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4,5-Epoxymorphinans

  • Chapter
Opioid Analgesics

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.

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References

  1. J. M. Gulland and R. Robinson, J. Chem. Soc. 980 (1923).

    Google Scholar 

  2. J. M. Gulland and R. Robinson, Mem. Proc. Manchester Lit. Phil Soc. 69, 79 (1925).

    CAS  Google Scholar 

  3. C. Schöfp, Justus Liebigs Ann. Chem. 452, 411 (1927).

    Google Scholar 

  4. M. Gates and G. Tschudi, J. Am. Chem. Soc. 74, 1109 (1952).

    CAS  Google Scholar 

  5. M. Gates and G. Tschudi, J. Am. Chem. Soc. 78, 1380 (1956).

    CAS  Google Scholar 

  6. D. H. R. Barton and T. Cohen, Festschrift Arthur Stoll, p. 117, Birckhauser, Basel (1957).

    Google Scholar 

  7. A. R. Battersby, Oxidative Coupling of Phenols, p. 119, Dekker, New York (1967).

    Google Scholar 

  8. K. W. Bentley, The Chemistry of the Morphine Alkaloids, Clarendon Press, Oxford (1954).

    Google Scholar 

  9. K. W. Bentley, “The Morphine Alkaloids,” in: Chemistry of Alkaloids, (S. W. Pelletier, ed.), Van Nostrand Reinhold, New York (1970).

    Google Scholar 

  10. S. F. Dyke, Some Aspects of the Chemistry of Opium, Royal Institute of Chemistry, Lecture Series No. 1 (1965).

    Google Scholar 

  11. D. Ginsburg, The Opium Alkaloids, Interscience, New York (1962).

    Google Scholar 

  12. C. A. Winter, in Analgetics (G. D. Stevens, ed.), Academic Press, New York (1965).

    Google Scholar 

  13. J. W. Lewis, K. W. Bentley, and A. Cowan, Ann. Rev. Pharmacol. Toxicol 11, 241 (1971).

    CAS  Google Scholar 

  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. 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. M. W. Adler, L. Manara, and R. Samanin, eds., Factors Affecting the Action of Narcotics, Raven Press, New York (1978).

    Google Scholar 

  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. J. H. Jaffe, p. 535, in Ref. 17.

    Google Scholar 

  19. C. I. Wright, J. Pharmacol. Exp. Ther. 71, 164 (1947).

    Google Scholar 

  20. E. L. Way, J. W. Kemp, J. M. Young, and D. R. Grassetti, J. Pharmacol. Exp. Ther. 129, 144 (1960).

    CAS  PubMed  Google Scholar 

  21. E. L. Way, J. W. Kemp, and J. M. Young, Bull. Narc. 17, 15 (1965).

    Google Scholar 

  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. T. Kametani, in The Total Synthesis of Natural Products (J. ApSimon, ed.), Vol. 3, Wiley-Interscience, New York (1977).

    Google Scholar 

  24. R. Grewe and A. Mondon, Chem. Ber. 81, 279 (1948).

    CAS  Google Scholar 

  25. R. Grewe, A. Mondon, and E. Nolte, Justus Liebigs Ann. Chem. 564, 161 (1949).

    CAS  Google Scholar 

  26. M. Gates, R. B. Woodward, W. F. Newhall, and R. Kunzli, J. Am. Chem. Soc. 72, 114 (1950).

    Google Scholar 

  27. D. Elad and D. Ginsburg, J. Am. Chem. Soc. 76, 312 (1954).

    CAS  Google Scholar 

  28. D. Elad and D. Ginsburg, J. Chem. Soc. 3052 (1954).

    Google Scholar 

  29. D. H. R. Barton, G. W. Kirby, W. Steglich, and G. M. Thomas, Proc. Chem. Soc. 203 (1963).

    Google Scholar 

  30. A. R Battersby, R. Binks, D. M. Foulkes, R. J. Francis, and D. J. McCaldin, Proc. Chem. Soc. 203 (1963).

    Google Scholar 

  31. A. R. Battersby, D. M. Foulkes, and R. Binks, J. Chem. Soc. 3323 (1965).

    Google Scholar 

  32. M. A. Schwartz and I. S. Mami, J. Am. Chem. Soc. 97, 1239 (1975).

    CAS  PubMed  Google Scholar 

  33. T. Kametani, M. Ihara, M. Fukumoto, and H. Yagi, J. Chem. Soc. (C) 2030 (1969).

    Google Scholar 

  34. J. D. White, G. Caravatti, T. B. Kline, E. Edstrom, K. C. Rice, and A. Brossi, Tetrahedron 39, 239 (1983).

    Google Scholar 

  35. A. T. Balaban, Rev. Roumaine Chim. 14, 1281 (1969).

    CAS  Google Scholar 

  36. K. C. Rice, J. Org. Chem. 45, 3135 (1980).

    CAS  Google Scholar 

  37. H. C. Beyerman, E. Buurman, and L. Maat, J. Chem. Soc, Chem. Comm. 918 (1972).

    Google Scholar 

  38. H. Brechbühler, H. Büchi, E. Hatz, J. Schreiber, and A. Eschenmoser, Helv. Chim. Acta 48, 1746 (1965).

    Google Scholar 

  39. G. C. Morrison, R. O. Waite, and J. Shavel, Tetrahedron Lett. 4055 (1967).

    Google Scholar 

  40. A. R. Brossi, Trends Pharmacol Sci. 3, 239 (1982).

    CAS  Google Scholar 

  41. H. C. Beyerman, E. Buurman, and L. Maat, J. Chem. Soc. Chem. Comm. 918, (1972).

    Google Scholar 

  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).

    CAS  Google Scholar 

  43. H. C. Beyerman, L. van Bommel, L. Maat, and C. Olieman, Recl. Trav. Chim. Pays-Bas 95, 312 (1976).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  45. T. S. Lie, L. Maat, and H. C. Beyerman, Red. Trav. Chim. Pays-Bas 98, 419 (1979).

    CAS  Google Scholar 

  46. H. C. Beyerman, E. Buurman, T. S. Lie, and L. Maat, Red Trav. Chim. Pays-Bas 95, 43 (1976).

    CAS  Google Scholar 

  47. P. R. Crabbendam, A. M. van Leersum, and L. Maat, Delft Prog. Rep. Chem. and Chem. Eng. 7, 77 (1982).

    CAS  Google Scholar 

  48. D. A. Evans, C. H. Mitch, R. C. Thomas, D. M. Zimmerman, and R. L. Robey, J. Am. Chem. Soc. 102, 5955 (1980).

    CAS  Google Scholar 

  49. D. A. Evans and C. H. Mitch, Tetrahedron Lett. 23, 258 (1982).

    Google Scholar 

  50. C. Schöpf and T. Pfeifer, Justus Liebigs, Ann. Chem. 483, 157 (1930).

    Google Scholar 

  51. C. Schöpf, T. Pfeifer, and H. Hirsch, Justus Liebigs Ann. Chem. 492, 213 (1932).

    Google Scholar 

  52. M. Gates and G. M. K. Hughes, Chem. Ind. (Lond.) 1506 (1956).

    Google Scholar 

  53. L. Small, H. M. Fitch, and W. E. Smith, J. Am. Chem. Soc. 58, 1457 (1936).

    CAS  Google Scholar 

  54. K. W. Bentley, Experientia 12, 251 (1956).

    CAS  PubMed  Google Scholar 

  55. M. Gates and M. S. Shepard, J. Am. Chem. Soc. 84, 4125 (1962).

    CAS  Google Scholar 

  56. D. D. Weiler and H. Rapport, J. Med. Chem. 19, 1171 (1976).

    Google Scholar 

  57. C. Olieman, L. Maat, and H. C. Beyerman, Red Trav. Chim. Pays-Bas 97, 31 (1978).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  59. M. Gates, J. Am. Chem. Soc. 75, 4340 (1953).

