The DOI matches its Crossref record.
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.
Overview
Integrity signals
Registry
Cites
Statistics
Verification
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
In the citing paper
“with one report finding that synthetic oral anabolic-androgenic steroids have been detected in up to 20% of performance-enhancing drugs sold legally over the counter (35,40,41).”
From Non-testosterone management of male hypogonadism: an examination of the existing literature (2020) · cites this paper as [41]
Citations
Cites
No references could be resolved yet.
Research works printed but not linked: 33
- 10.1016/0003-2670(93)80274-O · DOI
- 10.1093/clinchem/42.7.1001 · DOI
- 10.4155/bio.09.52 · DOI
- 10.4155/bio.10.57 · DOI
- 10.1210/en.2010-1501 · DOI
- 10.1002/rcm.722 · DOI
- 10.1002/rcm.1495 · DOI
- 10.1210/jc.2004-0033 · DOI
- 10.1021/ac050150y · DOI
- 10.1002/rcm.1858 · DOI
- 10.1016/j.jsbmb.2006.06.024 · DOI
- Kwok W.H., 2006, Proceedings of the 16th International Conference of Racing Analysts and Veterinarians, 120
- 10.1111/j.1365-2885.2008.01021.x · DOI
- 10.1007/978-3-540-79088-4_7 · DOI
- 10.1002/dta.250 · DOI
- 10.4155/bio.13.242 · DOI
- 10.1136/bjsports-2014-093526 · DOI
- 10.4155/bio.14.9 · DOI
- 10.1002/dta.273 · DOI
- 10.1016/j.aca.2006.08.025 · DOI
- 10.1248/cpb.11.1409 · DOI
- 10.1016/S0040-4039(01)87077-5 · DOI
- Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 1042047. Copies of the data can be obtained free of charge on application to CCDC 12 Union Road Cambridge CB2 1EZ UK (fax: +44‐(0)1223‐336033 or e‐mail:deposit@ccdc.cam.ac.uk).
- 10.4155/bio.13.40 · DOI
- 10.1021/ac102845y · DOI
- 10.3109/00498258009033771 · DOI
- 10.1021/ac60323a017 · DOI
- 10.1039/AN9941902537 · DOI
- 10.1002/mas.20107 · DOI
- 10.1016/j.jpba.2007.06.020 · DOI
- 10.1002/rcm.3826 · DOI
- deBoer D., 1992, Profiling anabolic androgens and corticosteroids in doping analysis, 38
- 10.1002/dta.88 · DOI
Cited by
Sorted by citations
Non-testosterone management of male hypogonadism: an examination of the existing literature
Krzastek, S. C., & Smith, R. P. (2020) · Translational Andrology and Urology · doi:10.21037/tau.2019.11.16 · Cited by 33
“Numerous other compounds with steroid-like structures are not regulated and have been identified in dietary supplements marketed to “enhance performance,” with one report finding that synthetic oral anabolic-androgenic steroids have been detected in up to 20% of performanceenhancing drugs sold legally over the counter…”
Background
Metadata
- Authors
- Cawley, A. T., Blakey, K., Waller, C. C., McLeod, M. D., Boyd, S., Heather, A., McGrath, K. C., Handelsman, D. J., & Willis, A. C.
- Affiliations
- Australian Racing Forensic Laboratory Racing NSW Randwick NSW Australia
- Queensland Health (AU)
- Australian National University (AU)
- Griffith University (AU)
- University of Technology Sydney (AU)
- The University of Sydney (AU)
- Corresponding author
- Cawley, Adam T.
- ORCID
- Venue
- Drug Testing and Analysis
- Publisher
- Wiley
- Published
- 2015-06-23
- Volume
- 8
- Issue
- 7
- Pages
- 621-632
- ISSN
- 1942-7603 (ISSN-L)
- 1942-7611
- OpenAlex
- W2113467400
- Cited by
- 16
- References
- 0
- Citations by year
- 2024: 1 · 2023: 1 · 2022: 2 · 2021: 2 · 2020: 3 · 2019: 1 · 2018: 1 · 2017: 4 · 2016: 1
- FWCI
- 6.63
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Drug Testing and Analysis (publishedVersion)
- PubMed (publishedVersion)
- ANU Open Research (Australian National University) (submittedVersion)
- Griffith Research Online (submittedVersion)
- Funders
- Australian Research Council (LP120200444)
- Topics
- Social Sciences › Sociology and Political Science › Doping in Sports
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Toxicology › Forensic Toxicology and Drug Analysis
- Life Sciences › Agricultural and Biological Sciences › Animal Science and Zoology › Pharmacological Effects and Assays
- Keywords
- designer steroids, halogenated steroids, androgenic activity, doping, steroid metabolism, precursor ion scanning
- MeSH terms
- Androgens, Androstanols, Animals, Cell Line, Horses, Humans, Liver, Gas Chromatography-Mass Spectrometry, Magnetic Resonance Spectroscopy, Steroids, Designer Drugs
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
