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4,5-Epoxymorphinans

  • Alan F. Casy
  • Robert T. Parfitt

Abstract

The latex obtained by incision of the unripe seed capsule of the poppy, Papaver somniferum, and known as opium is the source of several pharmacologically important alkaloids. Dioskurides, in about a.d. 77, referred to both the latex (opos) and a total plant extract (mekonion) and to the use of oral and inhaled (pipe-smoked) opium to induce a state of euphoria and sedation. Since before the Christian era the therapeutic properties of opium were evident, with the first written reference to poppy juice being by Theophrastus in the third century b.c.

Keywords

Opioid Receptor Analgesic Activity Antagonist Action Grignard Reagent Analgesic Potency 
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.
    J. M. Gulland and R. Robinson, J. Chem. Soc. 980 (1923).Google Scholar
  2. 2.
    J. M. Gulland and R. Robinson, Mem. Proc. Manchester Lit. Phil Soc. 69, 79 (1925).Google Scholar
  3. 3.
    C. Schöfp, Justus Liebigs Ann. Chem. 452, 411 (1927).Google Scholar
  4. 4.
    M. Gates and G. Tschudi, J. Am. Chem. Soc. 74, 1109 (1952).Google Scholar
  5. 5.
    M. Gates and G. Tschudi, J. Am. Chem. Soc. 78, 1380 (1956).Google Scholar
  6. 6.
    D. H. R. Barton and T. Cohen, Festschrift Arthur Stoll, p. 117, Birckhauser, Basel (1957).Google Scholar
  7. 7.
    A. R. Battersby, Oxidative Coupling of Phenols, p. 119, Dekker, New York (1967).Google Scholar
  8. 8.
    K. W. Bentley, The Chemistry of the Morphine Alkaloids, Clarendon Press, Oxford (1954).Google Scholar
  9. 9.
    K. W. Bentley, “The Morphine Alkaloids,” in: Chemistry of Alkaloids, (S. W. Pelletier, ed.), Van Nostrand Reinhold, New York (1970).Google Scholar
  10. 10.
    S. F. Dyke, Some Aspects of the Chemistry of Opium, Royal Institute of Chemistry, Lecture Series No. 1 (1965).Google Scholar
  11. 11.
    D. Ginsburg, The Opium Alkaloids, Interscience, New York (1962).Google Scholar
  12. 12.
    C. A. Winter, in Analgetics (G. D. Stevens, ed.), Academic Press, New York (1965).Google Scholar
  13. 13.
    J. W. Lewis, K. W. Bentley, and A. Cowan, Ann. Rev. Pharmacol. Toxicol 11, 241 (1971).Google Scholar
  14. 14.
    H. W. Kosterlitz, H. O. J. Collier, and J. E. Villarreal, eds., Agonist and Antagonist Actions of Narcotic Analgesic Drugs, University Park Press, Baltimore (1973).Google Scholar
  15. 15.
    W. R. Martin and J. W. Sloan, in Handbook of Experimental Pharmacology (W. R. Martin, ed), Vol. 45, p. 43, Springer-Verlag, Berlin (1977).Google Scholar
  16. 16.
    M. W. Adler, L. Manara, and R. Samanin, eds., Factors Affecting the Action of Narcotics, Raven Press, New York (1978).Google Scholar
  17. 17.
    J. H. Jaffe and W. R. Martin, in The Pharmacological Basis of Therapeutics (A. G. Gilman, L. S. Goodman, and A. Gilman, eds.), 6th ed., p. 494, Macmillan, New York (1980).Google Scholar
  18. 18.
    J. H. Jaffe, p. 535, in Ref. 17.Google Scholar
  19. 19.
    C. I. Wright, J. Pharmacol. Exp. Ther. 71, 164 (1947).Google Scholar
  20. 20.
    E. L. Way, J. W. Kemp, J. M. Young, and D. R. Grassetti, J. Pharmacol. Exp. Ther. 129, 144 (1960).PubMedGoogle Scholar
  21. 21.
    E. L. Way, J. W. Kemp, and J. M. Young, Bull. Narc. 17, 15 (1965).Google Scholar
  22. 22.
    C. Inturrisi, M. Max, J. Umans, M. Schultz, S. Shin, K. Foley, and R. D. Houde, Clin. Pharmacol. Ther. 31, 235 (1982).Google Scholar
  23. 23.
    T. Kametani, in The Total Synthesis of Natural Products (J. ApSimon, ed.), Vol. 3, Wiley-Interscience, New York (1977).Google Scholar
  24. 24.
    R. Grewe and A. Mondon, Chem. Ber. 81, 279 (1948).Google Scholar
  25. 25.
    R. Grewe, A. Mondon, and E. Nolte, Justus Liebigs Ann. Chem. 564, 161 (1949).Google Scholar
  26. 26.
    M. Gates, R. B. Woodward, W. F. Newhall, and R. Kunzli, J. Am. Chem. Soc. 72, 114 (1950).Google Scholar
  27. 27.
    D. Elad and D. Ginsburg, J. Am. Chem. Soc. 76, 312 (1954).Google Scholar
  28. 28.
    D. Elad and D. Ginsburg, J. Chem. Soc. 3052 (1954).Google Scholar
  29. 29.
    D. H. R. Barton, G. W. Kirby, W. Steglich, and G. M. Thomas, Proc. Chem. Soc. 203 (1963).Google Scholar
  30. 30.
    A. R Battersby, R. Binks, D. M. Foulkes, R. J. Francis, and D. J. McCaldin, Proc. Chem. Soc. 203 (1963).Google Scholar
  31. 31.
    A. R. Battersby, D. M. Foulkes, and R. Binks, J. Chem. Soc. 3323 (1965).Google Scholar
  32. 32.
    M. A. Schwartz and I. S. Mami, J. Am. Chem. Soc. 97, 1239 (1975).PubMedGoogle Scholar
  33. 33.
    T. Kametani, M. Ihara, M. Fukumoto, and H. Yagi, J. Chem. Soc. (C) 2030 (1969).Google Scholar
  34. 34.
    J. D. White, G. Caravatti, T. B. Kline, E. Edstrom, K. C. Rice, and A. Brossi, Tetrahedron 39, 239 (1983).Google Scholar
  35. 35.
    A. T. Balaban, Rev. Roumaine Chim. 14, 1281 (1969).Google Scholar
  36. 36.
    K. C. Rice, J. Org. Chem. 45, 3135 (1980).Google Scholar
  37. 37.
    H. C. Beyerman, E. Buurman, and L. Maat, J. Chem. Soc, Chem. Comm. 918 (1972).Google Scholar
  38. 38.
    H. Brechbühler, H. Büchi, E. Hatz, J. Schreiber, and A. Eschenmoser, Helv. Chim. Acta 48, 1746 (1965).Google Scholar
  39. 39.
    G. C. Morrison, R. O. Waite, and J. Shavel, Tetrahedron Lett. 4055 (1967).Google Scholar
  40. 40.
    A. R. Brossi, Trends Pharmacol Sci. 3, 239 (1982).Google Scholar
  41. 41.
    H. C. Beyerman, E. Buurman, and L. Maat, J. Chem. Soc. Chem. Comm. 918, (1972).Google Scholar
  42. 42.
    H. C. Beyerman, T. S. Lie, L. Maat, H. Bosman, E. Buurman, E. J. M. Bijsterveld, and H. J. M. Sinnige, Red Trav. Chim. Pays-Bas 95, 24 (1976).Google Scholar
  43. 43.
    H. C. Beyerman, L. van Bommel, L. Maat, and C. Olieman, Recl. Trav. Chim. Pays-Bas 95, 312 (1976).Google Scholar
  44. 44.
    H. C. Beyerman, J. van Berkel, T. S. Lie, L. Maat, and J. C. M. Wessels, Red. Trav. Chim. Pays-Bas 97, 127 (1978).Google Scholar
  45. 45.
    T. S. Lie, L. Maat, and H. C. Beyerman, Red. Trav. Chim. Pays-Bas 98, 419 (1979).Google Scholar
  46. 46.
    H. C. Beyerman, E. Buurman, T. S. Lie, and L. Maat, Red Trav. Chim. Pays-Bas 95, 43 (1976).Google Scholar
  47. 47.
    P. R. Crabbendam, A. M. van Leersum, and L. Maat, Delft Prog. Rep. Chem. and Chem. Eng. 7, 77 (1982).Google Scholar
  48. 48.
    D. A. Evans, C. H. Mitch, R. C. Thomas, D. M. Zimmerman, and R. L. Robey, J. Am. Chem. Soc. 102, 5955 (1980).Google Scholar
  49. 49.
    D. A. Evans and C. H. Mitch, Tetrahedron Lett. 23, 258 (1982).Google Scholar
  50. 50.
    C. Schöpf and T. Pfeifer, Justus Liebigs, Ann. Chem. 483, 157 (1930).Google Scholar
  51. 51.
    C. Schöpf, T. Pfeifer, and H. Hirsch, Justus Liebigs Ann. Chem. 492, 213 (1932).Google Scholar
  52. 52.
    M. Gates and G. M. K. Hughes, Chem. Ind. (Lond.) 1506 (1956).Google Scholar
  53. 53.
    L. Small, H. M. Fitch, and W. E. Smith, J. Am. Chem. Soc. 58, 1457 (1936).Google Scholar
  54. 54.
    K. W. Bentley, Experientia 12, 251 (1956).PubMedGoogle Scholar
  55. 55.
