Methandrostenolone metabolism in humans: potential problems associated with isolation and identification of metabolites

J Steroid Biochem. 1990 Aug 14;36(5):407-14. doi: 10.1016/0022-4731(90)90081-3.

Abstract

Methandrostenolone dose (amount and duration) and methods of isolation from urine can influence the identification and quantitation of methandrostenolone metabolites. Long-term use of methandrostenolone at high dosages led to the appearance of unmetabolized drug in the urine and contributed to the identification of a previously unreported metabolite, 3 beta, 6 section, 17 beta-trihydroxy-17 alpha-methyl-5 section-1-androstene. Exposure of methandrostenolone in vitro to acid conditions induced a retropinacol rearrangement in the D-ring of the methandrostenolone molecule, causing the formation of 18-nor-17,17-dimethyl-1,4,13(14)-androstatrien-3-one in large amounts. The same acidic conditions led to the addition of a hydroxyl at the 6 position of the B-ring of either the retropinacol rearrangement products or native methandrostenolone resulting in the formation of 6 beta-hydroxy-18-nor-17,17-dimethyl-1,4,13(14)-androstatrien-3-one, 6 alpha- hydroxy-18-nor-17,17-dimethyl-1,4,13(14)-androstatrien, 6 beta-17 alpha-methyl-1,4-androstadien-3-one and 6 alpha,17 beta-dihydroxy-17 alpha-methyl-1,4-androstadien-3-one. Hydroxylation of native methandrostenolone at the 6 position also occurs endogenously. However, no evidence of an endogenous retropinacol rearrangement was found. Silylating agents alone can induce the formation of small amounts of 6 beta-17 beta-dihydroxy-17 alpha-methyl-1,4-androstadien-3-one. Discrepancies between previously published reports on methandrostenolone metabolism in man are discussed and compared with an animal model.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Androgens / isolation & purification
  • Biotransformation
  • Chromatography, Gas
  • Gas Chromatography-Mass Spectrometry
  • Humans
  • Methandrostenolone / isolation & purification
  • Methandrostenolone / metabolism*
  • Methandrostenolone / urine
  • Molecular Structure
  • Sports

Substances

  • Androgens
  • Methandrostenolone