Methandienone or Turinabol: What's the Difference

Methandienone and turinabol are chemical «brothers»: turinabol is the same methandienone molecule with one chlorine atom added. However, this small change dramatically affects how the substance behaves in the body. The editorial team has broken down exactly what chlorination changes, where both compounds came from and what the differences in their risks are.

One atom of difference

Methandienone (methandrostenolone) is testosterone with two modifications: a double bond between the first and second carbon atoms in ring A and a methyl group at position 17α. The first change enhances the anabolic properties and slows some metabolic pathways, the second makes it possible to take the drug orally by protecting the molecule from rapid breakdown in the liver.

Turinabol, whose chemical name is 4-chlorodehydromethyltestosterone, has the same basis as methandienone but with a chlorine atom at the fourth position. This atom is located precisely in the part of the molecule with which the enzyme aromatase interacts, and effectively blocks the conversion of the steroid into estrogen.

The chlorine also changes the affinity for the androgen receptor and the interaction with metabolic enzymes. As a result, turinabol is considered a weaker androgen than methandienone, and its action is described as «without water» — that is, without estrogenic fluid retention.

Both substances are 17α-alkylated. Thus, the chlorine does not affect the main flaw of this class — hepatotoxicity. Both load the liver and worsen the lipid profile.

The history of two drugs

Methandienone was synthesized in the late 1950s, and the Swiss company Ciba released it under the name Dianabol. The American physician John Ziegler, who worked with the US weightlifting team, contributed to the spread of the drug among athletes, seeking to catch up with Soviet athletes. Later he himself expressed regret over the consequences of this decision.

The medical indications of methandienone were never broad, and in the USA the drug went out of circulation in the 1980s. However, in the sports community it became one of the most famous steroids in the world, and its production shifted mainly into the illegal sphere.

Turinabol appeared in the 1960s in the GDR thanks to the pharmaceutical enterprise Jenapharm. Created as a modification of methandienone with a «milder» profile, it became the basis of the state doping program, which after the archives were opened was described in detail by Franke and Berendonk (1997).

Thus, both substances have a «sports» rather than a clinical history. For neither of them are there modern randomized safety studies in humans that would meet current standards.

Aromatization and estrogenic effects

The most important practical difference between the substances lies in estrogenic activity. Methandienone is a substrate of aromatase and is converted into 17α-methylestradiol. Because of the 17α-methyl group, this estrogen is inactivated more slowly in the liver and has a pronounced estrogenic action.

The consequences of methandienone's estrogenic activity are fluid retention, edema, increased blood pressure and the risk of gynecomastia in men. Gynecomastia that has developed can be irreversible and in some cases requires surgical treatment.

Turinabol, because of the chlorine atom at the fourth position, practically does not aromatize. Therefore estrogenic fluid retention and estrogen-mediated gynecomastia are not characteristic of it. However, this does not mean the absence of hormonal side effects in general.

This difference explains why in sports culture methandienone is associated with rapid weight gain (largely due to fluid), and turinabol — with a slower but «drier» gain.

Androgenicity, liver, heart

Methandienone is a more pronounced androgen than turinabol. This manifests as acne, increased skin oiliness, acceleration of androgenic hair loss in predisposed people, and in women — rapid development of virilization. Turinabol is less androgenic, but, as the GDR experience shows, in women it also caused virilization, including irreversible.

With regard to the liver, both substances behave similarly. 17α-alkylation leads to the risk of cholestasis, elevation of liver enzymes, and with prolonged use — hepatic peliosis and tumors. The review by Solimini et al. (2017) describes cases of hepatotoxicity associated with steroids of this class.

On the cardiovascular side, methandienone has an additional «estrogenic» contribution: fluid retention enhances the rise in blood pressure. At the same time, both substances reduce HDL, and prolonged use of anabolic steroids is generally associated with myocardial hypertrophy and atherosclerosis (Baggish et al., 2017).

• Common: hepatotoxicity, dyslipidemia, suppression of the hormonal axis, infertility.
• More for methandienone: edema, gynecomastia, increased blood pressure, androgenic effects.
• More for turinabol: risks associated with the unknown composition of illegal products (the drug is not produced by pharmaceutical companies).

Psychological effects — irritability, mood swings, depression after withdrawal — are described for the class of anabolic steroids in general and apply to both substances.

Metabolism and detection

The metabolism of methandienone was studied in detail by Wilhelm Schänzer. His review (Schänzer, 1996) describes the main metabolites of anabolic steroids, and the group's later work (Schänzer et al., 2006) reported a new long-lived metabolite of methandienone, which significantly extended the window of its detection.

For turinabol, a similar breakthrough occurred in 2012, when Sobolevsky and Rodchenkov described new long-term metabolites. The reanalysis of samples from the 2008 and 2012 Olympic Games revealed a large number of positive results specifically for turinabol.

The chlorine in the turinabol molecule also affects metabolism: chlorinated metabolites have a characteristic «signature» in mass spectrometry, which facilitates their identification in the laboratory.

Both substances are included in class S1 of the WADA Prohibited List. The storage of samples for many years means that an athlete may receive sanctions much later than the date the sample was submitted.

Editorial conclusions

Turinabol is methandienone with a chlorine atom at position 4. This modification blocks aromatization and weakens the androgenic action, so turinabol does not cause the estrogenic fluid retention characteristic of methandienone.

At the same time, the chlorine does not eliminate the main risks: both substances are 17α-alkylated, load the liver, worsen the lipid profile and suppress the hormonal axis. The «mildness» of turinabol applies only to part of the side effects.

Both substances have a predominantly sports rather than medical history, and both are reliably detected by modern anti-doping methods.

We also recommend reading our materials «Methandienone vs Turinabol: what to choose and for whom», on gynecomastia in athletes and on the work of aromatase.

References

1. Kicman AT. Pharmacology of anabolic steroids. Br J Pharmacol. 2008;154(3):502–521.
2. Schänzer W. Metabolism of anabolic androgenic steroids. Clin Chem. 1996;42(7):1001–1020.
3. Schänzer W, Geyer H, Fusshöller G, et al. Mass spectrometric identification and characterization of a new long-term metabolite of metandienone in human urine. Rapid Commun Mass Spectrom. 2006;20(15):2252–2258.
4. Sobolevsky T, Rodchenkov G. Detection and mass spectrometric characterization of novel long-term dehydrochloromethyltestosterone metabolites in human urine. J Steroid Biochem Mol Biol. 2012;128(3–5):121–127.
5. Franke WW, Berendonk B. Hormonal doping and androgenization of athletes: a secret program of the German Democratic Republic government. Clin Chem. 1997;43(7):1262–1279.
6. Solimini R, Rotolo MC, Mastrobattista L, et al. Hepatotoxicity associated with illicit use of anabolic androgenic steroids in doping. Eur Rev Med Pharmacol Sci. 2017;21(1 Suppl):7–16.
7. Baggish AL, Weiner RB, Kanayama G, et al. Cardiovascular toxicity of illicit anabolic-androgenic steroid use. Circulation. 2017;135(21):1991–2002.