    CAS  Google Scholar 

  60. H. Rapoport, C. H. Lovell, H. R. Reist, and M. E. Warren, J. Am. Chem. Soc. 89, 1942 (1967).

    CAS  PubMed  Google Scholar 

  61. D. von Neubauer and K. Mothes, Planta Med. 11, 387 (1963).

    CAS  Google Scholar 

  62. N. Sharglii and L. Lalezari, Nature (Lond.) 213, 1244 (1967).

    Google Scholar 

  63. Science 190, 1274 (1975).

    Google Scholar 

  64. J. W. Fairbairn, Planta Med. 29, 26 (1976).

    CAS  PubMed  Google Scholar 

  65. M. Gordon, Ann. Rep. Med. Chem. 9, 38 (1973).

    Google Scholar 

  66. K. C. Rice, in Problems in Drug Dependence, 1981, (L. S. Harris, ed.), NIDA Research Monograph 41, 331 (1982).

    Google Scholar 

  67. K. C. Rice, Proc. Jap. Pharm. Soc. 64 (1983).

    Google Scholar 

  68. C. R. A. Wright, J. Chem. Soc. 27, 1031 (1874).

    Google Scholar 

  69. H. Dreser, Deut. Med. Wochenschr. 24, 185 (1898).

    Google Scholar 

  70. E. L. May and A. E. Jacobson, J. Pharm. Sci. 66, 285 (1977).

    CAS  PubMed  Google Scholar 

  71. H. Rapoport, C. H. Lovell, and B. M. Tolbert, J. Am. Chem. Soc. 73, 5900 (1951).

    CAS  Google Scholar 

  72. K. Goto and I. Yamamato, Proc. Jap. Acad. 30, 76 (1954) (Chem. Abs. 50, 1052h, 1956).

    Google Scholar 

  73. M. Takeda and H. Kugita, Japanese Patent 29153 (1971) (Chem. Abs. 75, 141030r (1971)).

    Google Scholar 

  74. H. Ioue, M. Takeda, and H. Kugita, Chem. Pharm. Bull 18, 1569 (1970).

    Google Scholar 

  75. K. C. Rice, J. Med. Chem. 20, 164 (1977).

    CAS  PubMed  Google Scholar 

  76. J. F. W. McOmie, M. L. Watts, and D. E. West, Tetrahedron 24, 2289 (1968).

    CAS  Google Scholar 

  77. J. A. Lawson and J. I. Degraw, J. Med. Chem. 20, 165 (1977).

    CAS  PubMed  Google Scholar 

  78. J. P. Garard, F. Kranz, and T. Rüll, Bull Soc. Chim. Fr. 486 (1965).

    Google Scholar 

  79. R. B. Barber and H. Rapoport, J. Med. Chem. 19, 1175 (1976).

    CAS  PubMed  Google Scholar 

  80. L. Knorr and H. Hortein, Chem. Ber. 39, 1409 (1906).

    CAS  Google Scholar 

  81. H. Hirsch, Justus Liebigs Ann. Chem. 489, 224 (1931).

    Google Scholar 

  82. H. Conroy, J. Am. Chem. Soc. 77, 5960 (1955).

    CAS  Google Scholar 

  83. M. Freund, Chem. Ber. 39, 844 (1906).

    CAS  Google Scholar 

  84. M. Yamada, Chem. Pharm. Bull. 10, 8712 (1962).

    Google Scholar 

  85. H. C. Brown and P. J. Geoghegan, J. Org. Chem. 35, 1844 (1970).

    CAS  Google Scholar 

  86. H. Rapoport, R. Naumann, E. R. Bissell, and R. M. Bonner, J. Org. Chem. 15, 1103 (1950).

    CAS  Google Scholar 

  87. I. Seki, Chem. Pharm. Bull. 18, 671 (1970).

    CAS  Google Scholar 

  88. H. Rapoport and H. N. Reist, J. Am. Chem. Soc. 77, 490 (1955).

    CAS  Google Scholar 

  89. R. B. Barber and H. Rapoport, J. Med. Chem. 18, 1074 (1975).

    CAS  PubMed  Google Scholar 

  90. E. L. Way and T. K. Alder, Pharmacol. Rev. 12, 383 (1960).

    CAS  PubMed  Google Scholar 

  91. T. Johannesson and J. Schou, Acta Pharmacol. Toxicol. 20, 165 (1963).

    CAS  Google Scholar 

  92. T. K. Aider, J. Pharmacol. Exp. Ther. 140, 155 (1963).

    Google Scholar 

  93. J. J. Kamm, V. B. Bastone, E. Mohacsi, and F. M. Vane, Xenobiotica 1, 273 (1971).

    CAS  PubMed  Google Scholar 

  94. P. H. Duquette, R. R. Erickson, and J. L. Holtzman, J. Med. Chem. 26, 1343 (1983).

    CAS  PubMed  Google Scholar 

  95. E. Mohacsi, W. Leimgruber, and H. Bamth, J. Med. Chem. 25, 1264 (1982).

    CAS  PubMed  Google Scholar 

  96. G. Papioannou, Eur. J. Med. Chem. 11, 287 (1976).

    Google Scholar 

  97. K. Shimomura, O. Kamata, S. Veki, S. Ida, K. Ogari, H. Yoshimura, and H. Tsukamoto. Tohoku. J. Exp. Med. 105, 45 (1971).

    CAS  PubMed  Google Scholar 

  98. M. Mori, K. Oguri, H. Yoshimura, O. Kamata, and S. Veki, Life Sci. 11, 525 (1972).

    CAS  Google Scholar 

  99. E. L. May and A. E. Jacobson, J. Pharm. Sci. 66, 285 (1977).

    CAS  PubMed  Google Scholar 

  100. C. E. Inturrisi, M. Schultz, S. Shin, J. G. Umans, L. Angel, and E. J. Simm, Life Sci. 33 (Suppl. 1), 773 (1983).

    CAS  PubMed  Google Scholar 

  101. L. H. Welsh, J. Org. Chem. 19, 1409 (1954).

    Google Scholar 

  102. E. L. Way, J. W. Kemp, J. M. Young, and D. R. Grasetti, J. Pharm. Exp. Ther. 129, 144 (1960).

    CAS  Google Scholar 

  103. K. C. Rice and A. E. Jacobson, J. Med. Chem. 18, 1033 (1975).

    CAS  PubMed  Google Scholar 

  104. J. von Mering, Merck’s Jahresb. 5, (1898).

    Google Scholar 

  105. R. Stockman and D. B. Dott, Br. Med. J. 189 (July 26, 1890).

    Google Scholar 

  106. H. Rapoport and J. B. Lavigne, J. Am. Chem. Soc. 75, 5329 (1953).

    CAS  Google Scholar 

  107. K. W. Bentley and H. M. E. Cardwell, J. Chem. Soc. 3252 (1955).

    Google Scholar 

  108. G. Stork and F. H. Clarke, J. Am. Chem. Soc. 78, 4619 (1956).

    CAS  Google Scholar 

  109. J. Kalvada, P. Buchscahcher, and O. Jeger, Helv. Chim. Acta. 38, 1847 (1955).

    Google Scholar 

  110. M. Mackay and D. C. Hodgkin, J. Chem. Soc. 3261 (1955).

    Google Scholar 

  111. L. Gylbert, Acta. Crystallogr. (B) 1630 (1973).

    Google Scholar 

  112. C. E. Brown, S. J. Roerig, J. M. Fujimoto, and V. T. Burger, J. Chem. Soc. Chem. Comm. 1506 (1983).

    Google Scholar 

  113. H. Kugita and M. Takeda, Chem. and Ind. (Lond.) 2099 (1964).

    Google Scholar 

  114. H. Kugita and M. Takeda, Chem. Pharm. Bull. 13, 1422 (1965).

    CAS  PubMed  Google Scholar 

  115. H. Kugita, M. Takeda, and H. Inoue, Tetrahedron Lett. 1277 (1967).

    Google Scholar 

  116. H. Kugita, M. Takeda, and H. Inoue, Tetrahedron 25, 4125 (1969).

    Google Scholar 

  117. S. Okuda, S. Yamaguchi, and K. Tsuda, Chem. Pharm. Bull. 13, 1092 (1965).

    CAS  PubMed  Google Scholar 

  118. F. G. Mann and M. J. Pragneil, J. Chem. Soc. 4120 (1965).

    Google Scholar 

  119. I. Iigima, J. Minamikawa, A. E. Jacobson, A. Brossi, and K. C. Rice, J. Org. Chem. 43, 1462 (1978).

    Google Scholar 

  120. Y. F. Jaquet, W. A. Klee, K. C. Rice, I. Iijima, and J. Minamikawa, Science 198, 842 (1977).

    Google Scholar 

  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. K. Goto and I. Yamamoto, Proc. Jap. Acad. 30, 769 (1954).

