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

Title
Isolation and identification of a sibutramine analogue adulterated in slimming dietary supplements
Authors
Ji Won KimSoon Jae KweonSeon Kyung ParkJung Yeon KimJi Hyun LeeKyoung Moon HanSooyeul ChoJinho KimSoon Young Han김형자Woo Seong Kim
Keywords
dietary supplements; sibutramine; sibutramin analogue; NMR; mass spectrum
Issue Date
2013-08
Publisher
FOOD ADDITIVES AND CONTAMINANTS PART A-CHEMISTRY ANALYSIS CONTROL EXPOSURE& RISK ASSESSMENT
Citation
VOL 30, NO 7, 1221-1229
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 chlorosibutramine 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.
URI
http://pubs.kist.re.kr/handle/201004/45768
ISSN
19440049
Appears in Collections:
KIST Publication > Article
Files in This Item:
There are no files associated with this item.
Export
RIS (EndNote)
XLS (Excel)
XML


qrcode

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.

BROWSE