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The Significance of Tryptophan, Phenylalanine, Tyrosine, and Their Metabolites in the Nervous System

  • Simon N. Young

Abstract

The aromatic amino acids tryptophan, phenylalanine, and tyrosine are important as precursors of 5-hydroxytryptamine (5-HT) and the catecholamines. The extent to which availability of these amino acids can influence biogenic amine synthesis and function is still a matter of active research. Other pathways of metabolism lead to the trace amines (discussed in Volume 1), the pineal indoles, and products of the kynurenine type in which the indole ring is cleaved. Until recently, methodological limitations have precluded adequate study of the metabolism of many of these compounds. For some, their significance in brain is a matter purely for speculation. For others, the data available point to some function, although exactly what is often not clear. The aromatic amino acids lead to such diversity of metabolites that they cannot all be discussed here. For example, condensation products, such as tetrahydro-β-carboline, have recently been demonstrated in brain using mass spectrometric methods1 and can influence neuronal activity in a variety of ways.2 Such condensation products, which can be formed from all three amino acids in the course of their metabolism, are not within the scope of this chapter. The purpose of this chapter is to follow tryptophan, phenylalanine, and tyrosine from the diet through the periphery to the brain, to review some of the metabolic processes that occur there, and to indicate to some extent what the significance of these processes may be.

Keywords

Aromatic Amino Acid Tryptophan Hydroxylase Catecholamine Synthesis Free Tryptophan Trace Amine 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    Honecker, H., and Rommelspacher, H., 1978, Naunyn Schmiedebergs Arch. Pharmacol. 305: 135–141.PubMedCrossRefGoogle Scholar
  2. 2.
    Buckholtz, N. S., 1980, Life Sci. 27: 893–903.PubMedCrossRefGoogle Scholar
  3. 3.
    Culley, W. J., Saunders, R. N., Mertz, E. T., and Jolly, D. H., 1963, Proc. Soc. Exp. Biol. Med. 113: 645–648.PubMedGoogle Scholar
  4. 4.
    Dickerson, J. W. T., and Pao, S. K., 1975, J. Neurochem. 25: 559–564.PubMedCrossRefGoogle Scholar
  5. 5.
    Fernstrom, J. D., and Wurtman, R. J., 1971, Nature [New Biol.] 234: 62–64.Google Scholar
  6. 6.
    Messing, R. B., Fisher, L. A., Phebus, L., and Lytle, L. D., 1976, Life Sci. 18: 707–714.PubMedCrossRefGoogle Scholar
  7. 7.
    Fernstrom, J. D., and Faller, D. V., 1978, J. Neurochem. 30: 1531–1538.PubMedCrossRefGoogle Scholar
  8. 8.
    Fernstrom, J. D., 1976, Metabolism26:207–223.Google Scholar
  9. 9.
    Perez-Cruet, J., Chase, T. N., and Murphy, D. L., 1979, Nature 248: 694–695.Google Scholar
  10. 10.
    Anderson, G. H., 1979, Can. J. Physiol. Pharmacol. 57: 1043–1057.PubMedCrossRefGoogle Scholar
  11. 11.
    Christensen, H. N., 1964, Mammalian Protein Metabolism, Volume 1 (H. N. Munro and J. B. Allison, Eds.), Academic Press, New York, pp. 564–566.Google Scholar
  12. 12.
    Munro, H. N., 1970, Mammalian Protein Metabolism, Volume 4 (H. N. Munro, ed.), Academic Press, New York, pp. 299–386.Google Scholar
  13. 13.
    Bloxam, D. L., Warren, W. H., and White, P. J., 1974, Life Sci. 15: 1443–1455.PubMedCrossRefGoogle Scholar
  14. 14.
    Munro, H. N., 1964, Mammalian Protein Metabolism, Volume 1 (H. N. Munro and J. B. Allison, Eds.), Academic Press, New York, pp. 381–481.Google Scholar
  15. 15.
    Sidransky, H., Sarma, D. S. R., Bongiorno, M., and Verney, E., 1968, J. Biol. Chem. 243: 1123–1132.PubMedGoogle Scholar
  16. 16.
    Majumdar, A. P. N., and Jorgensen, A. J. F., 1976, Biochem. Med. 16: 266–276.CrossRefGoogle Scholar
  17. 17.
