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New analogues of androgens that had never been available as approved drugs are marketed as “dietary supplement” recently. They are mainly advertised to promote muscle mass and are considered by the governmental authorities in various countries, as well as by the World Anti-doping Agency for sport, as being pharmacologically and/or chemically related to anabolic steroids.In the present study, we report...
The detection of misuse with naturally occuring steroids is a great challenge for doping control laboratories. Intake of natural anabolic steroids alters the steroid profile. Thus, screening for exogenous use of these steroids can be established by monitoring a range of endogenous steroids, which constitute the steroid profile, and evaluate their concentrations and ratios against reference ranges...
The product Orastan-A from Gaspari Nutrition was analyzed for its steroid content. According to the labeling, it is supposed to contain “5a-Androstano[2,3-c]furazan-17b-tetrahydropyranol ether”, also called furazadrol-THP ether. The GC–MS analyses of the liberated steroids (after extraction from the capsule matrix and cleavage of the THP ether, TMS-derivative and underivatized) revealed mass spectra...
Trenbolone (17β-hydroxy-estra-4,9,11-trien-3-one) and its derivatives such as 17α-methyltrenbolone represent a class of highly potent anabolic–androgenic steroids, which are prohibited in sports according to the regulation of the World Anti-Doping Agency (WADA). Due to marginal gas chromatographic properties of these compounds but excellent proton affinities resulting from a large and conjugated π-electron...
By means of gas chromatography/combustion/isotope ratio mass spectrometry (GC/C/IRMS) urinary steroids obtained from a reference population of 56 subjects were analyzed for their C13/C12-ratios. The analytes encompassed androsterone (A), etiocholanolone (E), 11β-hydroxyetiocholanolone (OHE), 11β-hydroxyandrosterone (OHA), and 5β-pregnane- 3α,20α-diol (PD). A and E represent androgen metabolites (AM)...
Enzyme-assisted in vitro synthesis of eleven glucuronide-conjugated anabolic androgenic steroid (AAS) metabolites was performed using biphenyl-induced rat liver microsomal enzymes. The substrates within the study were the main compounds and metabolites detected in human urine after dosing of, e.g. metandienone, metenolone, methyltestosterone, nandrolone, and testosterone. Yields of glucuronidation...
In human sports doping control analysis most of the steroids are analyzed after enzymatic hydrolysis of the glucuronides as per-trimethylsilyl (TMS) derivatives applying gas chromatography–mass spectrometry (GC–MS). According to the recommendations of the World Anti-Doping Agency the identification of analytes should be based on retention time and on mass spectrometric characterization. This study...
4-Hydroxyandrost-4-ene-3,17-dione is a second generation, irreversible aromatase inhibitor and commonly used as anti breast cancer medication for postmenopausal women. 4-Hydroxytestosterone is advertised as anabolic steroid and does not have any therapeutic indication. Both substances are prohibited in sports by the World Anti-Doping Agency, and, due to a considerable increase of structurally related...
A facile six-step synthesis of 2,2,3,4,4-d 5 -androsterone-β-d-glucuronide (1) starting from epiandrosterone (2) in 63% yield is described and compared with several alternative synthetic pathways. Compound 1 can be used as an internal standard in screening procedures for anabolic steroids to monitor the hydrolysis step of the steroid glucuronides prior to gas chromatography–mass spectrometry...
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