title: Analysis of non-ketoic steroids 17alpha-methylepithiostanol and desoxymethyl- testosterone in dietary supplements.
abstract: Dietary supplements containing 17alpha-methyl-2,3-epithio-5alpha-androstane-17beta-ol (17alpha-methylepithiostanol), which is a 17-methylated analogue of epithiostanol or a prodrug of desoxymethyltestosterone (17alpha-methyl-5alpha-androst-2-en-17beta-ol), have recently appeared on the Internet. 17alpha-Methylepithiostanol and desoxymethyltestosterone are classified as prohibited substances on the World Anti-Doping Agency (WADA) list. Two preparations, EPISTANE and P-PLEX, were obtained from the Internet so that their contents could be investigated. This study involved gas chromatography/mass spectrometry (GC/MS) analysis after trimethylsilyl (TMS) derivatization, liquid chromatography/mass spectrometry (LC/MS) in atmospheric pressure photoionization (APPI) mode and nuclear magnetic resonance (NMR) spectroscopy. Analysis using LC/MS in APPI mode would be a useful tool for detecting heat-labile and non-polar steroids.Although the labelling of EPISTANE indicates that it contains 17alpha-methyl-2alpha, 3alpha-epithio-5alpha-androstane-17beta-ol only, 17alpha-methyl-2beta,3beta-epithio-5alpha-androstane-17beta-ol and desoxymethyltestosterone were identified in the supplement. The results showed that P-PLEX contained desoxymethyltestosterone and its isomer 17alpha-methyl-5alpha-androst-3-en-17beta-ol. Urine samples can be screened after EPISTANE or P-PLEX administration using the normal screening procedure for anabolic steroids with GC/MS.
authors.affiliation: Anti-Doping Centre, Mitsubishi Chemical Medience Corporation, 3-30-1 Shimura, Itabashi-ku, Tokyo, Japan. Okano.Masato@mk.medience.co.jp
authors.forename: Masato
authors.initials: M
authors.lastname: Okano
authors.forename: Mitsuhiko
authors.initials: M
authors.lastname: Sato
authors.forename: Ayako
authors.initials: A
authors.lastname: Ikekita
authors.forename: Shinji
authors.initials: S
authors.lastname: Kageyama
mesh_terms: D000328:Adult; D000732:Androstanols / Q000032:analysis* / Q000652:urine; D000737:Androstenols / Q000032:analysis* / Q000652:urine; D019587:Dietary Supplements / Q000032:analysis*; D004300:Doping in Sports / Q000379:methods*; D006801:Humans; D008297:Male; D008875:Middle Aged; D013256:Steroids / Q000032:analysis* / Q000652:urine
chemical_list: C550524:17-methylepithiostanol; D000732:Androstanols; D000737:Androstenols; D013256:Steroids; C500374:17-methylandrost-2-en-17-ol