    Cocchi, D., di Giulio, A., Groppetti, A., Mantegazza, P., Muller, E. E., and Spano, P. F., 1975, Experientia 31: 384–386.PubMedCrossRefGoogle Scholar
  18. 18.
    Gessa, G. L., Biggio, G., Fadda, F., Corsini, G. V., andTagliamonte, A., 1974, J. Neurochem. 22: 869–870.PubMedCrossRefGoogle Scholar
  19. 19.
    Sjoerdsma, A., Weissbach, H., and Udenfriend, S., 1956, Am. J. Med. 20: 520–532.PubMedCrossRefGoogle Scholar
  20. 20.
    Young, S. N., St-Arnaud-McKenzie, D., and Sourkes, T. L., 1978, Biochem. Pharmacol. 27: 763–767.PubMedCrossRefGoogle Scholar
  21. 21.
    Green, A. R., Sourkes, T. L., and Young, S. N., 1975, Br. J. Pharmacol. 53: 287–292.PubMedCrossRefGoogle Scholar
  22. 22.
    Green, A. R., and Curzon, G., 1975, Biochem. Pharmacol. 24: 713–716.PubMedCrossRefGoogle Scholar
  23. 23.
    Green, A. R., Woods, H. F., Knott, P. J., and Curzon, G., 1975, Nature 255: 170.PubMedCrossRefGoogle Scholar
  24. 24.
    Young, S. N., and Sourkes, T. L., 1975, J. Biol. Chem. 250: 5009–5014.PubMedGoogle Scholar
  25. 25.
    Sourkes, T. L., 1971, Fed. Proc. 30: 897–903.PubMedGoogle Scholar
  26. 26.
    Joseph, M. H., Young, S. N., and Curzon, G., 1976, Biochem. Pharmacol. 25: 2599–2604.PubMedCrossRefGoogle Scholar
  27. 27.
    Young, S. N., and Oravec, M., 1979, Can. J. Biochem. 57: 517–522.PubMedGoogle Scholar
  28. 28.
    Jervis, G. A., 1960, Clin. Chim. Acta 5: 471–475.PubMedCrossRefGoogle Scholar
  29. 29.
    Kaufman, S., 1977, Advances in Neurochemistry, Volume 2 (B. W. Agranoff, and M. H. Aprison, Eds.), Plenum Press, New York, pp. 1–132.CrossRefGoogle Scholar
  30. 30.
    Cihak, A., Lamar, C., and Pitot, H. C., 1973, Arch. Biochem. Biophys. 156: 188–194.PubMedCrossRefGoogle Scholar
  31. 31.
    Knox, W. E., 1963, Trans. N.Y. Acad. Sci. 25: 503–512.PubMedCrossRefGoogle Scholar
  32. 32.
    Hager, C. B., and Kenney, F. T., 1968, J. Biol. Chem. 243: 3296–3300.PubMedGoogle Scholar
  33. 33.
    Wurtman, R. J., 1974, Life Sci. 15: 827–847.PubMedCrossRefGoogle Scholar
  34. 34.
    Wurtman, R. J., and Fernstrom, J. D., 1972, Perspectives in Neuropharmacology (S. H. Snyder, ed.), Oxford University Press, Oxford, pp. 143–193.Google Scholar
  35. 35.
    Laborit, H., and Thuret, F., 1977, Res. Commun. Chem. Pathol. Pharmacol. 17: 77–85.PubMedGoogle Scholar
  36. 36.
    Benkert, O., and Matussek, N., 1970, Nature 228 :13–15.Google Scholar
  37. 37.
    Oldendorf, W. H., and Szabo, J., 1976, Am. J. Physiol. 230: 94–98.PubMedGoogle Scholar
  38. 38.
    Pardridge, W. M., and Oldendorf, W. H., 1977, J. Neurochem. 28: 5–12.PubMedCrossRefGoogle Scholar
  39. 39.
    Pardridge, W. M., 1977, J. Neurochem. 28: 103–108.PubMedCrossRefGoogle Scholar
  40. 40.
    Pratt, O. E., 1979, J. Neural Transm. [Suppl.] 15: 29–42.Google Scholar
  41. 41.
    Soeters, P. B., and Fischer, J. E., 1976, Lancet 2: 880–882.PubMedCrossRefGoogle Scholar
  42. 42.
    McMenamy, R. H., Lund, C. C., and Oncley, J. L., 1957, J. Clin. Invest. 36: 1672–1679.PubMedCrossRefGoogle Scholar
  43. 43.