    CAS  Google Scholar 

  123. K. Goto and I. Yamamoto, Proc. Jap. Acad. 33, 477 (1957).

    CAS  Google Scholar 

  124. K. Goto and I. Yamamoto, Proc. Jap. Acad. 34, 60 (1958).

    Google Scholar 

  125. K. Goto, Sinomenine, an Optical Antipode of Morphine Alkaloids, p. 96, Kitasato Institute, Tokyo (1964).

    Google Scholar 

  126. K. Tagaki, H. Fukada, M. Watanabe, and M. Sato, Yakugaku Zasshi 80, 1506 (1960).

    Google Scholar 

  127. I. Iijima, Heterocycles 6, 1157 (1977).

    CAS  Google Scholar 

  128. I. Iijima, J. Minamikawa, A. E. Jacobson, A. E. Brossi, K. C. Rice, and W. Klee, J. Med. Chem. 21, 398 (1978).

    CAS  PubMed  Google Scholar 

  129. A. H. Beckett and A. F. Casy, J. Pharm. Pharmacol 6, 986 (1954).

    CAS  PubMed  Google Scholar 

  130. N. B. Eddy, Chem. and Ind. (Lond.) 1462 (1959).

    Google Scholar 

  131. A. H. Beckett, A. F. Casy, and N. J. Harper, J. Pharm. Pharmacol. 8, 874 (1956), and refs. there cited.

    CAS  PubMed  Google Scholar 

  132. N. B. Eddy, L. F. Small, J. H. Ager, and E. L. May, J. Org. Chem. 23, 1387 (1958).

    Google Scholar 

  133. R. L. Clark, A. A. Pessolano, J. Weijlard, and K. Pfister, J. Am. Chem. Soc. 75, 4963 (1953).

    CAS  Google Scholar 

  134. J. Weijlard, P. D. Orahovats, A. P. Sullivan, G. Purdue, F. K. Heath, and K. Pfister, J. Am. Chem. Soc. 78, 2342 (1956).

    CAS  Google Scholar 

  135. C. A. Winter, P. D. Orahovats, and E. G. Lehman, Arch. Int. Pharmacodyn. 110, 186 (1957).

    CAS  PubMed  Google Scholar 

  136. N. B. Eddy, H. Besendorf, and B. Pellmont, Bull. Narc. 10, 23 (1958).

    CAS  Google Scholar 

  137. J. Pohl, Zeitschr. Exp. Pathol. Therap. 17, 370 (1915).

    Google Scholar 

  138. J. von Braun, Chem. Ber. 49, 971 (1916).

    Google Scholar 

  139. J. von Braun, Chem. Ber. 49, 2655 (1916).

    Google Scholar 

  140. J. von Braun, M. Kuhn, and S. Siddiqui, Chem. Ber. 59, 1081 (1926).

    Google Scholar 

  141. K. C. Rice, J. Org. Chem. 40, 1850 (1975).

    CAS  PubMed  Google Scholar 

  142. K. C. Rice and E. L. May, J. Heterocycl. Chem. 14, 665 (1977).

    CAS  Google Scholar 

  143. W. L. McCawley, E. R. Hart, and D. F. Marsh, J. Am. Chem. Soc. 63, 314 (1941).

    CAS  Google Scholar 

  144. J. E. Echenhoff and J. D. Elder, Am. J. Med. Sci. 223, 191 (1952).

    Google Scholar 

  145. E. Costa and P. Greengard, eds. Adv. in Biochem. Pharmacol, Vol. 8, Narcotic Antagonists, Raven Press, New York (1973).

    Google Scholar 

  146. L. Lasagne and H. K. Beecher, J. Pharmacol. Exp. Ther. 112, 356 (1954).

    Google Scholar 

  147. A. S. Keats and J. Telford, J. Pharmacol. Exp. Ther. 177, 190 (1956).

    Google Scholar 

  148. P. Karrer and H. Heynemann, Helu. Chim. Acta. 31, 398 (1948).

    CAS  Google Scholar 

  149. M. Gates and T. Montzka, J. Med. Chem. 7, 127 (1964).

    CAS  PubMed  Google Scholar 

  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).

    CAS  PubMed  Google Scholar 

  151. C. Pert and S. Snyder, Mol. Pharmacol 10, 868 (1974).

    CAS  Google Scholar 

  152. V. M. Kolb, J. Pharm. Sci. 68, 1250 (1979).

    CAS  PubMed  Google Scholar 

  153. S. D. Darling, V. M. Kolb, G. S. Mandel, and N. S. Mandel, J. Pharm. Sci. 71, 763 (1982).

    CAS  PubMed  Google Scholar 

  154. G. Bianchi, R. Fiocchi, A. Tavani, and L. Manara, Life Sci. 30, 1875 (1982).

    CAS  PubMed  Google Scholar 

  155. J. Russell, P. Bass, L. I. Goldberg, C. R. Schuster, and H. Merz, Eur. J. Pharmacol. 78, 255 (1982).

    CAS  PubMed  Google Scholar 

  156. B. Kelenti, E. Stenszky, F. Czoller, L. Szlávik, and Z. Mészáros, Arzneim. Forsch. 7, 594 (1957).

    Google Scholar 

  157. K. Tagaki, H. Fukuda, and K. Yano, Yakugaku Zasshi 80, 1499 (1960).

    Google Scholar 

  158. O. J. Braendon, N. B. Eddy, and H. Halbach, Bull. World Health Org. 13, 937 (1955).

    Google Scholar 

  159. R. J. J. Ch. Lousberg and U. Weiss, Experientia 1440 (1974).

    Google Scholar 

  160. L. F. Small and S. G. Turnbull, J. Am. Chem. Soc. 59, 1541 (1937).

    CAS  Google Scholar 

  161. C. Olieman, L. Maat, and C. Beyerman, Recl Trav. Chim. Pays-Bas 95, 189 (1976).

    CAS  Google Scholar 

  162. L. F. Small and J. E. Mallonee, J. Org. Chem. 12, 558 (1947).

    CAS  PubMed  Google Scholar 

  163. E. Ochiai and T. Nakamura, Chem. Ber. 72, 684 (1939).

    Google Scholar 

  164. F. Kilivenyi and E. Vinkler, Pharmazie 34, 668 (1979).

    Google Scholar 

  165. M. A. Schwartz and M. F. Zoda, J. Org. Chem. 46, 4623 (1981).

    CAS  Google Scholar 

  166. F.-L. Hsu, K. C. Rice, and A. Brossi, Helv. Chim. Acta 63, 2042 (1980).

    CAS  Google Scholar 

  167. F.-L. Hsu, K. C. Rice, and A. Brossi, Helv Chim. Acta 65, 1576 (1982).

    CAS  Google Scholar 

  168. H. Auterhoff and W. Tiltjung, Arch. Pharm 313, 985 (1980).

    CAS  Google Scholar 

  169. L. F. Small and K. C. Yuen, J. Am. Chem. Soc 58, 192 (1936).

    CAS  Google Scholar 

  170. L. F. Small, H. M. Fitch, and W. E. Smith, J. Am. Chem. Soc. 58, 1457 (1936).

    CAS  Google Scholar 

  171. L. F. Small, S. G. Turnbull, and H. M. Fitch, J. Org. Chem. 3, 204 (1938).

    CAS  Google Scholar 

  172. G. Stork and L. Bauer, J. Am. Chem. Soc. 75, 4373 (1953).

    CAS  Google Scholar 

  173. L. F. Small and H. Rapoport, J. Org. Chem. 12, 284 (1947).

    CAS  PubMed  Google Scholar 

  174. N. B. Eddy, H. Halbach, and O. J. Braenden, Bull World Health Org. 14, 353 (1956).

    CAS  PubMed  Google Scholar 

  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. R. M. Boden, M. Gates, S. P. Ho, and P. Sundararaman, J. Org. Chem. 47, 1347 (1982).

