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  3. Evaluation Of The Short-term Stability Of 6α-chloro-testosterone, 6β-bromo-androstenedione And 6-oxo-androstenedione In Dimethylsulfoxide And Methanol Using Liquid And Gas Chromatography - Mass Spectrometry
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  3. Evaluation Of The Short-term Stability Of 6α-chloro-testosterone, 6β-bromo-androstenedione And 6-oxo-androstenedione In Dimethylsulfoxide And Methanol Using Liquid And Gas Chromatography - Mass Spectrometry

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Evaluation of the short-term stability of 6α-chloro-testosterone, 6β-bromo-androstenedione and 6-oxo-androstenedione

Dayamin Martínez Brito1, Patrizia Leogrande1, Xavier de la Torre1

  • 1Laboratorio Antidoping FMSI, Federazione Medico Sportiva Italiana, Rome, Italy.

Steroids
|March 11, 2025

View abstract on PubMed

Summary
This summary is machine-generated.
Keywords:
6-oxo-androstenedione6α-chloro-testosterone6β-bromo-androstenedioneDimethylsulfoxideShort-term stability

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Short-term stability of halogenated androgens 6α-chloro-testosterone (6-CT) and 6β-bromo-androstenedione (6-BrAED) was assessed. Degradation was higher in dimethylsulfoxide (DMSO) than methanol (MeOH), with 6-oxo-androstenedione (6-oxo-AED) showing stability.

Area of Science:

  • Analytical Chemistry
  • Steroid Chemistry
  • Chromatography

Background:

  • Accurate quantification of steroid compounds is crucial in various scientific fields.
  • Understanding the stability of steroid reference standards in different solvents and storage conditions is essential for reliable analytical results.
  • Halogenated androgens like 6α-chloro-testosterone (6-CT) and 6β-bromo-androstenedione (6-BrAED) are of interest, but their stability is not well-documented.

Purpose of the Study:

  • To evaluate the short-term stability of 6α-chloro-testosterone (6-CT), 6β-bromo-androstenedione (6-BrAED), and 6-oxo-androstenedione (6-oxo-AED) in methanol (MeOH) and dimethylsulfoxide (DMSO).
  • To investigate the impact of storage temperature (room temperature, +4°C, -20°C) on the stability of these steroid solutions.
  • To assess potential degradation during sample preparation for chromatographic analysis.

Main Methods:

  • Solutions of 6-CT, 6-BrAED, and 6-oxo-AED were prepared in MeOH and DMSO.
  • Samples were stored at different temperatures and analyzed at various time points (0, 7, 30, 60, 90 days).
  • Analysis was performed using liquid chromatography-tandem mass spectrometry (LC-MS/MS) and gas chromatography-high resolution mass spectrometry (GC-HRMS), including derivatization steps for GC-MS.

Main Results:

  • Extensive degradation of 6-CT and 6-BrAED was observed, with significantly higher degradation occurring in DMSO compared to MeOH.
  • 6-oxo-AED remained stable in both MeOH and DMSO under all tested conditions.
  • Degradation of 6-CT and 6-BrAED was also noted during the acidic derivatization process for GC-MS analysis, leading to halogen loss or dehydration to form Δ6 derivatives.

Conclusions:

  • DMSO promotes the degradation of halogenated androgens (6-CT, 6-BrAED) more than MeOH due to interactions with functional groups.
  • 6-oxo-AED exhibits excellent stability in both solvents, making it a reliable reference standard.
  • Analytical chemists must consider potential degradation of 6-CT and 6-BrAED during storage and sample preparation, especially under acidic conditions, to ensure accurate quantitative determinations.