88495-36-7Relevant academic research and scientific papers
Proton magnetic resonance spectra of 17ξ-hydroxy-17ξ-methyl-5ξ-androstane C-3 ketone and C-3ξ alcohol isomers in chloroform-d and pyridine-d5
Templeton,Choi Jackson
, p. 485 - 491 (1983)
17α-Hydroxy-17β-methyl-5β-androstan-3-one,17β-methyl-5α-androstane-3α ,17α-diol,17β-methyl-5α-androstane-3β,17α-diol, 17α-methyl-5β-androstane-3β,17β-diol,17β-methyl-5β-androstane- 3α,17α-diol and 17β-methyl-5β-androstane-3β,17α-diol were synthesized for the first time. 1H NMR spectra of all four 17ξ-hydroxy/17ξ-methyl C-3 ketones and all eight C-3 alcohols were recorded in chloroform-d and pyridine-d5. Pyridine-induced chemical shifts are discussed. Thin-layer chromatographic data are given.
New insights into themetabolism ofmethyltestosterone and metandienone: Detection of novel a-ring reducedmetabolites
Botrè, Francesco,Bureik, Matthias,Iannone, Michele,Keiler, Annekathrin Martina,Liu, Lingyu,Loke, Steffen,Parr, Maria Kristina,Scheffler, Heike,Schl?rer, Nils,Wenzel, Maxi,de la Torre, Xavier
, (2021/05/31)
Metandienone and methyltestosterone are orally active anabolic-androgenic steroids with a 17α-methyl structure that are prohibited in sports but are frequently detected in anti-doping analysis. Following the previously reported detection of long-term metabolites with a 17ξ-hydroxymethyl- 17ξ-methyl-18-nor-5ξ-androst-13-en-3ξ-ol structure in the chlorinated metandienone analog dehydrochloromethyltestosterone (“oral turinabol”), in this study we investigated the formation of similar metabolites of metandienone and 17α-methyltestosterone with a rearranged D-ring and a fully reduced A-ring. Using a semi-targeted approach including the synthesis of reference compounds, two diastereomeric substances, viz. 17α-hydroxymethyl-17β-methyl-18-nor-5β-androst-13-en-3α-ol and its 5α-analog, were identified following an administration of methyltestosterone. In post-administration urines of metandienone, only the 5β-metabolite was detected. Additionally, 3α,5β-tetrahydro-epi-methyltestosterone was identified in the urines of both administrations besides the classical metabolites included in the screening procedures. Besides their applicability for antidoping analysis, the results provide new insights into the metabolism of 17α-methyl steroids with respect to the order of reductions in the A-ring, the participation of different enzymes, and alterations to the D-ring.
17-Epimerization of 17α-methyl anabolic steroids in humans: metabolism and synthesis of 17α-hydroxy-17β-methyl steroids
Schaenzer, Willi,Opfermann, Georg,Donike, Manfred
, p. 537 - 550 (2007/10/02)
The 17-epimers of the anabolic steroids bolasterone (I), 4-chlorodehydromethyltestosterone (II), fluoxymesterone (III), furazabol (IV), methanedienone (V), mestanolone (VI), methyltestosterone (VII), methandriol (VIII), oxandrolone (IX), oxymesterone (X), oxymetholone (XI), stanozolol (XII), and the human metabolites 7α,17α-dimethyl-5β-androstane-3α,17β-diol (XIII) (metabolite of I), 6β-hydroxymetandienone (XIV) (metabolite of V), 17α-methyl-5β-androst-1-ene-3α,17β-diol (XV) (metabolite of V), 3'-hydroxystanozolol (XVI) (metabolite of XII), as well as the reference substances 17β-hydroxy-17α-methyl-5β-androstan-3-one (XVII), 17β-hydroxy-17α-methyl-5β-androst-1-en-3-one (XVIII) (also a metabolite of V), the four isomers 17α-methyl-5α-androstane-3α,17β-diol (XIX) (also a metabolite of VI, VII, and XI), 17α-methyl-5α-androstane-3β,17β-diol (XX), 17α-methyl-5β-androstane-3α,17β-diol (XXI) (also a metabolite of V, VII, and VIII), 17α-methyl-5β-androstane-3β,17β-diol (XXII), and 17β-hydroxy-7α,17α-dimethyl-5β-androstan-3-one (XXIII) were synthesized via a 17β-sulfate that spontaneously hydrolyzed in water to several dehydration products, and to the 17α-hydroxy-17β-methyl epimer.The 17β-sulfate was prepared by reaction of the 17β-hydroxy-17α-methyl steroid with sulfur trioxide pyridine complex.The 17β-methyl epimers are eluted in gas chromatography as trimethylsilyl derivatives from a capillary SE-54 or OV-1 column 70-170 methylen units before the corresponding 17α-methyl epimer.The electron impact mass spectra of the underivatized and trimethylsilylated epimers are in most cases identical and only for I, II, and V was a differentiation between the 17-epimers possible. 1H nuclear magnetic resonance (NMR) spectra show for the 17β-methyl epimer a chemical shift for the C-18 protons (singlet) of about 0.175 ppm (in deuterochloroform) to a lower field. 13C NMR spectra display differences for the 17-epimeric steroids in shielding effects for carbons 12-18 and 20.Excretion studies with I-XII with identification and quantification of 17-epimeric metabolites indicate that the extent of 17-epimerization depends on the A-ring structure and shows a great variation for the different 17α-methyl anabolic steroids.Keywords: anabolic steroids; 17-epimerization; nuclear magnetic resonance; Kovats indices; mass spectrometry; metabolism; gas chromatography