    CAS  Google Scholar 

  177. L. J. Sargent and E. L. May, J. Med. Chem. 13, 1061 (1970).

    CAS  PubMed  Google Scholar 

  178. A. Pohland and H. R. Sullivan, U. S. Patent 3,342,824 (1967).

    Google Scholar 

  179. G. M. Dyson and P. May, May’s Chemistry of Synthetic Drugs, 5th ed., p. 148, Longmans, London (1959).

    Google Scholar 

  180. N. B. Eddy, H. Halbach, and O. J. Braenden, Bull. World Health Org. 17, 569 (1957).

    CAS  PubMed  Google Scholar 

  181. L. F. Small, K. C. Yuen, and L. K. Eilers, J. Am. Chem. Soc. 55, 3863 (1933).

    CAS  Google Scholar 

  182. L. F. Small and H. Rapoport, J. Org. Chem. 12, 284 (1947).

    CAS  PubMed  Google Scholar 

  183. H. D. Brown, I. M. Rasmussen, G. B. Payne, and K. Pfister, J. Am. Chem. Soc. 75, 6238 (1953).

    CAS  Google Scholar 

  184. M. S. Chadha and H. Rapoport, J. Am. Chem. Soc. 70, 5730 (1957).

    Google Scholar 

  185. J. Fishman, U. S. Patent 3, 153,042 (1963).

    Google Scholar 

  186. R. Bognár and S. Makleit, Acta Chim. Acad. Sci. Hung. 59, 359 (1969).

    Google Scholar 

  187. J. Knoll, Pharmacol. Res. Comm. 5, 175 (1973).

    CAS  Google Scholar 

  188. J. Knoll, S. Fürst, and E. S. Vizi, Pharmacology 10, 354 (1973).

    CAS  PubMed  Google Scholar 

  189. R. C. Hill, D. Roemer, and H. Buescher, J. Pharmacol. Exp. Ther. 201, 580 (1977).

    CAS  PubMed  Google Scholar 

  190. S. C. Clarke, D. R. Jarinski, J. S. Pevnick, and J. D. Griffith, Clin. Pharmacol. Ther. 19, 295 (1976).

    Google Scholar 

  191. J. Knoll, S. Fürst, and K. Keleman, J. Pharm. Pharmacol. 25, 929 (1973).

    CAS  PubMed  Google Scholar 

  192. J. Knoll, Prog. Neuro-Psychopharmacol. 3, 95 (1979).

    CAS  Google Scholar 

  193. J. B. Jiang, R. Hanson, P. S. Portoghese, and A. E. Takemori, J. Med. Chem. 20, 1100 (1977).

    CAS  PubMed  Google Scholar 

  194. A Z. Ronai, F. F. Foldes, E. F. Hahn, and J. Fishman, J. Pharm. Exp. Ther. 200, 496 (1977).

    CAS  Google Scholar 

  195. W. Wieland and P. Kappelmeier, Justus Liebig’s Ann. Chem. 382, 306 (1911).

    CAS  Google Scholar 

  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. G. Stork and F. H. Clarke, J. Am. Chem. Soc. 78, 4619 (1956).

    CAS  Google Scholar 

  198. H. J. C. Yeh, R. S. Wilson, W. A. Klee, and A. E. Jacobson, J. Pharm. Sci. 65, 902 (1976).

    CAS  PubMed  Google Scholar 

  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. L. J. Sargent and A. E. Jacobson, J. Med. Chem. 15, 843 (1972).

    CAS  PubMed  Google Scholar 

  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. M. G. Lester, V. Petrow, and O. Stephenson, Tetrahedron 21, 711 (1965).