    McMenamy, R. H., 1964, J. Biol. Chem. 239: 2835–2841.PubMedGoogle Scholar
  44. 44.
    Curzon, G., and Knott, P. J., 1974, Br. J. Pharmacol. 50: 197–204.PubMedCrossRefGoogle Scholar
  45. 45.
    Gessa, G. L., and Tagliamonte, A., 1974, Serotonin: New Vistas: Biochemistry and Behavioral and Clinical Studies (E. Costa, G. L. Gessa, and M. Sandler, Eds.), Raven Press, New York, pp. 119–131.Google Scholar
  46. 46.
    Fernstrom, J. D., Hirsch, M. J., and Faller, D. V., 1976, Biochem. J. 106: 589–595.Google Scholar
  47. 47.
    Baumann, P., and Perey, M., 1977, Clin. Chim. Acta 76: 223–231.PubMedCrossRefGoogle Scholar
  48. 48.
    Fernstrom, J. D., Munro, H. N., and Wurtman, R. J., 1977, Nature 265: 277.PubMedCrossRefGoogle Scholar
  49. 49.
    Etienne, P., Young, S. N., and Sourkes, T. L., 1976, Nature 262: 144–145.PubMedCrossRefGoogle Scholar
  50. 50.
    Yuwiler, A., Oldendorf, W. H., Geller, E., and Braun, L., 1977, J. Neurochem. 28: 1015–1023.PubMedCrossRefGoogle Scholar
  51. 51.
    Pardridge, W. M., 1979, Life Sei. 25: 1519 - 1528.CrossRefGoogle Scholar
  52. 52.
    Daniel, P. M., Moorhouse, S. R., and Pratt, O. E., 1976, Psychol. Med. 6: 277–286.PubMedCrossRefGoogle Scholar
  53. 53.
    Toth, J., and Lajtha, A., 1977, Neurochem. Res. 2: 149–160.CrossRefGoogle Scholar
  54. 54.
    Sourkes, T. L., 1979, J. Neural Transm. [Suppl.] 15: 107–114.Google Scholar
  55. 55.
    Bruinvels, J., and Moleman, P., 1980, J. Neurochem. 34: 1065–1070.PubMedCrossRefGoogle Scholar
  56. 56.
    Morre, M. C., and Wurtman, R. J., 1981, Life Sci. 28: 65–75.PubMedCrossRefGoogle Scholar
  57. 57.
    Archer, E. G., Breakfield, X. O., and Sharata, M. N., 1977, J. Neurochem. 28: 127–135.PubMedCrossRefGoogle Scholar
  58. 58.
    Gershon, M. D., and Dreyfus, C. F., 1980, Brain Res. 184: 229–233.PubMedCrossRefGoogle Scholar
  59. 59.
    Lajtha, A., 1974, Aromatic Amino Acids in the Brain (G. E. W. Wolstenholme and D. W. Fitzsimons, Eds.), Elsevier, Amsterdam, pp. 25–41.Google Scholar
  60. 60.
    Wurtman, R. J., Shein, H. M., Axelrod, J., and Laren, F., 1969, Proc. Natl. Acad. Sci. U.S.A. 62: 749–755.PubMedCrossRefGoogle Scholar
  61. 61.
    Shaw, D. M., Riley, G., Tidmarsh, S., and Blazek, R., 1976, Lancet 1: 363–364.PubMedCrossRefGoogle Scholar
  62. 62.
    Johnson, T. C., and Chou, L., 1973, J. Neurochem. 20: 405–414.PubMedCrossRefGoogle Scholar
  63. 63.
    Johnson, T. C., and Luttges, M. W., 1966, J. Neurochem. 13: 545–552.PubMedCrossRefGoogle Scholar
  64. 64.
    Lin, C. C., Chung, C. H., and Lee, M. L., 1973, Biochem. J. 135: 367–373.Google Scholar
  65. 65.
    J0rgensen, A. J. F., and Majumdar, A. P. N., 1976, Biochem. Med. 16: 37–46.PubMedCrossRefGoogle Scholar
  66. 66.
    Weiss, B. F., Liebschutz, J. L., Wurtman, R. J., and Munro, H. N., 1975, J. Neurochem. 24: 1191–1195.PubMedCrossRefGoogle Scholar
  67. 67.
    Majumdar, A. P. N., 1980, Res. Commun. Chem. Pathol. Pharmacol. 28: 435–445.PubMedGoogle Scholar
  68. 68.