    M. Gates and M. S. Shepard, J. Am. Chem. Soc. 84, 4125 (1962).Google Scholar
  56. 56.
    D. D. Weiler and H. Rapport, J. Med. Chem. 19, 1171 (1976).Google Scholar
  57. 57.
    C. Olieman, L. Maat, and H. C. Beyerman, Red Trav. Chim. Pays-Bas 97, 31 (1978).Google Scholar
  58. 58.
    A. Brossi, F.-L. Hsu, K. C. Rice, M. D. Rozwadowska, H. Schmidhammer, C. D. Hufford, C. C. Chiang, and I. L. Karle, Helve. Chim. Acta 64, 1672, (1981).Google Scholar
  59. 59.
    M. Gates, J. Am. Chem. Soc. 75, 4340 (1953).Google Scholar
  60. 60.
    H. Rapoport, C. H. Lovell, H. R. Reist, and M. E. Warren, J. Am. Chem. Soc. 89, 1942 (1967).PubMedGoogle Scholar
  61. 61.
    D. von Neubauer and K. Mothes, Planta Med. 11, 387 (1963).Google Scholar
  62. 62.
    N. Sharglii and L. Lalezari, Nature (Lond.) 213, 1244 (1967).Google Scholar
  63. 63.
    Science 190, 1274 (1975).Google Scholar
  64. 64.
    J. W. Fairbairn, Planta Med. 29, 26 (1976).PubMedGoogle Scholar
  65. 65.
    M. Gordon, Ann. Rep. Med. Chem. 9, 38 (1973).Google Scholar
  66. 66.
    K. C. Rice, in Problems in Drug Dependence, 1981, (L. S. Harris, ed.), NIDA Research Monograph 41, 331 (1982).Google Scholar
  67. 67.
    K. C. Rice, Proc. Jap. Pharm. Soc. 64 (1983).Google Scholar
  68. 68.
    C. R. A. Wright, J. Chem. Soc. 27, 1031 (1874).Google Scholar
  69. 69.
    H. Dreser, Deut. Med. Wochenschr. 24, 185 (1898).Google Scholar
  70. 70.
    E. L. May and A. E. Jacobson, J. Pharm. Sci. 66, 285 (1977).PubMedGoogle Scholar
  71. 71.
    H. Rapoport, C. H. Lovell, and B. M. Tolbert, J. Am. Chem. Soc. 73, 5900 (1951).Google Scholar
  72. 72.
    K. Goto and I. Yamamato, Proc. Jap. Acad. 30, 76 (1954) (Chem. Abs. 50, 1052h, 1956).Google Scholar
  73. 73.
    M. Takeda and H. Kugita, Japanese Patent 29153 (1971) (Chem. Abs. 75, 141030r (1971)).Google Scholar
  74. 74.
    H. Ioue, M. Takeda, and H. Kugita, Chem. Pharm. Bull 18, 1569 (1970).Google Scholar
  75. 75.
    K. C. Rice, J. Med. Chem. 20, 164 (1977).PubMedGoogle Scholar
  76. 76.
    J. F. W. McOmie, M. L. Watts, and D. E. West, Tetrahedron 24, 2289 (1968).Google Scholar
  77. 77.
    J. A. Lawson and J. I. Degraw, J. Med. Chem. 20, 165 (1977).PubMedGoogle Scholar
  78. 78.
    J. P. Garard, F. Kranz, and T. Rüll, Bull Soc. Chim. Fr. 486 (1965).Google Scholar
  79. 79.
    R. B. Barber and H. Rapoport, J. Med. Chem. 19, 1175 (1976).PubMedGoogle Scholar
  80. 80.
    L. Knorr and H. Hortein, Chem. Ber. 39, 1409 (1906).Google Scholar
  81. 81.
    H. Hirsch, Justus Liebigs Ann. Chem. 489, 224 (1931).Google Scholar
  82. 82.
    H. Conroy, J. Am. Chem. Soc. 77, 5960 (1955).Google Scholar
  83. 83.
    M. Freund, Chem. Ber. 39, 844 (1906).Google Scholar
  84. 84.
    M. Yamada, Chem. Pharm. Bull. 10, 8712 (1962).Google Scholar
  85. 85.
    H. C. Brown and P. J. Geoghegan, J. Org. Chem. 35, 1844 (1970).Google Scholar
  86. 86.
    H. Rapoport, R. Naumann, E. R. Bissell, and R. M. Bonner, J. Org. Chem. 15, 1103 (1950).Google Scholar
  87. 87.
    I. Seki, Chem. Pharm. Bull. 18, 671 (1970).Google Scholar
  88. 88.
    H. Rapoport and H. N. Reist, J. Am. Chem. Soc. 77, 490 (1955).Google Scholar
  89. 89.
    R. B. Barber and H. Rapoport, J. Med. Chem. 18, 1074 (1975).PubMedGoogle Scholar
  90. 90.
    E. L. Way and T. K. Alder, Pharmacol. Rev. 12, 383 (1960).PubMedGoogle Scholar
  91. 91.
    T. Johannesson and J. Schou, Acta Pharmacol. Toxicol. 20, 165 (1963).Google Scholar
  92. 92.
    T. K. Aider, J. Pharmacol. Exp. Ther. 140, 155 (1963).Google Scholar
  93. 93.
    J. J. Kamm, V. B. Bastone, E. Mohacsi, and F. M. Vane, Xenobiotica 1, 273 (1971).PubMedGoogle Scholar
  94. 94.
    P. H. Duquette, R. R. Erickson, and J. L. Holtzman, J. Med. Chem. 26, 1343 (1983).PubMedGoogle Scholar
  95. 95.
    E. Mohacsi, W. Leimgruber, and H. Bamth, J. Med. Chem. 25, 1264 (1982).PubMedGoogle Scholar
  96. 96.
    G. Papioannou, Eur. J. Med. Chem. 11, 287 (1976).Google Scholar
  97. 97.
    K. Shimomura, O. Kamata, S. Veki, S. Ida, K. Ogari, H. Yoshimura, and H. Tsukamoto. Tohoku. J. Exp. Med. 105, 45 (1971).PubMedGoogle Scholar
  98. 98.
    M. Mori, K. Oguri, H. Yoshimura, O. Kamata, and S. Veki, Life Sci. 11, 525 (1972).Google Scholar
  99. 99.
    E. L. May and A. E. Jacobson, J. Pharm. Sci. 66, 285 (1977).PubMedGoogle Scholar
  100. 100.
    C. E. Inturrisi, M. Schultz, S. Shin, J. G. Umans, L. Angel, and E. J. Simm, Life Sci. 33 (Suppl. 1), 773 (1983).PubMedGoogle Scholar
  101. 101.
    L. H. Welsh, J. Org. Chem. 19, 1409 (1954).Google Scholar
  102. 102.
    E. L. Way, J. W. Kemp, J. M. Young, and D. R. Grasetti, J. Pharm. Exp. Ther. 129, 144 (1960).Google Scholar
  103. 103.
    K. C. Rice and A. E. Jacobson, J. Med. Chem. 18, 1033 (1975).PubMedGoogle Scholar
  104. 104.
    J. von Mering, Merck’s Jahresb. 5, (1898).Google Scholar
  105. 105.
    R. Stockman and D. B. Dott, Br. Med. J. 189 (July 26, 1890).Google Scholar
  106. 106.
    H. Rapoport and J. B. Lavigne, J. Am. Chem. Soc. 75, 5329 (1953).Google Scholar
  107. 107.
    K. W. Bentley and H. M. E. Cardwell, J. Chem. Soc. 3252 (1955).Google Scholar
  108. 108.
    G. Stork and F. H. Clarke, J. Am. Chem. Soc. 78, 4619 (1956).Google Scholar
  109. 109.
    J. Kalvada, P. Buchscahcher, and O. Jeger, Helv. Chim. Acta. 38, 1847 (1955).Google Scholar
  110. 110.
    M. Mackay and D. C. Hodgkin, J. Chem. Soc. 3261 (1955).Google Scholar
  111. 111.
    L. Gylbert, Acta. Crystallogr. (B) 1630 (1973).Google Scholar
  112. 112.
    C. E. Brown, S. J. Roerig, J. M. Fujimoto, and V. T. Burger, J. Chem. Soc. Chem. Comm. 1506 (1983).Google Scholar
  113. 113.
    H. Kugita and M. Takeda, Chem. and Ind. (Lond.) 2099 (1964).Google Scholar
  114. 114.
    H. Kugita and M. Takeda, Chem. Pharm. Bull. 13, 1422 (1965).PubMedGoogle Scholar
  115. 115.
    H. Kugita, M. Takeda, and H. Inoue, Tetrahedron Lett. 1277 (1967).Google Scholar
  116. 116.
    H. Kugita, M. Takeda, and H. Inoue, Tetrahedron 25, 4125 (1969).Google Scholar
  117. 117.
    S. Okuda, S. Yamaguchi, and K. Tsuda, Chem. Pharm. Bull. 13, 1092 (1965).PubMedGoogle Scholar
  118. 118.
    F. G. Mann and M. J. Pragneil, J. Chem. Soc. 4120 (1965).Google Scholar
  119. 119.
    I. Iigima, J. Minamikawa, A. E. Jacobson, A. Brossi, and K. C. Rice, J. Org. Chem. 43, 1462 (1978).Google Scholar
  120. 120.
    Y. F. Jaquet, W. A. Klee, K. C. Rice, I. Iijima, and J. Minamikawa, Science 198, 842 (1977).Google Scholar
  121. 121.
