Detection and mass spectrometric characterization of novel long-term dehydrochloromethyltestosterone metabolites in human urine

@article{Sobolevsky2012DetectionAM,
  title={Detection and mass spectrometric characterization of novel long-term dehydrochloromethyltestosterone metabolites in human urine},
  author={Tim Sobolevsky and Grigory M Rodchenkov},
  journal={The Journal of Steroid Biochemistry and Molecular Biology},
  year={2012},
  volume={128},
  pages={121-127}
}

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References

SHOWING 1-10 OF 15 REFERENCES

Mass spectrometric identification and characterization of a new long-term metabolite of metandienone in human urine.

TLDR
A new metabolite generated from metandienone has been identified as 18-nor-17beta-hydroxymethyl,17alpha-methyl-androst-1,4,13-trien-3-one in excretion study urine samples providing a valuable tool for the long-term detection of metandiensone abuse by athletes in sports drug testing.

GC and capillary column GC/MS determination of synthetic anabolic steroids. II. 4-chloro-methandienone (oral turinabol) and its metabolites.

The determination of oral turinabol (4-chloro-17 alpha-methyl-17 beta-hydroxy-1,4-androstadien-3-one) [1] in the 'free' fraction of human urine samples by gas chromatography and capillary column gas

Metabolism of anabolic steroids in humans: synthesis of 6 beta-hydroxy metabolites of 4-chloro-1,2-dehydro-17 alpha-methyltestosterone, fluoxymesterone, and metandienone.

TLDR
Human excretion studies showed that 6 beta-hydroxylation is the major metabolic pathway in the metabolism of 4-chloro-1,2-dehydro-17 alpha-methyltestosterone, fluoxymesterone, and metandienone, whereas for boldenone, 17 alpha-nakedosterone, and testosterone, 6 alpha-hydroxyation is negligible.

17-Epimerization of 17 alpha-methyl anabolic steroids in humans: metabolism and synthesis of 17 alpha-hydroxy-17 beta-methyl steroids.

TLDR
It is shown that the extent of 17-epimerization depends on the A-ring structure and shows a great variation for the different 17 alpha-methyl anabolic steroids.

Detection of the misuse of steroids in doping control

Metabolism of anabolic androgenic steroids.

TLDR
A review of the metabolism of AAS is presented and Testosterone is the principal androgenic steroid and its metabolism is compared with that of Aas.