G. B., Christian S. T. Identification and quantification of 1,2,3,4-tetrahydro-β-carboline, 2-methyl-1,2,3,4-tetrahydro-β-carboline and 6-methoxy-1,2,3,4-tetrahydro-β-carboline as in vivo constituents of rat brain and adrenal gland. Biochem. Pharmacol 1981; 30: 9–17
   PubMed Web of Science ®Google Scholar
• Honecker H., Rommelspacher H. Tetrahydronorharmane (tetra-hydro-β-carboline), a physiologically occurring compound of indole metabolism. Naunyn-Schmiedeberg'sArch. Pharmacol 1978; 305: 135–141
   PubMed Web of Science ®Google Scholar
• Honecker H., Coper H., Fähndrich C., Rommelspacher H. “Identification of tetrahydronorharmane (tetrahydro-β-carboline) in human blood platelets”. J. Clin. Chem. Clin. Biochem. 1980; 18: 133–135
   PubMedGoogle Scholar
• Bidder T. G., Schoemaker D. W., Boettger H. G., Evans M., Cummins J. T. “Harman in human platelets”. Life ScL 1979; 25: 157–164
   PubMed Web of Science ®Google Scholar
• Schoemaker D. W., Cummins J. T., Bidder T. G., Boettger H. G., Evans M. “Identification of harman in the rat arcuate nucleus”. Naunyn-Schmiedeberg's Arch. Pharmacol 1980; 310: 227–230
   Google Scholar
• Kari I., Peura P., Airaksinen M. M. Quantitative gas chromatographic mass spectrometric determination of 1,2,3,4-tetrahydro-β-carboline in human plasma and platelets. Biomed. Mass Spectrom. 1980; 7: 549–552
   PubMedGoogle Scholar
• Allen J. R. F., Beck O., Borg S., Skröder R. Analysis of 1-methyl-1,2,3,4-tetrahydro-β-carboline in human urine and cerebrospinal fluid by gas chromatography mass spectrometry. Eur. J. Mass. Spectrom. Biochem. Med. Environ. Res. 1980; 1: 171–177
   Google Scholar
• Mesnil M., Testa B., Jenner P. “Xenobiotic metabolism by brain monooxygenases and other cerebral enzymes”. Adv. Drug Res. 1984; 13: 95–207
   Google Scholar
• Rommelspacher H., Damm H., Strauss S., Schmidt G. “Ethanol induces an increase of harman in the brain and urine of rats”. Naunyn-Schmiedeberg's Arch. Pharmacol. 1984; 327: 107–113
   Google Scholar
• Susilo R., Rommelspacher H. Formation of a β-carboline (1,2,3,4-tetrahydro-1-methyl-β-carboline-1-carboxylic acid) following intracerebroventricular injection of tryptamine and pyruvic acid. Naunyn-Schmiedeberg's Arch. Pharmacol 1987; 335: 70–76
   Google Scholar
• Susilo R., Rommelspacher H. “Formation of 1-methyl-β-carbolines in rats from their possible carboxylic acid precursor”. Naunyn-Schmiedeberg's Arch. Pharmacol 1988; 337: 566–571
   Google Scholar
• Collins M. A., Neafsey E. J., Cheng B. Y., Hurley-Gius K., Ung-Chhun N. A., Pronger D. A., Christensen M. A., Hurley-Gius D. Endogenous analogs of N-methyl-4-pheny 1–1,2,3,6-tetrahydropyridine: Indoleamine derived tetrahydro-β-carbolines as potential causative factors in Parkinson's disease. Adv. Neurol 1986; 45: 179–182
   Google Scholar
• Perry T. L., Yong V. W., Wall R. A., Jones K. Paraquat and two endogenous analogues of the neurotoxic substance N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine do not damage dopaminergic nigrostriatal neurons in the mouse. Neurosci. Lett. 1986; 69: 285–289
   PubMed Web of Science ®Google Scholar
• Rollema H., Booth R. G., Castagnoli N., Jr. In vivo dopaminergic neurotoxicity of the 2-β-methylcarbolinium ion, a potential endogenous MPP+ analog. Eur. J. Pharmacol 1988; 153: 131–134
   PubMed Web of Science ®Google Scholar
• Schouten M. J., Bruinvels J. “Endogenously formed norharman (β-carboline) in platelet rich plasma obtained from porphyric rats”. Pharmacol. Biochem. Behav. 1986; 24: 1219–1223
   PubMed Web of Science ®Google Scholar
• Booth R. G., Trevor A., Singer T. P., Castagnoli N., Jr. Studies on semirigid tricyclic analogues of the nigrostriatal toxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine,7. Med. Chem. 1989; 32: 473–477
   Web of Science ®Google Scholar
• Greiner B., Rommelspacher H. “Two metabolic pathways of tetrahydronorharmane (tetrahydro-β-carboline) in rats”. Naunyn-Schmiedeberg's Arch. Pharmacol. 1984; 325: 349–355
   Google Scholar
• Kohno M., Ohta S., Hirobe M. “Tetrahydroisoquinoline and 1-methyl-tetrahydroisoquinoline as novel endogenous amines in rat brain”. Biochem. Biophys. Res. Commun. 1986; 140: 448–454
   PubMed Web of Science ®Google Scholar
• Niwa T., Takeda N., Kaneda N., Hashizume Y., Nagatsu T. “Presence of tetrahydroisoquinoline and 2-methyl-tetrahydroisoquinoline in parkinsonian and normal human brains”. Biochem. Biophys. Res. Commun. 1987; 144: 1084–1089
   PubMed Web of Science ®Google Scholar
• Ohta S., Kohno M., Makino Y., Tachikawa O., Hirobe M. “Tetrahydroisoquinoline and 1-methyl-tetrahydroisoquinoline are present in the human brain: Relation to Parkinson's disease”. Biomed. Res. 1987; 8: 453–456
   Web of Science ®Google Scholar
• Weiner H. A model to estimate the in vivo level of tetrahydroisoquinoline in brain during the consumption of ethanol. Beta-carbolines and Tetrahydroisoquinolines, F. Bloom, et al. Alan R. Liss, New York 1982; 69–79
   Google Scholar
• Melchior C., Collins M. A. “The route and significance of endogenous synthesis of alkaloids in animals”. CRC Crit. Rev. Toxicol. 1982; 9: 313–356
   Web of Science ®Google Scholar
• Perry T. L., Jones K., Hansen S. “Tetrahydroisoquinoline lacks dopaminergic nigrostriatal neurotoxicity in mice”. Neurosci. Lett. 1988; 85: 101–104
   PubMed Web of Science ®Google Scholar
• Suzuki K., Mizuno Y., Yoshida M. “Inhibition of mitochondrial NADH-ubiquinone oxidoreductase activity and ATP synthesis by tetrahydroisoquinoline”. Neurosci. Lett. 1988; 86: 105–108
   PubMed Web of Science ®Google Scholar
• Oreland L., Arai Y., Stenström A. Age, neuropsychiatric diseases and brain monoamine oxidase. Monoamine Oxidase and Disease, T. Tipton, P. Dostert, M. Strolin-, Benedetti. Academic Press, London 1984; 291–300
   Google Scholar
• Irwin I., Ricaurte G. A., DeLanney L. E., Langston J. W. The sensitivity of nigrostriatal dopamine neurons to MPP+ does not increase with age. Neurosci. Lett. 1988; 87: 51–56
   PubMed Web of Science ®Google Scholar