17β-methyl-5α-androstane-3α,17α-diol | 88729-24-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 17β-methyl-5α-androstane-3α,17α-diol
• 英文别名: 5alpha-Androstane-3alpha,17beta-diol, 17-methyl-；(3R,5S,8R,9S,10S,13S,14S,17R)-10,13,17-trimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthrene-3,17-diol
• CAS: 88729-24-2
• 化学式: C₂₀H₃₄O₂
• 分子量: 306.489
• InChiKey: QGKQXZFZOIQFBI-YBXIWKLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  17β-methyl-5α-androstane-3α,17α-diol 在 硫酸氢铵 、 碳酸氢铵 、 5’-三磷酸腺苷 、 magnesium chloride 作用下， 以 水 为溶剂， 生成 17β-methyl-5α-androstane-3α,17α-diol 3-sulfate
  参考文献：
  名称：

  磺基共轭代谢物的表征和定量，用于检测甲基睾酮滥用并通过 LC-MS 直接识别。

  摘要：

  甲基睾酮（MT）是兴奋剂控制分析中发现的最常被滥用的合成代谢雄激素类固醇之一。 MT 在人体中的代谢产生多种 І 相代谢物及其相应的 Ⅱ 相结合物。先前的研究假设17α-甲基-5β-雄甾烷-3α,17β-二醇(S2)的3α-磺基缀合物是MT的主要硫酸盐代谢物，检测窗口超过10天。然而，迄今为止，尚未对该代谢物的结构进行最终直接且明确的确认。在本研究中，我们建立了一种检测和识别 S2 的方法，使用液相色谱联用串联质谱 (LC-MS/MS) 进行完整分析，无需复杂的样品预处理。一项体外研究得出了所有 3-硫酸化 17-甲基雄甾烷-3,17-二醇非对映异构体的 LC-MS/MS 参考保留时间，从而可以对潜在检测到的代谢物进行准确的结构分配。在对一名健康男性志愿者进行的体内排泄研究中，单次口服 10 mg MT 后证实了代谢物 S2 的存在。参考标准是化学合成的，通过精确质谱 (MS) 和核磁共振

  DOI：

  10.1016/j.jsbmb.2024.106527
• 作为产物：
  描述：

  17beta-甲基-5alpha-雄甾烷-3alpha,17beta-二醇 在 吡啶 、 氢氧化钾 、 三氧化硫吡啶 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 17β-methyl-5α-androstane-3α,17α-diol
  参考文献：
  名称：

  人类中17种α-甲基同化类固醇的17-表异构化：17种α-羟基-17β-甲基类固醇的代谢和合成。

  摘要：

  17个β-二醇（XIX）（也是VI，VII和XI的代谢物），17个α-甲基-5α-雄甾烷3β，17个β-二醇（XX），17个α-甲基-5β-雄烷醇-3 alpha，17 beta-diol（XXI）（也是V，VII和VIII的代谢物），17 alpha-methyl-5 beta-androstane-3 beta，17 beta-diol（XXII）和17 beta-hydroxy -7α，17α-二甲基-5β-雄烷-3-酮（XXIII）是通过17β-硫酸盐合成的，该硫酸盐在水中自发水解成几种脱水产物，再合成为17α-羟基-17β-甲基差向异构体。通过使17β-羟基-17α-甲基甾族化合物与三氧化硫吡啶配合物反应来制备17β-硫酸盐。在相应的17个α-甲基差向异构体之前，从毛细管SE-54或OV-1色谱柱的70-170个亚甲基单元中，将17种β-甲基差向异构体作为三甲基甲硅烷基衍生物从气

  DOI：

  10.1016/0039-128x(92)90023-3

文献信息

• New Insights into the Metabolism of Methyltestosterone and Metandienone: Detection of Novel A-Ring Reduced Metabolites
  作者：Steffen Loke、Lingyu Liu、Maxi Wenzel、Heike Scheffler、Michele Iannone、Xavier de la Torre、Nils Schlörer、Francesco Botrè、Annekathrin Martina Keiler、Matthias Bureik、Maria Kristina Parr