    Google Scholar 

  203. H. Rapoport and L. F. Small, J. Org. Chem. 12, 834 (1947).

    CAS  PubMed  Google Scholar 

  204. J. O. Polazzi, J. Org. Chem. 46, 4262 (1981).

    CAS  Google Scholar 

  205. S. J. DeSolms, J. Org. Chem. 41, 2650 (1976).

    CAS  Google Scholar 

  206. H. Tada, M. Kobayashi, and Y. K. Sawa, Tetrahedron Lett. 1805 (1969).

    Google Scholar 

  207. R. M. Allen and G. W. Kirby, J. Chem. Soc. 363 (1973).

    Google Scholar 

  208. M. P. Kotick, D. L. Leland, J. O. Polazzi, J. F. Howes, and A. R. Bousquet, J. Med. Chem. 24, 1445 (1981).

    CAS  PubMed  Google Scholar 

  209. R. F. Abdulla and K. H. Fuhr, J. Org. Chem. 43, 4284 (1978).

    Google Scholar 

  210. D. Leland, J. O. Polazzi, and M. P. Kotick, J. Org. Chem. 45, 4026 (1980).

    CAS  Google Scholar 

  211. C. Mannich and M. Schulte, Arch. Pharm. 276, 593 (1938).

    CAS  Google Scholar 

  212. D. L. Leland and M. P. Kotick, J. Med. Chem. 24, 717 (1981).

    CAS  PubMed  Google Scholar 

  213. M. P. Kotick, D. L. Leland, J. O. Polazzi, J. F. Howes, and A. Bousquet, J. Med. Chem. 26, 1050 (1983).

    CAS  PubMed  Google Scholar 

  214. D. L. Leland, J. O. Polazzi, and M. P. Kotick, J. Org. Chem. 45, 4026 (1980).

    CAS  Google Scholar 

  215. D. L. Leland, J. Heterocycl. Chem. 18, 1101 (1981).

    CAS  Google Scholar 

  216. J. O. Polazzi, M. P. Kotick, J. F. Howes, and A. R. Bousquet, J. Med. Chem. 24, 1516 (1981).

    CAS  PubMed  Google Scholar 

  217. D. L. Leland and M. P. Kotick, J. Org. Chem. 48, 1813 (1983).

    CAS  Google Scholar 

  218. J. Quick, P. Herlihy, R. K. Razdan, and J. F. Howes, J. Med. Chem. 25, 983 (1982).

    PubMed  Google Scholar 

  219. M. P. Kotick, J. Med. Chem. 24, 722 (1981).

    CAS  PubMed  Google Scholar 

  220. W. Fleischhacker and A. Klement, Monatsch. Chem. 106, 1513 (1975).

    CAS  Google Scholar 

  221. M. Boes and W. Fleischhacker, Justus Liebig’s Ann. Chem. 1994 (1981).

    Google Scholar 

  222. I. Iijima, J. Minamikawa, K. C. Rice, and A. E. Jacobson, J. Med. Chem. 21, 1320 (1978).

    CAS  PubMed  Google Scholar 

  223. S. Y. Yeh, H. A. Krebs, and C. W. Gorodetzky, J. Pharm. Sci. 68, 133 (1979).

    CAS  PubMed  Google Scholar 

  224. K. Uba, N. Miyata, K. Watanabe, and M. Hirobe, Chem. Pharm. Bull 28, 356 (1980).

    CAS  PubMed  Google Scholar 

  225. K. Uba, N. Miyata, K. Watanabe, and M. Hirobe, Chem. Pharm. Bull 27, 2257 (1979).

    CAS  Google Scholar 

  226. N. Miyata, K. Uba, K. Watanabe, and M. Hirobe, Chem. Pharm. Bull. 28, 3722 (1980).

    CAS  PubMed  Google Scholar 

  227. I. Takayang, R. Shibata, F. Konno, N. Miyata, and M. Chika, J. Pharmacobiodyn. 5, 505 (1982).

    Google Scholar 

  228. G. D. Smith and J. F. Griffin, Science 199, 1214 (1978).

    CAS  PubMed  Google Scholar 

  229. M. Kotick, D. L. Leland, J. O. Polazzi, and R. N. Schut, J. Med. Chem. 23, 166 (1980).

    CAS  PubMed  Google Scholar 

  230. G. H. Posner, Org. React. 19, 1 (1972).

    CAS  Google Scholar 

  231. F. Ghozland, P. Maroni, I. Viloria, and J. Cros, Eur. J. Med. Chem. 18, 22 (1983).

    CAS  Google Scholar 

  232. P. D. Gesellchen and D. M. Zimmerman, Ann. Rep. Med. Chem. 16, 43 (1981).

    Google Scholar 

  233. D. L. Leland, J. O. Polazzi, and M. P. Kotick, J. Org. Chem. 46, 4012 (1981).

    CAS  Google Scholar 

  234. M. P. Kotick, J. Med. Chem. 24, 722 (1981).

    CAS  PubMed  Google Scholar 

  235. R. Okum and H. W. Elliot, J. Pharmacol. Exp. Ther. 124, 225 (1958).

    Google Scholar 

  236. J. Fishman and M. J. Lewenstein, U. S. Patent 3,162,639 (1964).

    Google Scholar 

  237. O. Isler, H. Gutman, M. Montavon, R. Rüegg, G. Ryser, and P. Zeller, Helv. Chim. Acta 40, 1247 (1957).

    Google Scholar 

  238. E. F. Hahn, J. Fishman, and R. D. Heilman, J. Med. Chem. 18, 259 (1975).

    CAS  PubMed  Google Scholar 

  239. M. P. Kotick and J. O. Polazzi, J. Heterocycl. Chem. 18, 1029 (1981).

    CAS  Google Scholar 

  240. W. Fleischacker and B. Richter, Chem. Ber. 113, 3866 (1980).

    Google Scholar 

  241. G. H. Herman and M.-N. N. Kan, Biomed. Mass Spec. 1, 350 (1974).

    CAS  Google Scholar 

  242. S. P. Findlay and L. F. Small, J. Am. Chem. Soc. 73, 4001 (1951).

    CAS  Google Scholar 

  243. U. Weiss, J. Org. Chem. 22, 1505 (1957).

    CAS  Google Scholar 

  244. M. Freund and E. Speyer, J. Prakt. Chem. 94, 135 (1916).

    CAS  Google Scholar 

  245. F. M. Hauser, T.-K. Chen, and F. I. Carroll, J. Med. Chem. 17, 117 (1974).

    Google Scholar 

  246. U. Weiss, J. Am. Chem. Soc. 77, 5891 (1955).

    CAS  Google Scholar 

  247. M. J. Lewenstein, Br. Patent, 955, 493 (1964).

    Google Scholar 

  248. H. Blumberg, H. B. Dayton, G. M. Rapoport, and D. N. Rapoport, Fed. Proc. 20, 311 (1961).

    Google Scholar 

  249. L. Lasagna, Proc. Roy. Soc. Med. 58, 978 (1965).

    CAS  PubMed  Google Scholar 

  250. M. J. Lewenstein and J. Fishman, U. S. Patent 3,320,262, (1967).

    Google Scholar 

  251. H. Blumberg, I. J. Pachter, and Z. Metossian, U. S. Patent, 3,332,950 (1967).

    Google Scholar 

  252. N. Chatterjie, C. E. Inturrisi, H. B. Dayton, and H. Blumberg, J. Med. Chem. 18, 490 (1975).

    CAS  PubMed  Google Scholar 

  253. H. L. Holmes and C. C. Lee, J. Am. Chem. Soc. 69, 1966 (1947).

    Google Scholar 

  254. I. Brown and M. Martin-Smith, J. Chem. Soc. 4139 (1960).

    Google Scholar 

  255. M. A. Schwartz and R. A. Wallace, J. Med. Chem. 24, 1525 (1981).

    CAS  PubMed  Google Scholar 

  256. J. Knoll, S. Fürst, and S. Makeleit, J. Pharm. Pharmacol. 27, 99 (1975).

    CAS  PubMed  Google Scholar 

  257. J. B. Taylor, J. Chem. Soc. (C) 1506 (1968).

    Google Scholar 

  258. G. W. Pasternak and E. F. Hahn, J. Med. Chem. 23, 674 (1980).

    CAS  PubMed  Google Scholar 

  259. G. W. Pasternak, S. R. Childers, and S. H. Snyder, J. Pharmacol. Exp. Ther. 214, 455 (1980).

    CAS  PubMed  Google Scholar 

  260. S. R. Childers and G. W. Pasternak, Cell Mol. Neurobiol. 2, 93 (1982).

    CAS  Google Scholar 

  261. E. F. Hahn, M. Carroll-Buatti, and G. W. Pasternak, J. Neurosci. 2, 572 (1982).

    CAS  PubMed  Google Scholar 

  262. H. Merz, K. Stockhaus, and H. Wick, J. Med. Chem. 18, 996 (1975).

    CAS  PubMed  Google Scholar 

  263. H. Merz, K. Stockhaus, and H. Wick, J. Med. Chem. 20, 844 (1977).

    CAS  PubMed  Google Scholar 

  264. E. Kutter, A. Herz, H. J. Teschemacher, and R. Hess, J. Med. Chem. 13, 801 (1970).

    CAS  PubMed  Google Scholar 

  265. G. H. Loew and D. S. Berkowitz, J. Med. Chem. 18, 656 (1975).

    CAS  PubMed  Google Scholar 

  266. G. H. Loew and D. S. Berkowitz, in Opiates and Endogenous Opioid Peptides, p. 399, Elsevier, Amsterdam (1976).

    Google Scholar 

  267. J. Knoll, Neuropharmacology 14, 921 (1975).

    CAS  PubMed  Google Scholar 

  268. G. H. Loew and D. S. Berkowitz, J. Med. Chem. 21, 101 (1978).

    CAS  PubMed  Google Scholar 

  269. B. Belleau, T. Conway, F. R. Ahmed, and A. D. Hardy, J. Med. Chem. 17, 907 (1974).

    CAS  PubMed  Google Scholar 

  270. S. Shiotani, T. Kometani, Y. Iitaka, and A. Itai, J. Med. Chem. 21, 153 (1978).

    CAS  PubMed  Google Scholar 

  271. V. M. Kolb, J. Pharm. Sci. 67, 999 (1978).

    CAS  PubMed  Google Scholar 

  272. Ref. 266, p. 387.

    Google Scholar 

  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).

    CAS  PubMed  Google Scholar 

  274. G. Heinisch, V. Kintz, and F. Vieböck, Monatsch. Chem. 102, 530 (1971).

    CAS  Google Scholar 

  275. R. M. Allen and G. W. Kirby, J. Chem. Soc. Perkin Trans. I 363 (1973).

    Google Scholar 

  276. A. C. Currie, J. Gillon, G. T. Newbold, and F. S. Spring, J. Chem. Soc. 773 (1960).

    Google Scholar 

  277. L. J. Sargent, L. H. Schwartzman, and L. F. Small, J. Org. Chem. 23, 1247 (1958).

    CAS  Google Scholar 

  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. W. R. Buckett, M. E. Farguharson, and C. G. Haining, J. Pharm. Pharmacol. 16, 174 (1964).

    CAS  PubMed  Google Scholar 

  280. W. R. Buckett, J. Pharm. Pharmacol. 16, 68T (1964).

    Google Scholar 

  281. C. Linder and J. Fishman, J. Med. Chem. 16, 553 (1973).

    CAS  PubMed  Google Scholar 

  282. D. L. Leland, J. O. Polazzi, and M. P. Kotick, J. Org. Chem. 46, 4012 (1981).

    CAS  Google Scholar 

  283. M. P. Kotick, J. Org. Chem. 48, 1819 (1983).

    CAS  Google Scholar 

  284. P. Osei-Gyimah and S. Archer, J. Med. Chem. 23, 162 (1980).

    CAS  PubMed  Google Scholar 

  285. S. Archer and P. Osei-Gyimah, J. Heterocycl. Chem. 16, 389 (1979).

    CAS  Google Scholar 

  286. R. M. Allen and G. W. Kirby, J. Chem. Soc. Chem. Comm. 1346 (1970).

    Google Scholar 

  287. R. M. Allen, G. W. Kirby, and D. J. McDougall, J. Chem. Soc. Perkin Trans I 1143 (1981).

    Google Scholar 

  288. L. S. Schwab, J. Med. Chem. 23, 698 (1980).

    CAS  PubMed  Google Scholar 

  289. W. R. Buckett, Br. J. Pharmacol. 76, 269P (1982).

    Google Scholar 

  290. W. Fleischhacker and B. Richter, Sd Pharm. 49, 118 (1981).

    Google Scholar 

  291. W. Fleischhacker and B. Richter, Chem. Ber. 112, 3054 (1979).

    CAS  Google Scholar 

  292. E. J. Simon and J. M. Hiller, Ann. Rev. Pharmacol. Toxicol. 18, 371 (1978).

    CAS  Google Scholar 

  293. P. S. Portoghese, V. G. Telang, A. E. Takemori, and G. Hayashi, J. Med. Chem. 14, 144 (1971).

    CAS  PubMed  Google Scholar 

  294. A. E. Takemori, A. Ward, P. S. Portoghese, and V. G. Telang, J. Med. Chem. 17, 1051 (1974).

    CAS  PubMed  Google Scholar 

  295. K. C. Rice, S. Shiotani, C. R. Creveling, A. E. Jacobson, and W. A. Klee, J. Med. Chem. 20, 673 (1977).

    CAS  PubMed  Google Scholar 

  296. M. May, I. Czoncha, D. R. Garrison, and D. J. Triggle, J. Pharm. Sci. 57, 884 (1968).

    CAS  PubMed  Google Scholar 

  297. R. Schultz and A. Goldstein, Life Sci. 16, 1843 (1975).

    Google Scholar 

  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. J. B. Jiang, R. N. Hanson, P. S. Portoghese, and A. E. Takemori, J. Med. Chem. 20, 1100 (1977).

