Studies on anabolic steroids—6. Identification of urinary metabolites of stenbolone acetate (17β-acetoxy-2-methyl-5α-androst-1-en-3-one) in human by gas chromatography/mass spectrometry

Goudreault, Danielle; Massé, Robert

doi:10.1016/0960-0760(91)90323-w

Cited by 18 publications

(14 citation statements)

References 15 publications

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“…A further loss of CH 3 • yields m/z 275. Consistent with this conclusion is the appearance of the ions at the same mass in the spectrum of the 2‐methyl analogue of 3α‐17‐dihydroxy‐5α‐androstan‐1,16‐diene TMS ether and in the spectrum of mixed d 0 ‐TMS (enol group) and d 9 ‐TMS (3‐position) (Goudreault & Massé, ) steroid.…”

Section: Trimethylsilyl Derivativesmentioning

confidence: 65%

“…In common with the spectra of steroids with enol‐TMS groups only at C17, the molecular and [M − 15] + ions are abundant and there is a characteristic ion at m/z 169. Two very prominent ions at m/z 290 and 275 characterize the 3‐TMSO‐Δ 5 ‐function (Goudreault & Massé, ; Parr et al, ; Schänzer & Donike, ). The ion at m/z 290 represents loss of C1‐C4 with the 3‐TMSO‐group (CH 2 =CH‐CH(OTMS)=CH 2 ) from the A ring (ion of type iy ).…”

Section: Trimethylsilyl Derivativesmentioning

confidence: 99%

“…The spectrum of the 17-oxo-analogue, with a 2methyl group (140 Fig. 44c) (Goudreault & Massé, 1991), shows major ions at m/z 141 (base peak, equivalent to m/z 127 in the spectrum of 139) and m/z 156 (equivalent to m/z 142).…”

Section: Iic10a Diagnostic Ions For Specific Steroid Hydroxylationmentioning

confidence: 99%

“…(Adapted from Parr et al (2011)), (b) 3β,17β-dihydroxy-5α-androstan-1-ene 139), (Adapted from Parr et al, (2011)) and (c) 3α-hydroxy-2-methyl-5α-androstan-17-one (140). (Adapted from Goudreault and Massé (1991)). 2007)).…”

Section: Iic10a Diagnostic Ions For Specific Steroid Hydroxylationmentioning

confidence: 99%

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Mass Spectrometric Fragmentation of Trimethylsilyl and Related Alkylsilyl Derivatives

Harvey

Vouros

2019

Mass Spectrometry Reviews

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This review describes the mass spectral fragmentation of trimethylsilyl (TMS) and related alkylsilyl derivatives used for preparing samples for analysis, mainly by combined gas chromatography and mass spectrometry (GC/MS). The review is divided into three sections. The first section is concerned with the TMS derivatives themselves and describes fragmentation of derivatized alcohols, thiols, amines, ketones, carboxylic acids and bifunctional compounds such as hydroxy‐ and amino‐acids, halo acids and hydroxy ethers. More complex compounds such as glycerides, sphingolipids, carbohydrates, organic phosphates, phosphonates, steroids, vitamin D, cannabinoids, and prostaglandins are discussed next. The second section describes intermolecular reactions of siliconium ions such as the TMS cation and the third section discusses other alkylsilyl derivatives. Among these latter compounds are di‐ and trialkyl‐silyl derivatives, various substituted‐alkyldimethylsilyl derivatives such as the tert‐butyldimethylsilyl ethers, cyclic silyl derivatives, alkoxysilyl derivatives, and 3‐pyridylmethyldimethylsilyl esters used for double bond location in fatty acid spectra. © 2019 Wiley Periodicals, Inc. Mass Spec Rev 0000:1–107, 2019

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Section: Trimethylsilyl Derivativesmentioning

confidence: 65%

Section: Trimethylsilyl Derivativesmentioning

confidence: 99%

Section: Iic10a Diagnostic Ions For Specific Steroid Hydroxylationmentioning

confidence: 99%

Section: Iic10a Diagnostic Ions For Specific Steroid Hydroxylationmentioning

confidence: 99%

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Mass Spectrometric Fragmentation of Trimethylsilyl and Related Alkylsilyl Derivatives

Harvey

Vouros

2019

Mass Spectrometry Reviews

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“…Besides the 16-hydroxy and 17-keto metabolites [108] a minor metabolite hydroxylated at C-18, 2-methyl-5␣-androst-1-ene-18-ol-3,17-dione, was also found [109,110].…”

Section: Stenbolonementioning

confidence: 99%

Metabolism and excretion of anabolic steroids in doping control—New steroids and new insights

Eenoo

Delbeke

2006

The Journal of Steroid Biochemistry and Molecular Biology

107

114

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Metabolism of methylstenbolone studied with human liver microsomes and the uPA^+/+‐SCID chimeric mouse model

Geldof

Lootens

Polet

et al. 2014

Biomedical Chromatography

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Anti-doping laboratories need to be aware of evolutions on the steroid market and elucidate steroid metabolism to identify markers of misuse. Owing to ethical considerations, in vivo and in vitro models are preferred to human excretion for nonpharmaceutical grade substances. In this study the chimeric mouse model and human liver microsomes (HLM) were used to elucidate the phase I metabolism of a new steroid product containing, according to the label, methylstenbolone. Analysis revealed the presence of both methylstenbolone and methasterone, a structurally closely related steroid. Via HPLC fraction collection, methylstenbolone was isolated and studied with both models. Using HLM, 10 mono-hydroxylated derivatives (U1-U10) and a still unidentified derivative of methylstenbolone (U13) were detected. In chimeric mouse urine only di-hydroxylated metabolites (U11-U12) were identified. Although closely related, neither methasterone nor its metabolites were detected after administration of isolated methylstenbolone. Administration of the steroid product resulted mainly in the detection of methasterone metabolites, which were similar to those already described in the literature. Methylstenbolone metabolites previously described were not detected. A GC-MS/MS multiple reaction monitoring method was developed to detect methylstenbolone misuse. In one out of three samples, previously tested positive for methasterone, methylstenbolone and U13 were additionally detected, indicating the applicability of the method.

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Studies on anabolic steroids—6. Identification of urinary metabolites of stenbolone acetate (17β-acetoxy-2-methyl-5α-androst-1-en-3-one) in human by gas chromatography/mass spectrometry

Cited by 18 publications

References 15 publications

Mass Spectrometric Fragmentation of Trimethylsilyl and Related Alkylsilyl Derivatives

Mass Spectrometric Fragmentation of Trimethylsilyl and Related Alkylsilyl Derivatives

Metabolism and excretion of anabolic steroids in doping control—New steroids and new insights

Metabolism of methylstenbolone studied with human liver microsomes and the uPA^+/+‐SCID chimeric mouse model

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Studies on anabolic steroids—6. Identification of urinary metabolites of stenbolone acetate (17β-acetoxy-2-methyl-5α-androst-1-en-3-one) in human by gas chromatography/mass spectrometry

Cited by 18 publications

References 15 publications

Mass Spectrometric Fragmentation of Trimethylsilyl and Related Alkylsilyl Derivatives

Mass Spectrometric Fragmentation of Trimethylsilyl and Related Alkylsilyl Derivatives

Metabolism and excretion of anabolic steroids in doping control—New steroids and new insights

Metabolism of methylstenbolone studied with human liver microsomes and the uPA+/+‐SCID chimeric mouse model

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Product

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Metabolism of methylstenbolone studied with human liver microsomes and the uPA^+/+‐SCID chimeric mouse model