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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.
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“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]
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Cited by
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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
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- CoChat. (2026). Citation check: Detection and metabolic investigations of a novel designer steroid: 3‐chloro‐17α‐methyl‐5α‐androstan‐17β‐ol. https://app.cochat.ai/papers/10.1002/dta.1832
- The paper
- Cawley, A. T., Blakey, K., Waller, C. C., McLeod, M. D., Boyd, S., Heather, A., McGrath, K. C., Handelsman, D. J., & Willis, A. C. (2016). Detection and metabolic investigations of a novel designer steroid: 3‐chloro‐17α‐methyl‐5α‐androstan‐17β‐ol. Drug Testing and Analysis. https://doi.org/10.1002/dta.1832
