Isoquinoline neurotoxins in the brain and Parkinson's disease

Neuroscience Research

Volumn 29, Issue 2, 1997, Pages 99-111

  Nagatsu, Toshiharu ^a  

^a FUJITA HEALTH UNIVERSITY SCHOOL OF MEDICINE   (Japan)

Author keywords

Complex I; Dopamine; Isoquinolines; Monoamine oxidase; Nigrostriatal neurons; Parkinson's disease; Tyrosine 3 monooxygenase (tyrosine hydroxylase)

Indexed keywords

1 METHYL 4 PHENYLPYRIDINIUM; 1,2,3,6 TETRAHYDRO 1 METHYL 4 PHENYLPYRIDINE; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; ISOQUINOLINE DERIVATIVE; NEUROTOXIN; TETRAHYDROISOQUINOLINE;

BRAIN; DOPAMINERGIC NERVE CELL; HUMAN; MONKEY; NEUROTOXICITY; NIGRONEOSTRIATAL SYSTEM; NONHUMAN; PARKINSON DISEASE; PARKINSONISM; PRIORITY JOURNAL; REVIEW;

BRAIN; HUMANS; ISOQUINOLINES; NEUROTOXINS; PARKINSON DISEASE; TYROSINE 3-MONOOXYGENASE;

EID: 0030840624     PISSN: 01680102     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0168-0102(97)00083-7     Document Type: Review

References (89)