    H. L. Holmes, in: Alkaloids (R. H. F. Manske and H. L. Holmes, eds.), Vol. 2, p. 219, Academic Press, New York (1952).Google Scholar
  122. 122.
    K. Goto and I. Yamamoto, Proc. Jap. Acad. 30, 769 (1954).Google Scholar
  123. 123.
    K. Goto and I. Yamamoto, Proc. Jap. Acad. 33, 477 (1957).Google Scholar
  124. 124.
    K. Goto and I. Yamamoto, Proc. Jap. Acad. 34, 60 (1958).Google Scholar
  125. 125.
    K. Goto, Sinomenine, an Optical Antipode of Morphine Alkaloids, p. 96, Kitasato Institute, Tokyo (1964).Google Scholar
  126. 126.
    K. Tagaki, H. Fukada, M. Watanabe, and M. Sato, Yakugaku Zasshi 80, 1506 (1960).Google Scholar
  127. 127.
    I. Iijima, Heterocycles 6, 1157 (1977).Google Scholar
  128. 128.
    I. Iijima, J. Minamikawa, A. E. Jacobson, A. E. Brossi, K. C. Rice, and W. Klee, J. Med. Chem. 21, 398 (1978).PubMedGoogle Scholar
  129. 129.
    A. H. Beckett and A. F. Casy, J. Pharm. Pharmacol 6, 986 (1954).PubMedGoogle Scholar
  130. 130.
    N. B. Eddy, Chem. and Ind. (Lond.) 1462 (1959).Google Scholar
  131. 131.
    A. H. Beckett, A. F. Casy, and N. J. Harper, J. Pharm. Pharmacol. 8, 874 (1956), and refs. there cited.PubMedGoogle Scholar
  132. 132.
    N. B. Eddy, L. F. Small, J. H. Ager, and E. L. May, J. Org. Chem. 23, 1387 (1958).Google Scholar
  133. 133.
    R. L. Clark, A. A. Pessolano, J. Weijlard, and K. Pfister, J. Am. Chem. Soc. 75, 4963 (1953).Google Scholar
  134. 134.
    J. Weijlard, P. D. Orahovats, A. P. Sullivan, G. Purdue, F. K. Heath, and K. Pfister, J. Am. Chem. Soc. 78, 2342 (1956).Google Scholar
  135. 135.
    C. A. Winter, P. D. Orahovats, and E. G. Lehman, Arch. Int. Pharmacodyn. 110, 186 (1957).PubMedGoogle Scholar
  136. 136.
    N. B. Eddy, H. Besendorf, and B. Pellmont, Bull. Narc. 10, 23 (1958).Google Scholar
  137. 137.
    J. Pohl, Zeitschr. Exp. Pathol. Therap. 17, 370 (1915).Google Scholar
  138. 138.
    J. von Braun, Chem. Ber. 49, 971 (1916).Google Scholar
  139. 139.
    J. von Braun, Chem. Ber. 49, 2655 (1916).Google Scholar
  140. 140.
    J. von Braun, M. Kuhn, and S. Siddiqui, Chem. Ber. 59, 1081 (1926).Google Scholar
  141. 141.
    K. C. Rice, J. Org. Chem. 40, 1850 (1975).PubMedGoogle Scholar
  142. 142.
    K. C. Rice and E. L. May, J. Heterocycl. Chem. 14, 665 (1977).Google Scholar
  143. 143.
    W. L. McCawley, E. R. Hart, and D. F. Marsh, J. Am. Chem. Soc. 63, 314 (1941).Google Scholar
  144. 144.
    J. E. Echenhoff and J. D. Elder, Am. J. Med. Sci. 223, 191 (1952).Google Scholar
  145. 145.
    E. Costa and P. Greengard, eds. Adv. in Biochem. Pharmacol, Vol. 8, Narcotic Antagonists, Raven Press, New York (1973).Google Scholar
  146. 146.
    L. Lasagne and H. K. Beecher, J. Pharmacol. Exp. Ther. 112, 356 (1954).Google Scholar
  147. 147.
    A. S. Keats and J. Telford, J. Pharmacol. Exp. Ther. 177, 190 (1956).Google Scholar
  148. 148.
    P. Karrer and H. Heynemann, Helu. Chim. Acta. 31, 398 (1948).Google Scholar
  149. 149.
    M. Gates and T. Montzka, J. Med. Chem. 7, 127 (1964).PubMedGoogle Scholar
  150. 150.
    J. I DeGraw, J. A. Lawson, J. L. Crase, H. L. Johnson, M. Ellis, E. T. Vyeno, G. H. Loew, and D. S. Berkowitz, J. Med. Chem. 21, 415 (1978).PubMedGoogle Scholar
  151. 151.
    C. Pert and S. Snyder, Mol. Pharmacol 10, 868 (1974).Google Scholar
  152. 152.
    V. M. Kolb, J. Pharm. Sci. 68, 1250 (1979).PubMedGoogle Scholar
  153. 153.
    S. D. Darling, V. M. Kolb, G. S. Mandel, and N. S. Mandel, J. Pharm. Sci. 71, 763 (1982).PubMedGoogle Scholar
  154. 154.
    G. Bianchi, R. Fiocchi, A. Tavani, and L. Manara, Life Sci. 30, 1875 (1982).PubMedGoogle Scholar
  155. 155.
    J. Russell, P. Bass, L. I. Goldberg, C. R. Schuster, and H. Merz, Eur. J. Pharmacol. 78, 255 (1982).PubMedGoogle Scholar
  156. 156.
    B. Kelenti, E. Stenszky, F. Czoller, L. Szlávik, and Z. Mészáros, Arzneim. Forsch. 7, 594 (1957).Google Scholar
  157. 157.
    K. Tagaki, H. Fukuda, and K. Yano, Yakugaku Zasshi 80, 1499 (1960).Google Scholar
  158. 158.
    O. J. Braendon, N. B. Eddy, and H. Halbach, Bull. World Health Org. 13, 937 (1955).Google Scholar
  159. 159.
    R. J. J. Ch. Lousberg and U. Weiss, Experientia 1440 (1974).Google Scholar
  160. 160.
    L. F. Small and S. G. Turnbull, J. Am. Chem. Soc. 59, 1541 (1937).Google Scholar
  161. 161.
    C. Olieman, L. Maat, and C. Beyerman, Recl Trav. Chim. Pays-Bas 95, 189 (1976).Google Scholar
  162. 162.
    L. F. Small and J. E. Mallonee, J. Org. Chem. 12, 558 (1947).PubMedGoogle Scholar
  163. 163.
    E. Ochiai and T. Nakamura, Chem. Ber. 72, 684 (1939).Google Scholar
  164. 164.
    F. Kilivenyi and E. Vinkler, Pharmazie 34, 668 (1979).Google Scholar
  165. 165.
    M. A. Schwartz and M. F. Zoda, J. Org. Chem. 46, 4623 (1981).Google Scholar
  166. 166.
    F.-L. Hsu, K. C. Rice, and A. Brossi, Helv. Chim. Acta 63, 2042 (1980).Google Scholar
  167. 167.
    F.-L. Hsu, K. C. Rice, and A. Brossi, Helv Chim. Acta 65, 1576 (1982).Google Scholar
  168. 168.
    H. Auterhoff and W. Tiltjung, Arch. Pharm 313, 985 (1980).Google Scholar
  169. 169.
    L. F. Small and K. C. Yuen, J. Am. Chem. Soc 58, 192 (1936).Google Scholar
  170. 170.
    L. F. Small, H. M. Fitch, and W. E. Smith, J. Am. Chem. Soc. 58, 1457 (1936).Google Scholar
  171. 171.
    L. F. Small, S. G. Turnbull, and H. M. Fitch, J. Org. Chem. 3, 204 (1938).Google Scholar
  172. 172.
    G. Stork and L. Bauer, J. Am. Chem. Soc. 75, 4373 (1953).Google Scholar
  173. 173.
    L. F. Small and H. Rapoport, J. Org. Chem. 12, 284 (1947).PubMedGoogle Scholar
  174. 174.
    N. B. Eddy, H. Halbach, and O. J. Braenden, Bull World Health Org. 14, 353 (1956).PubMedGoogle Scholar
  175. 175.
    L. F. Small, N. B. Eddy, E. Mossetig, and C. K. Himmelsbach, Studies on Drug Addiction, Suppl. 138, Washington D. C. (1938).Google Scholar
  176. 176.
    R. M. Boden, M. Gates, S. P. Ho, and P. Sundararaman, J. Org. Chem. 47, 1347 (1982).Google Scholar
  177. 177.
    L. J. Sargent and E. L. May, J. Med. Chem. 13, 1061 (1970).PubMedGoogle Scholar
  178. 178.
    A. Pohland and H. R. Sullivan, U. S. Patent 3,342,824 (1967).Google Scholar
  179. 179.
    G. M. Dyson and P. May, May’s Chemistry of Synthetic Drugs, 5th ed., p. 148, Longmans, London (1959).Google Scholar
  180. 180.
    N. B. Eddy, H. Halbach, and O. J. Braenden, Bull. World Health Org. 17, 569 (1957).PubMedGoogle Scholar
  181. 181.
    L. F. Small, K. C. Yuen, and L. K. Eilers, J. Am. Chem. Soc. 55, 3863 (1933).Google Scholar
  182. 182.
    L. F. Small and H. Rapoport, J. Org. Chem. 12, 284 (1947).PubMedGoogle Scholar
  183. 183.
