Oxidation of testosterone by permanganate and its implication in sports drug testing

Kuzhiumparambil, U; Watanabe, S; Fu, S

Oxidation of testosterone by permanganate and its implication in sports drug testing

Kuzhiumparambil, U

Watanabe, S

Fu, S

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Publication Type:: Journal Article
Citation:: New Journal of Chemistry, 2015, 39 (3), pp. 1597 - 1602
Issue Date:: 2015-03-01

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Field	Value	Language
dc.contributor.author	Kuzhiumparambil, U https://orcid.org/0000-0003-0582-6779	en_US
dc.contributor.author	Watanabe, S https://orcid.org/0000-0001-5211-3283	en_US
dc.contributor.author	Fu, S https://orcid.org/0000-0002-6238-3612	en_US
dc.date.issued	2015-03-01	en_US
dc.identifier.citation	New Journal of Chemistry, 2015, 39 (3), pp. 1597 - 1602	en_US
dc.identifier.issn	1144-0546	en_US
dc.identifier.uri	http://hdl.handle.net/10453/36134
dc.identifier.uri	http://hdl.handle.net/10453/36722
dc.description.abstract	© The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015. Manipulations of urine samples by urine substitution, urine dilution, and urine adulteration with highly oxidative chemicals to escape detection in doping control analysis have been reported in the past. Adulteration of urine with oxidising chemicals such as potassium permanganate, cerium ammonium nitrate, pyridinium chlorochromate etc. can lead to considerable changes in the endogenous steroidal profile parameters and thus mask the abnormality in the steroidal profile following steroid abuse. In this study we have identified the formation of two stable oxidation products upon reaction of potassium permanganate with testosterone, an important endogenous urinary steroid. Isolation and characterisation of these oxidation products were performed using chromatography and spectroscopy and the products were elucidated as 4α,5α-dihydroxytestosterone and 4β,5β-dihydroxytestosterone. Formation of these two molecules in human urine after adulteration with potassium permanganate has been demonstrated by liquid chromatography-mass spectrometry (LC-MS) analysis. The products 4α,5α-dihydroxytestosterone and 4β,5β-dihydroxytestosterone have not been previously reported in urine and hence have the potential to be included in the routine drug testing program for monitoring possible testosterone abuse and permanganate adulteration of urine.	en_US
dc.relation.ispartof	New Journal of Chemistry	en_US
dc.relation.isbasedon	10.1039/c4nj01478b	en_US
dc.subject.classification	General Chemistry	en_US
dc.title	Oxidation of testosterone by permanganate and its implication in sports drug testing	en_US
dc.type	Journal Article
utslib.citation.volume	3	en_US
utslib.citation.volume	39	en_US
utslib.for	0305 Organic Chemistry	en_US
utslib.for	0399 Other Chemical Sciences	en_US
utslib.for	03 Chemical Sciences	en_US
pubs.embargo.period	Not known	en_US
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 Mathematical and Physical Sciences
pubs.organisational-group	/University of Technology Sydney/Strength - C3 - Climate Change Cluster
pubs.organisational-group	/University of Technology Sydney/Strength - CCET - Centre for Clean Energy Technology
pubs.organisational-group	/University of Technology Sydney/Strength - CFS - Centre for Forensic Science
pubs.organisational-group	/University of Technology Sydney/Students
utslib.copyright.status	open_access
pubs.issue	3	en_US
pubs.publication-status	Published	en_US
pubs.volume	39	en_US

Abstract:

© The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015. Manipulations of urine samples by urine substitution, urine dilution, and urine adulteration with highly oxidative chemicals to escape detection in doping control analysis have been reported in the past. Adulteration of urine with oxidising chemicals such as potassium permanganate, cerium ammonium nitrate, pyridinium chlorochromate etc. can lead to considerable changes in the endogenous steroidal profile parameters and thus mask the abnormality in the steroidal profile following steroid abuse. In this study we have identified the formation of two stable oxidation products upon reaction of potassium permanganate with testosterone, an important endogenous urinary steroid. Isolation and characterisation of these oxidation products were performed using chromatography and spectroscopy and the products were elucidated as 4α,5α-dihydroxytestosterone and 4β,5β-dihydroxytestosterone. Formation of these two molecules in human urine after adulteration with potassium permanganate has been demonstrated by liquid chromatography-mass spectrometry (LC-MS) analysis. The products 4α,5α-dihydroxytestosterone and 4β,5β-dihydroxytestosterone have not been previously reported in urine and hence have the potential to be included in the routine drug testing program for monitoring possible testosterone abuse and permanganate adulteration of urine.

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http://hdl.handle.net/10453/36134