    Joh, T. H., Shikimi, T., Pickel, V. M., and Reis, D. J., 1975, Proc. Natl. Acad. Sci. U.S.A. 72: 3575–3579.PubMedCrossRefGoogle Scholar
  69. 69.
    Hess, S. M., and Doepfner, W., 1961, Arch. Int. Pharmacodyn. 134: 89–99.PubMedGoogle Scholar
  70. 70.
    Ashcroft, G. W., Eecleston, D., and Crawford, T. B. B., 1965, J. Neurochem. 12: 489–492.CrossRefGoogle Scholar
  71. 71.
    Fernstrom, J. D., and Wurtman, R. J., 1971, Science 173: 149–152.PubMedCrossRefGoogle Scholar
  72. 72.
    Grahame-Smith, D. G., 1971, J. Neurochem. 18: 1053–1066.PubMedCrossRefGoogle Scholar
  73. 73.
    Carlsson, A., and Lindqvist, M., 1978, Naunyn Schmiedebergs Arch. Pharmacol. 303: 157–164.PubMedCrossRefGoogle Scholar
  74. 74.
    Friedman, P. A., Kappelman, A. H., and Kaufman, S., 1972, J. Biol. Chem. 247: 4165–4173.PubMedGoogle Scholar
  75. 75.
    Ichiyama, A., Nakamura, S., Nishizuka, Y., and Hayaishi, O., 1970, J. Biol. Chem. 245: 1699–1709.PubMedGoogle Scholar
  76. 76.
    Gal, E. M., Young, R. B., and Sherman, A. D., 1978, J. Neurochem. 31: 237–244.PubMedCrossRefGoogle Scholar
  77. 77.
    Gibson, C. J., Deikel, S. M., Young, S. N., and Binik, Y. M., 1981, Psychopharmacology 76: 118–121.CrossRefGoogle Scholar
  78. 78.
    Curzon, G., Kantamaneni, B. D., Bartlett, J. R., and Bridges, P. K., 1976, J. Neurochem. 26: 613–615.PubMedCrossRefGoogle Scholar
  79. 79.
    Vapalaliti, M., Hyyppa, M. T., Nieminen, V., and Rinne, U. K., 1978, J. Neurosurg. 48: 58–63.CrossRefGoogle Scholar
  80. 80.
    Young, S. N., Gauthier, S., Anderson, G. M., and Purdy, W. C., 1980, J. Neurol. Neurosurg, Psychiatry 43: 438–445.CrossRefGoogle Scholar
  81. 81.
    Eccleston, D., Ashcroft, G. W., Crawford, T. B. B., Stanton, J. B., Wood, D., and McTurk, P. H., 1970, J. Neurol. Neurosurg. Psychiatry 33: 269–272.CrossRefGoogle Scholar
  82. 82.
    Young, S. N., and Gauthier, S., 1981, J. Neurol. Neurosurg. Psychiatry 44: 323–328.PubMedCrossRefGoogle Scholar
  83. 83.
    Smith, J. E., Hingten, J. N., Lane, J. D., and Aprison, M. H., 1976, J. Neurochem. 26: 537–541.PubMedCrossRefGoogle Scholar
  84. 84.
    Raleigh, M. J., Brammer, G. L., Yuwiler, A., Flannery, J. W., McGuire, M. T., and Geller, E., 1980, Exp. Neurol. 68: 322–334.PubMedCrossRefGoogle Scholar
  85. 85.
    Tricklebank, M. D., Drewitt, P. N., and Curzon, G., 1980, Psychopharmacology 69: 173–177.PubMedCrossRefGoogle Scholar
  86. 86.
    Marsden, C. A., and Curzon, G., 1976, Neuropharmacology 15: 165–171.PubMedCrossRefGoogle Scholar
  87. 87.
    Patkina, N. A., and Lapin, I. P., 1976, Pharmacol. Biochem. Behav. 5: 241–245.PubMedCrossRefGoogle Scholar
  88. 88.
    Modigh, K., 1973, Psychopharmacology 30: 123–134.CrossRefGoogle Scholar
  89. 89.
    Fernando, J. C. R., and Curzon, G., 1981, Neuropharmacology 20: 115–122.PubMedCrossRefGoogle Scholar
  90. 90.
    Gallager, D. W., and Aghajanian, G. K., 1976, Neuropharmacology 15: 149–156.PubMedCrossRefGoogle Scholar
  91. 91.