    H. D. Brown, I. M. Rasmussen, G. B. Payne, and K. Pfister, J. Am. Chem. Soc. 75, 6238 (1953).Google Scholar
  184. 184.
    M. S. Chadha and H. Rapoport, J. Am. Chem. Soc. 70, 5730 (1957).Google Scholar
  185. 185.
    J. Fishman, U. S. Patent 3, 153,042 (1963).Google Scholar
  186. 186.
    R. Bognár and S. Makleit, Acta Chim. Acad. Sci. Hung. 59, 359 (1969).Google Scholar
  187. 187.
    J. Knoll, Pharmacol. Res. Comm. 5, 175 (1973).Google Scholar
  188. 188.
    J. Knoll, S. Fürst, and E. S. Vizi, Pharmacology 10, 354 (1973).PubMedGoogle Scholar
  189. 189.
    R. C. Hill, D. Roemer, and H. Buescher, J. Pharmacol. Exp. Ther. 201, 580 (1977).PubMedGoogle Scholar
  190. 190.
    S. C. Clarke, D. R. Jarinski, J. S. Pevnick, and J. D. Griffith, Clin. Pharmacol. Ther. 19, 295 (1976).Google Scholar
  191. 191.
    J. Knoll, S. Fürst, and K. Keleman, J. Pharm. Pharmacol. 25, 929 (1973).PubMedGoogle Scholar
  192. 192.
    J. Knoll, Prog. Neuro-Psychopharmacol. 3, 95 (1979).Google Scholar
  193. 193.
    J. B. Jiang, R. Hanson, P. S. Portoghese, and A. E. Takemori, J. Med. Chem. 20, 1100 (1977).PubMedGoogle Scholar
  194. 194.
    A Z. Ronai, F. F. Foldes, E. F. Hahn, and J. Fishman, J. Pharm. Exp. Ther. 200, 496 (1977).Google Scholar
  195. 195.
    W. Wieland and P. Kappelmeier, Justus Liebig’s Ann. Chem. 382, 306 (1911).Google Scholar
  196. 196.
    G. Stork, in: The Alkaloids (R. H. F. Manske and H. L. Holmes, eds.), Vol. 2, p. 176, Academic Press, New York (1952).Google Scholar
  197. 197.
    G. Stork and F. H. Clarke, J. Am. Chem. Soc. 78, 4619 (1956).Google Scholar
  198. 198.
    H. J. C. Yeh, R. S. Wilson, W. A. Klee, and A. E. Jacobson, J. Pharm. Sci. 65, 902 (1976).PubMedGoogle Scholar
  199. 199.
    L. F. Small and R. E. Lutz, Chemistry of Opium Alkaloids, Suppl. 103 to the Public Health Reports, US Government Printing Office, Washington D. C. (1932).Google Scholar
  200. 200.
    L. J. Sargent and A. E. Jacobson, J. Med. Chem. 15, 843 (1972).PubMedGoogle Scholar
  201. 201.
    P. A. J. Janssen and C. A. M. Van Der Eycken, in: Drugs Affecting the CNS (A. Burger, ed.), Vol. 2, p. 25, Dekker, New York (1968).Google Scholar
  202. 202.
    M. G. Lester, V. Petrow, and O. Stephenson, Tetrahedron 21, 711 (1965).Google Scholar
  203. 203.
    H. Rapoport and L. F. Small, J. Org. Chem. 12, 834 (1947).PubMedGoogle Scholar
  204. 204.
    J. O. Polazzi, J. Org. Chem. 46, 4262 (1981).Google Scholar
  205. 205.
    S. J. DeSolms, J. Org. Chem. 41, 2650 (1976).Google Scholar
  206. 206.
    H. Tada, M. Kobayashi, and Y. K. Sawa, Tetrahedron Lett. 1805 (1969).Google Scholar
  207. 207.
    R. M. Allen and G. W. Kirby, J. Chem. Soc. 363 (1973).Google Scholar
  208. 208.
    M. P. Kotick, D. L. Leland, J. O. Polazzi, J. F. Howes, and A. R. Bousquet, J. Med. Chem. 24, 1445 (1981).PubMedGoogle Scholar
  209. 209.
    R. F. Abdulla and K. H. Fuhr, J. Org. Chem. 43, 4284 (1978).Google Scholar
  210. 210.
    D. Leland, J. O. Polazzi, and M. P. Kotick, J. Org. Chem. 45, 4026 (1980).Google Scholar
  211. 211.
    C. Mannich and M. Schulte, Arch. Pharm. 276, 593 (1938).Google Scholar
  212. 212.
    D. L. Leland and M. P. Kotick, J. Med. Chem. 24, 717 (1981).PubMedGoogle Scholar
  213. 213.
    M. P. Kotick, D. L. Leland, J. O. Polazzi, J. F. Howes, and A. Bousquet, J. Med. Chem. 26, 1050 (1983).PubMedGoogle Scholar
  214. 214.
    D. L. Leland, J. O. Polazzi, and M. P. Kotick, J. Org. Chem. 45, 4026 (1980).Google Scholar
  215. 215.
    D. L. Leland, J. Heterocycl. Chem. 18, 1101 (1981).Google Scholar
  216. 216.
    J. O. Polazzi, M. P. Kotick, J. F. Howes, and A. R. Bousquet, J. Med. Chem. 24, 1516 (1981).PubMedGoogle Scholar
  217. 217.
    D. L. Leland and M. P. Kotick, J. Org. Chem. 48, 1813 (1983).Google Scholar
  218. 218.
    J. Quick, P. Herlihy, R. K. Razdan, and J. F. Howes, J. Med. Chem. 25, 983 (1982).PubMedGoogle Scholar
  219. 219.
    M. P. Kotick, J. Med. Chem. 24, 722 (1981).PubMedGoogle Scholar
  220. 220.
    W. Fleischhacker and A. Klement, Monatsch. Chem. 106, 1513 (1975).Google Scholar
  221. 221.
    M. Boes and W. Fleischhacker, Justus Liebig’s Ann. Chem. 1994 (1981).Google Scholar
  222. 222.
    I. Iijima, J. Minamikawa, K. C. Rice, and A. E. Jacobson, J. Med. Chem. 21, 1320 (1978).PubMedGoogle Scholar
  223. 223.
    S. Y. Yeh, H. A. Krebs, and C. W. Gorodetzky, J. Pharm. Sci. 68, 133 (1979).PubMedGoogle Scholar
  224. 224.
    K. Uba, N. Miyata, K. Watanabe, and M. Hirobe, Chem. Pharm. Bull 28, 356 (1980).PubMedGoogle Scholar
  225. 225.
    K. Uba, N. Miyata, K. Watanabe, and M. Hirobe, Chem. Pharm. Bull 27, 2257 (1979).Google Scholar
  226. 226.
    N. Miyata, K. Uba, K. Watanabe, and M. Hirobe, Chem. Pharm. Bull. 28, 3722 (1980).PubMedGoogle Scholar
  227. 227.
    I. Takayang, R. Shibata, F. Konno, N. Miyata, and M. Chika, J. Pharmacobiodyn. 5, 505 (1982).Google Scholar
  228. 228.
    G. D. Smith and J. F. Griffin, Science 199, 1214 (1978).PubMedGoogle Scholar
  229. 229.
    M. Kotick, D. L. Leland, J. O. Polazzi, and R. N. Schut, J. Med. Chem. 23, 166 (1980).PubMedGoogle Scholar
  230. 230.
    G. H. Posner, Org. React. 19, 1 (1972).Google Scholar
  231. 231.
    F. Ghozland, P. Maroni, I. Viloria, and J. Cros, Eur. J. Med. Chem. 18, 22 (1983).Google Scholar
  232. 232.
    P. D. Gesellchen and D. M. Zimmerman, Ann. Rep. Med. Chem. 16, 43 (1981).Google Scholar
  233. 233.
    D. L. Leland, J. O. Polazzi, and M. P. Kotick, J. Org. Chem. 46, 4012 (1981).Google Scholar
  234. 234.
    M. P. Kotick, J. Med. Chem. 24, 722 (1981).PubMedGoogle Scholar
  235. 235.
    R. Okum and H. W. Elliot, J. Pharmacol. Exp. Ther. 124, 225 (1958).Google Scholar
  236. 236.
    J. Fishman and M. J. Lewenstein, U. S. Patent 3,162,639 (1964).Google Scholar
  237. 237.
    O. Isler, H. Gutman, M. Montavon, R. Rüegg, G. Ryser, and P. Zeller, Helv. Chim. Acta 40, 1247 (1957).Google Scholar
  238. 238.
    E. F. Hahn, J. Fishman, and R. D. Heilman, J. Med. Chem. 18, 259 (1975).PubMedGoogle Scholar
  239. 239.
    M. P. Kotick and J. O. Polazzi, J. Heterocycl. Chem. 18, 1029 (1981).Google Scholar
  240. 240.
    W. Fleischacker and B. Richter, Chem. Ber. 113, 3866 (1980).Google Scholar
  241. 241.
    G. H. Herman and M.-N. N. Kan, Biomed. Mass Spec. 1, 350 (1974).Google Scholar
  242. 242.
    S. P. Findlay and L. F. Small, J. Am. Chem. Soc. 73, 4001 (1951).Google Scholar
  243. 243.
    U. Weiss, J. Org. Chem. 22, 1505 (1957).Google Scholar
  244. 244.
    M. Freund and E. Speyer, J. Prakt. Chem. 94, 135 (1916).Google Scholar
  245. 245.
