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Morphinans

  • Alan F. Casy
  • Robert T. Parfitt

Abstract

Once the structure of morphine had been established,(1,2) attempts at its synthesis were started. Although early efforts were frustrated, independent proposals by Robinson(3) and Schöpf(4) regarding the biosynthesis of the morphine skeleton from a 1-benzyltetrahydroisoquinoline prompted Grewe(5–7) to embark upon a synthesis which led to racemic N-methylmorphinan 4 (Scheme 3.1). Grewe demonstrated that 4, although possessing only the nitrogen functional group of morphine, retained similar analgesic properties (1/5 × morphine). This observation resulted in many studies that it was hoped would produce analgesics with a more clinically acceptable pharmacological profile than morphine, but possessing the morphinan structure (5). Inclusion of a 3-OH was found to enhance analgesia considerably without unduly affecting undesirable pharmacological properties.

Keywords

Opioid Receptor Tartaric Acid Total Synthesis Antinociceptive Activity Methyl Vinyl Ketone 
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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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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