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Reaction scheme for 17α-hydroxymethyl-17β-methyl-18-nor-5ξ-androst-13-en-3ξ-ol steroids.

Journal: Molecules

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

doi: 10.3390/molecules26051354

Figure Lengend Snippet: Reaction scheme for 17α-hydroxymethyl-17β-methyl-18-nor-5ξ-androst-13-en-3ξ-ol steroids.

Article Snippet: 17β-Methyltestosterone (epi-MT, 9 ) was obtained from Santa Cruz Biotechnology (Heidelberg, Germany).

Techniques:

Mass spectrum (GC-EI-QTOF-MS, 70 eV) of 17α-hydroxymethyl-17β-methyl-18-nor-5β-androst-13-en-3α-ol ( 8 ), bis- trimethylsilyl) (TMS (x-axis: m / z ; y-axis: relative abundance).

Journal: Molecules

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

doi: 10.3390/molecules26051354

Figure Lengend Snippet: Mass spectrum (GC-EI-QTOF-MS, 70 eV) of 17α-hydroxymethyl-17β-methyl-18-nor-5β-androst-13-en-3α-ol ( 8 ), bis- trimethylsilyl) (TMS (x-axis: m / z ; y-axis: relative abundance).

Article Snippet: 17β-Methyltestosterone (epi-MT, 9 ) was obtained from Santa Cruz Biotechnology (Heidelberg, Germany).

Techniques:

Retention times (GC-QQQ-MS), molecular ions (M •+ ) in low electron ionization (LEI, 20 eV), and mass difference to exact mass ( m / z ther 448.3187, C 26 H 48 O 2 Si 2 +• ) of diasteromeric  17α-hydroxymethyl-17β-methyl-18-nor-5ξ-androst-13-en-3ξ-ols  as per-TMS derivatives.

Journal: Molecules

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

doi: 10.3390/molecules26051354

Figure Lengend Snippet: Retention times (GC-QQQ-MS), molecular ions (M •+ ) in low electron ionization (LEI, 20 eV), and mass difference to exact mass ( m / z ther 448.3187, C 26 H 48 O 2 Si 2 +• ) of diasteromeric 17α-hydroxymethyl-17β-methyl-18-nor-5ξ-androst-13-en-3ξ-ols as per-TMS derivatives.

Article Snippet: 17β-Methyltestosterone (epi-MT, 9 ) was obtained from Santa Cruz Biotechnology (Heidelberg, Germany).

Techniques:

1 H and 13 C NMR spectral data of  17α-hydroxymethyl-17β-methyl-18-nor-5β-androst-13-en-3α-ol  ( 8 ) and 17α-hydroxymethyl-17β-methyl-18-nor-5α-androst-13-en-3α-ol ( 8a ). Multiplicity of signals indicated as singlet (s), doublet (d).

Journal: Molecules

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

doi: 10.3390/molecules26051354

Figure Lengend Snippet: 1 H and 13 C NMR spectral data of 17α-hydroxymethyl-17β-methyl-18-nor-5β-androst-13-en-3α-ol ( 8 ) and 17α-hydroxymethyl-17β-methyl-18-nor-5α-androst-13-en-3α-ol ( 8a ). Multiplicity of signals indicated as singlet (s), doublet (d).

Article Snippet: 17β-Methyltestosterone (epi-MT, 9 ) was obtained from Santa Cruz Biotechnology (Heidelberg, Germany).

Techniques:

Synthesis route for 17β-methyl-5β-androstane-3α,17α-diol ( 11 ).

Journal: Molecules

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

doi: 10.3390/molecules26051354

Figure Lengend Snippet: Synthesis route for 17β-methyl-5β-androstane-3α,17α-diol ( 11 ).

Article Snippet: 17β-Methyltestosterone (epi-MT, 9 ) was obtained from Santa Cruz Biotechnology (Heidelberg, Germany).

Techniques:

Mass spectrum (GC-EI-QTOF-MS, 70 eV) of 17β-methyl-5β-androstane-3α,17α-diol ( 11 ), bis TMS (x-axis: m / z ; y-axis: relative abundance).

Journal: Molecules

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

doi: 10.3390/molecules26051354

Figure Lengend Snippet: Mass spectrum (GC-EI-QTOF-MS, 70 eV) of 17β-methyl-5β-androstane-3α,17α-diol ( 11 ), bis TMS (x-axis: m / z ; y-axis: relative abundance).

Article Snippet: 17β-Methyltestosterone (epi-MT, 9 ) was obtained from Santa Cruz Biotechnology (Heidelberg, Germany).

Techniques:

Retention times (GC-QQQ-MS) and ion transitions of currently targeted metabolites in anti-doping analysis.

Journal: Molecules

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

doi: 10.3390/molecules26051354

Figure Lengend Snippet: Retention times (GC-QQQ-MS) and ion transitions of currently targeted metabolites in anti-doping analysis.

Article Snippet: 17β-Methyltestosterone (epi-MT, 9 ) was obtained from Santa Cruz Biotechnology (Heidelberg, Germany).

Techniques:

Proposed metabolism of methyltestosterone (black, 18 ) and metandienone (red, 12 ) to the found metabolites 17α-hydroxymethyl-17β-methyl-18-nor-5β-androst-13-en-3α-ol ( 8 ), 17α-hydroxymethyl-17β-methyl-18-nor-5α-androst-13-en-3α-ol ( 8a ), and 17β-methyl-5β-androstane-3α,17α-diol ( 11 ) except last step of metandienone. The question marks represent reactions whose enzymes have not been elucidated yet.

Journal: Molecules

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

doi: 10.3390/molecules26051354

Figure Lengend Snippet: Proposed metabolism of methyltestosterone (black, 18 ) and metandienone (red, 12 ) to the found metabolites 17α-hydroxymethyl-17β-methyl-18-nor-5β-androst-13-en-3α-ol ( 8 ), 17α-hydroxymethyl-17β-methyl-18-nor-5α-androst-13-en-3α-ol ( 8a ), and 17β-methyl-5β-androstane-3α,17α-diol ( 11 ) except last step of metandienone. The question marks represent reactions whose enzymes have not been elucidated yet.

Article Snippet: 17β-Methyltestosterone (epi-MT, 9 ) was obtained from Santa Cruz Biotechnology (Heidelberg, Germany).

Techniques: