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Quantification and Stereochemical Composition of R-(-) and S-(+)-Clenbuterol Enantiomers in Bovine Urine by Liquid Chromatography-Tandem Mass Spectrometry.
J Anal Toxicol. 2020 Apr 30; 44(3):237-244.JA

Abstract

Clenbuterol (4-amino-α-[(tert-butylamino)methyl]-3,5-dichlorobenzylalcohol) is a β2-adrenergic agonist. The consumption of meat contaminated with clenbuterol can lead to increased heart rate, blood pressure, anxiety, palpitations and skeletal muscle tremors. Several analytical methods have been developed to identify and quantify clenbuterol in different biological matrices. In this report, we have developed a specific and sensitive analytical method for quantifying clenbuterol and performed an in-depth enantiomeric analysis in bovine urine. The method was evaluated in accordance with international guidelines, and we used an isotopically labeled analog as an internal standard. The extraction efficiency for clenbuterol in bovine urine was > 98%, the limit of detection was 0.05 ng/mL and the limit of quantification was 0.10 ng/mL. Our assay showed high specificity, no carryover was observed and the assay was linear in the range 0.10-8.0 ng/mL. Fifteen bovine urine samples were analyzed (containing clenbuterol), and an enantiomeric analysis was performed. The clenbuterol concentration range was 0.10-10.56 ng/mL across these samples. The levorotatory enantiomer was detected at greater concentrations than the dextrorotatory enantiomer, the ratio being 1.7 ± 0.6 (n = 15), and a statistical difference was observed (P < 0.05) using the Wilcoxon test.

Authors+Show Affiliations

Sección de Química Orgánica, Departamento de Ciencias Químicas, Facultad de Estudios Superiores Cuautitlán, Universidad Nacional Autónoma de México, Av 1 de mayo S/N, Col. Sta María las Torres, Cuautitlán Izcalli, CP54740, Estate of México, Mexico. Laboratorio Nacional de Prevención y Control del Dopaje-CONADE, Camino a Sta Teresa 482, Col. Peña Pobre, Alcaldía Tlalpan, CP14060, Mexico city, Mexico.Laboratorio Nacional de Prevención y Control del Dopaje-CONADE, Camino a Sta Teresa 482, Col. Peña Pobre, Alcaldía Tlalpan, CP14060, Mexico city, Mexico.Laboratorio Nacional de Prevención y Control del Dopaje-CONADE, Camino a Sta Teresa 482, Col. Peña Pobre, Alcaldía Tlalpan, CP14060, Mexico city, Mexico.Laboratorio de Desarrollo Farmacéutico-LEDEFAR, Facultad de Estudios Superiores Cuautitlán, Universidad Nacional Autónoma de México, Carretera Cuautitlán-Teoloyucan km 2.5, San Sebastián Xhala CP 54714, Estate of México, Mexico.Departamento de Química de Biomacromoléculas, Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Alcaldía Coyoacán, CP04510, Mexico City, Mexico.División de Estudios de Posgrado e Investigación del, Tecnológico Nacional de México/División de Estudios de Posgrado e Investigación del, Instituto Tecnológico de Altamira, Carretera Tampico-Mante Km 24.5. CP 89600, Altamira, Tamaulipas, Mexico.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31681961

Citation

Velasco-Bejarano, Benjamín, et al. "Quantification and Stereochemical Composition of R-(-) and S-(+)-Clenbuterol Enantiomers in Bovine Urine By Liquid Chromatography-Tandem Mass Spectrometry." Journal of Analytical Toxicology, vol. 44, no. 3, 2020, pp. 237-244.
Velasco-Bejarano B, Bautista J, Rodríguez ME, et al. Quantification and Stereochemical Composition of R-(-) and S-(+)-Clenbuterol Enantiomers in Bovine Urine by Liquid Chromatography-Tandem Mass Spectrometry. J Anal Toxicol. 2020;44(3):237-244.
Velasco-Bejarano, B., Bautista, J., Rodríguez, M. E., López-Arellano, R., Arreguín-Espinosa, R., & Carrillo, R. V. (2020). Quantification and Stereochemical Composition of R-(-) and S-(+)-Clenbuterol Enantiomers in Bovine Urine by Liquid Chromatography-Tandem Mass Spectrometry. Journal of Analytical Toxicology, 44(3), 237-244. https://doi.org/10.1093/jat/bkz087
Velasco-Bejarano B, et al. Quantification and Stereochemical Composition of R-(-) and S-(+)-Clenbuterol Enantiomers in Bovine Urine By Liquid Chromatography-Tandem Mass Spectrometry. J Anal Toxicol. 2020 Apr 30;44(3):237-244. PubMed PMID: 31681961.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Quantification and Stereochemical Composition of R-(-) and S-(+)-Clenbuterol Enantiomers in Bovine Urine by Liquid Chromatography-Tandem Mass Spectrometry. AU - Velasco-Bejarano,Benjamín, AU - Bautista,Jahir, AU - Rodríguez,Martha E, AU - López-Arellano,Raquel, AU - Arreguín-Espinosa,Roberto, AU - Carrillo,Ricardo Velasco, PY - 2019/02/08/received PY - 2019/06/13/revised PY - 2019/08/25/accepted PY - 2019/11/5/pubmed PY - 2020/5/21/medline PY - 2019/11/5/entrez KW - Clenbuterol quantification KW - UHPLC-MS/MS KW - mass spectrometry KW - stereochemical composition KW - β2-agonist SP - 237 EP - 244 JF - Journal of analytical toxicology JO - J Anal Toxicol VL - 44 IS - 3 N2 - Clenbuterol (4-amino-α-[(tert-butylamino)methyl]-3,5-dichlorobenzylalcohol) is a β2-adrenergic agonist. The consumption of meat contaminated with clenbuterol can lead to increased heart rate, blood pressure, anxiety, palpitations and skeletal muscle tremors. Several analytical methods have been developed to identify and quantify clenbuterol in different biological matrices. In this report, we have developed a specific and sensitive analytical method for quantifying clenbuterol and performed an in-depth enantiomeric analysis in bovine urine. The method was evaluated in accordance with international guidelines, and we used an isotopically labeled analog as an internal standard. The extraction efficiency for clenbuterol in bovine urine was > 98%, the limit of detection was 0.05 ng/mL and the limit of quantification was 0.10 ng/mL. Our assay showed high specificity, no carryover was observed and the assay was linear in the range 0.10-8.0 ng/mL. Fifteen bovine urine samples were analyzed (containing clenbuterol), and an enantiomeric analysis was performed. The clenbuterol concentration range was 0.10-10.56 ng/mL across these samples. The levorotatory enantiomer was detected at greater concentrations than the dextrorotatory enantiomer, the ratio being 1.7 ± 0.6 (n = 15), and a statistical difference was observed (P < 0.05) using the Wilcoxon test. SN - 1945-2403 UR - https://www.unboundmedicine.com/medline/citation/31681961/Quantification_and_Stereochemical_Composition_of_R_____and_S__+__Clenbuterol_Enantiomers_in_Bovine_Urine_by_Liquid_Chromatography_Tandem_Mass_Spectrometry_ L2 - https://academic.oup.com/jat/article-lookup/doi/10.1093/jat/bkz087 DB - PRIME DP - Unbound Medicine ER -