    Trulson, M. E., and Jacobs, B. L., 1979, Brain Res. 163: 135–150.PubMedCrossRefGoogle Scholar
  92. 92.
    Hery, F., Simonnet, G., Bourgoin, S., Soubrie, P., Artaud, F., Hamon, M., and Glowinski, J., 1979, Brain Res. 169: 317–334.PubMedCrossRefGoogle Scholar
  93. 93.
    Puizillout, J. J., Gaudin-Chazal, G., Daszuta, A., Seyfritz, N., and Ternaux, J. P., 1979, J. Physiol [Paris] 75: 531–537.Google Scholar
  94. 94.
    Trulson, M. E., and Jacobs, B. L., 1976, Neuropharmacology 15: 339–344.PubMedCrossRefGoogle Scholar
  95. 95.
    Ternaux, J. P., Boireau, A., Bourgoin, S., Hamon, M., Hery, F., and Glowinski, J., 1976, Brain Res. 101: 533–548.PubMedCrossRefGoogle Scholar
  96. 96.
    Marsden, C. A., Conti, J., Strope, E., Curzon, G., and Adams, R. N., 1979, Brain Res. 171: 85–99.PubMedCrossRefGoogle Scholar
  97. 97.
    Karobath, M., and Baldessarini, R. J., 1972, Nature 236: 206–208.Google Scholar
  98. 98.
    Bagchi, S. P., and Zarycki, E. P., 1975, Biochem. Pharmacol. 24: 1381–1390.CrossRefGoogle Scholar
  99. 99.
    Katz, I., Lloyd, T., and Kaufman, S., 1976, Biochim. Biophys. Acta 445: 567–578.PubMedCrossRefGoogle Scholar
  100. Kapatos, G., and Zigmond, M., 1977, J. Neurochem. 28:1109–1119Google Scholar
  101. 101.
    Carlsson, A., and Lindqvist, M., 1978, Naunyn Schmiedebergs Arch. Pharmacol. 303: 157–164.PubMedCrossRefGoogle Scholar
  102. 102.
    Laborit, H., London, A., and Weber, B., 1970, Agressologie 11: 139–151.PubMedGoogle Scholar
  103. 103.
    Wurtman, R. J., Larin, F., Mostafapour, S., and Fernstroin, J. D., 1974, Science 185: 183–184.PubMedCrossRefGoogle Scholar
  104. 104.
    Gibson, C. J., and Wurtman, R. J., 1978, Life Sci. 22: 1399–1406.PubMedCrossRefGoogle Scholar
  105. 105.
    Scally, M. C., Ulus, I., and Wurtman, R. J., 1977, J. Neural. Trans. 41: 1–6.CrossRefGoogle Scholar
  106. 106.
    Sved, A. F., Fernstrom, J. D., and Wurtman, R. J., 1979, Life Sci. 25: 1293–1300.PubMedCrossRefGoogle Scholar
  107. 107.
    Melamed, E., Hefti, F., and Wurtman, R. J., 1980, Proc. Natl. Acad. Sci. U.S.A. 77: 4305–4309.PubMedCrossRefGoogle Scholar
  108. 108.
    Aghajanian, G. K., 1978, Essays in Neurochemistry and Neuropharmacology, Volume 3 (M. B. H. Youdim, W. Lovenberg, D. F. Sharman, and J. R. Lagnado, Eds.), John Wiley & Sons, New York, Chichester, pp. 1–32.Google Scholar
  109. 109.
    Thurmond, J. B., Lasley, S. M., Conkin, A. L., and Brown, J. W., 1977, Pharmacol. Biochem. Behav. 6: 475–478.PubMedCrossRefGoogle Scholar
  110. 110.
    Snodgrass, S. R., 1974, J. Pharm. Pharmacol. 26: 931–936.PubMedCrossRefGoogle Scholar
  111. 111.
    Snodgrass, S. R., and Horn, A. S., 1973, J. Neurochem. 21: 687–696.PubMedCrossRefGoogle Scholar
  112. 112.
    Sloan, J. W., Martin, W. R., Clements, T. H., Buehwald, W. F., and Bridges, S. R., 1975, J. Neurochem. 24: 523–532.PubMedCrossRefGoogle Scholar
  113. 113.
    Saavedra, J. M., and Axelrod, J., 1973, J. Pharmacol. Exp. Ther. 185: 523–529.PubMedGoogle Scholar
  114. 114.
