Understanding Turinabol from a Scientific Perspective
Oral Turinabol has the scientific name of Chlorodehydromethyltestosterone, also referred to as Dehydrochlormethyltestosterone or DHCMT. Broadly, all anabolic steroids can be classified into two categories: endogenous steroids and exogenous steroids. Endogenous steroids are ones naturally produced by the human body such as testosterone and dihydrotestosterone. Exogenous steroids are altered versions of endogenous steroids designed by pharmaceutical companies in an attempt to create steroids with more desirable properties including oral bio-availability, increased anabolic effects and lowered androgenic or masculinizing side effects (Hoffman et al, 2009).
Structurally, Turinabol is a cross between two anabolic steroids: Dianabol and Clostebol. Turinabol has the same base structure as Dianabol, but also contains the added chlorine atom at the fourth carbon, which is the unique feature of Clostebol.
Overall, these structural alterations make Turinabol a milder cousin of Dianabol, as it exerts no estrogenic side effects (such as gynecomastia) and, in general, is less androgenic (or masculinising) (Llewellyn, 2011).
Where did Turinabol come from?
Chlorodehydromethyltestosterone was first described in 1962 (Doerner and Schubert, 1962). Soon after this point, the East German pharmaceutical company Jenapharm released the drug for prescription sale and medical usage, under the brand name Oral-Turinabol (Llewellyn, 2011).
Oral-Turinabol was subsequently exploited by East Germany in a state-sponsored doping programme designed to accelerate athletic performance at the Olympic Stage (Ungerleider, 2001).
The East German State-Sponsored Doping Program
The atrocity of the East German state-sponsored doping program was only fully unrelieved after athletes medical reports were released in the early 1990’s. At the height of the program, over 1,500 doctors and scientists were employed, and perhaps as many as 10,000 athletes were affected. The vast majority of athletes were unaware of the oral anabolic steroids they were taking because they were described as “vitamin pills that would compensate for their lack of nutrition” (Costello, 2013 ). Doping was carried out on male and female athletes, some of which were as young as 10 years old, and particularly for female athletes, resulted in permanent masculinization of body parts (Ungerleider, 2001).
Over 1,000 sportsmen and women are thought to have experienced serious long-lasting physiological and psychological damage from the doping programme and a compensation fund of £2.5 million was set up by the German Government to compensate these athletes for the horrors they were unknowingly subjected to (Costello, 2013 ).
Due to all of the negative press of the use of Oral-Turinabol by the East German state-sponsored doping program, the original manufacturer of Oral-Turinabol (Jenapharm) discontinued the drug.
Since this point, Chlorodehydromethyltestosterone has not existed as a prescription drug product. However, this anabolic is still available and is produced by a small number of underground manufacturers (Llewellyn, 2011).
How do we test for Turinabol?
Long Term Metabolites & The Russian Doping Scandal
Turinabol is detected by identifying distinct metabolites in the urine of the athlete.
In general, this is the case for most oral-exogenous steroids. When oral-exogenous steroids enter the body, they are heavily metabolized by the gastrointestinal tract and liver resulting in the creation of structurally distinct metabolites, excreted into the urine (Kicman, 2008). Anti-doping tests are intended to identify these unique metabolites in the urine of the athlete, using techniques such as gas chromatography-mass spectrometry (GC-MS). These metabolites will be excreted by the body for a period of time, after which Oral-Turinabol itself can no longer be detected in the urine (Kicman, 2008).
The initial tests could only identify Oral-Turinabol based metabolites that would be excreted for a few days in the urine.
However, as research expanded on the drug and additional metabolites were discovered, the window for detection for these newer metabolites was extended to around 20 days (Catlin, 2016).
In the last several years, a new long-term metabolite, referred to as the M4 metabolite, was identified that increases the window of detection to at least 40-50 days. The chemistry of Oral-Turinabol, however, appears to be such that after 20 days only the long-term metabolite would be detectable, while the parent and other identifying metabolites would no longer be detectable.
While not many drugs in the WADA system rely on the presence of a single metabolite to demonstrate the presence of a drug, doing so is certainly acceptable (Catlin, 2016).
Interestingly it was Grigory Rodchenkov, who was heavily involved in the recent Russian Doping scandal, that first described the new long-term metabolite test (Rodchenkov & Sobolevsky , 2012). At the time of his publication in the Journal of Steroid Biochemistry and Molecular Biology, Rodchenkov was the Director of the Anti-Doping Laboratory in Moscow. However, it would later be revealed that for 2011 through 2015 he was involved in the Russian state-sponsored doping program, in which over 1,000 Russian Olympic athletes are implicated in having benefited from manipulations to conceal positive doping tests (McLaren, 2016).