    F. M. Hauser, T.-K. Chen, and F. I. Carroll, J. Med. Chem. 17, 117 (1974).Google Scholar
  246. 246.
    U. Weiss, J. Am. Chem. Soc. 77, 5891 (1955).Google Scholar
  247. 247.
    M. J. Lewenstein, Br. Patent, 955, 493 (1964).Google Scholar
  248. 248.
    H. Blumberg, H. B. Dayton, G. M. Rapoport, and D. N. Rapoport, Fed. Proc. 20, 311 (1961).Google Scholar
  249. 249.
    L. Lasagna, Proc. Roy. Soc. Med. 58, 978 (1965).PubMedGoogle Scholar
  250. 250.
    M. J. Lewenstein and J. Fishman, U. S. Patent 3,320,262, (1967).Google Scholar
  251. 251.
    H. Blumberg, I. J. Pachter, and Z. Metossian, U. S. Patent, 3,332,950 (1967).Google Scholar
  252. 252.
    N. Chatterjie, C. E. Inturrisi, H. B. Dayton, and H. Blumberg, J. Med. Chem. 18, 490 (1975).PubMedGoogle Scholar
  253. 253.
    H. L. Holmes and C. C. Lee, J. Am. Chem. Soc. 69, 1966 (1947).Google Scholar
  254. 254.
    I. Brown and M. Martin-Smith, J. Chem. Soc. 4139 (1960).Google Scholar
  255. 255.
    M. A. Schwartz and R. A. Wallace, J. Med. Chem. 24, 1525 (1981).PubMedGoogle Scholar
  256. 256.
    J. Knoll, S. Fürst, and S. Makeleit, J. Pharm. Pharmacol. 27, 99 (1975).PubMedGoogle Scholar
  257. 257.
    J. B. Taylor, J. Chem. Soc. (C) 1506 (1968).Google Scholar
  258. 258.
    G. W. Pasternak and E. F. Hahn, J. Med. Chem. 23, 674 (1980).PubMedGoogle Scholar
  259. 259.
    G. W. Pasternak, S. R. Childers, and S. H. Snyder, J. Pharmacol. Exp. Ther. 214, 455 (1980).PubMedGoogle Scholar
  260. 260.
    S. R. Childers and G. W. Pasternak, Cell Mol. Neurobiol. 2, 93 (1982).Google Scholar
  261. 261.
    E. F. Hahn, M. Carroll-Buatti, and G. W. Pasternak, J. Neurosci. 2, 572 (1982).PubMedGoogle Scholar
  262. 262.
    H. Merz, K. Stockhaus, and H. Wick, J. Med. Chem. 18, 996 (1975).PubMedGoogle Scholar
  263. 263.
    H. Merz, K. Stockhaus, and H. Wick, J. Med. Chem. 20, 844 (1977).PubMedGoogle Scholar
  264. 264.
    E. Kutter, A. Herz, H. J. Teschemacher, and R. Hess, J. Med. Chem. 13, 801 (1970).PubMedGoogle Scholar
  265. 265.
    G. H. Loew and D. S. Berkowitz, J. Med. Chem. 18, 656 (1975).PubMedGoogle Scholar
  266. 266.
    G. H. Loew and D. S. Berkowitz, in Opiates and Endogenous Opioid Peptides, p. 399, Elsevier, Amsterdam (1976).Google Scholar
  267. 267.
    J. Knoll, Neuropharmacology 14, 921 (1975).PubMedGoogle Scholar
  268. 268.
    G. H. Loew and D. S. Berkowitz, J. Med. Chem. 21, 101 (1978).PubMedGoogle Scholar
  269. 269.
    B. Belleau, T. Conway, F. R. Ahmed, and A. D. Hardy, J. Med. Chem. 17, 907 (1974).PubMedGoogle Scholar
  270. 270.
    S. Shiotani, T. Kometani, Y. Iitaka, and A. Itai, J. Med. Chem. 21, 153 (1978).PubMedGoogle Scholar
  271. 271.
    V. M. Kolb, J. Pharm. Sci. 67, 999 (1978).PubMedGoogle Scholar
  272. 272.
    Ref. 266, p. 387.Google Scholar
  273. 273.
    R. J. Kobylecki, R. W. Carling, J. A. H. Lord, C. F. C. Smith, and A. C. Lane, J. Med Chem. 25, 116 (1982).PubMedGoogle Scholar
  274. 274.
    G. Heinisch, V. Kintz, and F. Vieböck, Monatsch. Chem. 102, 530 (1971).Google Scholar
  275. 275.
    R. M. Allen and G. W. Kirby, J. Chem. Soc. Perkin Trans. I 363 (1973).Google Scholar
  276. 276.
    A. C. Currie, J. Gillon, G. T. Newbold, and F. S. Spring, J. Chem. Soc. 773 (1960).Google Scholar
  277. 277.
    L. J. Sargent, L. H. Schwartzman, and L. F. Small, J. Org. Chem. 23, 1247 (1958).Google Scholar
  278. 278.
    H. Krueyer, N. B. Eddy, and M. Sumwalt in The Pharmacology of the Opium Alkaloids, part 2, p. 944, U. S. Government Printing Office, Washington, D. C. (1943).Google Scholar
  279. 279.
    W. R. Buckett, M. E. Farguharson, and C. G. Haining, J. Pharm. Pharmacol. 16, 174 (1964).PubMedGoogle Scholar
  280. 280.
    W. R. Buckett, J. Pharm. Pharmacol. 16, 68T (1964).Google Scholar
  281. 281.
    C. Linder and J. Fishman, J. Med. Chem. 16, 553 (1973).PubMedGoogle Scholar
  282. 282.
    D. L. Leland, J. O. Polazzi, and M. P. Kotick, J. Org. Chem. 46, 4012 (1981).Google Scholar
  283. 283.
    M. P. Kotick, J. Org. Chem. 48, 1819 (1983).Google Scholar
  284. 284.
    P. Osei-Gyimah and S. Archer, J. Med. Chem. 23, 162 (1980).PubMedGoogle Scholar
  285. 285.
    S. Archer and P. Osei-Gyimah, J. Heterocycl. Chem. 16, 389 (1979).Google Scholar
  286. 286.
    R. M. Allen and G. W. Kirby, J. Chem. Soc. Chem. Comm. 1346 (1970).Google Scholar
  287. 287.
    R. M. Allen, G. W. Kirby, and D. J. McDougall, J. Chem. Soc. Perkin Trans I 1143 (1981).Google Scholar
  288. 288.
    L. S. Schwab, J. Med. Chem. 23, 698 (1980).PubMedGoogle Scholar
  289. 289.
    W. R. Buckett, Br. J. Pharmacol. 76, 269P (1982).Google Scholar
  290. 290.
    W. Fleischhacker and B. Richter, Sd Pharm. 49, 118 (1981).Google Scholar
  291. 291.
    W. Fleischhacker and B. Richter, Chem. Ber. 112, 3054 (1979).Google Scholar
  292. 292.
    E. J. Simon and J. M. Hiller, Ann. Rev. Pharmacol. Toxicol. 18, 371 (1978).Google Scholar
  293. 293.
    P. S. Portoghese, V. G. Telang, A. E. Takemori, and G. Hayashi, J. Med. Chem. 14, 144 (1971).PubMedGoogle Scholar
  294. 294.
    A. E. Takemori, A. Ward, P. S. Portoghese, and V. G. Telang, J. Med. Chem. 17, 1051 (1974).PubMedGoogle Scholar
  295. 295.
    K. C. Rice, S. Shiotani, C. R. Creveling, A. E. Jacobson, and W. A. Klee, J. Med. Chem. 20, 673 (1977).PubMedGoogle Scholar
  296. 296.
    M. May, I. Czoncha, D. R. Garrison, and D. J. Triggle, J. Pharm. Sci. 57, 884 (1968).PubMedGoogle Scholar
  297. 297.
    R. Schultz and A. Goldstein, Life Sci. 16, 1843 (1975).Google Scholar
  298. 298.
    P. S. Portoghese, R. N. Hanson, V. G. Telang, J. L. Winger, and A. E. Takemori, J. Med. Chem. 20, 1920 (1977).Google Scholar
  299. 299.
    J. B. Jiang, R. N. Hanson, P. S. Portoghese, and A. E. Takemori, J. Med. Chem. 20, 1100 (1977).PubMedGoogle Scholar
  300. 300.
    E. F. Hahn, J. Fishman, and R. D. Heilman, J. Med. Chem. 18, 259 (1975).PubMedGoogle Scholar
  301. 301.
    N. Chatterjie, C. E. Inturrisi, H. B. Dayton, and H. Blumberg, J. Med. Chem. 18, 490 (1975).PubMedGoogle Scholar
  302. 302.
    P. S. Portoghese, D. L. Larson, J. B. Jiang, A. E. Takemori, and T. P. Caruso, J. Med. Chem. 21, 598 (1978).PubMedGoogle Scholar
  303. 303.
    P. S. Portoghese, D. L. Larson, J. B. Jiang, T. P. Caruso, and A. E. Takemori, J. Med. Chem. 22, 168 (1979).PubMedGoogle Scholar
  304. 304.
    D. Julius and P. Renault, eds. Res. Monograph Ser. Nat. Inst. Drug Abuse (U. S.) 9, (1976) Google Scholar
  305. 305.
    G. A. Wiley, R. L. Hershkowitw, B. M. Rein, and B. C. Chung, J. Am. Chem. Soc. 86, 964 (1964).Google Scholar
  306. 306.