1. Bail, M., Miller, S., Cohen, G., 1980. Selective 7-O-methylation of salsolinol in rat brain and heart in vivo. Life Sci. 26, 2051-2060.
2. Chiba, K., Trevor, A., Castagnoli, N. Jr., 1984. Metabolism of the neurotoxic tertiary amine, MPTP by brain monoamine oxidase. Biochem. Biophys. Res. Commun. 120, 574-578.
3. Cohen, G., Collins, M., 1970. Alkaloids from catecholamines in adrenal tissue: possible role in alcoholism. Science 167, 1749-1751.
4. Collins, M.A., Num, W.P., Borge, G.F., Teas, G., Goldforb, C., 1979. Dopamine related tetrahydroisoquinolines: significant urinary excretion by alcoholics after alcohol consumption. Science 206, 1184-1186.
5. Collins, M.A., Neafsey, E.J., 1985. Beta-carboline analogues of N-methyl-4-phenyltetrahydropyridine (MPTP): endogenous factors underlying idiopathic parkinsonism. Neurosci. Lett. 55, 179-184.
6. Davis, V.E., Walsh, M.J., 1970. Alcohol, amines, and alkaloids: a possible biochemical basis for alcohol addiction. Science 167, 1005-1007.
7. Davis, G.C.B., Williams, A.C., Markey, S.P., Ebert, M.H., Caine, E.D., Reichert, C.M., Kopin, I.J., 1979. Chronic parkinsonism secondary to intravenous injection of meperidine analogues. Psychiatry Res. 1, 249-254.
8. Deng, Y., Maruyama, W., Kawai, M., Dostert, P., Yamamura, H., Takahashi, T., Naoi, M., 1997. Assay for the (R)- and (S)-enantiomers of salsolinols in biological samples and foods with ionpair high-performance liquid chromatography using β-cyclodextrin as a chiral mobile phase addictive. J. Chromatogr. B689, 313-320.
9. Dostert, P., Strolin Benedetti, M., Dordain, G., Vernay, D., 1989. Enatiomeric composition of urinary salsolinol in parkinsonian patients after Medopar. J. Neural Transm. Parkinson's Dis. Dementia Sect. 1, 269-278.
10. Duncan, M.W., Smythe, G.A., 1985. Gas chromatography/mass spectrometric methodology for simultaneous assay of salsolinol, dopamine, norepinephrine, dihydroxyphenylacetic acid and dihydroxyphenylethanol. Biomed. Mass Spectrom. 12, 108-114.
11. Greenfield, S.A., 1992. Cell death in Parkinson's disease. In: Tipton, K.F. (Ed.), Essays in Biochemistry. Portland Press, London, pp. 103-118.
12. Heikkila, R.E., Hess, A., Duvoisin, R.C., 1984. Dopaminergic neurotoxicity of 1-methyl-1,2,5,6-tetrahydropyridine in mice. Science 224, 1451-1453.
13. Hirata, Y., Nagatsu, T., 1985a. Inhibition of tyrosine hydroxylation in tissue slices of rat striatum by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine. Brain Res. 337, 193-196.
14. Hirata, Y., Nagatsu, T., 1985b. Inhibition of tyrosine hydroxylation in rat striatal tissue slices by 1-methyl-4-phenylpyridinium ion. Neurosci. Lett. 57, 301-305.
15. Hirata, Y., Nagatsu, T., 1986. Early and late effects of systemically administered 1 - methyl - 4 - phenyl - 1, 2, 3, 6 - tetrahydropyridine (MPTP) on tyrosine hydroxylase activity in vitro and on tyrosine hydroxylation in tissue slices of mouse striatum. Neurosci. Lett. 68, 245-248.
16. +), on tyrosine hydroxylation in rat striatal tissue slices. Brain Res. 397, 341-344.
17. Ishida, J., Yamaguchi, M., Nakamura, M., 1991. High-performance liquid chromatographic determination of 1,2,3,4-tetrahydroisoquinoline in rat brain with fluorescence detection. Anal. Biochem. 195, 168-171.
18. Kajita, M., Niwa, T., Takeda, N., Yoshizumi, H., Tatematsu, A., Watanabe, K., Nagatsu, T., 1993. Presence of N-methyl-dopamine in parkinsonian and normal human brains. J. Chromatogr. B613, 1-8.
19. Kajita, M., Niwa, T., Maruyama, W., Nakahara, D., Takeda, N., Yoshizumi, H., Tatematsu, A., Watanabe, K., Naoi, M., Nagatsu, T., 1994. Endogenous synthesis of N-methylnorsalsolinol in rat brain during in vivo microdialysis with epinine. J. Chromatogr. B654, 263-269.
20. Kajita, M., Niwa, T., Fujisaki, M., Ueki, M., Niimura, K., Sato, M., Egami, K., Naoi, M., Yoshida, M., Nagatsu, T., 1995. Detection of 1-phenyl-N-methyl-1,2,3,4-tetrahydroisoquinoline and 1-phenyl-1,2,3,4-tetrahydroisoquinoline in human brain by gas chromatography-tandem mass spectrometry. J. Chromatogr. B669, 345-351.
