Clandestine chemists at it again
Drug testers could be one step ahead of the latest attempt to add to the list of unsporting performance-enhancing drugs. The news follows the discovery of a second 'designer steroid' - a drug designed to enhance sporting performance but breeze through a drug test undetected.
The first designer steroid, tetrahydrogestrinone (THG) (see Chemistry World, October 2004, p54), was discovered in 2003 after an anonymous tip-off. The latest drug to enter the athletic underworld is desoxy-methyl-testosterone (DMT).
This was a professional job. 'The chemistry that is needed [for DMT synthesis] is far more complex than for THG,' says Olivier Rabin, director of science for the World Anti-Doping Authority (WADA). 'I cannot do this in my kitchen, even with the proper recipe.'
Last year, customs officials seized a suspicious shipment of bottles at the US/Canadian border. An anonymous e-mail sent to the WADA headquarters in Montreal, Canada, subsequently drew the drug testers into the picture. Since then, WADA scientists have been working hard to identify what was in the bottles. The transparent liquid was far from pure, says Rabin. 'There are a lot of chemical residues that can give you some hints about the chemical pathways that have been used to synthesise this product.'
Christiane Ayotte, head of the WADA laboratory in Montreal, pored over these residues to decipher what the illicit chemists had been up to. 'We were very impressed at the level of sophistication of the chemical reaction that was used to produce this substance,' she says.
It seems, however, that there was a flaw in their design. GC-MS highlights a particularly prominent peak characteristic of a methyl group at the 17-alpha position, says Rabin.
Conveniently, this feature of the DMT molecule is unlikely to be altered by the body's metabolism and would probably have been picked up by the existing drug-testing regime, he says.
The methyltestosterone signature has been used to test for signs of DMT in stored urine samples from several sports. So far, none has turned up positive, suggesting that this new steroid may not be in widespread use, says Rabin. 'This puts us ahead of the dopers.'
The structure of DMT will be published shortly and in vivo models are being established to work out how it is metabolised by the body and what effect it might have on performance.