    CAS  PubMed  Google Scholar 

  300. E. F. Hahn, J. Fishman, and R. D. Heilman, J. Med. Chem. 18, 259 (1975).

    CAS  PubMed  Google Scholar 

  301. N. Chatterjie, C. E. Inturrisi, H. B. Dayton, and H. Blumberg, J. Med. Chem. 18, 490 (1975).

    CAS  PubMed  Google Scholar 

  302. P. S. Portoghese, D. L. Larson, J. B. Jiang, A. E. Takemori, and T. P. Caruso, J. Med. Chem. 21, 598 (1978).

    CAS  PubMed  Google Scholar 

  303. P. S. Portoghese, D. L. Larson, J. B. Jiang, T. P. Caruso, and A. E. Takemori, J. Med. Chem. 22, 168 (1979).

    CAS  PubMed  Google Scholar 

  304. D. Julius and P. Renault, eds. Res. Monograph Ser. Nat. Inst. Drug Abuse (U. S.) 9, (1976)

    Google Scholar 

  305. G. A. Wiley, R. L. Hershkowitw, B. M. Rein, and B. C. Chung, J. Am. Chem. Soc. 86, 964 (1964).

    CAS  Google Scholar 

  306. L. M. Sayre and P. S. Portoghese, J. Org. Chem. 45, 3366 (1980).

    CAS  Google Scholar 

  307. T. P. Caruso, A. E. Takemori, D. L. Larson, and P. S. Portoghese, Science 204, 316 (1979).

    CAS  PubMed  Google Scholar 

  308. P. S. Portoghese, D. L. Larson, L. M. Sayre, D. S. Fries, and A. E. Takemori, J. Med. Chem. 23, 233 (1980).

    CAS  PubMed  Google Scholar 

  309. P. S. Portoghese, J. Med. Chem. 8, 609 (1965).

    CAS  PubMed  Google Scholar 

  310. S. J. Ward, P. S. Portoghese, and A. E. Takemori, J. Pharmacol. Exp. Ther. 220, 494 (1982).

    CAS  PubMed  Google Scholar 

  311. S. J. Ward, P. S. Portoghese, and A. E. Takemori, Eur. J. Pharmacol. 80, 377 (1982).

    CAS  PubMed  Google Scholar 

  312. A. E. Takemori, D. L. Larson, and P. S. Portoghese, Eur. J. Pharmacol. 70, 445 (1981).

    CAS  PubMed  Google Scholar 

  313. L. M. Sayre, D. L. Larson, D. S. Fries, A. E. Takemori, and P. S. Portoghese, J. Med. Chem. 26, 1229 (1983).

    CAS  PubMed  Google Scholar 

  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. P. S. Portoghese and A. E. Takemori, J. Med. Chem. 26, 1341 (1983).

    CAS  PubMed  Google Scholar 

  316. M. Erez, A. E. Takemori, and P. S. Portoghese, J. Med. Chem. 25, 847 (1982).

    CAS  PubMed  Google Scholar 

  317. P. S. Portoghese, G, Ronsisvalle, D. L. Larson, C. B. Yim, L. M. Sayre, and A. E. Takemori, Life Sci. 31, 1283 (1982).

    CAS  PubMed  Google Scholar 

  318. E. J. P. Fear, J. Thornower, and J. Veitch, J. Chem. Soc. 1322 (1958).

    Google Scholar 

  319. M. Newcomb, S. S. Moore, and D. J. Cram, J. Am. Chem. Soc. 99, 6405 (1977).

    CAS  Google Scholar 

  320. E. Hazum, K. J. Chang, H. J. Leighton, O. W. Lever, and P. Cuatrecasas, Biochem. Biophys. Res. Comm. 104, 347 (1982).

    CAS  PubMed  Google Scholar 

  321. A. C. Allen, J. M. Moore, and D. A. Cooper, J. Org. Chem. 48, 3951 (1983).

    CAS  Google Scholar 

  322. K. W. Bentley and D. G. Hardy, Proc. Chem. Soc. 220 (1963).

    Google Scholar 

  323. K. W. Bentley and A. F. Thomas, J. Chem. Soc. 1863 (1956).

    Google Scholar 

  324. K. W. Bentley and D. G. Hardy, J. Am. Chem. Soc. 89, 3267 (1967).

    CAS  Google Scholar 

  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).

    CAS  PubMed  Google Scholar 

  326. J. W. Lewis, M. J. Readhead, and A. C. B. Smith, J. Med. Chem. 16, 9 (1973).

    CAS  PubMed  Google Scholar 

  327. J. W. Lewis, Adv. Biochem. Psychopharmacol. 8, 123 (1974).

    Google Scholar 

  328. R. G. Twycross, Pain 3, 93 (1977).

    CAS  PubMed  Google Scholar 

  329. A. F. Casy, Prog. Drug. Res. 22, 149 (1978).

    CAS  PubMed  Google Scholar 

  330. K. W. Bentley, D. G. Hardy, and B. Meek, J. Am. Chem. Soc. 89, 3273 (1967).

    CAS  PubMed  Google Scholar 

  331. K. W. Bentley and D. G. Hardy, J. Am. Chem. Soc. 98, 3281 (1967).

    Google Scholar 

  332. K. W. Bentley, Br. Patent 1,136,214 (1968).

    Google Scholar 

  333. G. F. Blane, A. L. A. Boura, A. E. Fitzgerald, and R. E. Lister, Br. J. Pharmacol. 30, 11 (1967).

    CAS  Google Scholar 

  334. D. Campbell, R. E. Lister, and G. W. McNicol, Clin. Pharmacol. Ther. 5, 193 (1964).

    CAS  PubMed  Google Scholar 

  335. J. D. Wallach, Vet. Med. 64, 53 (1961).

    Google Scholar 

  336. J. M. King and B. Carter, Afr. Wildlife J. 3, 19 (1965).

    Google Scholar 

  337. A. M. Hartshoorn, J. Am. Vet. Med. Assoc. 149, 875 (1966).

    Google Scholar 

  338. J. D. Wallach, J. Am. Vet. Med. Assoc. 149, 871 (1966).

    CAS  PubMed  Google Scholar 

  339. G. F. Blane, J. Pharm. Pharmacol 19, 367 (1967).

    CAS  PubMed  Google Scholar 

  340. H. W. Kosterlitz and A. J. Watt, Br. J. Pharmacol 33, 266 (1968).

    CAS  Google Scholar 

  341. G. F. Blane and D. Dugdall, J. Pharm. Pharmacol 20, 547 (1968).

    CAS  PubMed  Google Scholar 

  342. A. Cowan, Adv. Biochem. Psychopharmacol 8, 427 (1974).

    Google Scholar 

  343. A. Cowan, J. C. Doxey, and E. J. R. Harry, Br. J. Pharmacol. 60, 547 (1977).

    CAS  PubMed  Google Scholar 

  344. W. F. Michne, R. L. Salsbury, and S. J. Michalec, J. Med. Chem. 20, 682 (1977).

    CAS  PubMed  Google Scholar 

  345. S. C. Clarke, Clin. Pharmacol Ther. 19, 295 (1976).

    Google Scholar 

  346. S. N. Downing, W. P. Leary, and E. S. White, Br. J. Anaesth. 47, 251 (1977).

    Google Scholar 

  347. A. B. Dobkin, Can. Anaesth. Soc. J. 24, 186 (1977).

    CAS  PubMed  Google Scholar 

  348. K. W. Bentley, D. G. Hardy, and B. Meek, J. Am. Chem. Soc. 89, 3293 (1967).

    CAS  PubMed  Google Scholar 

  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).

    CAS  PubMed  Google Scholar 

  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. K. W. Bentley, D. G. Hardy, H. P. Crocker, D. I. Haddlesey, and P. A. Mayor, J. Am. Chem. Soc. 89, 3312 (1967).

    CAS  PubMed  Google Scholar 

  352. K. Kanematsu and T. Sasaki, J. Chem. Soc. Chem. Comm. 988 (1967).

    Google Scholar 

  353. K. W. Bentley and B. Meek, J. Chem. Soc. (C) 2233 (1969).

    Google Scholar 

  354. K. W. Bentley, D. G. Hardy, and A. C. B. Smith, J. Chem. Soc. (C) 2235, (1969).

    Google Scholar 

  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. K. W. Bentley, J. D. Bower, and J. W. Lewis, J. Chem. Soc. (C) 2569 (1969).

    Google Scholar 

  357. K. W. Bentley, J. D. Bower, and A. C. B. Smith, J. Chem. Soc. (C) 2241 (1969).

    Google Scholar 

  358. J. W. Lewis and M. J. Readhead, J. Med. Chem. 13, 525 (1970).

    CAS  PubMed  Google Scholar 

  359. K. W. Bentley, D. G. Hardy, and P. A. Mayor, J. Chem. Soc. (C) 2385 (1969).

    Google Scholar 

  360. D. I. Haddlesey, J. W. Lewis, P. A. Mayor, and G. R. Young J. Chem. Soc. Perkin I 872 (1972).

    Google Scholar 

  361. J. W. Lewis, M. J. Rance, and G. R. Young, J. Med. Chem. 17, 465 (1974).

    CAS  PubMed  Google Scholar 

  362. D. I. Haddlesey, J. W. Lewis, and P. A. Mayor, J. Chem. Soc. Perkin I 875 (1972).

    Google Scholar 

  363. J. W. Lewis, P. A. Mayor, and D. I. Haddlesey, J. Med. Chem. 16, 12 (1973).

    CAS  PubMed  Google Scholar 

  364. C. W. Hutchins, G. K. Cooper, S. Purro, and H. Rapoport, J. Med. Chem. 24, 773 (1981).

    CAS  PubMed  Google Scholar 

  365. G. H. Loew and D. S. Berkowitz, J. Med. Chem. 22, 603 (1979).

    CAS  PubMed  Google Scholar 

  366. A. P. Feinberg, I. Cresse, and S. H. Snyder, Proc. Natl. Acad. Sci. USA 73, 4215 (1976).

    CAS  PubMed  Google Scholar 

  367. P. R. Crabbendam, L. Maat, and H. C. Beyerman, Reel Trav. Chim. Pays-Bas 100, 293 (1981).

    CAS  Google Scholar 

  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. J. W. Lewis, M. J. Readhead, and A. C. B. Smith, J. Med. Chem. 16, 9 (1973).