Rodchenkov was recently featured in the drug-scandal film Icarus and is currently living in America under the witness protection programme, although a warrant has recently been released for his arrest in Russia (Sky Sports, 2017).
Discovering the Duchess
Dr Rodchenkov’s breakthrough in 2012 in the discovery of the long-term metabolite of Turinabol was heralded as a significant contribution to Anti-Doping research recognized by the heads of other WADA accredited laboratories (McLaren, 2016). However, the independent investigation into the Russian doping scandal later revealed the following:
“He was working at cross-purposes. While appearing to be at the forefront of the development of doping detection science he was secretly developing a cocktail of drugs with a very short detection window, colloquially known as the “Duchess,” to assist athletes to dope and evade doping control processes. In other words, he was simultaneously improving the doping control system while using that knowledge to undermine its efficacy and integrity”. (McLaren, 2016).
The “Duchess” cocktail Rodchenkov had developed was precise.
To speed up the absorption of steroids and shorten the detection window, he dissolved the drugs in alcohol — Chivas whiskey for men, Martini vermouth for women (Schwirtz & Ruiz, 2016). Dr Rodchenkov’s formula was precise: one milligram of the steroid mixture for every millilitre of alcohol. The athletes were instructed to swish the liquid around in their mouths, under the tongue, to absorb the drug sublingually. (Schwirtz & Ruiz, 2016).
Sublingual administration of steroids means they can diffuse straight into venous circulation and therefore bypass the degradation they would usually be subjected to if they were swallowed and passed through the gastrointestinal tract and the liver. This means many of the signature longer-term metabolites that are created after metabolization of these steroids by the gastrointestinal tract and liver are no longer present in the urine.
Rodchenkov’s discovery of a long-term metabolite of Turinabol resulted in the composition of the steroids used for the “Duchess” cocktail changing in composition. Turinabol was substituted for trenbolone, enabling Russian athletes to continue taking this cocktail of steroids (trenbolone, oxandrolone and methenalone) but still test negative (McLaren, 2016).
The recent increase in the number of positive tests for Turinabol
Rodchenkov’s new test for the long-term metabolite for Turinabol has resulted in many retrospective positive test results from the 2008 and 2012 Olympics. For both these events, frozen urine samples were defrosted and reanalyzed with this new technique. In total, 99 athletes gave retrospective positive results, with a total of 136 positive results for banned substances. Of these 136 positive results, 64 came from Turinabol (Roger Pielke, 2016). In addition, 11 weightlifters tested positive at the 2015 IWF World Weightlifting Championships for Turinabol, and it was the most commonly detected anabolic steroid (Hammer, 2015).
Baseball has also seen an increase in the number of positive drug tests. According to the Anti-Doping Database, Turinabol was reported five times in 2012, 72 times in 2013, then dropped to 17 in 2014 and to 14 in 2015. Prior to 2012, it was only reported one or two times a year (BSCG, 2016).
In March 2017, UFC Athlete Frank Mir tested positive for the long-term metabolite for Turinabol, and received a two year suspension (USADA, 2017). In June 2017, Jon Jones tested positive for the same metabolite after his weigh in for UFC 214, where he beat Daniel Cormier for the Light Heavyweight title (Brown, 2017).
So why have so many athletes been recently caught taking Turinabol?
There are three possible hypotheses.
Turinabol Taking Over: The Three Hypotheses
First, the athletes took the drug itself, and with the improved testing, they have tested positive.
The second hypothesis is the athletes took a dietary supplement that was contaminated with Turinabol (perhaps without their knowing), and the third being a designer steroid present in a supplement could convert or metabolize into Turinabol. (BSCG, 2016).
All three of these hypotheses are confounded by the improvements in detection capabilities, which could be resulting in the recent spike of positives. An off-season Turinabol doping regimen that would previously be expected to clear the body quickly based on experience may not be useable anymore with the improved detection capabilities. Given that many of the positives from baseball came from preseason or early season testing, this hypothesis seems plausible for this sport (BSCG, 2016).
The risk for contamination with Turinabol inside a supplement is very real. The United States Anti-Doping Agency (USADA) keeps an up-to-date record of so-called “High Risk” supplements available for purchase online. You can create an account and search this list for yourself at www.supplement411.org.
