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Chromatographic and spectroscopic study of impurities present in thebaine obtained from Papaver bracteatum Lindl.

Xiaoli Zhou, Ming Yuan, Li Li, Jingwen Wang, Yuelin Zeng, and Hua Chen

National Institutes for Food and Drug Control, Beijing, China

 

E-mail: zhouxiaoli@nifdc.org.cn

Received: 9 October 2020  Accepted: 24 June 2021

Abstract:

Thebaine is an important opiate alkaloid derived from opium that can be converted into various pharmaceutical compounds. However, only a few studies have focused on the quality and purity control of thebaine. In this study, the impurities present in a thebaine raw material sample, which was extracted from Papaver bracteatum Lindl., were studied through directed syntheses and structural identification using mass spectrometry, nuclear magnetic resonance spectroscopy, and circular dichroism. The thebaine sample was analyzed using high-performance liquid chromatography, the impurities present were identified by two-dimensional ultra-performance liquid chromatography coupled with tandem mass spectrometry, and their structures were elucidated by mass spectrometry. Following the preparation of identified impurities, their structures were characterized and confirmed to be northebaine and thebaine N-oxide by nuclear magnetic resonance spectroscopy and circular dichroism. The identification of these impurities and the development of a synthetic route toward these compounds will be expected to lay the foundation for the analysis of thebaine-related substances and for the preparation of related reference substances.

Keywords: Liquid chromatography; Mass spectrometry; Thebaine; Thebaine N-oxide; Northebaine

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-021-01757-x

 

Chemical Papers 75 (11) 5825–5837 (2021)

Monday, February 06, 2023

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