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Resolution of R-(-) and S-(+)- enantiomers of clenbuterol in pharmaceutical preparations and black-market products using liquid chromatography-tandem mass spectrometry.
Drug Test Anal. 2017 Nov; 9(11-12):1738-1743.DT

Abstract

Several banned substances are illegally used by athletes in racemic mixtures for performance enhancement. These include clenbuterol, methyl hexaneamine, methamphetamines, and amphetamines. Clenbuterol is present in a large number of doping samples from Olympic and non-Olympic athletes that have adverse analytical findings (AAFs). In some cases, the presence of these substances could be the result of consumption of meat contaminated with clenbuterol. In other cases, the origin is not clear. In this study, 27 products with racemic clenbuterol were evaluated using a new analytical methodology for the resolution of R-(-) and S-(+)-enantiomers of clenbuterol by liquid chromatography-tandem mass spectrometry (LC-MS/MS) using a chiral column in 15 min with good separation. The method developed can also be used for the analysis of other biological matrices such as urine, serum, and meat. The resolution between two peaks' (Rs) value obtained using chromatographic data was 1.03. Both clenbuterol enantiomers were present in all products analyzed and the ratio was nearly 1. The origin of the product was not important for determining the presence of one or both enantiomers. All products displayed a 50:50 ratio of clenbuterol enantiomers. To the best of our knowledge, clenbuterol ratio determination of a large number of pharmaceutical preparations and black-market products has not been reported previously. The information shown could be used by national anti-doping organizations and the athletes with AAFs attributed to clenbuterol. Copyright © 2017 John Wiley & Sons, Ltd.

Authors+Show Affiliations

Facultad de Estudios Superiores Cuautitlán-UNAM, Departamento de Ciencias Químicas, Sección de Química Orgánica, Av. 1 de mayo S/N, Col. Sta. María las Torres, Cuautitlán Izcalli, Estado de México, México, C.P. 54740. Laboratorio Nacional de Prevención y Control del Dopaje-CONADE, Dirección de Medicina y Ciencias Aplicadas, Camino a Santa Teresa No. 482, Col. Peña Pobre, Delegación Tlalpan, Ciudad de México, México, C. P. 14060.Laboratorio Nacional de Prevención y Control del Dopaje-CONADE, Dirección de Medicina y Ciencias Aplicadas, Camino a Santa Teresa No. 482, Col. Peña Pobre, Delegación Tlalpan, Ciudad de México, México, C. P. 14060.Facultad de Estudios Superiores Cuautitlán-UNAM, Departamento de Ciencias Químicas, Sección de Química Orgánica, Av. 1 de mayo S/N, Col. Sta. María las Torres, Cuautitlán Izcalli, Estado de México, México, C.P. 54740.Laboratorio Nacional de Prevención y Control del Dopaje-CONADE, Dirección de Medicina y Ciencias Aplicadas, Camino a Santa Teresa No. 482, Col. Peña Pobre, Delegación Tlalpan, Ciudad de México, México, C. P. 14060.Laboratorio Nacional de Prevención y Control del Dopaje-CONADE, Dirección de Medicina y Ciencias Aplicadas, Camino a Santa Teresa No. 482, Col. Peña Pobre, Delegación Tlalpan, Ciudad de México, México, C. P. 14060.Laboratorio Nacional de Prevención y Control del Dopaje-CONADE, Dirección de Medicina y Ciencias Aplicadas, Camino a Santa Teresa No. 482, Col. Peña Pobre, Delegación Tlalpan, Ciudad de México, México, C. P. 14060.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

28856822

Citation

Velasco-Bejarano, Benjamín, et al. "Resolution of R-(-) and S-(+)- Enantiomers of Clenbuterol in Pharmaceutical Preparations and Black-market Products Using Liquid Chromatography-tandem Mass Spectrometry." Drug Testing and Analysis, vol. 9, no. 11-12, 2017, pp. 1738-1743.
Velasco-Bejarano B, Bautista J, Noguez MO, et al. Resolution of R-(-) and S-(+)- enantiomers of clenbuterol in pharmaceutical preparations and black-market products using liquid chromatography-tandem mass spectrometry. Drug Test Anal. 2017;9(11-12):1738-1743.
Velasco-Bejarano, B., Bautista, J., Noguez, M. O., Camacho, E., Rodríguez, M. E., & Rodríguez, L. (2017). Resolution of R-(-) and S-(+)- enantiomers of clenbuterol in pharmaceutical preparations and black-market products using liquid chromatography-tandem mass spectrometry. Drug Testing and Analysis, 9(11-12), 1738-1743. https://doi.org/10.1002/dta.2294
Velasco-Bejarano B, et al. Resolution of R-(-) and S-(+)- Enantiomers of Clenbuterol in Pharmaceutical Preparations and Black-market Products Using Liquid Chromatography-tandem Mass Spectrometry. Drug Test Anal. 2017;9(11-12):1738-1743. PubMed PMID: 28856822.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Resolution of R-(-) and S-(+)- enantiomers of clenbuterol in pharmaceutical preparations and black-market products using liquid chromatography-tandem mass spectrometry. AU - Velasco-Bejarano,Benjamín, AU - Bautista,Jahir, AU - Noguez,Ma Olivia, AU - Camacho,Evangelina, AU - Rodríguez,Martha E, AU - Rodríguez,Leonardo, Y1 - 2017/10/23/ PY - 2017/07/13/received PY - 2017/08/10/revised PY - 2017/08/23/accepted PY - 2017/9/1/pubmed PY - 2018/8/23/medline PY - 2017/9/1/entrez KW - anti-doping KW - clenbuterol KW - enantiomeric composition KW - enantioselective resolution SP - 1738 EP - 1743 JF - Drug testing and analysis JO - Drug Test Anal VL - 9 IS - 11-12 N2 - Several banned substances are illegally used by athletes in racemic mixtures for performance enhancement. These include clenbuterol, methyl hexaneamine, methamphetamines, and amphetamines. Clenbuterol is present in a large number of doping samples from Olympic and non-Olympic athletes that have adverse analytical findings (AAFs). In some cases, the presence of these substances could be the result of consumption of meat contaminated with clenbuterol. In other cases, the origin is not clear. In this study, 27 products with racemic clenbuterol were evaluated using a new analytical methodology for the resolution of R-(-) and S-(+)-enantiomers of clenbuterol by liquid chromatography-tandem mass spectrometry (LC-MS/MS) using a chiral column in 15 min with good separation. The method developed can also be used for the analysis of other biological matrices such as urine, serum, and meat. The resolution between two peaks' (Rs) value obtained using chromatographic data was 1.03. Both clenbuterol enantiomers were present in all products analyzed and the ratio was nearly 1. The origin of the product was not important for determining the presence of one or both enantiomers. All products displayed a 50:50 ratio of clenbuterol enantiomers. To the best of our knowledge, clenbuterol ratio determination of a large number of pharmaceutical preparations and black-market products has not been reported previously. The information shown could be used by national anti-doping organizations and the athletes with AAFs attributed to clenbuterol. Copyright © 2017 John Wiley & Sons, Ltd. SN - 1942-7611 UR - https://www.unboundmedicine.com/medline/citation/28856822/Resolution_of_R_____and_S__+___enantiomers_of_clenbuterol_in_pharmaceutical_preparations_and_black_market_products_using_liquid_chromatography_tandem_mass_spectrometry_ L2 - https://doi.org/10.1002/dta.2294 DB - PRIME DP - Unbound Medicine ER -