Metenolone: Uses, Interactions, Mechanism of Action DrugBank Online

After failure to confirm an anabolic action of testosterone and its derivatives in rats, methandienone (‘Dianabol’, an “anabolic steroid” used by athletes) has been given to 11 athletic men during a course of weight-training, in a double-blind, crossover experiment. Body weight and composition, muscular strength and performance, and indices of endocrine function were studied. Compared with the placebo period, on methandienone the subjects gained weight (mean 3-3 kg +/- 0-6 kg) and accumulated a disproportionately large amount of potassium (420+/-68 mmol); the increase in weight was confined to the lean part of the body, and the muscles increased in size. Strength and performance improved over each training period, but not significantly differently on drug and placebo. On the drug, plasma-cortisol concentration and urinary cortisol excretion increased, and plasma-testosterone decreased. Although the weight and body-composition changes may demonstrate an anabolic action of methandienone in man, they may alternatively have been caused Buy Testosterone Enanthate online by an increase in intracellular fluid, and the question of anabolic action therefore remains open.

New Insights into the Metabolism of Methyltestosterone and Metandienone: Detection of Novel A-Ring Reduced Metabolites

They are also different from the majority of metabolites of analogous 17-methyl steroids [30,31,38,39,40,41,42]. A spatula tip of epi-mestanolon (10a) was dissolved in 2 mL of absolute THF, 80 µL of K-Selectride was added and the mixture was stirred for 1 h at ambient temperature. Afterwards, 100 µL of aqueous hydrochloric acid (1 M) was added until there was no formation of bubbles anymore. Then, 150 µL of potassium hydroxide solution (1 M) was added and the mixture was extracted three times with 5 mL of hexane. Both potential ways represent the last step of the proposed formation of the metabolites 8 and 11. The other reactions of the metabolism of both investigated compounds are displayed in Figure 11.

Doping in sports

• A spatula tip of epi-mestanolon (10a) was dissolved in 2 mL of absolute THF, 80 µL of K-Selectride was added and the mixture was stirred for 1 h at ambient temperature.
• The detection and structure identification of the above-mentioned substances in the urine samples help to gain further insights into human metabolism of metandienone and 17α-methyltestosterone.
• As the first step of synthesis, attachment of an additional carbon-atom at C17 was achieved using Nysted reagent.
• Anti-doping laboratories mostly target the parent compound (12), 6-OH-metandienone (13), epi-metandienone (14), epi-metendiol (15), nor-epi-metendiol (16), and 20βOH-nor-metandienone (17) [18,22,23].
• The 17-epimer was found in the urines after the intake of both mentioned anabolic-androgenic steroids.

Metandienone and methyltestosterone are orally active anabolic-androgenic steroids with a 17α-methyl structure that are prohibited in sports but are frequently detected in anti-doping analysis. Using a semi-targeted approach including the synthesis of reference compounds, two diastereomeric substances, viz. 17α-hydroxymethyl-17β-methyl-18-nor-5β-androst-13-en-3α-ol and its 5α-analog, were identified following an administration of methyltestosterone. In post-administration urines of metandienone, only the 5β-metabolite was detected.

Two more diastereomers with 17α-methyl-17β-hydroxy configurations (17α-methyl-5α-androstane-3α,17β-diol (19) and 17α-methyl-5β-androstane-3α,17β-diol (20)) were commercially available and used for retention time comparison and urinary metabolite identification. The common metabolites of MT (18) and MD (12) were detected by comparison of retention time and quantifier and qualifier transitions, as reported in Table 3. Corresponding chromatograms are available as supplemental material (S3). Chemical structures of phase I metabolites of methyltestosterone reported in the literature. Retention times (GC-QQQ-MS) and ion transitions of currently targeted metabolites in anti-doping analysis.

In addition to the commonly monitored metabolites, the two synthesized 17-hydroxymethyl-17-methyl steroids were found in p.a. Urines of methyltestosterone (17α-hydroxymethyl-17β-methyl-18-nor-5α-androst-13-en-3α-ol, 8a, 17α-hydroxymethyl-17β-methyl-18-nor-5β-androst-13-en-3α-ol, 8) by GC-MS comparison. As the chemical structures of metandienone (12) and methyltestosterone (18) are similar to dehydrochloromethyltestosterone, it is conceivable that intake of these substances results in metabolites with a related structure.