DMT (Desoxymethyltestosterone)

New Designer Steroid (correctly) Identified

            In December, 2003, Canadian sprinter Derek Dueck was crossing back into Alberta when Canadian customs officials flagged his vehicle for inspection. Perhaps he was acting suspicious when answering the routine questions, or perhaps his car was just in the wrong spot in line. Whatever the reason, a search quickly yielded two unidentified vials of liquid and 70 vials of human growth hormone. Dueck was held on smuggling charges. One of the vials was later reported to contain THG (tetrahydrogestrinone), the designer steroid at the heart of the BALCO doping scandal. The world would not learn of the exact contents of that second vial for more than a year, however. When they did, they would be introduced to yet another new previously undetectable anabolic steroid. In the process, global media interest in the "dark and shady" underground world of designer steroids was once again invigorated.

            DMT Identified (Sort of)

                The slow public identification of this new steroid was not entirely intentional. Although officials at the Canadian Border Service Agency's lab learned upon early analysis that the vial likely contained a derivative of testosterone, they were unable to say for certain what was in it. The vial would sit on an evidence shelf, unidentified, for approximately seven months. It would take an anonymous e-mail in June, 2004, warning doping officials that the seized product likely contained a new designer anabolic agent, to push the Canadian government to gain the assistance of the World Anti-Doping Agency (WADA). A joint and serious effort was thereafter undertaken to identify the mystery drug. At the direction of Christiane Ayotte, director of the Olympic lab in Montreal, the drug was soon identified and given the name desoxymethyltestosterone (DMT). Ayotte reports of the detailed synthesis of DMT to Chemical and Engineering News on February 11, 2005:

            "Their synthesis starts with epiandrosterone, a natural reduction product of testosterone that is excreted in urine. 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 intermediaries with methyllithium adds methyl group to C-17 and converts the keto group there to a hydroxyl group, resulting in DMT."

            Dangerous and Ineffective?

            In addition to giving this drug a label, Ayotte had a number of other things to say about it. To begin with, she claimed DMT was a mixture of poor quality products and that it was contaminated with flammable and toxic chemicals. "There was no purification," reports Ayotte. "Anyone who takes the drug would be extremely stupid." Impurities, at least in regard to steroidal contaminants, do legitimately seem to be an issue with DMT, given that several different steroids (androst-2-ene-17b-ol, androst-3-ene-17b-ol, 17a-methyl-androst-2-ene-17b-ol, and 17a-methyl-androst-3-ene-17b-ol) were isolated in the solution. But honestly, I see nothing unusually dangerous or toxic about these steroids, at least that we know if. That aside, I'm obviously in no position to discuss the safety of other chemical contaminants, having neither the samples to examine, nor the requisite background to judge them. But at least the drugs themselves don't seem immediately "scary." But Ayotte goes a step further, claiming DMT  "... might have the unintended effects of being toxic yet ineffective because of the chemical changes made to the base drug, testosterone." Toxic is one thing, but ineffective? Would someone invest such time and money in a steroid that doesn't work?  

            Androst-2-ene Compounds: Overlooked

            In many regards, Ayotte's public comments about DMT being ineffective underline just how little WADA knows about the drugs it's responsible for policing. Had Ayotte possessed a very thorough background in anabolic steroid chemistry, she would have been able to quickly identify the merit in one of these modifications in particular, the 2-ene products. The papers on these steroids are not all that difficult to find. For example, in 1964, a group of Czech researchers published experiments on a novel 2-ene derivative of testosterone, specifically ansrost-2-ene-17b-ol.[1] They reported that this steroid had a very protracted duration of activity and overall potency compared to its parent steroid. This new 2-ene produced a 50 percent stronger anabolic response than did regular testosterone, while at the same time possessed 55 percent less androgenic activity.

Other researchers put the numbers at 160%/60%[2] and 150%/50%.[3] Later, in 1967, one of the same researchers helped publish another paper attributing much of the increased activity and duration of effect of androst-2-ene to a marked resistance to metabolism.[4] The steroid is so potent because, among other things, it sticks around the body for a longer time than does regular testosterone. This modified 2-ene testosterone derivative was shaping up to be a very interesting steroid indeed, far from ineffective, as Ayotte suggested.

            In 1966, experiments were also published on a 17-alpha methylated derivative of androst- 2-ene.[5] They demonstrated even more striking properties inherent in this new orally active anabolic steroid. The methyl-androst-2-ene turned out to be 12 times more anabolic than methyltestosterone, the most common standard of comparison for c-17-alpha alkylated oral steroids at the time. Its androgenic component was less than double that of methyltestosterone, giving this new anabolic an extremely high anabolic to androgenic ratio (more than six to one). That is a tremendous difference, both in potency and overall androgenicity.

To give you a little perspective, methandrostenolone (Dianabol), which is a popular known derivative of methyltestosterone, only tests out to be twice as anabolic as methyltestosterone. Oxandrolone (Anavar), one of the most potent commercial steroids known (on paper), comes in about three to six times more potent than methyltestosterone. When you go down the list, you quickly realize that methyl-androst-2-ene-17b-ol (on paper) is significantly more potent milligram for milligram than any commercially available prescription anabolic steroid. Had Ayotte missed the studies on androst-2-ene compounds completely?  

            DMT: Final Identification

            Due to the impurities in the product, as well as the obvious lack of familiarity with the compounds present, WADA never made a final identification of DMT. They simply dubbed it a mixture of different steroidal components and left it at that. Upon more serious consideration, I do not believe that was the intended case at all. I believe strongly that the maker or makers of DMT were focused on one specific compound all the time, the most potent compound: 17a-methyl-androst-2-ene-17b-ol. This is what I am going to give the name DMT, as it seems most logical.

Our new specific DMT compound is an inordinately powerful anabolic steroid when you compare it to those steroids already commercially available, and is also structurally incapable of converting to estrogen, which is a favorable trait for athletes in speed and endurance sports. Its metabolites are also likely all of the androst-2-ene type, which is unique enough that cross-identification as another known anabolic steroid during a drug screen should be highly unlikely. In the end, I believe an inability to manufacture the drug in its pure form was the reason it was being found in a mixture as it was. The producer probably just didn't feel a need to worry about some contamination by other 2-ene and 3-ene steroids, perhaps knowing they would not show up on a drug screen. So, in the end, we are making a concrete identification of DMT where WADA was unable to do so. How surprising! Maybe I should see if they need some help with their steroid identification (just kidding!). 

STEPHEN: SAME BIO

References

[1] On the protracted action of androst-2-en-17b-ol. Cekan, Vesely et al. Steroids, Jan 1965 113-16.

[2] Kincl, F. A. and Dorfman, R. I. Steroids, 3, 109 (1964)

[3] Bowers, Cross, Edwards et al. J Med Chem, 6 156 (1963)

[4] The causes of the prolonged action of 5a-androst-2-en-17b-ol. Cekan, Bartosek. Steroids, 10:1 75-81

[5] J Med Chem, 9, 685 (1966) R. E. Counsell, G. W. Adelstein, P. D. Klimstra et al.