  DOI：10.3390/molecules26051354

  日期：——

  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

  美二烯酮和甲基睾酮是口服活性合成代谢雄激素类固醇，具有 17α-甲基结构，在体育运动中被禁止，但在反兴奋剂分析中经常被检测到。继之前报道在氯化间二烯酮类似物脱氢氯甲基睾酮（“口服特力补”）中检测到具有 17ψ-羟甲基-17ψ-甲基-18-nor-5ψ-androst-13-en-3ψ-ol 结构的长期代谢物后，在这项研究中，我们研究了具有重新排列的 D 环和完全还原的 A 环的间二烯酮和 17α-甲基睾酮的类似代谢物的形成。使用半靶向方法，包括合成参考化合物、两种非对映异构体物质，即。 17α-羟甲基-17β-甲基-18-nor-5β-androst-13-en-3α-ol 及其 5α-类似物在施用甲基睾酮后被鉴定。在美二酮给药后的尿液中，仅检测到 5β-代谢物。此外，除了筛选程序中包含的经典代谢物外，在两次给药的尿液中还鉴定出了 3α,5β-四氢表甲基睾酮。除了适用于反兴奋剂分析之外，这些结果还为
• 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
  作者：John F. Templeton、Chung-Ja Choi Jackson

  DOI：10.1016/0039-128x(83)90088-0

  日期：1983.4

  17 alpha-Hydroxy-17 beta-methyl-5 beta-androstan-3-one,17 beta-methyl-5 alpha-androstane-3 alpha,17 alpha-diol,17 beta-methyl-5 alpha-androstane-3 beta,17 alpha-diol,17 alpha-methyl-5 beta-androstane-3 beta,17 beta-diol,17 beta-methyl-5 beta-androstane-3 alpha,17 alpha-diol and 17 beta-methyl-5 beta-androstane-3 beta,17 alpha-diol were synthesized for the first time. 1H NMR spectra of all four 17 xi-hydroxy/17 xi-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.
• Alternative long-term markers for the detection of methyltestosterone misuse
  作者：C. Gómez、O.J. Pozo、J. Marcos、J. Segura、R. Ventura

  DOI：10.1016/j.steroids.2012.10.008

  日期：2013.1

  Methyltestosterone (MT) is one of the most frequently detected anabolic androgenic steroids in doping control analysis. MT misuse is commonly detected by the identification of its two main metabolites excreted as glucuronide conjugates, 17 alpha-methyl-5 alpha-androstan-3 alpha,17 beta-diol and 17 alpha-methyl-5 beta-androstan-3 alpha,17 beta-diol. The detection of these metabolites is normally performed by gas chromatography-mass spectrometry, after previous hydrolysis with beta-glucuronidase enzymes, extraction and derivatization steps. The aim of the present work was to study the sulphate fraction of MT and to evaluate their potential to improve the detection of the misuse of the drug in sports. MT was administered to healthy volunteers and urine samples were collected up to 30 days after administration. After an extraction with ethyl acetate, urine extracts were analysed by liquid chromatography tandem mass spectrometry using electrospray ionisation in negative mode by monitoring the transition m/z 385 to m/z 97. Three diol sulphate metabolites (S1, S2 and S3) were detected. Potential structures for these metabolites were proposed after solvolysis and mass spectrometric experiments: S1, 17 alpha-methyl-5 beta-androstan-3 alpha,17 beta-diol 3 alpha-sulphate; S2, 17 beta-methyl-5 alpha-androstan-3 alpha,17 alpha-diol 3 alpha-sulphate; and S3, 17 beta-methyl-5 beta-androstan-3 alpha,17 alpha-diol 3 alpha-sulphate. Synthesis of reference compounds will be required in order to confirm the structures. The retrospectivity of these sulphate metabolites in the detection of MT misuse was compared with the obtained with previously described metabolites. Metabolite S2 was detected up to 21 days after MT administration, improving between 2 and 3 times the retrospectivity of the detection compared to the last long-term metabolite of MT previously described, 17 alpha-hydroxy-17 beta-methylandrostan-4,6-dien-3-one. (c) 2012 Elsevier Inc. All rights reserved.