    Philips, S. R., Durden, D. A., and Boulton, A. A., 1974, Can. J. Biochem. 52: 447–451.PubMedGoogle Scholar
  115. 115.
    Warsh, J. J., Godse, D. D., Stancer, H. C., Chan, P. W., and Coscina, D. V., 1977, Biochem. Med. 18: 10–20.PubMedCrossRefGoogle Scholar
  116. 116.
    Artigas, F., and Gelpi, E., 1979, Anal. Biochem. 92: 233–242.PubMedCrossRefGoogle Scholar
  117. 117.
    Philips, S. R., Durden, D. A., and Boulton, A. A., 1974, Can. J. Biochem. 52: 447–451.PubMedGoogle Scholar
  118. 118.
    Warsh, J. J., Coscina, D. V., Godse, D. D., and Chan, P. W., 1979, J. Neurchem. 32: 1191–1196.CrossRefGoogle Scholar
  119. 119.
    Young, S. N., Anderson, G. M., and Purdy, W. C., 1980, J. Neurochem. 34: 309–315.PubMedCrossRefGoogle Scholar
  120. 120.
    Oldendorf, W. H., and Braun, L. D., 1976, Brain Res. 113: 219–224.PubMedCrossRefGoogle Scholar
  121. 121.
    Young, S. N., Anderson, G. M., Gauthier, S., and Purdy, W. C., 1980, J. Neurochem. 34: 1087–1092.PubMedCrossRefGoogle Scholar
  122. 122.
    Jones, R. S. G., and Boulton, A. A., 1980, Life Sci. 27: 1849–1856.PubMedCrossRefGoogle Scholar
  123. 123.
    Gillin, J. G., Kaplan, J., Stillman, R., and Wyatt, R. J., 1976, Am. J. Psychiatry 133:203–208.Google Scholar
  124. 124.
    Luchins, D., Ban, T. A., and Lehmann, H. E., 1978, Int. Pharmacopsychiatry 13: 16–33.PubMedGoogle Scholar
  125. 125.
    Fuller, R. W., 1976, Life Sci. 19: 625–628.PubMedCrossRefGoogle Scholar
  126. 126.
    Oon, M. C. H., Murray, R. M., Rodnight, R., Murphy, M. P., and Birley, J. L. T., 1977, Psychopharmacology 54: 171–175.PubMedCrossRefGoogle Scholar
  127. 127.
    Raisanen, M., and Karkkainen, J., 1979, J. Chromatogr. 162: 579–584.PubMedCrossRefGoogle Scholar
  128. 128.
    Walker, R. W., Mandel, L. R., Kleinman, J. E., Gillin, J. C., Wyatt, R. J., and Vandenheuvel, W. J. A., 1979, J. Chromatogr. 162: 539–546.PubMedCrossRefGoogle Scholar
  129. 129.
    Reiter, R. J., 1980, The Pineal, Volume 5, Eden Press, Westmount, Quebec.Google Scholar
  130. 130.
    Illnerova, H., Backstrom, M., Saaf, J., Wetterberg, L., and Vangbo, B., 1978, Neurosci. Lett. 9: 189–193.PubMedCrossRefGoogle Scholar
  131. 131.
    Arendt, J., Wirz-Justice, A., Bradtke, K., and Kornemark, M., 1979, Ann. Clin. Biochem. 16: 307–312.PubMedGoogle Scholar
  132. 132.
    Shaw, K. M., 1979, Adv. Drug Res. 11: 75–96.Google Scholar
  133. 133.
    Anton-Tay, F., and Wurtman, R. J., 1969, Nature 221: 474–475.PubMedCrossRefGoogle Scholar
  134. 134.
    Niles, L. P., Wong, Y. W., Mishra, R. K., and Brown, G. M., 1979, Eur. J. Pharmacol. 55: 219–220.PubMedCrossRefGoogle Scholar
  135. 135.
    Cardinali, D. P., Vacas, M. I., and Boyer, E. E., 1979, Endocrinology 105: 437–441.PubMedCrossRefGoogle Scholar
  136. 136.
    Pang, S. F., Yu, H. S., Suen, H. C., and Brown, G. M., 1980, J. Endocrinol. 87: 89–93.PubMedCrossRefGoogle Scholar
  137. 137.
    Bubenik, G. A., 1980, Horm. Res. 12: 313–323.PubMedCrossRefGoogle Scholar
  138. 138.