    CAS  PubMed  Google Scholar 

  370. J. W. Lewis and M. J. Readhead, J. Med. Chem. 16, 84 (1973).

    CAS  PubMed  Google Scholar 

  371. C. W. Hutchins and H. Rapoport, J. Med. Chem. 27, 521 (1984).

    CAS  PubMed  Google Scholar 

  372. A. F. Bradbury, D. G. Smyth, and C. R. Small, Nature 260, 165 (1976).

    CAS  PubMed  Google Scholar 

  373. M. P. Kotick, D. L. Leland, J. O. Polazzi, J. F. Howes, and A. Bousquet, J. Med. Chem. 26, 1050 (1983).

    CAS  PubMed  Google Scholar 

  374. H. Rapoport and P. Sheldrick, J. Am. Chem. Soc. 85, 1636 (1983).

    Google Scholar 

  375. A. Singh, S. Archer, K. Hoogsteen, and J. Hirshfield, J. Org. Chem. 47, 752 (1982).

    CAS  Google Scholar 

  376. K. Hayakawa, S. Motohiro, I. Fujii, and K. Kanematsu, J. Am. Chem. Soc. 103, 4605 (1981).

    CAS  Google Scholar 

  377. G. W. Kirby, K. W. Bentley, P. Horsewood, and S. Singh, J. Chem. Soc. Perkin I 3064 (1979).

    Google Scholar 

  378. G. W. Kirby and J. G. Sweeney, J. Chem. Soc. Perkin I 3250, (1981).

    Google Scholar 

  379. M. Boes and W. Fleischhacker, Justus Liebigs Ann. Chem. 2002 (1981).

    Google Scholar 

  380. R. Bognár, S. Makleit, L. Radies, and I. Seki, Org. Prep. Proc. Int. 5, 49 (1973).

    Google Scholar 

  381. G. M. Badger and R. B. Bradbury, J. Chem. Soc. 445 (1960).

    Google Scholar 

  382. W. K. Hart, S. R. Johns, J. A. Lamberton, and J. K. Saunders, Tetrahedron Lett. 2891 (1968).

    Google Scholar 

  383. A. R. Battersby, M. H. G. Munro, R. B. Bradbury, and F. Santary, J. Chem. Soc. Chem. Comm. 695 (1968).

    Google Scholar 

  384. M. Tomita, T. Ibuka, Y. Inubush, and K. Takeda, Tetrahedron Lett. 3605 (1964).

    Google Scholar 

  385. L. J. Sargent and B. C. Joshi, J. Med. Chem. 11, 336 (1968).

    CAS  PubMed  Google Scholar 

  386. S. Okuda, S. Yamaguchi, Y. Kawazoe, and K. Tsuda, Chem. Pharm. Bull. 12, 104 (1964).

    CAS  PubMed  Google Scholar 

  387. N. Karplus, J. Chem Phys. 30, 11 (1959).

    CAS  Google Scholar 

  388. D. Elad and D. Ginsburg, J. Am. Chem. Soc. 78, 3691 (1956).

    CAS  Google Scholar 

  389. T. Rüll, Bull, Soc. Chim. Fr. 586 (1963).

    Google Scholar 

  390. A. E. Jacobson, H. J. Yeh, and L. J. Sargent, Org. Mag. Reson, 4, 875 (1972).

    CAS  Google Scholar 

  391. T. J. Batterham, K. H. Bell, and U. Weiss, Aust. J. Chem. 18, 1799 (1965).

    CAS  Google Scholar 

  392. J. A. Glasel, Biochem. Biophys. Res. Comm. 102, 703 (1981).

    CAS  PubMed  Google Scholar 

  393. S. K. Burt, G. H. Loew, and G. M. Hashimoto, Ann. N. Y. Acad. Sci. 367, 219 (1981).

    CAS  PubMed  Google Scholar 

  394. S. Yamaguchi, S. Okuda, and N. Nakagawa, Chem. Pharm. Bull. 11, 1465 (1963).

    CAS  PubMed  Google Scholar 

  395. T. Rüll and D. Gagnaire, Bull. Soc. Chim. Fr. 2189 (1963).

    Google Scholar 

  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).

    CAS  PubMed  Google Scholar 

  397. Y. Terui, K. Tori, S. Maeda, and Y. K. Sawa, Tetrahedron Lett. 2853 (1975).

    Google Scholar 

  398. F. I. Carroll, C. G. Moreland, G. A. Brine, and J. A. Kepler, J. Org. Chem. 41, 996 (1976).

    CAS  PubMed  Google Scholar 

  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. J. H. van den Hende and N. R. Nelson, J. Am. Chem. Soc. 89, 2901 (1967).

    PubMed  Google Scholar 

  401. V. M. Kolb, J. Pharm. Sci. 68, 1250 (1979).

    CAS  PubMed  Google Scholar 

  402. V. M. Kolb, G. S. Mandel, and N. S. Mandel, J. Pharm. Sci. 71, 763 (1982).

    PubMed  Google Scholar 

  403. S. Shiotani, T. Kometani, Y. Iitaka, and A. Itai, J. Med. Chem. 21, 153 (1978).

    CAS  PubMed  Google Scholar 

  404. E. E. Eliel, S. Morris-Natschke, and V. M. Kolb, Org. Magn. Resort. 22, 258 (1984).

    CAS  Google Scholar 

  405. A. P. Feinberg, I. Creese, and S. H. Snyder, Proc. Natl. Acad. Sci. USA 73, 4215 (1976).

    CAS  PubMed  Google Scholar 

  406. J. M. Bobbit, W. Weiss, and D. D. Hanessian, J. Org. Chem. 24, 1582 (1959).

    Google Scholar 

  407. U. Weiss and T. Rüll, Bull. Soc. Chim. Fr. 3707 (1965).

    Google Scholar 

  408. T. Rüll, Bull. Soc. Chim. Fr. 3715 (1965).

    Google Scholar 

  409. A. F. Casy and M. M. A. Hassan, J. Pharm. Pharmacol. 19, 132 (1967).

    CAS  Google Scholar 

  410. H. Inoue, M. Takeda, and H. Kugita, Chem. Pharm. Bull. 21, 2004 (1973).

    CAS  Google Scholar 

  411. H. Audier, H. Fetison, D. Ginsburg, A. Mandelbaum, and T. Rüll, Tetrahedron Lett. 13 (1965).

    Google Scholar 

  412. H. Nakata, Y. Hirata, A. Tatematsu, H. Tada, and Y. K. Sawa, Tetrahedron Lett. 829 (1965).

    Google Scholar 

  413. A. Mandelbaum and D. Ginsburg, Tetrahedron Lett. 2479 (1965).

    Google Scholar 

  414. D. M. S. Wheeler, T. H. Kinstle, and K. L. Rinehart, J. Am. Chem. Soc. 89, 4494 (1967).

    CAS  PubMed  Google Scholar 

  415. J. Fridrichsons, M. F. Mackay, and A. M. Mathieson, Tetrahedron Lett. 2887 (1968).

    Google Scholar 

  416. J. Fridrichsons, M. F. Mackay, and A. M. Mathieson, Tetrahedron 26, 1969 (1970).

    Google Scholar 

  417. G. Kartha, F. R. Ahmed, and W. H. Barnes, Acta Cryst. 15, 326 (1962).

    CAS  Google Scholar 

  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. W. H. Olendorf, S. Hyman, L. Braun, and S. Z. Olendorf, Science 178, 984 (1972).