    L. M. Sayre and P. S. Portoghese, J. Org. Chem. 45, 3366 (1980).Google Scholar
  307. 307.
    T. P. Caruso, A. E. Takemori, D. L. Larson, and P. S. Portoghese, Science 204, 316 (1979).PubMedGoogle Scholar
  308. 308.
    P. S. Portoghese, D. L. Larson, L. M. Sayre, D. S. Fries, and A. E. Takemori, J. Med. Chem. 23, 233 (1980).PubMedGoogle Scholar
  309. 309.
    P. S. Portoghese, J. Med. Chem. 8, 609 (1965).PubMedGoogle Scholar
  310. 310.
    S. J. Ward, P. S. Portoghese, and A. E. Takemori, J. Pharmacol. Exp. Ther. 220, 494 (1982).PubMedGoogle Scholar
  311. 311.
    S. J. Ward, P. S. Portoghese, and A. E. Takemori, Eur. J. Pharmacol. 80, 377 (1982).PubMedGoogle Scholar
  312. 312.
    A. E. Takemori, D. L. Larson, and P. S. Portoghese, Eur. J. Pharmacol. 70, 445 (1981).PubMedGoogle Scholar
  313. 313.
    L. M. Sayre, D. L. Larson, D. S. Fries, A. E. Takemori, and P. S. Portoghese, J. Med. Chem. 26, 1229 (1983).PubMedGoogle Scholar
  314. 314.
    P. S. Portoghese and A. E. Takemori, in: The Chemical Regulation of Biological Mechanisms (A. M. Creighton and S. Turner, eds.) p. 181, Royal Society of Chemistry, London (1982).Google Scholar
  315. 315.
    P. S. Portoghese and A. E. Takemori, J. Med. Chem. 26, 1341 (1983).PubMedGoogle Scholar
  316. 316.
    M. Erez, A. E. Takemori, and P. S. Portoghese, J. Med. Chem. 25, 847 (1982).PubMedGoogle Scholar
  317. 317.
    P. S. Portoghese, G, Ronsisvalle, D. L. Larson, C. B. Yim, L. M. Sayre, and A. E. Takemori, Life Sci. 31, 1283 (1982).PubMedGoogle Scholar
  318. 318.
    E. J. P. Fear, J. Thornower, and J. Veitch, J. Chem. Soc. 1322 (1958).Google Scholar
  319. 319.
    M. Newcomb, S. S. Moore, and D. J. Cram, J. Am. Chem. Soc. 99, 6405 (1977).Google Scholar
  320. 320.
    E. Hazum, K. J. Chang, H. J. Leighton, O. W. Lever, and P. Cuatrecasas, Biochem. Biophys. Res. Comm. 104, 347 (1982).PubMedGoogle Scholar
  321. 321.
    A. C. Allen, J. M. Moore, and D. A. Cooper, J. Org. Chem. 48, 3951 (1983).Google Scholar
  322. 322.
    K. W. Bentley and D. G. Hardy, Proc. Chem. Soc. 220 (1963).Google Scholar
  323. 323.
    K. W. Bentley and A. F. Thomas, J. Chem. Soc. 1863 (1956).Google Scholar
  324. 324.
    K. W. Bentley and D. G. Hardy, J. Am. Chem. Soc. 89, 3267 (1967).Google Scholar
  325. 325.
    K. W. Bentley, A. L. A. Boura, A. E. Fitzgerald, D. G. Hardy, A. McCoubrey, M. L. Aikman, and R. E. Lister, Nature 206, 102 (1965).PubMedGoogle Scholar
  326. 326.
    J. W. Lewis, M. J. Readhead, and A. C. B. Smith, J. Med. Chem. 16, 9 (1973).PubMedGoogle Scholar
  327. 327.
    J. W. Lewis, Adv. Biochem. Psychopharmacol. 8, 123 (1974).Google Scholar
  328. 328.
    R. G. Twycross, Pain 3, 93 (1977).PubMedGoogle Scholar
  329. 329.
    A. F. Casy, Prog. Drug. Res. 22, 149 (1978).PubMedGoogle Scholar
  330. 330.
    K. W. Bentley, D. G. Hardy, and B. Meek, J. Am. Chem. Soc. 89, 3273 (1967).PubMedGoogle Scholar
  331. 331.
    K. W. Bentley and D. G. Hardy, J. Am. Chem. Soc. 98, 3281 (1967).Google Scholar
  332. 332.
    K. W. Bentley, Br. Patent 1,136,214 (1968).Google Scholar
  333. 333.
    G. F. Blane, A. L. A. Boura, A. E. Fitzgerald, and R. E. Lister, Br. J. Pharmacol. 30, 11 (1967).Google Scholar
  334. 334.
    D. Campbell, R. E. Lister, and G. W. McNicol, Clin. Pharmacol. Ther. 5, 193 (1964).PubMedGoogle Scholar
  335. 335.
    J. D. Wallach, Vet. Med. 64, 53 (1961).Google Scholar
  336. 336.
    J. M. King and B. Carter, Afr. Wildlife J. 3, 19 (1965).Google Scholar
  337. 337.
    A. M. Hartshoorn, J. Am. Vet. Med. Assoc. 149, 875 (1966).Google Scholar
  338. 338.
    J. D. Wallach, J. Am. Vet. Med. Assoc. 149, 871 (1966).PubMedGoogle Scholar
  339. 339.
    G. F. Blane, J. Pharm. Pharmacol 19, 367 (1967).PubMedGoogle Scholar
  340. 340.
    H. W. Kosterlitz and A. J. Watt, Br. J. Pharmacol 33, 266 (1968).Google Scholar
  341. 341.
    G. F. Blane and D. Dugdall, J. Pharm. Pharmacol 20, 547 (1968).PubMedGoogle Scholar
  342. 342.
    A. Cowan, Adv. Biochem. Psychopharmacol 8, 427 (1974).Google Scholar
  343. 343.
    A. Cowan, J. C. Doxey, and E. J. R. Harry, Br. J. Pharmacol. 60, 547 (1977).PubMedGoogle Scholar
  344. 344.
    W. F. Michne, R. L. Salsbury, and S. J. Michalec, J. Med. Chem. 20, 682 (1977).PubMedGoogle Scholar
  345. 345.
    S. C. Clarke, Clin. Pharmacol Ther. 19, 295 (1976).Google Scholar
  346. 346.
    S. N. Downing, W. P. Leary, and E. S. White, Br. J. Anaesth. 47, 251 (1977).Google Scholar
  347. 347.
    A. B. Dobkin, Can. Anaesth. Soc. J. 24, 186 (1977).PubMedGoogle Scholar
  348. 348.
    K. W. Bentley, D. G. Hardy, and B. Meek, J. Am. Chem. Soc. 89, 3293 (1967).PubMedGoogle Scholar
  349. 349.
    K. W. Bentley, D. G. Hardy, C. F. Howell, W. Fulmor, J. E. Lancaster, J. J. Brown, G. O. Morton, and R. A. Hardy, J. Am Chem. Soc. 89, 3303 (1967).PubMedGoogle Scholar
  350. 350.
    K. W. Bentley, D. G. Hardy, B. Meek, J. B. Taylor, J. J. Brown, and G. O. Morton, J. Chem. Soc. (C) 2229 (1969).Google Scholar
  351. 351.
    K. W. Bentley, D. G. Hardy, H. P. Crocker, D. I. Haddlesey, and P. A. Mayor, J. Am. Chem. Soc. 89, 3312 (1967).PubMedGoogle Scholar
  352. 352.
    K. Kanematsu and T. Sasaki, J. Chem. Soc. Chem. Comm. 988 (1967).Google Scholar
  353. 353.
    K. W. Bentley and B. Meek, J. Chem. Soc. (C) 2233 (1969).Google Scholar
  354. 354.
    K. W. Bentley, D. G. Hardy, and A. C. B. Smith, J. Chem. Soc. (C) 2235, (1969).Google Scholar
  355. 355.
    K. W. Bentley, J. D. Bower, J. W. Lewis, M. J. Readhead, A. C. B. Smith, and G. R. Young, J. Chem. Soc. (C) 2237 (1969).Google Scholar
  356. 356.
    K. W. Bentley, J. D. Bower, and J. W. Lewis, J. Chem. Soc. (C) 2569 (1969).Google Scholar
  357. 357.
    K. W. Bentley, J. D. Bower, and A. C. B. Smith, J. Chem. Soc. (C) 2241 (1969).Google Scholar
  358. 358.
    J. W. Lewis and M. J. Readhead, J. Med. Chem. 13, 525 (1970).PubMedGoogle Scholar
  359. 359.
    K. W. Bentley, D. G. Hardy, and P. A. Mayor, J. Chem. Soc. (C) 2385 (1969).Google Scholar
  360. 360.
    D. I. Haddlesey, J. W. Lewis, P. A. Mayor, and G. R. Young J. Chem. Soc. Perkin I 872 (1972).Google Scholar
  361. 361.
    J. W. Lewis, M. J. Rance, and G. R. Young, J. Med. Chem. 17, 465 (1974).PubMedGoogle Scholar
  362. 362.
    D. I. Haddlesey, J. W. Lewis, and P. A. Mayor, J. Chem. Soc. Perkin I 875 (1972).Google Scholar
  363. 363.
    J. W. Lewis, P. A. Mayor, and D. I. Haddlesey, J. Med. Chem. 16, 12 (1973).PubMedGoogle Scholar
  364. 364.
