Detection and metabolic investigations of a novel designer steroid: 3-chloro-17α-methyl-5α-androstan-17β-ol

Cawley, AT; Blakey, K; Waller, CC; Mcleod, MD; Boyd, S; Heather, A; Mcgrath, KC; Handelsman, DJ; Willis, AC

Detection and metabolic investigations of a novel designer steroid: 3-chloro-17α-methyl-5α-androstan-17β-ol

Cawley, AT Blakey, K Waller, CC Mcleod, MD Boyd, S Heather, A Mcgrath, KC Handelsman, DJ Willis, AC

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Publisher:: WILEY-BLACKWELL
Publication Type:: Journal Article
Citation:: Drug Testing and Analysis, 2016, 8, (7), pp. 621-632
Issue Date:: 2016-07-01

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Field	Value	Language
dc.contributor.author	Cawley, AT
dc.contributor.author	Blakey, K
dc.contributor.author	Waller, CC
dc.contributor.author	Mcleod, MD
dc.contributor.author	Boyd, S
dc.contributor.author	Heather, A
dc.contributor.author	Mcgrath, KC
dc.contributor.author	Handelsman, DJ
dc.contributor.author	Willis, AC
dc.date.accessioned	2022-03-24T03:14:52Z
dc.date.available	2015-05-28
dc.date.available	2022-03-24T03:14:52Z
dc.date.issued	2016-07-01
dc.identifier.citation	Drug Testing and Analysis, 2016, 8, (7), pp. 621-632
dc.identifier.issn	1942-7603
dc.identifier.issn	1942-7611
dc.identifier.uri	http://hdl.handle.net/10453/155499
dc.description.abstract	© 2015 John Wiley & Sons, Ltd. 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.
dc.format	Print-Electronic
dc.language	eng
dc.publisher	WILEY-BLACKWELL
dc.relation.ispartof	Drug Testing and Analysis
dc.relation.isbasedon	10.1002/dta.1832
dc.rights	info:eu-repo/semantics/closedAccess
dc.subject	0301 Analytical Chemistry, 0601 Biochemistry and Cell Biology, 1115 Pharmacology and Pharmaceutical Sciences
dc.subject.classification	Analytical Chemistry
dc.subject.mesh	Androgens
dc.subject.mesh	Androstanols
dc.subject.mesh	Animals
dc.subject.mesh	Cell Line
dc.subject.mesh	Designer Drugs
dc.subject.mesh	Gas Chromatography-Mass Spectrometry
dc.subject.mesh	Horses
dc.subject.mesh	Humans
dc.subject.mesh	Liver
dc.subject.mesh	Magnetic Resonance Spectroscopy
dc.subject.mesh	Steroids
dc.subject.mesh	Liver
dc.subject.mesh	Cell Line
dc.subject.mesh	Animals
dc.subject.mesh	Horses
dc.subject.mesh	Humans
dc.subject.mesh	Steroids
dc.subject.mesh	Androstanols
dc.subject.mesh	Designer Drugs
dc.subject.mesh	Androgens
dc.subject.mesh	Magnetic Resonance Spectroscopy
dc.subject.mesh	Gas Chromatography-Mass Spectrometry
dc.title	Detection and metabolic investigations of a novel designer steroid: 3-chloro-17α-methyl-5α-androstan-17β-ol
dc.type	Journal Article
utslib.citation.volume	8
utslib.location.activity	England
utslib.for	1115 Pharmacology and Pharmaceutical Sciences
utslib.for	0601 Biochemistry and Cell Biology
utslib.for	0301 Analytical Chemistry
utslib.for	0601 Biochemistry and Cell Biology
utslib.for	1115 Pharmacology and Pharmaceutical Sciences
pubs.organisational-group	/University of Technology Sydney
pubs.organisational-group	/University of Technology Sydney/Faculty of Science
pubs.organisational-group	/University of Technology Sydney/Faculty of Science/School of Medical and Molecular Sciences
pubs.organisational-group	/University of Technology Sydney/Strength - CHT - Health Technologies
pubs.organisational-group	/University of Technology Sydney/Faculty of Science/School of Life Sciences
pubs.organisational-group	/University of Technology Sydney/Centre for Health Technologies (CHT)
utslib.copyright.status	closed_access	*
pubs.consider-herdc	false
dc.date.updated	2022-03-24T03:14:50Z
pubs.issue	7
pubs.publication-status	Accepted
pubs.volume	8
utslib.citation.issue	7

Abstract:

© 2015 John Wiley & Sons, Ltd. 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.

Please use this identifier to cite or link to this item:

http://hdl.handle.net/10453/155499