Seven different supplements, all sold from different companies, are known to contain Turinabol or its metabolites, after they have been batch tested by USADA. Some of these supplements intentionally state they contain Turinabol, whereas others don’t.
Since Turinabol and DHCMT derivates are prevalent online, it is clear that oral-Turinabol remains available, likely through raw material providers in China or elsewhere. Unfortunately, many of these raw material providers also offer legitimate and legal supplement ingredients to the supplement marketplace, leaving open the real possibility for inadvertent contamination of benign products. (Catlin, 2016).
In this regard, athletes should resort to taking supplements certified to be free of banned substances by an independent third party. Examples of companies that do this third-party testing are BSCG Certified Drug Free, Aegis Certified, Cologne List, Informed Sport and NSF Certified for Sport.
As USADA states, “ No resource can protect you completely. The reality is the use of dietary supplements can be risky, and that awareness, caution, education, and common sense must be exercised when considering their use.” (USADA, 2017).
The prevalence of Turinabol and its derivates in the supplement industry is alarming and does lead to the possibility of contaminated supplements causing a positive test. The problem here lies in that we can’t determine if the metabolite came from actual Turinabol or a contaminated supplement. The detected long-term metabolite is the same in both scenarios, which means we are left with the athletes reasoning for the positive result.
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About the author
Alex Kolliari-Turner has a Biological Sciences degree from the University of Oxford and is a self-funded PhD student conducting research into developing new tests for Anabolic steroids, based out of the University of Brighton, England. He runs the @antidopingscience Instagram page, and hosts the Anti-Doping Science Podcast.
Brown, 2017 . Independant. [Online]
Available at: http://www.independent.co.uk/sport/general/mma/jon-jnes-fails-drugs-test-usada-daniel-cormier-ufc-214-light-heavyweight-a7907636.html
BSCG, 2016 . BSCG Blog. [Online]
Available at: http://www.espn.com/espn/otl/story/_/id/15458724/more-ped-busts-coming-major-league-baseball-soon
Catlin, 2016. The Catlin Perspective. [Online]
Available at: https://thecatlinperspective.wordpress.com/2016/07/31/colabello-oral-turinabol-and-the-mlb-positive-drug-tests/
Costello, 2013 . BBC Sport. [Online]
Available at: http://www.bbc.co.uk/sport/athletics/22269445
Doerner and Schubert, 1962. Proc. Intern. Congr. Hormonal Steroids, Milan , Excerpta Med. Intern. Congr. Ser.. Volume No. 51, 210..
Hammer, A., 2015. Floe Elite. [Online]
Available at: http://www.floelite.com/article/38697-17-new-positive-tests-from-iwf-worlds#.WdiYjGiPJaQ
Hoffman et al, 2009. POSITION STAND ON ANDROGEN AND HUMAN GROWTH HORMONE USE. Journal of Strength and Conditioning Research, p. 23(Supplement 5)/S1–S59.
Kicman, 2008. Pharmacology of anabolic steroids. British Journal of Pharmacology, pp. 154, 502–521.
Llewellyn, 2011. Anabolics. Molecular Nutrition .
McLaren, P. R. H., 2016. THE INDEPENDENT PERSON 2nd REPORT WADA INVESTIGATION OF SOCHI ALLEGATIONS, s.l.: WADA.
Rodchenkov & Sobolevsky , 2012. Detection and mass spectrometric characterization of novel long-term dehydrochloromethyltestosterone metabolites in human urine. The Journal of Steroid Biochemistry and Molecular Biology, 128(3-5), pp. 121-127 .
Roger Pielke, J., 2016. The Least Thing. [Online]
Available at: http://leastthing.blogspot.co.uk/2016/11/a-summary-of-olympic-drug-re-testing-so.html
Schwirtz & Ruiz, 2016. The New York Times. [Online]
Available at: https://www.nytimes.com/2016/05/13/sports/russia-doping-sochi-olympics-2014.html?_r=1
Sky Sports, 2017. Sky Sports. [Online]
Available at: http://www.skysports.com/more-sports/athletics/news/29175/11057195/russia-issues-arrest-warrant-for-whistleblower-grigory-rodchenkov
Ungerleider, S., 2001. Faust Gold: Inside the East German Doping Machine. New York: Thomas Dunne Books.
USADA, 2017 . UFC USADA. [Online]
Available at: https://ufc.usada.org/francisco-mir-receives-doping-sanction/
[Accessed 21 April 2017].
USADA, 2017 . USADA Supplement 411. [Online]
Available at: https://www.usada.org/substances/supplement-411/