title: Detection and metabolic investigations of a novel designer steroid: 3-chloro-17α-methyl-5α-androstan-17β-ol.
abstract: In 2012, seized capsules containing white powder were analyzed to show the presence of unknown steroid-related compounds. Subsequent gas chromatography-mass spectrometry (GC-MS) and nuclear magnetic resonance (NMR) investigations identified a mixture of 3α- and 3β- isomers of the novel compound; 3-chloro-17α-methyl-5α-androstan-17β-ol. Synthesis of authentic reference materials followed by comparison of NMR, GC-MS and gas chromatography-tandem mass spectrometry (GC-MS/MS) data confirmed the finding of a new 'designer' steroid. Furthermore, in vitro androgen bioassays showed potent activity highlighting the potential for doping using this steroid. Due to the potential toxicity of the halogenated steroid, in vitro metabolic investigations of 3α-chloro-17α-methyl-5α-androstan-17β-ol using equine and human S9 liver fractions were performed. For equine, GC-MS/MS analysis identified the diagnostic 3α-chloro-17α-methyl-5α-androstane-16α,17β-diol metabolite. For human, the 17α-methyl-5α-androstane-3α,17β-diol metabolite was found. Results from these studies were used to verify the ability of GC-MS/MS precursor-ion scanning techniques to support untargeted detection strategies for designer steroids in anti-doping analyses. Copyright © 2015 John Wiley & Sons, Ltd.
authors.affiliation: Australian Racing Forensic Laboratory, Racing NSW, Randwick, NSW, Australia.
authors.forename: Adam T
authors.initials: AT
authors.lastname: Cawley
authors.affiliation: Forensic and Scientific Services, Health Support Queensland, Department of Health, Queensland Government, Archerfield, QLD, Australia.
authors.forename: Karen
authors.initials: K
authors.lastname: Blakey
authors.affiliation: Research School of Chemistry, Australian National University, Canberra, ACT, Australia.
authors.forename: Christopher C
authors.initials: CC
authors.lastname: Waller
authors.affiliation: Research School of Chemistry, Australian National University, Canberra, ACT, Australia.
authors.forename: Malcolm D
authors.initials: MD
authors.lastname: McLeod
authors.affiliation: Magnetic Resonance Facility, School of Natural Sciences, Griffith University, Nathan, QLD, Australia.
authors.forename: Sue
authors.initials: S
authors.lastname: Boyd
authors.affiliation: Faculty of Science, University of Technology, Sydney, NSW, Australia.|Currently with the Department of Physiology, University of Otago, Dunedin, New Zealand.
authors.forename: Alison
authors.initials: A
authors.lastname: Heather
authors.affiliation: Faculty of Science, University of Technology, Sydney, NSW, Australia.
authors.forename: Kristine C
authors.initials: KC
authors.lastname: McGrath
authors.affiliation: ANZAC Research Institute, University of Sydney, Concord, NSW, Australia.
authors.forename: David J
authors.initials: DJ
authors.lastname: Handelsman
authors.affiliation: Research School of Chemistry, Australian National University, Canberra, ACT, Australia.
authors.forename: Anthony C
authors.initials: AC
authors.lastname: Willis
mesh_terms: D000728:Androgens / Q000032:analysis / Q000378:metabolism* / Q000652:urine*; D000732:Androstanols / Q000032:analysis / Q000378:metabolism* / Q000652:urine*; D000818:Animals; D002460:Cell Line; D015198:Designer Drugs / Q000032:analysis / Q000378:metabolism* / Q000493:pharmacokinetics*; D008401:Gas Chromatography-Mass Spectrometry; D006736:Horses; D006801:Humans; D008099:Liver / Q000187:drug effects / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D013256:Steroids
chemical_list: C000615633:3-chloro-17alpha-methyl-5alpha-androstan-17beta-ol; D000728:Androgens; D000732:Androstanols; D015198:Designer Drugs; D013256:Steroids
keywords: androgen bioassay; anti-doping; designer steroids; gas chromatography-tandem mass spectrometry; steroid metabolism