Determination of 19-nortestosterone, testosterone and trenbolone by gas chromatography-negative-ion mass spectrometry after formation of the pentafluorobenzylcarboxymethoxime-trimethylsilyl derivatives

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Abstract

The known reaction of 3-ketosteroids with carboxymethoxylamine (to form the corresponding carboxymethoximes), followed by esterification of the carboxyl group with pentafluorobenzyl bromide, has been used to obtain derivatives of 19-nortestosterone, testosterone and trenbolone suitable for high-sensitivity detection with gas chromatography-negative-ion chemical ionization mass spectrometry. These derivatives, after further silylation of the alcoholic groups of the steroids, showed excellent chromatographic and spectrometric characteristics and were detectable in the low picogram range. The derivatization gave rise to the formation of two isomers which were distinguishable by gas chromatography. The existence of the two isomers was also confirmed by high-performance liquid chromatography. Examples of the usefulness of this derivatization procedure are given for the analysis of 19-nortestosterone, testosterone and trenbolone in meat and urine samples. By the use of immunoaffinity extraction and addition of deuterated internal standards (synthesized by isotopic exchange), the new derivatization procedure allowed a correct identification and quantitation of the steroids and reached very low detection limits [0.02 ppb (109) for 19-nortestosterone and testosterone, 0.06 ppb for trenbolone].

Original languageEnglish
Pages (from-to)325-334
Number of pages10
JournalJournal of Chromatography A
Volume547
Issue numberC
DOIs
Publication statusPublished - Jun 28 1991

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Trenbolone Acetate
Nandrolone
Gas chromatography
Gas Chromatography
Mass spectrometry
Testosterone
Mass Spectrometry
Negative ions
Ions
Derivatives
Isomers
Steroids
Ketosteroids
Meats
Esterification
High performance liquid chromatography
Meat
Ionization
Limit of Detection
High Pressure Liquid Chromatography

ASJC Scopus subject areas

  • Analytical Chemistry
  • Clinical Biochemistry
  • Molecular Medicine

Cite this

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title = "Determination of 19-nortestosterone, testosterone and trenbolone by gas chromatography-negative-ion mass spectrometry after formation of the pentafluorobenzylcarboxymethoxime-trimethylsilyl derivatives",
abstract = "The known reaction of 3-ketosteroids with carboxymethoxylamine (to form the corresponding carboxymethoximes), followed by esterification of the carboxyl group with pentafluorobenzyl bromide, has been used to obtain derivatives of 19-nortestosterone, testosterone and trenbolone suitable for high-sensitivity detection with gas chromatography-negative-ion chemical ionization mass spectrometry. These derivatives, after further silylation of the alcoholic groups of the steroids, showed excellent chromatographic and spectrometric characteristics and were detectable in the low picogram range. The derivatization gave rise to the formation of two isomers which were distinguishable by gas chromatography. The existence of the two isomers was also confirmed by high-performance liquid chromatography. Examples of the usefulness of this derivatization procedure are given for the analysis of 19-nortestosterone, testosterone and trenbolone in meat and urine samples. By the use of immunoaffinity extraction and addition of deuterated internal standards (synthesized by isotopic exchange), the new derivatization procedure allowed a correct identification and quantitation of the steroids and reached very low detection limits [0.02 ppb (109) for 19-nortestosterone and testosterone, 0.06 ppb for trenbolone].",
author = "Renzo Bagnati and Roberto Fanelli",
year = "1991",
month = "6",
day = "28",
doi = "10.1016/S0021-9673(01)88656-8",
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T1 - Determination of 19-nortestosterone, testosterone and trenbolone by gas chromatography-negative-ion mass spectrometry after formation of the pentafluorobenzylcarboxymethoxime-trimethylsilyl derivatives

AU - Bagnati, Renzo

AU - Fanelli, Roberto

PY - 1991/6/28

Y1 - 1991/6/28

N2 - The known reaction of 3-ketosteroids with carboxymethoxylamine (to form the corresponding carboxymethoximes), followed by esterification of the carboxyl group with pentafluorobenzyl bromide, has been used to obtain derivatives of 19-nortestosterone, testosterone and trenbolone suitable for high-sensitivity detection with gas chromatography-negative-ion chemical ionization mass spectrometry. These derivatives, after further silylation of the alcoholic groups of the steroids, showed excellent chromatographic and spectrometric characteristics and were detectable in the low picogram range. The derivatization gave rise to the formation of two isomers which were distinguishable by gas chromatography. The existence of the two isomers was also confirmed by high-performance liquid chromatography. Examples of the usefulness of this derivatization procedure are given for the analysis of 19-nortestosterone, testosterone and trenbolone in meat and urine samples. By the use of immunoaffinity extraction and addition of deuterated internal standards (synthesized by isotopic exchange), the new derivatization procedure allowed a correct identification and quantitation of the steroids and reached very low detection limits [0.02 ppb (109) for 19-nortestosterone and testosterone, 0.06 ppb for trenbolone].

AB - The known reaction of 3-ketosteroids with carboxymethoxylamine (to form the corresponding carboxymethoximes), followed by esterification of the carboxyl group with pentafluorobenzyl bromide, has been used to obtain derivatives of 19-nortestosterone, testosterone and trenbolone suitable for high-sensitivity detection with gas chromatography-negative-ion chemical ionization mass spectrometry. These derivatives, after further silylation of the alcoholic groups of the steroids, showed excellent chromatographic and spectrometric characteristics and were detectable in the low picogram range. The derivatization gave rise to the formation of two isomers which were distinguishable by gas chromatography. The existence of the two isomers was also confirmed by high-performance liquid chromatography. Examples of the usefulness of this derivatization procedure are given for the analysis of 19-nortestosterone, testosterone and trenbolone in meat and urine samples. By the use of immunoaffinity extraction and addition of deuterated internal standards (synthesized by isotopic exchange), the new derivatization procedure allowed a correct identification and quantitation of the steroids and reached very low detection limits [0.02 ppb (109) for 19-nortestosterone and testosterone, 0.06 ppb for trenbolone].

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