Synthesis of a doxycycline-[(13) CD3 ] standard

J Labelled Comp Radiopharm. 2016 Jun 15;59(7):291-3. doi: 10.1002/jlcr.3397. Epub 2016 Apr 6.

Abstract

A stable isotope labelled mass spectrometry internal standard of the antibiotic doxycycline was prepared to assist in pharmacokinetic analyses. Our approach was to first N-demethylate doxycycline using a non-classical Polonovski reaction and then re-methylate using methyl-[(13) CD3 ] iodide, which gave doxycycline-[(13) CD3 ] with an isotopic purity of 99%.

Keywords: MS internal standard; antibiotic; demethylation; doxycycline.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Chemistry Techniques, Synthetic
  • Doxycycline / chemical synthesis*
  • Doxycycline / chemistry*
  • Isotope Labeling
  • Radiochemistry / standards*
  • Reference Standards

Substances

  • Doxycycline