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Does the analysis of the enantiomeric composition of clenbuterol in human urine enable the differentiation of illicit clenbuterol administration from food contamination in sports drug testing?
Rapid Commun Mass Spectrom. 2013 Feb 28; 27(4):507-12.RC

Abstract

RATIONALE

Clenbuterol (4-amino-α-[(tert-butylamino)methyl]-3,5-dichlorobenzyl alcohol) is approved for human and veterinary use primarily for the treatment of pulmonary afflictions. Despite the authorized administration in cases of medical indications, the misuse of clenbuterol in animal husbandry as well as elite and amateur sport has frequently been reported, arguably due to growth-promoting properties. Due to various recent incidences of doping control specimens containing clenbuterol, strategies towards the discrimination of a surreptitious application from unintended intake via animal-derived edibles or dietary supplements were required.

METHODS

The enantiomeric compositions of clenbuterol in human urine samples derived from administration studies with therapeutic amounts of the β(2)-agonist and authentic doping control specimens were determined. Due to the facts that therapeutic clenbuterol consists of a racemic mixture of (+)- and (-)-stereoisomers and that the first mentioned (dextrorotatory) stereoisomer is retained to a greater extent in edible animal tissue, the differentiation of a recent administration of therapeutic (and thus racemic) clenbuterol from food contamination (stereoisomerically depleted clenbuterol) was considered. Employing deuterated clenbuterol as internal standard, the target analytes were extracted from human urine by means of concerted liquid-liquid and solid-phase extractions and subjected to chiral liquid chromatography hyphenated to high resolution/high accuracy mass spectrometry with electrospray ionization.

RESULTS

Both enantiomers of clenbuterol were baseline separated and relative abundances of corresponding labeled and unlabeled stereoisomers were determined, demonstrating that the therapeutic use of clenbuterol results in racemic mixtures in urine for at least 24 h while adverse analytical findings presumably originating from food contaminations can yield (-)-clenbuterol-depleted pairs of analytes.

CONCLUSIONS

The determination of relative abundances of clenbuterol enantiomers can indicate the ingestion of clenbuterol via contaminated food; however, depletion of (-)-clenbuterol in edible animal tissue is time-dependent and thus results can still be inconclusive as to the inadvertent ingestion of clenbuterol when clenbuterol administration to animals was conducted until slaughter.

Authors+Show Affiliations

Center for Preventive Doping Research - Institute of Biochemistry, German Sport University Cologne, Cologne, Germany. m.thevis@biochem.dshs-koeln.deNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

23322656

Citation

Thevis, Mario, et al. "Does the Analysis of the Enantiomeric Composition of Clenbuterol in Human Urine Enable the Differentiation of Illicit Clenbuterol Administration From Food Contamination in Sports Drug Testing?" Rapid Communications in Mass Spectrometry : RCM, vol. 27, no. 4, 2013, pp. 507-12.
Thevis M, Thomas A, Beuck S, et al. Does the analysis of the enantiomeric composition of clenbuterol in human urine enable the differentiation of illicit clenbuterol administration from food contamination in sports drug testing? Rapid Commun Mass Spectrom. 2013;27(4):507-12.
Thevis, M., Thomas, A., Beuck, S., Butch, A., Dvorak, J., & Schänzer, W. (2013). Does the analysis of the enantiomeric composition of clenbuterol in human urine enable the differentiation of illicit clenbuterol administration from food contamination in sports drug testing? Rapid Communications in Mass Spectrometry : RCM, 27(4), 507-12. https://doi.org/10.1002/rcm.6485
Thevis M, et al. Does the Analysis of the Enantiomeric Composition of Clenbuterol in Human Urine Enable the Differentiation of Illicit Clenbuterol Administration From Food Contamination in Sports Drug Testing. Rapid Commun Mass Spectrom. 2013 Feb 28;27(4):507-12. PubMed PMID: 23322656.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Does the analysis of the enantiomeric composition of clenbuterol in human urine enable the differentiation of illicit clenbuterol administration from food contamination in sports drug testing? AU - Thevis,Mario, AU - Thomas,Andreas, AU - Beuck,Simon, AU - Butch,Anthony, AU - Dvorak,Jiri, AU - Schänzer,Wilhelm, PY - 2012/11/09/received PY - 2012/11/30/revised PY - 2012/12/04/accepted PY - 2013/1/17/entrez PY - 2013/1/17/pubmed PY - 2013/6/20/medline SP - 507 EP - 12 JF - Rapid communications in mass spectrometry : RCM JO - Rapid Commun. Mass Spectrom. VL - 27 IS - 4 N2 - RATIONALE: Clenbuterol (4-amino-α-[(tert-butylamino)methyl]-3,5-dichlorobenzyl alcohol) is approved for human and veterinary use primarily for the treatment of pulmonary afflictions. Despite the authorized administration in cases of medical indications, the misuse of clenbuterol in animal husbandry as well as elite and amateur sport has frequently been reported, arguably due to growth-promoting properties. Due to various recent incidences of doping control specimens containing clenbuterol, strategies towards the discrimination of a surreptitious application from unintended intake via animal-derived edibles or dietary supplements were required. METHODS: The enantiomeric compositions of clenbuterol in human urine samples derived from administration studies with therapeutic amounts of the β(2)-agonist and authentic doping control specimens were determined. Due to the facts that therapeutic clenbuterol consists of a racemic mixture of (+)- and (-)-stereoisomers and that the first mentioned (dextrorotatory) stereoisomer is retained to a greater extent in edible animal tissue, the differentiation of a recent administration of therapeutic (and thus racemic) clenbuterol from food contamination (stereoisomerically depleted clenbuterol) was considered. Employing deuterated clenbuterol as internal standard, the target analytes were extracted from human urine by means of concerted liquid-liquid and solid-phase extractions and subjected to chiral liquid chromatography hyphenated to high resolution/high accuracy mass spectrometry with electrospray ionization. RESULTS: Both enantiomers of clenbuterol were baseline separated and relative abundances of corresponding labeled and unlabeled stereoisomers were determined, demonstrating that the therapeutic use of clenbuterol results in racemic mixtures in urine for at least 24 h while adverse analytical findings presumably originating from food contaminations can yield (-)-clenbuterol-depleted pairs of analytes. CONCLUSIONS: The determination of relative abundances of clenbuterol enantiomers can indicate the ingestion of clenbuterol via contaminated food; however, depletion of (-)-clenbuterol in edible animal tissue is time-dependent and thus results can still be inconclusive as to the inadvertent ingestion of clenbuterol when clenbuterol administration to animals was conducted until slaughter. SN - 1097-0231 UR - https://www.unboundmedicine.com/medline/citation/23322656/Does_the_analysis_of_the_enantiomeric_composition_of_clenbuterol_in_human_urine_enable_the_differentiation_of_illicit_clenbuterol_administration_from_food_contamination_in_sports_drug_testing L2 - https://doi.org/10.1002/rcm.6485 DB - PRIME DP - Unbound Medicine ER -