Isolation and identification of a sibutramine analogue adulterated in slimming dietary supplements

Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2013;30(7):1221-9. doi: 10.1080/19440049.2013.793826. Epub 2013 Jun 25.

Abstract

A suspected sibutramine analogue was detected in a slimming functional food by an ultra performance liquid chromatography-electrospray ionisation-time of flight mass spectrometry (UPLC-ESI-TOF/MS) method. The ultraviolet (UV) spectrum of this suspected compound showed close similarity to that of sibutramine. The sample was extracted with 70% MeOH and isolated by semi-preparative column chromatography. The structure of this compound was identified by spectroscopic analyses (nuclear magnetic resonance [NMR] technique, mass and tandem mass etc.). The structure of the unknown compound was demonstrated to be [(±)-dimethyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]-N,N,3-trimethylbutan-1-amine (molecular formula C17H25NCl2) and named as chloro-sibutramine. Compared with sibutramine, it has one more chlorine atom than the 3-cholorophenyl group so was switched to 3,4-dichlorophenyl. Until now, chloro-sibutramine was isolated for the first time from the undeclared ingredient included in dietary supplements. Although the safety of chloro-sibutramine is unknown, there is a potential health risk to consumers because of a similar skeleton to sibutramine. For public health, this sibutramine analogue has been included in the inspection list of illegal adulterants in Korea.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Appetite Depressants / analysis*
  • Chromatography, Liquid
  • Cyclobutanes / analysis*
  • Cyclobutanes / chemistry
  • Dietary Supplements*
  • Drug Contamination*
  • Magnetic Resonance Spectroscopy

Substances

  • Appetite Depressants
  • Cyclobutanes
  • sibutramine