21. Kikuchi, K., Nagatsu, Y., Makino, Y., Mashino, T., Ohta, S., Hirobe, M., 1991. Metabolism and penetration through blood-brain barrier of parkinsonism-related compounds, 1,2,3,4-tetrahydroisoquinoline and 1-methyl-1,2,3,4-tetrahydroisoquinoline. Drug Metab. Dispos. 19, 257-262.
22. Kiuchi, K., Hagiwara, M., Hidaka, H., Nagatsu, T., 1988. Effect of the 1-methyl-4-phenylpyridinium ion on phosphorylation of tyrosine hydroxylase in rat pheochromacytoma PC12 cells. Neurosci. Lett. 89, 209-215.
23. Kohno, M., Ohta, S., Hirobe, M., 1986. Tetrahydroisoquinoline and 1-methyl-tetrahydroisoquinoline as novel endogenous amines in rat brain. Biochem. Biophys. Res. Commun. 140, 448-454.
24. Kotake, Y., Tasaki, Y., Makino, Y., Ohta, S., Hirobe, M., 1995. 1-Benzyl-1,2,3,4-tetrahydroisoquinoline as a parkinsonism-inducing agent: a novel endogenous amine in mouse brain and parkinsonian brain. J. Neurochem. 65, 2633-2638.
25. Langston, J.W., Ballard, P., Tetrud, J.W., Irwin, I., 1983. Chronic parkinsonism in humans due to a product of meperidine-analog synthesis. Science 219, 979-980.
26. Lasala, J.M., Coscia, C.J., 1979. Accumulation of a tetrahydroisoquinoline in phenylketonuria. Science 203, 283-284.
27. Liptrot, J., Holdup, D., Phillipson, O., 1994. 1,2,3,4-Tetrahydro-2-methyl-4,6,7-isoquinolinetriol inhibits tyrosine hydroxylase activity in rat striatal synaptosomes. J. Neural Transm. Gen. Sect. 96, 51-62.
28. Makino, Y., Ohta, S., Tachikawa, O., Hirobe, M., 1988. Presence of tetrahydroisoquinoline and 1-methyl-tetrahydroisoquinoline in foods: compounds related to Parkinson's disease. Life Sci. 43, 373-378.
29. Makino, Y., Tasaki, Y., Ohta, S., Hirobe, M., 1990. Confirmation of the enantiomers of 1-methyl-1,2,3,4-tetrahydroisoquinoline in the mouse brain and foods applying gas chromatography/mass spectrometry with negative ion chemical ionization. Biomed. Environ. Mass Spectrom. 19, 415-419.
30. Maruyama, W., Nakahara, D., Ota, M., Takahashi, T., Takahashi, A., Nagatsu, T., Naoi, M., 1993. N-Methylation of dopamine-derived 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, (R)-salsolinol in rat brains: in vivo microdialysis study. J. Neurochem. 59, 395-400.
31. Maruyama, W., Dostert, P., Matsubara, K., Naoi, M., 1995. N-methyl-(R)salsolinol produces hydroxy radicals: involvement to neurotoxicity. Free Radic. Biol. Med. 19, 67-75.
32. Maruyama, W., Abe, T., Tohgi, H., Dostert, P., Naoi, M., 1996. A dopaminergic neurotoxin, (R)-N-methylsalsolinol increases in parkinsonian cerebrospinal fluid. Ann. Neurol. 40, 119-122.
33. Matsubara, K., Akane, A., Maseda, C., Takahashi, S., Fukui, Y., 1985. Salsolinol in urine of nonalcoholic individuals after long-term moderate drinking. Alcohol Drug Res. 6, 281-288.
34. Matsubara, K., Fukushima, S., Fukui, Y., 1987. A systematic regional study of brain salsolinal levels during and immediately following chronic ethanol ingestion in rats. Brain Res. 413, 336-343.
35. Minami, M., Takahashi, T., Maruyama, W., Takahashi, A., Dostert, P., Nagatsu, T., Naoi, M., 1992. Inhibition of tyrosine hydoxylase by R and S enantiomers of salsolinol, 1-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline. J. Neurochem. 58, 2097-2101.
36. Minami, M., Maruyama, W., Dostert, P., Nagatsu, T., Naoi, M., 1993. Inhibition of type A and B monoamine oxidase by 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolines and their N-methylated derivatives. J. Neural Transm. Gen. Sect. 92, 125-135.
37. Mogi, M., Harada, M., Kojima, K., Kiuchi, K., Nagatsu, I., Nagatsu, T., 1987. Effects of repeated systemic administration of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) on striatal tyrosine hydroxylase activity in vitro and tyrosine hydroxylase content. Neurosci. Lett. 80, 213-218.
