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Pharmaceutisch Weekblad

, Volume 7, Issue 5, pp 202–207 | Cite as

Structure elucidation of two isomeric steroids: Photolytical and thermal reaction products from norethisterone studied by two-dimensional nuclear magnetic resonance

  • A. G. J. Sedee
  • G. M. J. Beijersbergen Van Henegouwen
  • W. Guijt
  • C. A. G. Haasnoot
Original Articles

Abstract

Two-dimensional nuclear magnetic resonance was used for the structure elucidation of two isomeric photoproducts of norethisterone, a commonly used progestogen in oral contraceptives. The predominant one of the two isolated products derived from photochemical decomposition of norethisterone upon irradiation with UV-B light (280–320 nm) was 5α,17β-dihydroxy-19-nor-17α-pregn-20-yn-3-one. The minor photoproduct appeared to be the analogous 5β-isomer,i.e.

5β,17β-dihydroxy-19-nor-17α-pregn-20-yn-3-one. The latter compound was also obtained from the thermal reduction of norethisterone-4β,5β-epoxide using aluminium amalgam in isopropanol. Two-dimensional NMR appeared to be superior to mass and IR spectrometry in identifying the isomers.

Keywords

Public Health Aluminium Steroid Internal Medicine Nuclear Magnetic Resonance 
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

© Bohn, Scheltema & Holkema 1985

Authors and Affiliations

  • A. G. J. Sedee
    • 1
  • G. M. J. Beijersbergen Van Henegouwen
    • 1
  • W. Guijt
    • 2
  • C. A. G. Haasnoot
    • 2
  1. 1.Department of Pharmacochemistry, Center for Bio-Pharmaceutical SciencesState University of LeidenRA LeidenThe Netherlands
  2. 2.Laboratory of Biophysical Chemistry, Faculty of ScienceUniversity of NijmegenED NijmegenThe Netherlands

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