    C. W. Hutchins, G. K. Cooper, S. Purro, and H. Rapoport, J. Med. Chem. 24, 773 (1981).PubMedGoogle Scholar
  365. 365.
    G. H. Loew and D. S. Berkowitz, J. Med. Chem. 22, 603 (1979).PubMedGoogle Scholar
  366. 366.
    A. P. Feinberg, I. Cresse, and S. H. Snyder, Proc. Natl. Acad. Sci. USA 73, 4215 (1976).PubMedGoogle Scholar
  367. 367.
    P. R. Crabbendam, L. Maat, and H. C. Beyerman, Reel Trav. Chim. Pays-Bas 100, 293 (1981).Google Scholar
  368. 368.
    J. W. Lewis, M. J. Readhead, I. A. Selby, A. C. B. Smith, and C. A. Young, J. Chem. Soc. (C) 1158 (1971).Google Scholar
  369. 369.
    J. W. Lewis, M. J. Readhead, and A. C. B. Smith, J. Med. Chem. 16, 9 (1973).PubMedGoogle Scholar
  370. 370.
    J. W. Lewis and M. J. Readhead, J. Med. Chem. 16, 84 (1973).PubMedGoogle Scholar
  371. 371.
    C. W. Hutchins and H. Rapoport, J. Med. Chem. 27, 521 (1984).PubMedGoogle Scholar
  372. 372.
    A. F. Bradbury, D. G. Smyth, and C. R. Small, Nature 260, 165 (1976).PubMedGoogle Scholar
  373. 373.
    M. P. Kotick, D. L. Leland, J. O. Polazzi, J. F. Howes, and A. Bousquet, J. Med. Chem. 26, 1050 (1983).PubMedGoogle Scholar
  374. 374.
    H. Rapoport and P. Sheldrick, J. Am. Chem. Soc. 85, 1636 (1983).Google Scholar
  375. 375.
    A. Singh, S. Archer, K. Hoogsteen, and J. Hirshfield, J. Org. Chem. 47, 752 (1982).Google Scholar
  376. 376.
    K. Hayakawa, S. Motohiro, I. Fujii, and K. Kanematsu, J. Am. Chem. Soc. 103, 4605 (1981).Google Scholar
  377. 377.
    G. W. Kirby, K. W. Bentley, P. Horsewood, and S. Singh, J. Chem. Soc. Perkin I 3064 (1979).Google Scholar
  378. 378.
    G. W. Kirby and J. G. Sweeney, J. Chem. Soc. Perkin I 3250, (1981).Google Scholar
  379. 379.
    M. Boes and W. Fleischhacker, Justus Liebigs Ann. Chem. 2002 (1981).Google Scholar
  380. 380.
    R. Bognár, S. Makleit, L. Radies, and I. Seki, Org. Prep. Proc. Int. 5, 49 (1973).Google Scholar
  381. 381.
    G. M. Badger and R. B. Bradbury, J. Chem. Soc. 445 (1960).Google Scholar
  382. 382.
    W. K. Hart, S. R. Johns, J. A. Lamberton, and J. K. Saunders, Tetrahedron Lett. 2891 (1968).Google Scholar
  383. 383.
    A. R. Battersby, M. H. G. Munro, R. B. Bradbury, and F. Santary, J. Chem. Soc. Chem. Comm. 695 (1968).Google Scholar
  384. 384.
    M. Tomita, T. Ibuka, Y. Inubush, and K. Takeda, Tetrahedron Lett. 3605 (1964).Google Scholar
  385. 385.
    L. J. Sargent and B. C. Joshi, J. Med. Chem. 11, 336 (1968).PubMedGoogle Scholar
  386. 386.
    S. Okuda, S. Yamaguchi, Y. Kawazoe, and K. Tsuda, Chem. Pharm. Bull. 12, 104 (1964).PubMedGoogle Scholar
  387. 387.
    N. Karplus, J. Chem Phys. 30, 11 (1959).Google Scholar
  388. 388.
    D. Elad and D. Ginsburg, J. Am. Chem. Soc. 78, 3691 (1956).Google Scholar
  389. 389.
    T. Rüll, Bull, Soc. Chim. Fr. 586 (1963).Google Scholar
  390. 390.
    A. E. Jacobson, H. J. Yeh, and L. J. Sargent, Org. Mag. Reson, 4, 875 (1972).Google Scholar
  391. 391.
    T. J. Batterham, K. H. Bell, and U. Weiss, Aust. J. Chem. 18, 1799 (1965).Google Scholar
  392. 392.
    J. A. Glasel, Biochem. Biophys. Res. Comm. 102, 703 (1981).PubMedGoogle Scholar
  393. 393.
    S. K. Burt, G. H. Loew, and G. M. Hashimoto, Ann. N. Y. Acad. Sci. 367, 219 (1981).PubMedGoogle Scholar
  394. 394.
    S. Yamaguchi, S. Okuda, and N. Nakagawa, Chem. Pharm. Bull. 11, 1465 (1963).PubMedGoogle Scholar
  395. 395.
    T. Rüll and D. Gagnaire, Bull. Soc. Chim. Fr. 2189 (1963).Google Scholar
  396. 396.
    W. Fulmor, J. E. Lancaster, G. O. Morton, J. J. Brown, C. F. Howell, C. T. Nora, and R. A. Hardy, J. Am. Chem. Soc. 89, 3322 (1967).PubMedGoogle Scholar
  397. 397.
    Y. Terui, K. Tori, S. Maeda, and Y. K. Sawa, Tetrahedron Lett. 2853 (1975).Google Scholar
  398. 398.
    F. I. Carroll, C. G. Moreland, G. A. Brine, and J. A. Kepler, J. Org. Chem. 41, 996 (1976).PubMedGoogle Scholar
  399. 399.
    D. W. Hughes and D. B. MacLean, in: The Alkaloids (R. H. F. Manske and R. G. A. Rodrigo, eds.) 18, 228 (1981).Google Scholar
  400. 400.
    J. H. van den Hende and N. R. Nelson, J. Am. Chem. Soc. 89, 2901 (1967).PubMedGoogle Scholar
  401. 401.
    V. M. Kolb, J. Pharm. Sci. 68, 1250 (1979).PubMedGoogle Scholar
  402. 402.
    V. M. Kolb, G. S. Mandel, and N. S. Mandel, J. Pharm. Sci. 71, 763 (1982).PubMedGoogle Scholar
  403. 403.
    S. Shiotani, T. Kometani, Y. Iitaka, and A. Itai, J. Med. Chem. 21, 153 (1978).PubMedGoogle Scholar
  404. 404.
    E. E. Eliel, S. Morris-Natschke, and V. M. Kolb, Org. Magn. Resort. 22, 258 (1984).Google Scholar
  405. 405.
    A. P. Feinberg, I. Creese, and S. H. Snyder, Proc. Natl. Acad. Sci. USA 73, 4215 (1976).PubMedGoogle Scholar
  406. 406.
    J. M. Bobbit, W. Weiss, and D. D. Hanessian, J. Org. Chem. 24, 1582 (1959).Google Scholar
  407. 407.
    U. Weiss and T. Rüll, Bull. Soc. Chim. Fr. 3707 (1965).Google Scholar
  408. 408.
    T. Rüll, Bull. Soc. Chim. Fr. 3715 (1965).Google Scholar
  409. 409.
    A. F. Casy and M. M. A. Hassan, J. Pharm. Pharmacol. 19, 132 (1967).Google Scholar
  410. 410.
    H. Inoue, M. Takeda, and H. Kugita, Chem. Pharm. Bull. 21, 2004 (1973).Google Scholar
  411. 411.
    H. Audier, H. Fetison, D. Ginsburg, A. Mandelbaum, and T. Rüll, Tetrahedron Lett. 13 (1965).Google Scholar
  412. 412.
    H. Nakata, Y. Hirata, A. Tatematsu, H. Tada, and Y. K. Sawa, Tetrahedron Lett. 829 (1965).Google Scholar
  413. 413.
    A. Mandelbaum and D. Ginsburg, Tetrahedron Lett. 2479 (1965).Google Scholar
  414. 414.
    D. M. S. Wheeler, T. H. Kinstle, and K. L. Rinehart, J. Am. Chem. Soc. 89, 4494 (1967).PubMedGoogle Scholar
  415. 415.
    J. Fridrichsons, M. F. Mackay, and A. M. Mathieson, Tetrahedron Lett. 2887 (1968).Google Scholar
  416. 416.
    J. Fridrichsons, M. F. Mackay, and A. M. Mathieson, Tetrahedron 26, 1969 (1970).Google Scholar
  417. 417.
    G. Kartha, F. R. Ahmed, and W. H. Barnes, Acta Cryst. 15, 326 (1962).Google Scholar
  418. 418.
    R. W. Houde, S. L. Wallenstein, and W. T. Beaver, Analgetics, (G. d Stevens, ed.), p. 75, Academic Press, New York (1965).Google Scholar
  419. 419.
    W. H. Olendorf, S. Hyman, L. Braun, and S. Z. Olendorf, Science 178, 984 (1972).Google Scholar
  420. 420.
    J. G. Nutt and D. R. Jasinski, Clin. Pharmacol. Ther. 15, 156 (1974).PubMedGoogle Scholar
  421. 421.
    S. H. Weinstein, M. Pfeffer and J. Schor, Adv. Biochem. Psychopharmacol. 8, 525 (1973).PubMedGoogle Scholar
  422. 422.