    Friedhoff, A. J., and Miller, J. C., 1977, Res. Commun. Chem. Pathol. Pharmacol. 16: 225–244.PubMedGoogle Scholar
  139. 139.
    Bubenik, G. A., Brown, G. M., and Grota, L. G., 1976, Brain Res. 118: 417–427.PubMedCrossRefGoogle Scholar
  140. 140.
    Bosin, T. R., Jonsson, G., and Beck, O., 1979, Brain Res. 173: 79–88.PubMedCrossRefGoogle Scholar
  141. 141.
    Quay, W. B., 1974, Pineal Chemistry, Charles C. Thomas, Springifeld, Illinois.Google Scholar
  142. 142.
    Narasimhachari, N., Kempster, E., and Anbar, M., 1980, Biomed. Mass Spectrom. 7: 231–235.PubMedCrossRefGoogle Scholar
  143. 143.
    Duncan, R. J. S., and Sourkes, T. L., 1974, J. Neurochem. 22: 663–669.PubMedCrossRefGoogle Scholar
  144. 144.
    Turner, A. J., Illingsworth, J. A., and Tipton, K. J., 1974, Biochem. J. 144: 353–360.PubMedGoogle Scholar
  145. 145.
    Cheifetz, S., and Warsh, J. J., 1980, J. Neurochem. 34: 1093–1099.PubMedCrossRefGoogle Scholar
  146. 146.
    Anderson, G. M., Young, J. G., Young, S. N., Batter, D. K., Cohen, D. J., and Shaywitz, B. A., 1981, J. Chromatogr. 224: 315–320.CrossRefGoogle Scholar
  147. 147.
    Beck, O., Borg, S., Holmstedt, B., and Stibler, H., 1980, Biochem. Pharmacol. 29: 693–696.PubMedCrossRefGoogle Scholar
  148. 148.
    Wilson, B. W., Lynch, H. J., and Ozaki, Y., 1978, Life Sci. 23: 1019 - 1024.PubMedCrossRefGoogle Scholar
  149. 149.
    Cornford,E.M.,Bocash, W.D.,Braun,L.D.,Crane,P. D.,Oldendorf,W.H.,andMaclnnis, A. J., 1979, /. Clin. Invest. 63: 1241–1248.Google Scholar
  150. 150.
    Reiter, R. J., and Vaughan, M. K., 1977, Life Sei. 21: 159–172.CrossRefGoogle Scholar
  151. 151.
    Seed, J. R., and Sechelski, J., 1977, Life Sei. 21: 1603–1610.CrossRefGoogle Scholar
  152. 152.
    Gäl, E. M., Armstrong, J. C., and Ginsberg, B., 1966, J. Neurochem. 13: 643–654.PubMedCrossRefGoogle Scholar
  153. 153.
    Yoshida, R., and Hayaishi, O., 1978, Proc. Natl. Acad. Sei. U.S.A. 75: 3998–4000.CrossRefGoogle Scholar
  154. 154.
    Tsuda, H., Noguchi, T., and Kido, R., 1972, J. Neurochem l9 M7–890.Google Scholar
  155. 155.
    Hirata, F., Hayaishi, O., Tokuyama, T., and Senoh, S., 1974, J. Biol. Chem. 249: 1311–1313.Google Scholar
  156. 156.
    Fujiwara, M., Shibata, M., Watanabe, Y., Nukiwa, T., Hirata, F., Mizuno, N., and Hayaishi, O., 1978, J. Biol. Chem. 253: 6081–6085.PubMedGoogle Scholar
  157. 157.
    Makino, K., Joh, Y., and Hasegauva, F., 1962, Biochem. Biophys. Res. Commun. 6: 432–437.PubMedCrossRefGoogle Scholar
  158. 158.
    Toda, N., 1975, J. Pharmacol. Exp. Ther. 193: 385–392.PubMedGoogle Scholar
  159. 159.
    Christenson, J. G., Dairman, W., and Udenfriend, S., 1970, Arch. Biochem. Biophys. 141: 356–367.PubMedCrossRefGoogle Scholar
  160. 160.
    Saavedra, J. M., 1974, Neurochem. 22: 211–216.CrossRefGoogle Scholar
  161. 161.
    Fulton, T. R., Triano, T., Rabe, A., and Loo, Y. H., 1980, Life Sci. 27: 1271–1281.PubMedCrossRefGoogle Scholar
  162. 162.