38. Moser, A., Kömpf, D., 1992. Presence of methyl-6,7-dihydroxy-1,2,3,6-tetrahydroisoquinolines, derivatives of the neurotoxin isoquinoline, in parkinsonian lumbar CSF. Life Sci. 50, 1885-1891.
39. Musshoff, F., Daldrup, Th., Bonte, W., 1993. Gas chromatographic-mass spectrometric screening procedure for the identification of formaldehyde-derived tetrahydroisoquinolines in human urine. J. Chromatogr. B619, 235-242.
40. Myers, R.D., Melchior, C.L., 1977. Alcohol drinking: abnormal intake caused by tetrahydropapaveroline in brain. Science 196, 554-556.
41. +) and the structurally related compounds in vitro and in vivo. Eur. Neurol. 26 (Suppl. 1), 11-15.
42. Nagatsu, T., Yoshida, M., 1988. An endogenous substance of the brain, tetrahydroisoquinoline, produces parkinsonism in primates with decreased dopamine, tyrosine hydroxylase and biopterin in the nigrostriatal regions. Neurosci. Lett. 87, 178-182.
43. Nagatsu, T., Naoi, M., Niwa, T., Yoshida, M., 1994. Endogenous MPTP-like amines in the brain: isoquinolines. In: Mizuno, Y., Caine, D.B., Horowski, R. (Eds.), Advances in Research on Neurodegeneration II. Birkhäuser, Boston, pp. 149-159.
44. Naoi, M., Hirata, Y., Nagatsu, T., 1987. Inhibition of monoamine oxidase by N-methylisoquinolinium ion. J. Neurochem. 48, 709-712.
45. Naoi, M., Nagatsu, T., 1988. Inhibition of type A monoamine oxidase by methylquinolines and structurally related compounds. J. Neurochem. 50, 1105-1110.
46. Naoi, M., Matsuura, S., Takahashi, T., Nagatsu, T., 1989a. An N-methyltransferase in human brain catalyzes N-methylation of 1,2,3,4-tetrahydroisoquinoline into N-methyl-1,2,3,4-tetrahydroisoquinoline, a precursor of a dopaminergic neurotoxin, N-methylisoquinolinium ion. Biochem. Biophys. Res. Commun. 161, 1213-1219.
47. Naoi, M., Matsuura, S., Parvez, H., Takahashi, T., Hirata, Y., Minami, M., Nagatsu, T., 1989b. Oxidation of N-methyl-1,2,3,4-tetrahydroisoquinoline into N-methylisoquinolinium ion by monoamine oxidase. J. Neurochem. 52, 653-655.
48. Naoi, M., Dostert, P., Yoshida, M., Nagatsu, T., 1993a. N-Methylated tetrahydroisoquinolines as dopaminergic neurotoxins. In: Narabayashi, H., Nagatsu, T., Yanagisawa, N., Mizuno, Y. (Eds.), Advances in Neurology, vol. 60. Raven Press, New York, pp. 212-217.
49. Naoi, M., Parvez, H., Nagatsu, T., 1993b. Isoquinolines and quinolines as inhibitors and substrates of monoamine oxidase. In: Yasuhara, H., Parvez, S.H., Oguchi, Y., Sandler, M., Nagatsu, T. (Eds.), Monoamine Oxidase. VSP, Utrecht, pp. 45-60.
50. Naoi, M., Maruyama, W., Dostert, P., 1994a. Binding of 1,2[N]-dimehtyl-6,7-dihydroxyisoquinolinium ion to melanin: effects of ferrous and ferric ion on the binding. Neurosci. Lett. 171, 9-12.
51. Naoi, M., Maruyama, W., Niwa, T., Nagatsu, T., 1994b. Novel toxins and Parkinson's disease: N-methylation and oxidation as metabolic bioactivation of neurotoxin. J. Neural Transm. Suppl. 41, 197-205.
52. Naoi, M., Maruyama, W., Dostert, P., Hashizume, Y., 1996a. Animal model of Parkinson's disease induced by naturally-occurring 1(R), 2(N)-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline. Biog. Amines 12, 135-147.
53. Naoi, M., Maruyama, Y., Dostert, P., Hashizume, Y., Nakahara, D., Takahashi, T., Ota, M., 1996b. Dopamine-derived endogenous 1(R), 2(N)-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, N-methyl-(R)-salsolinol, induced parkinsonism in rats: biochemical, pathological and behavioral studies. Brain Res. 709, 285-295.
54. Naoi, M., Maruyama, W., Dostert, P., Kohda, K., Kaiya, T., 1996c. A novel enzyme enantiomer selectively synthesizes (R) salsolinol, a precursor of a dopaminergic neurotoxin, N-methyl (R) salsolinol. Neurosci. Lett. 212, 183-186.
55. +) destroys cultured mesencephalic dopamine neurons. Biog. Amines 8, 61-67.
