Metandienone Wikipedia

Laboratories mainly screen for the parent compound itself (18) and two reduced derivatives (3α5α-THMT, 19; 3α5β-THMT, 20). The metabolites of both substances are frequently monitored by gas chromatography-mass spectrometry after hydrolysis of the glycosidic bond of glucuronides as aglycons [22,23]. Many metabolites related to the intake of metandienone are reported in the literature, and a number of these have been known for decades. These are generated by both phase I and phase II drug metabolizing enzymes.

The discovery of such new metabolites may help in extending the time of detection after the intake of metandienone (12) or methyltestosterone (18), which would be a considerable contribution to the fight against doping, as cheating may be traced back over a longer period. Additionally, such findings may help to further elucidate the metabolism of synthetic steroids and therefore improve the understanding of human biotransformation. After cooling to 0 °C, Nysted reagent (20%) was diluted with absolute tetrahydrofurane (THF abs.), and titanium tetrachloride was added dropwise.

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

Afterwards, the mixture was poured into water and extracted three times with dichloromethane. The organic phases were washed with brine and then dried over sodium sulfate. The 3α,5β-epi-tetrahydromethyltestosterone was identified as the first peak in positive urine samples of metandienone and methyltestosterone at 9.56 min (Figure 8).

As before, a dose of 100 mg of methandienone/day was given alternately with the placebo in a double-blind crossover experiment. The treatment periods lasted 6 weeks and were separated by an interval of 6 weeks. Body weight, potassium and nitrogen, muscle size, and leg performance and strength increased significantly during training on the drug, but not during the placebo period. The https://laboratoriobioxil.com/primobolan-injections-steroid-course-2/ finding of increased body nitrogen suggested that the weight gain was not only intracellular fluid.

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• After the intake of MD, this was also found earlier, but with a problem in separation of the four diastereomers [15].
• Phase I reactions include the introduction of a double bond at position 6, the reduction of double bonds in the A-ring, the reduction of the 3-oxo group, hydroxylations in positions 6, 11, 12, 16, or 18, epimerization in position 17, and rearrangement of the D-ring [8,9,10,11,12,13,14,15].
• And X.d.l.T.; investigation, S.L., L.L., H.S., M.W., M.I., X.d.l.T. and N.S.; resources, M.K.P., N.S., A.M.K., M.B.

Phase I reactions include the introduction of a double bond at position 6, the reduction of double bonds in the A-ring, the reduction of the 3-oxo group, hydroxylations in positions 6, 11, 12, 16, or 18, epimerization in position 17, and rearrangement of the D-ring [8,9,10,11,12,13,14,15]. With respect to phase II reactions, both glucuronidation and sulfonation have been reported [16,17]. In recent years, new investigations on long-term metabolites of MD (12) identified further metabolites with 17β-hydroxymethyl-17α-methyl-13-ene structure [18,19,20,21]. 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]. Aberrantly, only 17α-hydroxymethyl-17β-methyl-18-nor-5β-androst-13-en-3α-ol (8) was confirmed in the p.a. The stereochemistry at C17 is the opposite of the currently monitored long-term metabolite of MD and also to 17β-hydroxymethyl-17α-methyl-18-nor-androsta-4,13-dien-3-one, which was detected earlier after administration of MT [38].

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.

2. Urinary Metabolites

Based on preliminary data, the mentioned substances are detected for at least 48 h after the intake of parent compounds. Excretion studies with a higher number of volunteers and prolonged sample collection will be performed in the near future to evaluate the detection windows of the new metabolites. Interestingly, the structure of the long-term metabolite of 4-chlorometandienone with modified D-ring structure and a fully reduced A-ring (Sobolevsky’s “M3”) was assigned to 4α-chloro-17β-hydroxymethyl-17α-methyl-18-nor-5α-androst-13-en-3α-ol by Forsdahl et al. [31]. The metabolites proposed for MT and MD as described above show an inverse stereochemistry at the D-ring in comparison to these assignments. For other steroids with a similar structure, such as dehydrochloromethyltestosterone, there is a metabolite described with a fully reduced A-ring and a rearranged D-ring [30], which was synthesized in 2018 [31,32].

The 17-epimer was found in the urines after the intake of both mentioned anabolic-androgenic steroids. In the case of MT administration, the metabolite 11 was also described earlier, but found with shorter detection times than the 17α-methyl analogs 19 and 20 [38]. After the intake of MD, this was also found earlier, but with a problem in separation of the four diastereomers [15].