Sulfate esters of morphine derivatives: Synthesis and characterization

András Váradi, András Gergely, Szabolcs Béni, Péter Jankovics, Béla Noszál, Sándor Hosztafi

Research output: Article

12 Citations (Scopus)

Abstract

Sixteen 3-O- and 6-O-sulfate esters of morphine, codeine and some of their N-methyl quaternary derivatives were synthesized by means of sulfation with pyridine-SO3 complex and sulfuric acid/N,N′- dicyclohexylcarbodiimide. Complete 1H- and 13C-NMR assignments are given for each of the synthesized compounds based on one- and two-dimensional homo- and heteronuclear measurements. Comparative analysis of chiral properties by circular dichroism and optical rotatory dispersion revealed characteristic differences in the spectra due to changes in charge, polarity and intramolecular association by strong hydrogen bonds in aqueous solution. The synthesized sulfate esters are prospective peripheral analgesics lacking central side effects and are also useful as reference substances for various analytical studies involving sulfate ester metabolites.

Original languageEnglish
Pages (from-to)65-72
Number of pages8
JournalEuropean Journal of Pharmaceutical Sciences
Volume42
Issue number1-2
DOIs
Publication statusPublished - jan. 18 2011

ASJC Scopus subject areas

  • Pharmaceutical Science

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