56. Nimitkitpaisan, Y., Skolnick, P., 1978. Catecholamine receptors and cyclic AMP formation in the central nervous system: effects of tetrahydroisoquinoline derivatives. Life Sci. 23, 375-382.
57. +) and tetrahydroisoquinoline derivatives on dopaminergic neurons in ventral mesencephalic-striatal co-culture. Neurodegeneration 3, 33-42.
58. Niwa, T., Takada, N., Kaneda, N., Hashizumi, Y., Nagatsu, T., 1987. Presence of tetrahydroisoquinoline and 2-methyl-tetrahydroisoquinoline in parkinsonian and normal human brains. Biochem. Biophys. Res. Commun. 144, 1084-1089.
59. Niwa, T., Takeda, N., Tatematsu, A., Matsuura, S., Yoshida, M., Nagatsu, T., 1988. Migration of tetrahydroisoquinoline a possible parkinsonian neurotoxin, into monkey brain from blood as proved by gas chromatography-mass spectrometry. J. Chromatogr. B452, 85-91.
60. Niwa, T., Takeda, N., Sasaoka, T., Kaneda, N., Hashizume, Y., Yoshizumi, H., Tatematsu, A., Nagatsu, T., 1989a. Detection of tetrahydroisoquinoline, in parkinsonian brain as an endogenous amine by use of gas chromatography-mass spectrometry. J. Chromatogr. B491, 397-403.
61. Niwa, T., Yoshizumi, H., Tatematsu, A., Matsuura, S., Nagatsu, T., 1989b. Presence of tetrahydroisoquinoline, a parkinsonism-related compound, in food. J. Chromatogr. B493, 347-352.
62. Niwa, T., Takeda, N., Yoshizumi, H., Tatematsu, A., Yoshida, M., Dostert, P., Naoi, M., Nagatsu, T., 1991. Presence of 2-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline and 1,2-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, novel endogenous amines, in parkinsonian and normal human brains. Biochem. Biophys. Res. Commun. 177, 603-609.
63. Niwa, T., Maruyama, W., Nakahara, D., Takeda, N., Yoshizumi, H., Tatematsu, A., Takahashi, A., Dostert, P., Naoi, M., Nagatsu, T., 1992. Endogenous synthesis of N-methylsalsolinol, an analogue of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, in rat brain during in vivo microdialysis with salsolinol, as demonstrated by gas chromatography-mass spectrometry. J. Chromatogr. B578, 109-115.
64. Niwa, T., Naoi, M., Yoshida, M., Nagatsu, T., 1993. Analysis of tetrahydroisoquinolines in the brain by gas chromatography/mass spectrometry. In: Parvez, S.H., Naoi, M., Nagatsu, T., Parvez, S. (Eds.), Methods in Neurotransmitter and Neuropeptide Research. Elsevier, Amsterdam, pp. 255-278.
65. Ogawa, M., Ogura, K., Nagatsuka, Y., Ohta, S., Imai, H., Nagatsu, I., Nagatsu, T., Yoshida, M., 1995. Effects of chronic administration of 1,2,3,4-tetrahydroisoquinoline and its derivatives on the monkey: immunohistochemical study. In: Hanin, I., Yoshida, M., Fisher, A. (Eds.), Alzheimer's and Parkinson's Diseases. Plenum, New York, pp. 583-587.
66. Ohta, S., Kohno, M., Makino, Y., Tachikawa, O., Hirobe, O., 1987. Tetrahydroisoquinoline and 1-methyl-tetrahydroisoquinoline are present in the human brain: relation to Parkinson's disease. Biomed. Res. 8, 453-456.
67. Ohta, S., Tachikawa, O., Makino, Y., Tasaki, Y., Hirobe, O., 1990. Metabolism and brain accumulation of tetrahydroisoquinoline (TIQ): a possible parkinsonism inducing substance in an animal model of a poor debrisoquine metabolizer. Life Sci. 46, 599-605.
68. Origitano, T.C., Collins, M.A., 1980. Confirmation of an unexpected brain O-methylation pattern for the dopamine-derived tetrahydroisoquinoline, salsolinol. Life Sci. 26, 2061-2065.
69. Riggin, R.M., Kissinger, P.T., 1977. Determination of tetrahydroisoquinoline alkaloids in biological materials with high performance liquid chromatography. Anal. Chem. 49, 530-533.
70. Saitoh, T., Mizuno, Y., Nagatsu, T., Yoshida, M., 1988. Effect of long-term administration of 1,2,3,4-tetrahydroisoquinoline (TIQ) on striatal dopamine and 3,4-dihydroxyphenylacetic acid (DOPAC) content in mice. Neurosci. Lett. 92, 321-324.
71. Sandler, M., Bonham-Carter, S., Hunter, K.R., Stern, G.M., 1973. Tetrahydroisoquinoline alkaloids: in vivo metabolites of L-dopa in man. Nature 241, 439-443.
