Rapid screening and structural elucidation of a novel sibutramine analogue in a weight loss supplement: 11-Desisobutyl-11-benzylsibutramine

Journal of Pharmaceutical and Biomedical Analysis

Volumn 83, Issue , 2013, Pages 122-128

  Mans, Daniel J ^a   Gucinski, Ashley C ^a   Dunn, Jamie D ^a   Gryniewicz Ruzicka, Connie M ^a   Mecker Pogue, Laura C ^a   Kao, Jeff L F ^b   Ge, Xia ^b  

^a CENTER FOR DRUG EVALUATION AND RESEARCH   (United States)

^b WASHINGTON UNIVERSITY   (United States)

Author keywords

Dietary supplement; Ion mobility spectrometry; Mass spectrometry; Nuclear magnetic resonance; Sibutramine

Indexed keywords

11 DESISOBUTYL 11 BENZYLSIBUTRAMINE; ANTIOBESITY AGENT; BENZYL DERIVATIVE; SEROTONIN NORADRENALIN REUPTAKE INHIBITOR; SIBUTRAMINE; SODIUM HYDROXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DIET SUPPLEMENTATION; DRUG DESIGN; DRUG SCREENING; FOOD AND DRUG ADMINISTRATION; ION MOBILITY SPECTROMETRY; LIQUID CHROMATOGRAPHY TANDEM MASS SPECTROMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; TANDEM MASS SPECTROMETRY; WEIGHT REDUCTION;

CHROMATOGRAPHY, LIQUID; CYCLOBUTANES; DIETARY SUPPLEMENTS; MAGNETIC RESONANCE SPECTROSCOPY; TANDEM MASS SPECTROMETRY; WEIGHT LOSS;

EID: 84878802135     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2013.02.031     Document Type: Article

References (20)

1. Overweight and obesity. http://www.cdc.gov/obesity/data/facts.html.
2. Hiatt W.R., Thomas A., Goldfine A.B. What cost weight loss?. Circulation 2012, 125:1171-1177.
3. FDA approves weight-management drug Qsymia. http://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm312468.htm.
4. Jeffery J.E., Whybrow D. N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine hydrochloride monohydrate for use in treating depression. Brit. UK Pat. Appl. GB 1987, 2184122A.
5. Ryan D.H., Kaiser P., Bray G.A. Sibutramine: a novel new agent for obesity treatment. Obes. Res. 1995, 3:553-559.
6. Jeffery J.E., Kerrigan F., Miller T.K., Smith G.J., Tometzki G.B. Synthesis of sibutramine, a novel cyclobutylalkylamine useful in the treatment of obesity, and its major human metabolites. J. Chem. Soc. Perkin Trans. 1996, 1:2583-2589.
7. Buckett W.R., Thomas P.C., Luscombe G.P. The pharmacology of sibutramine hydrochloride (BTS 54 524), a new antidepressant which induces rapid noradrenergic down-regulation. Prog. Neuro-Psychoph. 1988, 12:575-584.
8. Meridia® (sibutramine hydrochloride monohydrate) Sponsor Briefing Document - EMDAC Meeting 13 August 2010. http://www.fda.gov/downloads/AdvisoryCommittees/CommitteesMeetingMaterials/Drugs/EndocrinologicandMetabolicDrugsAdvisoryCommittee/UCM225573.pdf.
9. Abbott Laboratories agrees to withdraw its obesity drug Meridia. http://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm228812.htm.
10. Dunn J.D., Gryniewicz-Ruzicka C.M., Kauffman J.F., Westenberger B.J., Buhse L.F. Using a portable ion mobility spectrometer to screen dietary supplements for sibutramine. J. Pharm. Biomed. Anal. 2011, 54:469-474.
11. Dunn J.D., Gryniewicz-Ruzicka C.M., Mans D.J., Mecker-Pogue L.C., Kauffman J.F., Westenberger B.J., Buhse L.F. Qualitative screening for adulterants in weight-loss supplements by ion mobility spectrometry. J. Pharm. Biomed. Anal. 2012, 71:18-26.
12. Lai K.-C., Liu Y.-C., Tseng M.-C., Lin Y.-L., Lin J.-H. Isolation and identification of a sibutramine analogue in a healthy food for weight loss. Y. Ship. Fen. 2007, 15:20-24.
13. Thevis M., Sigmund G., Schiffer A.-K., Schaenzer W. Determination of N-desmethyl- and N-bisdesmethyl metabolites of Sibutramine in doping control analysis using liquid chromatography-tandem mass spectrometry. Eur. J. Mass Spectrom. 2006, 12:129-136.
14. Arzhantsev S., Li X., Kauffman J.F. Rapid limit tests for metal impurities in pharmaceutical materials by X-ray fluorescence spectroscopy using wavelet transform filtering. Anal. Chem. 2011, 83:1061-1068.
15. Gryniewicz C.M., Reepmeyer J.C., Kauffman J.F., Buhse L.F. Detection of undeclared erectile dysfunction drugs and analogues in dietary supplements by ion mobility spectrometry. J. Pharm. Biomed. Anal. 2009, 49:601-606.
16. Gryniewicz C.M., Spencer J.A., Hankins M., Kauffman J.F. Spectroscopic methods for rapid determination of diethylene glycol in glycerin. Am. Pharm. Rev. 2007, 10:24-30.
17. Gryniewicz-Ruzicka C.M., Arzhantsev S., Pelster L.N., Westenberger B.J., Buhse L.F., Kauffman J.F. Multivariate calibration and instrument standardization for the rapid detection of diethylene glycol in glycerin by Raman spectroscopy. Appl. Spectrosc. 2011, 65:334-341.
18. Kauffman J.F., Gryniewicz-Ruzicka C.M., Arzhantsev S., Dunn J.D., Spencer J.A., Wolfgang S., Li X., Pelster L.N., Westenberger B.J., Buhse L.F. Pharmaceutical surveillance with rapid spectroscopic screening technologies. Am. Pharm. Rev. 2010, 13:58-62.
19. Li X., Arzhantsev S., Kauffman J.F., Spencer J.A. Detection of diethylene glycol adulteration in propylene glycol - method validation through a multi-instrument collaborative study. J. Pharm. Biomed. Anal. 2011, 54:1001-1006.
20. Mans D.J., Callahan R.J., Dunn J.D., Gryniewicz-Ruzicka C.M. Rapid-screening detection of acetildenafils, sildenafils and avanafil by ion mobility spectrometry. J. Pharm. Biomed. Anal. 2013, 75:153-157.