    Google Scholar 

  420. J. G. Nutt and D. R. Jasinski, Clin. Pharmacol. Ther. 15, 156 (1974).

    CAS  PubMed  Google Scholar 

  421. S. H. Weinstein, M. Pfeffer and J. Schor, Adv. Biochem. Psychopharmacol. 8, 525 (1973).

    CAS  PubMed  Google Scholar 

  422. W. R. Martin, D. R. Jasinski, and P. A. Mansky, Arch. Gen. Psychiatry, 28, 784 (1973).

    CAS  PubMed  Google Scholar 

  423. K. Vereby, J. Volarka, S. Mule, and R. Resnick, Clin. Pharmacol. Ther. 20, 315 (1976).

    Google Scholar 

  424. E. L. Way and T. K. Adler, in: The Biological Disposition of Morphine and Its Surrogates, WHO, Geneva (1962).

    Google Scholar 

  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. L. Lemberger and A. Rubin, Physiological Disposition of Drugs, Chap. 5, Spectrum Publications, New York (1976).

    Google Scholar 

  427. H. Yoshimura, K. Oguri, and H. Tsukamoto, Tetrahedron Lett. 483 (1968).

    Google Scholar 

  428. S. Y. Yeh, C. W. Gorodetzky, and H. A. Krebs, J. Pharm. Sci. 66, 1288 (1977).

    CAS  PubMed  Google Scholar 

  429. H. Yoshimura, J. Pharmacobiodyn 3, S6 (1980).

    Google Scholar 

  430. S. Y. Yeh, J. Pharmacol. Exp. Ther. 192, 201 (1975).

    CAS  PubMed  Google Scholar 

  431. J. W. Miller and H. H. Anderson, J. Pharmacol. Exp. Ther. 112, 191 (1954).

    CAS  PubMed  Google Scholar 

  432. J. W. Miller and H. W. Elliot, J. Pharmacol. Exp. Ther. 113, 283 (1955).

    CAS  PubMed  Google Scholar 

  433. A. H. Beckett, A. F. Casy, and N. J. Harper, J. Pharm. Pharmacol. 8, 874 (1956).

    CAS  PubMed  Google Scholar 

  434. C. Ellison, H. W. Elliot, M. Look, and H. Rapoport, J. Med. Chem. 6, 237 (1963).

    Google Scholar 

  435. J. B. Schenkman, H. Remmer, and R. W. Estabrook, Mol Pharmacol. 3, 113 (1967).

    CAS  PubMed  Google Scholar 

  436. S. Y. Yeh, R. L. McQuinn, H. A. Krebs, and C. W. Gorodetzky, J. Pharm. Sci. 67, 878 (1978).

    CAS  PubMed  Google Scholar 

  437. S. Y. Yeh, Pharmacologist 18, 178 (1976).

    Google Scholar 

  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. T. K. Alder, J. M. Fujimoto, E. L. Way, and E. M. Baker, J. Pharmacol Exp. Ther. 114, 251 (1955).

    Google Scholar 

  440. K. Klutch, Drug, Metab. Disp. 2, 23 (1974).

    CAS  Google Scholar 

  441. S. Y. Yeh, Fed. Proc. 35, 469 (1976).

    Google Scholar 

  442. C. Ellison and H. W. Elliot, J. Pharmacol Exp. Ther. 144, 265 (1964).

    Google Scholar 

  443. D. Borner and S. Abbott, Experientia 29, 180 (1973).

    CAS  PubMed  Google Scholar 

  444. S. Y. Yeh, Experientia 30, 264 (1974).

    CAS  PubMed  Google Scholar 

  445. L. S. Abrams and H. W. Elliot, J. Pharm. Exp. Ther. 189, 285 (1974).

    CAS  Google Scholar 

  446. J. Daly, J. K. Inscoe, and J. Axelrod, J. Med. Chem. 8, 1953 (1965).

    Google Scholar 

  447. A. L. Misra, N. L. Vadlamani, R. B. Pontani, and S. J. Mulé, Biochem. Pharmacol. 22, 2129 (1973).

    CAS  PubMed  Google Scholar 

  448. S. Y. Yeh, H. A. Krebs, and C. W. Gorodetzky, J. Pharm. Sci. 68, 133 (1979).

    CAS  PubMed  Google Scholar 

  449. N. Miyata, K. Uba, K. Watanabe, and M. Hirobe, J. Pharmacobiodyn. 4, 57 (1981).

    Google Scholar 

  450. I. Takayanagi, F. Konno, N. Miyata, K. Watanabe, and M. Hirobe, Jap. J. Pharmacol 32, 387 (1982).

    CAS  PubMed  Google Scholar 

  451. E. L. Way, J. M. Young, and J. W. Kemp, Bull Narc. 17, 25 (1965).

    CAS  Google Scholar 

  452. E. R. Garrett and T. Gurkan, J. Pharm. Sci. 69, 1116 (1980).

    CAS  PubMed  Google Scholar 

  453. S. Y. Yeh and R. L. McQuinn, J. Pharm. Sci. 64, 1237 (1975).

    CAS  PubMed  Google Scholar 

  454. S. Y. Yeh, C. W. Gorodetzky, and R. L. McQuinn, J. Pharmacol. Exp. Ther. 196, 249 (1976).

    CAS  PubMed  Google Scholar 

  455. S. Y. Yeh, R. L. McQuinn, and C. W. Gorodetzky, J. Pharm. Sci. 66, 201 (1977).

    CAS  PubMed  Google Scholar 

  456. S. H. Weinstein, M. Pfeffer, J. M. Schor, L. Indindoli, and M. Mintz, J. Pharm. Sci. 60, 1567 (1971).

    CAS  PubMed  Google Scholar 

  457. J. M. Fujimoto, J. Pharmacol. Exp. Ther. 168, 180 (1969).

    CAS  PubMed  Google Scholar 

  458. J. M. Tujimoto, Proc. Soc. Exp. Biol Med. 133, 317 (1970).

    Google Scholar 

  459. M. E. Wall, D. R. Brine, and M. Perez-Reyez, Drug Metab. Disposition 9, 369 (1981).

    CAS  Google Scholar 

  460. E. J. Cone, Tetrahedron Lett. 2607 (1973).

    Google Scholar 

  461. A. H. Beckett and A. F. Casy, Proc. Med. Chem. 4, 171 (1965).

    CAS  Google Scholar 

  462. N. B. Eddy and E. L. May, Science 181, 407 (1973).

    CAS  PubMed  Google Scholar 

  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. A. S. Horn and J. R. Rogers, J. Pharm. Pharmacol 29, 257 (1977).

    CAS  PubMed  Google Scholar 

  465. G. de Stevens (ed.), Analgetics, Academic Press, New York (1965).

    Google Scholar 

  466. D. Lednicer (ed.), Central Analgetics, John Wiley and Sons, New York (1982).

    Google Scholar 

  467. E. L. May, J. Med. Chem. 23, 225 (1980).

    CAS  PubMed  Google Scholar 

  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. P. S. Portoghese, Acc. Chem. Res. 11, 21 (1978).

    CAS  Google Scholar 

  470. E. Kutter, A. Herz, H.-J. Teschemacher, and R. Hess, J. Med. Chem. 13, 801 (1970).

    CAS  PubMed  Google Scholar 

  471. J. J. Kaufman, N. M. Semo, and W. S. Koski, J. Med. Chem. 18, 647 (1975).

    CAS  PubMed  Google Scholar 

  472. R. H. F. Manske and H. L. Holmes (eds.), The Alkaloids, Academic Press, New York (1952).

    Google Scholar 

  473. K. W. Bentley, in: The Alkaloids (R. H. F. Manske, ed.), Vol. 13, p. 1, Academic Press, New York (1971).

    Google Scholar 

  474. H. W. Kosterlitz and A. A. Waterfield, Ann. Rev. Pharmacol. 15, 29 (1975).

    CAS  PubMed  Google Scholar 

  475. H. W. Kosterlitz, J. A. H. Lord, S. J. Paterson, and A. A. Waterfield, Br. J. Pharmacol 68, 333 (1980).

    CAS  PubMed  Google Scholar 

  476. C. E. Brown, S. C. Roerig, J. M. Fujimoto, and V. T. Burger, J. Chem. Soc, Chem. Commun. 1506 (1983).

    Google Scholar 

  477. J. A. Glasel and H. W. Reiher, Org. Magn. Reson. 23, 236 (1985).

    CAS  Google Scholar 

  478. S. Fang, A. E. Takemori, and P. S. Portoghese, J. Med. Chem. 27, 1361 (1984).

    CAS  PubMed  Google Scholar 

  479. J. Reden, M. F. Reich, K. C. Rice, A. H. Jacobson and A. Brossi, J. Med. Chem. 22, 256 (1979).

    CAS  PubMed  Google Scholar 

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Casy, A.F., Parfitt, R.T. (1986). 4,5-Epoxymorphinans. In: Opioid Analgesics. Springer, Boston, MA. https://doi.org/10.1007/978-1-4899-0585-7_2

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