17β-hydroxy-17α-methyl-5α-androstan-3-ene | 62797-46-0

• 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-hydroxy-17α-methyl-5α-androstan-3-ene
• 英文别名: 17α-Methyl-5α-androst-3-en-17β-ol
• CAS: 62797-46-0；94901-78-7；1229-05-6
• 化学式: C₂₀H₃₂O
• 分子量: 288.473
• InChiKey: VIJIZSMDFAAMIH-PAPWGAKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  21.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  17β-hydroxy-17α-methyl-5α-androstan-3-ene 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 四氢呋喃 为溶剂， 以0.2251 g的产率得到3α-bromo-4ξ,17β-dihydroxy-17α-methyl-5α-androstane
  参考文献：
  名称：

  Characterization of desoxymethyltestosterone main urinary metabolite produced from cultures of human fresh hepatocytes

  摘要：

  Desoxymethyltestosterone (DMT; 17 beta-hydroxy-17 alpha-methyl-5 alpha-androst-2-ene) is a designer steroid present in hormonal supplements distributed illegally as such or in combination with other steroids, for self-administration. It figures on the list of substances prohibited in sports and its detection in athlete's urine samples is based upon the presence of the parent compound or the main urinary metabolite, which has not been characterized yet. Following its isolation from cultures of human fresh hepatocytes and S9 fractions of liver homogenates, we were able to identify this metabolite as being 17 alpha-methyl-2 beta,3 alpha,17 beta-trihydroxy-5 alpha-androstane. Other minor metabolites were also characterized. The production, isolation, NMR, mass spectral analyses and chemical synthesis are presented. (c) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.02.008
• 作为产物：
  描述：

  雄烯二酮 在 溶剂黄146 、 锌 作用下， 以 乙醚 为溶剂， 反应 21.67h， 生成 17β-hydroxy-17α-methyl-5α-androstan-3-ene
  参考文献：
  名称：

  Characterization of desoxymethyltestosterone main urinary metabolite produced from cultures of human fresh hepatocytes

  摘要：

  Desoxymethyltestosterone (DMT; 17 beta-hydroxy-17 alpha-methyl-5 alpha-androst-2-ene) is a designer steroid present in hormonal supplements distributed illegally as such or in combination with other steroids, for self-administration. It figures on the list of substances prohibited in sports and its detection in athlete's urine samples is based upon the presence of the parent compound or the main urinary metabolite, which has not been characterized yet. Following its isolation from cultures of human fresh hepatocytes and S9 fractions of liver homogenates, we were able to identify this metabolite as being 17 alpha-methyl-2 beta,3 alpha,17 beta-trihydroxy-5 alpha-androstane. Other minor metabolites were also characterized. The production, isolation, NMR, mass spectral analyses and chemical synthesis are presented. (c) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.02.008

文献信息

• <i>In vitro</i>metabolism studies of desoxy-methyltestosterone (DMT) and its five analogues, and<i>in vivo</i>metabolism of desoxy-vinyltestosterone (DVT) in horses
  作者：Wai Him Kwok、Karen Y. Kwok、David K. K. Leung、Gary N. W. Leung、Colton H. F. Wong、Jenny K. Y. Wong、Terence S. M. Wan

  DOI：10.1002/jms.3613

  日期：2015.8

  communities. This paper describes the in vitro metabolism studies of DMT and five of its structural analogues with different substituents at the 17α position (RH, ethyl, vinyl, ethynyl and 2 H3 -methyl). In addition, the in vivo metabolism of desoxy-vinyltestosterone (DVT) in horses will be presented. The in vitro studies revealed that the metabolic pathways of DMT and its analogues occurred predominantly

  2002年降冰片酮和2003年四氢孕酮的人体运动员样本的阳性结果证实，设计类固醇确实在人体运动中被滥用。2005年，在美加边境的政府官员扣押了设计类固醇家族的另一种产品，称为“ Madol”（也称为脱氧甲基睾丸激素（DMT））。两年后，在混合武术运动员的样本中报告了DMT的阳性发现。在人类运动中同样会滥用人类运动中使用的掺杂剂，这并不罕见。因此，专门设计的类固醇会对赛马和马术社区构成类似的威胁。本文介绍了DMT及其5个在17α位具有不同取代基的结构类似物（RH，乙基，乙烯基，乙炔基和2 H3-甲基）。此外，还将介绍马体内脱氧乙烯基睾丸激素（DVT）的体内代谢。体外研究表明，DMT及其类似物的代谢途径主要通过烯酮形成，羟基化和还原的结合而在A环中发生。对于DMT及其一些类似物，还观察到涉及17α-烷基羟基化的其他生物转化。口服实验表明DVT被广泛代谢，尿液中未检测到母体药物。在给药后最多4
• Synthesis of 3-trifluoromethyl steroids
  作者：Manfred Ernst Wolff、Abraham F. Pascual

  DOI：10.1021/jm00284a021

  日期：1971.2