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Philipp, Anika A.; Wissenbach, Dirk K.; Weber, Armin A.; Zapp, Josef; Maurer, Hans H.

Phase I and II metabolites of speciogynine, a diastereomer of the main Kratom alkaloid mitragynine, identified in rat and human urine by liquid chromatography coupled to low‐ and high‐resolution linear ion trap mass spectrometry

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  • Media type: E-Article
  • Title: Phase I and II metabolites of speciogynine, a diastereomer of the main Kratom alkaloid mitragynine, identified in rat and human urine by liquid chromatography coupled to low‐ and high‐resolution linear ion trap mass spectrometry
  • Contributor: Philipp, Anika A.; Wissenbach, Dirk K.; Weber, Armin A.; Zapp, Josef; Maurer, Hans H.
  • imprint: Wiley, 2010
  • Published in: Journal of Mass Spectrometry
  • Language: English
  • DOI: 10.1002/jms.1848
  • ISSN: 1076-5174; 1096-9888
  • Keywords: Spectroscopy
  • Origination:
  • Footnote:
  • Description: <jats:title>Abstract</jats:title><jats:p><jats:italic>Mitragyna speciosa</jats:italic> (<jats:italic>Kratom</jats:italic> in Thai), a Thai medical plant, is misused as herbal drug of abuse. Besides the most abundant alkaloids mitragynine (MG) and paynantheine (PAY), several other alkaloids were isolated from <jats:italic>Kratom</jats:italic> leaves, among them the third abundant alkaloid is speciogynine (SG), a diastereomer of MG. The aim of this present study was to identify the phase I and II metabolites of SG in rat urine after the administration of a rather high dose of the pure alkaloid and then to confirm these findings using human urine samples after <jats:italic>Kratom</jats:italic> use. The applied liquid chromatography coupled to low‐ and high‐resolution mass spectrometry (LC–HRMS‐MS) provided detailed information on the structure in the MS<jats:sup><jats:italic>n</jats:italic></jats:sup> mode particularly with high resolution. For the analysis of the human samples, the LC separation had to be improved markedly allowing the separation of SG and its metabolites from its diastereomer MG and its metabolites. In analogy to MG, besides SG, nine phase I and eight phase II metabolites could be identified in rat urine, but only three phase I and five phase II metabolites in human urine. These differences may be caused by the lower SG dose applied by the user of <jats:italic>Kratom</jats:italic> preparations. SG and its metabolites could be differentiated in the human samples from the diastereomeric MG and its metabolites comparing the different retention times determined after application of the single alkaloids to rats. In addition, some differences in MS<jats:sup>2</jats:sup> and/or MS<jats:sup>3</jats:sup> spectra of the corresponding diastereomers were observed. Copyright © 2010 John Wiley &amp; Sons, Ltd.</jats:p>