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Second 'Designer' Steroid Uncovered
Chemists identify compound and propose possible synthesis
Chemical & Engineering News
STEVE RITTER
February 11, 2005
Canadian scientists have identified a new “designer” steroid
purportedly synthesized to avoid detection in standard drug
tests, but there’s no evidence so far that athletes have used
it.
The World Anti-Doping Agency (WADA), based in Montreal,
announced the discovery of desoxymethyltestosterone (DMT)
during a conference call with reporters on Feb. 1. According
to WADA and press reports, the steroid was among drugs
confiscated by Canadian customs agents at a U.S.-Canadian
border crossing in December 2003. Last June, WADA officials
received an anonymous e-mail tip that the steroid was part of
the seizure. WADA then worked with customs officials to obtain
samples, which were tested at the Doping Control Laboratory at
the University of Quebec, in Montreal.
DMT is the second designer steroid to be discovered. The first
was tetrahydrogestrinone (THG), which was identified in 2003
by chemists at the Olympic Analytical Laboratory at the
University of California, Los Angeles (C&EN, Nov. 17, 2003,
page 66).
The Montreal lab, directed by Christiane Ayotte, has
collaborated with medicinal chemist Donald Poirier and his
group at the University of Laval, in Sainte-Foy, Quebec, to
further study DMT and to work out a possible synthesis.
Their synthesis starts with epiandrosterone, a natural
reduction product of testosterone that is excreted in urine,
Ayotte tells C&EN. They react epiandrosterone with
p-toluenesulfonyl chloride and trimethylpyridine to remove the
hydroxyl group at C-3 of the steroid ring system. A pair of
olefin isomers form, the 3-ene and 2-ene. Reaction of these
intermediates with methyllithium adds a methyl group to C-17
and converts the keto group there to a hydroxyl group,
resulting in DMT. Ayotte believes this is the likely approach
used by the chemist who originally made the steroid because
her team detected the two intermediate isomers as impurities
in the seized material.
The Montreal lab is conducting liver cell culture studies on
DMT to identify metabolites and plans a research paper to
report the physiological properties of the steroid, Ayotte
says.
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[Definitie:] "An ergogenic aid is any substance or phenomenon that enhances performance."
(Wilmore and Costill) 