    Durden, D. A., and Philips, S. R., 1980, J. Neurochem. 34: 1725–1732.PubMedCrossRefGoogle Scholar
  163. 163.
    Oldendorf, W. H., 1971, Am. J. Physiol. 221: 1629–1639.PubMedGoogle Scholar
  164. 164.
    Durden, D. A., Philips, S. R., and Boulton, A. A., 1973, Can. J. Biochem. 51: 995–1002.PubMedCrossRefGoogle Scholar
  165. 165.
    Sandler, M., Ruthven, C. R. J., Goodwin, B. L., and Coppen, A., 1979, Clin. Chim. Acta 93: 169–171.PubMedCrossRefGoogle Scholar
  166. 166.
    Sabelli, H. C., Borison, R. L., Diamond, B. I., Havdala, H. S., and Narasimhachari, N., 1978, Biochem. Pharmacol 27: 1708–1711.CrossRefGoogle Scholar
  167. 167.
    Danielson, T. J., Boulton, A. A., and Robertson, H. A., 1977, J. Neurochem. 29: 1131–1135.PubMedCrossRefGoogle Scholar
  168. 168.
    Boulton, A. A., Dyck, L. E., and Durden, D. A., 1974, Life Sci. 14: 1673–1683.CrossRefGoogle Scholar
  169. 169.
    Fellman, J. H., Roth, E. S., and Fujita, T. S., 1976, Arch. Biochem. Biophys. 174: 562–567.PubMedCrossRefGoogle Scholar
  170. 170.
    Boulton, A. A., and Dyck, L. E., 1974, Life Sei. 14: 2497–2506.CrossRefGoogle Scholar
  171. 171.
    Brandau, K., and Axelrod, J., 1972, Naunyn Schmiedebergs Arch. Pharmacol. 273: 123–133.PubMedCrossRefGoogle Scholar
  172. 172.
    Karoum, F., Bunney, W., Gillin, J. C., Jimerson, D., Van Kämmen, D., and Wyatt, R. J., 1977, Biochem. Pharmacol. 26: 629–632.PubMedCrossRefGoogle Scholar
  173. 173.
    Bosin, T. R., Hathaway, D. R., and Maickel, R. P., 1974, Arch. Int. Pharmacodyn. Ther. 212: 32–35.PubMedGoogle Scholar
  174. 174.
    Yuwiler, A., 1973, J. Neurochem. 20: 1099–1109.PubMedCrossRefGoogle Scholar
  175. 175.
    Loh, H. H., and Berg, C. P., 1971, J. Nutr. 101: 1351–1358.PubMedGoogle Scholar
  176. 176.
    Budny, J., Dow, R. C., Eccleston, D., Hill, A. G., and Ritchie, I. M., 1976, Br. J. Pharmacol. 58: 3–7.PubMedCrossRefGoogle Scholar
  177. 177.
    Hankes, L. V., Brown, R. R., Leklem, J., Schmaeler, M., and Jesseph, J., 1972, J. Invest. Dermatol. 58: 85–95.PubMedCrossRefGoogle Scholar
  178. 178.
    Borison, R. L., Maple, P. J., Havdala, H. S., and Diamond, B. I., 1978, Res. Commun. Chem. Pathol. Pharmacol. 21: 363–366.PubMedGoogle Scholar
  179. 179.
    Mann, J., Peselow, E. D., Snyderman, S., and Gershon, S., 1980, Am. J. Psychiatry 137: 1611–1612.PubMedGoogle Scholar
  180. 180.
    Fernández Pardal, J., 1980, J. Neurosci. Res. 5: 155–161.CrossRefGoogle Scholar
  181. 181.
    Bodnar, R. J., Lattner, M., and Wallace, M. M., 1980, Pharmacol. Biochem. Behav. 13: 829–833.PubMedCrossRefGoogle Scholar
  182. 182.
    Tokuhisa, S., Saisu, K., Naruse, K., Yoshikawa, H., and Baba, S., 1981, Chem. Pharm. Bull. 29: 514–518.PubMedCrossRefGoogle Scholar
  183. 183.
    Shalita, B., and Dikstein, S., 1979, Pfluegers Arch. 379: 245–250.CrossRefGoogle Scholar

Copyright information

© Plenum Press, New York 1983

Authors and Affiliations

  • Simon N. Young
    • 1
  1. 1.Department of PsychiatryMcGill UniversityMontrealCanada

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