    W. R. Martin, D. R. Jasinski, and P. A. Mansky, Arch. Gen. Psychiatry, 28, 784 (1973).PubMedGoogle Scholar
  423. 423.
    K. Vereby, J. Volarka, S. Mule, and R. Resnick, Clin. Pharmacol. Ther. 20, 315 (1976).Google Scholar
  424. 424.
    E. L. Way and T. K. Adler, in: The Biological Disposition of Morphine and Its Surrogates, WHO, Geneva (1962).Google Scholar
  425. 425.
    J. T. Scrapfani and D. H. Clouet, in: Narcotic Drugs (D. H. Clouet, ed.), Chap. 6, Plenum Press, New York (1971).Google Scholar
  426. 426.
    L. Lemberger and A. Rubin, Physiological Disposition of Drugs, Chap. 5, Spectrum Publications, New York (1976).Google Scholar
  427. 427.
    H. Yoshimura, K. Oguri, and H. Tsukamoto, Tetrahedron Lett. 483 (1968).Google Scholar
  428. 428.
    S. Y. Yeh, C. W. Gorodetzky, and H. A. Krebs, J. Pharm. Sci. 66, 1288 (1977).PubMedGoogle Scholar
  429. 429.
    H. Yoshimura, J. Pharmacobiodyn 3, S6 (1980).Google Scholar
  430. 430.
    S. Y. Yeh, J. Pharmacol. Exp. Ther. 192, 201 (1975).PubMedGoogle Scholar
  431. 431.
    J. W. Miller and H. H. Anderson, J. Pharmacol. Exp. Ther. 112, 191 (1954).PubMedGoogle Scholar
  432. 432.
    J. W. Miller and H. W. Elliot, J. Pharmacol. Exp. Ther. 113, 283 (1955).PubMedGoogle Scholar
  433. 433.
    A. H. Beckett, A. F. Casy, and N. J. Harper, J. Pharm. Pharmacol. 8, 874 (1956).PubMedGoogle Scholar
  434. 434.
    C. Ellison, H. W. Elliot, M. Look, and H. Rapoport, J. Med. Chem. 6, 237 (1963).Google Scholar
  435. 435.
    J. B. Schenkman, H. Remmer, and R. W. Estabrook, Mol Pharmacol. 3, 113 (1967).PubMedGoogle Scholar
  436. 436.
    S. Y. Yeh, R. L. McQuinn, H. A. Krebs, and C. W. Gorodetzky, J. Pharm. Sci. 67, 878 (1978).PubMedGoogle Scholar
  437. 437.
    S. Y. Yeh, Pharmacologist 18, 178 (1976).Google Scholar
  438. 438.
    H. W. Elliot, B. M. Tolbert, T. K. Alder, and H. H. Anderson, Proc. Soc. Exp. Biol Med. 85, 77 (1954).Google Scholar
  439. 439.
    T. K. Alder, J. M. Fujimoto, E. L. Way, and E. M. Baker, J. Pharmacol Exp. Ther. 114, 251 (1955).Google Scholar
  440. 440.
    K. Klutch, Drug, Metab. Disp. 2, 23 (1974).Google Scholar
  441. 441.
    S. Y. Yeh, Fed. Proc. 35, 469 (1976).Google Scholar
  442. 442.
    C. Ellison and H. W. Elliot, J. Pharmacol Exp. Ther. 144, 265 (1964).Google Scholar
  443. 443.
    D. Borner and S. Abbott, Experientia 29, 180 (1973).PubMedGoogle Scholar
  444. 444.
    S. Y. Yeh, Experientia 30, 264 (1974).PubMedGoogle Scholar
  445. 445.
    L. S. Abrams and H. W. Elliot, J. Pharm. Exp. Ther. 189, 285 (1974).Google Scholar
  446. 446.
    J. Daly, J. K. Inscoe, and J. Axelrod, J. Med. Chem. 8, 1953 (1965).Google Scholar
  447. 447.
    A. L. Misra, N. L. Vadlamani, R. B. Pontani, and S. J. Mulé, Biochem. Pharmacol. 22, 2129 (1973).PubMedGoogle Scholar
  448. 448.
    S. Y. Yeh, H. A. Krebs, and C. W. Gorodetzky, J. Pharm. Sci. 68, 133 (1979).PubMedGoogle Scholar
  449. 449.
    N. Miyata, K. Uba, K. Watanabe, and M. Hirobe, J. Pharmacobiodyn. 4, 57 (1981).Google Scholar
  450. 450.
    I. Takayanagi, F. Konno, N. Miyata, K. Watanabe, and M. Hirobe, Jap. J. Pharmacol 32, 387 (1982).PubMedGoogle Scholar
  451. 451.
    E. L. Way, J. M. Young, and J. W. Kemp, Bull Narc. 17, 25 (1965).Google Scholar
  452. 452.
    E. R. Garrett and T. Gurkan, J. Pharm. Sci. 69, 1116 (1980).PubMedGoogle Scholar
  453. 453.
    S. Y. Yeh and R. L. McQuinn, J. Pharm. Sci. 64, 1237 (1975).PubMedGoogle Scholar
  454. 454.
    S. Y. Yeh, C. W. Gorodetzky, and R. L. McQuinn, J. Pharmacol. Exp. Ther. 196, 249 (1976).PubMedGoogle Scholar
  455. 455.
    S. Y. Yeh, R. L. McQuinn, and C. W. Gorodetzky, J. Pharm. Sci. 66, 201 (1977).PubMedGoogle Scholar
  456. 456.
    S. H. Weinstein, M. Pfeffer, J. M. Schor, L. Indindoli, and M. Mintz, J. Pharm. Sci. 60, 1567 (1971).PubMedGoogle Scholar
  457. 457.
    J. M. Fujimoto, J. Pharmacol. Exp. Ther. 168, 180 (1969).PubMedGoogle Scholar
  458. 458.
    J. M. Tujimoto, Proc. Soc. Exp. Biol Med. 133, 317 (1970).Google Scholar
  459. 459.
    M. E. Wall, D. R. Brine, and M. Perez-Reyez, Drug Metab. Disposition 9, 369 (1981).Google Scholar
  460. 460.
    E. J. Cone, Tetrahedron Lett. 2607 (1973).Google Scholar
  461. 461.
    A. H. Beckett and A. F. Casy, Proc. Med. Chem. 4, 171 (1965).Google Scholar
  462. 462.
    N. B. Eddy and E. L. May, Science 181, 407 (1973).PubMedGoogle Scholar
  463. 463.
    A. F. Casy, in: Guide to Molecular Pharmacology—Toxicology (R. M. Featherstone, ed.), Part 1, p. 217, Dekker, New York (1973).Google Scholar
  464. 464.
    A. S. Horn and J. R. Rogers, J. Pharm. Pharmacol 29, 257 (1977).PubMedGoogle Scholar
  465. 465.
    G. de Stevens (ed.), Analgetics, Academic Press, New York (1965).Google Scholar
  466. 466.
    D. Lednicer (ed.), Central Analgetics, John Wiley and Sons, New York (1982).Google Scholar
  467. 467.
    E. L. May, J. Med. Chem. 23, 225 (1980).PubMedGoogle Scholar
  468. 468.
    G. H. Loew, D. Berkowitz, H. Weinstein, and S. Srebrenik, in: Molecular and Quantum Pharmacology (E. Bergmann and B. Pullman, eds.), p. 355, D. Reidel, Dordrecht, Holland (1974).Google Scholar
  469. 469.
    P. S. Portoghese, Acc. Chem. Res. 11, 21 (1978).Google Scholar
  470. 470.
    E. Kutter, A. Herz, H.-J. Teschemacher, and R. Hess, J. Med. Chem. 13, 801 (1970).PubMedGoogle Scholar
  471. 471.
    J. J. Kaufman, N. M. Semo, and W. S. Koski, J. Med. Chem. 18, 647 (1975).PubMedGoogle Scholar
  472. 472.
    R. H. F. Manske and H. L. Holmes (eds.), The Alkaloids, Academic Press, New York (1952).Google Scholar
  473. 473.
    K. W. Bentley, in: The Alkaloids (R. H. F. Manske, ed.), Vol. 13, p. 1, Academic Press, New York (1971).Google Scholar
  474. 474.
    H. W. Kosterlitz and A. A. Waterfield, Ann. Rev. Pharmacol. 15, 29 (1975).PubMedGoogle Scholar
  475. 475.
    H. W. Kosterlitz, J. A. H. Lord, S. J. Paterson, and A. A. Waterfield, Br. J. Pharmacol 68, 333 (1980).PubMedGoogle Scholar
  476. 476.
    C. E. Brown, S. C. Roerig, J. M. Fujimoto, and V. T. Burger, J. Chem. Soc, Chem. Commun. 1506 (1983).Google Scholar
  477. 477.
    J. A. Glasel and H. W. Reiher, Org. Magn. Reson. 23, 236 (1985).Google Scholar
  478. 478.
    S. Fang, A. E. Takemori, and P. S. Portoghese, J. Med. Chem. 27, 1361 (1984).PubMedGoogle Scholar
  479. 479.
    J. Reden, M. F. Reich, K. C. Rice, A. H. Jacobson and A. Brossi, J. Med. Chem. 22, 256 (1979).PubMedGoogle Scholar

Copyright information

© Springer Science+Business Media New York 1986

Authors and Affiliations

  • Alan F. Casy
    • 1
  • Robert T. Parfitt
    • 1
    • 2
  1. 1.University of BathBathUK
  2. 2.Canberra College of Advanced EducationBelconnenAustralia

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