72. Sasaoka, T., Kaneda, N., Niwa, T., Hashizume, Y., Nagatsu, T., 1988. Analysis of salsolinol in human brain using high-performance liquid chromatography with electrochemical detection. J. Chromatogr. B428, 152-155.
73. Shapira, A.H.V., 1996. Neurotoxicity and the mechanism of cell death in Parkinson's disease. In: Battistin, L., Scarlato, G., Caraceni, T., Ruggieri, S. (Eds.), Advances in Neurology, vol.60. Lippincott-Raven, Philadelphia, pp. 161-165.
74. Sjöquist, B., Magnuson, E., 1980. Analysis of salsolinol and salsoline in biological samples using deuterium labelled internal standards and gas chromatography-mass spectrometry. J. Chromatogr. B183, 17-24.
75. Sjöquist, B., Eriksson, A., Winbland, B., 1982a. Brain salsolinol levels in alcoholism. Lancet 675, 675-676.
76. Sjöquist, B., Ljungquist, S., Engel, J., 1982b. Increased salsolinol levels in rat striatum and limbic forebrain following chronic ethanol treatment. J. Neurochem. 39, 259-262.
77. Sjöquist, B., Ljungquist, C., 1985. Identification and quantification of 1-carboxysalsolinol and salsolinol in biological samples by gas chromatography-mass spectrometry. J. Chromatogr. B343, 1-8.
78. Soto-Otero, R., Riguera-Vega, R., Méndez-Alvarez, E., Sánchez-Sellero, I., López-Rivadulla Lamas, M., 1996. Interaction of 1,2,3,4-tetrahydroisoquinoline with some components of cigarette smoke: potential implications for Parkinson's disease. Biochem. Biophys. Res. Commun. 222, 607-611.
79. Sourkes, T.L., 1971. Possible new metabolites mediating actions of L-Dopa. Nature 229, 413-414.
80. Strolin-Benedetti, M., Bellotti, V., Pianezzala, E., More, E., Carminati, P., Dostert, P., 1989. Ratio of the R and S enatiomers of salsolinol in food and human urine. J. Neural Transm. 77, 47-53.
81. Suzuki, M., Mizuno, Y., Tamauchi, Y., Nagatsu, T., Yoshida, M., 1992. Selective inhibition of complex I by N-methylisoquinolinium ion and N-methyl-1,2,3,4-tetrahydroisoquinoline in isolated mitochondria prepared from mouse brain. J. Neurol. Sci. 109, 219-223.
82. Takahashi, T., Maruyama, W., Deng, Y., Dostert, P., Nakamura, D., Niwa, T., Ohta, S., Naoi, M., 1997. Cytotoxicity of endogenous isoquinoline to human dopaminergic neuroblastoma SH-SY5Y cells. J. Neural Transm. 104, 59-66.
83. Tasaki, Y., Makino, Y., Ohta, S., Hirobe, M., 1991. 1-Methyl-1,2,3,4-tetrahydroisoquinoline, decreased in 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-treated mouse, prevents parkinsonism-like behavior abnormalities. J. Neurochem. 57, 1940-1943.
84. Ung-Chhum, N., Cheng, B.Y., Pronger, D.A., Serrano, P., Chavez, B., Fernandez Perrez, R., Morales, J., Collins, M.A., 1985. Alkaloid adducts in human brain: coexistence of 1-carboxylated and noncarboxylated isoquinolines and β-carbolines in alcholics and nonalcoholics. Prog. Clin. Biol. Res. 183, 125-136.
85. Weiner, H., 1981. Possible steady-state concentrations of tetrahydroisoquinolines in brain after the consumption of ethanol. Fed. Proc., Fed. Am. Soc. Exp. Biol. 40, 2082-2085.
86. Weiner, C.D., Collins, M.A., 1978. Tetrahydroisoquinolines derived from catecholamines or dopa: effects on brain tyrosine hydroxylase activity. Biochem. Pharmacol. 27, 2699-2703.
87. Wu, R.F., Miura, S., Ichikawa, Y., 1992. Neurotoxins: 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, 1,2,3,4-tetrahydroisoquinoline and 1-methyl-6,7-dihydroxy-tetrahydroisoquinoline as substrate for FAD-containing monooxygenase of porcine liver microsomes. Biochem. Pharmacol. 44, 2079-2081.
88. Yoshida, M., Niwa, T., Nagatsu, T., 1990. Parkinsonism in monkeys produced by chronic administration of an endogenous substance of the brain, tetrahydroisoquinoline: the behavioral and biochemical changes. Neurosci. Lett. 119, 109-113.
89. Zarrang de Ysern, M.E., Ordoñez, L.A., 1981. Tetrahydroisoquinolines. Prog. Neuro-Psychopharmacol. Biol. Psychiatry 5, 343-355.