雄甾酮-[D4] | 89685-10-9

• 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
• 中文名称: 雄甾酮-[D4]
• 英文名称: (d4-2,2,4,4)-(3α,5α)-3-hydroxyandrostan-17-one
• 英文别名: Androsterone-d4；(3R,5S,8R,9S,10S,13S,14S)-2,2,4,4-tetradeuterio-3-hydroxy-10,13-dimethyl-1,3,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one
• CAS: 89685-10-9
• 化学式: C₁₉H₃₀O₂
• 分子量: 294.414
• InChiKey: QGXBDMJGAMFCBF-NGIKVBDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  雄甾酮-[D4] 、 七氟丁酸酐 以 乙酸乙酯 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Simultaneous quantification of GABAergic 3α,5α/3α,5β neuroactive steroids in human and rat serum

  摘要：

  The 3 alpha,5 alpha- and 3 alpha,5 beta-reduced derivatives of progesterone, deoxycorticosterone, dehydroepiandrosterone and testosterone enhance GABAergic neurotransmission and produce inhibitory neurobehavioral and anti-inflammatory effects. Despite Substantial information oil the progesterone derivative (3 alpha,5 alpha)-3-hydroxypregnan-20-one (3 alpha,5 alpha-THP, allopregnanolone), the physiological significance of the other endogenous GABAergic neuroactive steroids has remained elusive. Here, we describe the validation of a method using gas chromatography-mass spectrometry to simultaneously identify serum levels of the eight 3 alpha,5 alpha- and 3 alpha,5 beta-reduced derivatives of progesterone, deoxycorticosterone, dehydroepiandrosterone and testosterone. The method shows specificity. sensitivity and enhanced throughput compared to other methods already available for neuroactive steroid quantification. Administration of pregnenolone to rats and progesterone to women produced selective effects on the 3 alpha,5 alpha- and 3 alpha,5 beta-reduced neuroactive steroids, indicating differential regulation of their biosynthetic pathways. Pregnenolone administration increased serum levels of 3 alpha,5 alpha-THP (+1488%, p<0.001), (3 alpha,5 alpha)-3,21-dihydroxypregnan-20-one (3 alpha,5 alpha-THDOC, +205%, p<0.01), (3 alpha,5 alpha)-3-hydroxyandrostan-17-one (3 alpha,5 alpha-A, +216%, p<0.001), (3 alpha,5 alpha,17 beta)-androstane-3,17-diol (3 alpha,5 alpha-A-diol, +190%, p<0.01). (3 alpha,5 beta)-3-hydroxypregnan-20-one (3 alpha,5 beta-THP) and (3 alpha,5 beta)-3-hydroxyandrostan-17-one (3 alpha,5 beta-A) were not altered, while (3 alpha,5 beta)-3,21-dihydroxypregnan-20-one (3 alpha,5 beta-THDOC) and (3 alpha,5 beta,17 beta)-androstane-3,17-diol (3 alpha,5 beta-A-diol) were increased from undetectable levels to 271 +/- 100 and 2.4 +/- 0.9 pg +/- SEM, respectively (5/8 rats). Progesterone administration increased serum levels of 3 alpha,5 beta-THP (+1806%, p<0.0001), 3 alpha,5 beta-THP (+575%, p<0.001), 3 alpha,5 beta-THDOC (+309%, p<0.001). 3 alpha,5 beta-THDOC levels were increased by 307%, although this increase was not significant because this steroid was detected only in 3/16 control Subjects. Levels of 3 alpha,5 alpha-A, 3 alpha,5 beta-A and pregnenolone were not altered. This method can be used to investigate the physiological and pathological role of neuroactive steroids and to develop bioinarkers and new therapeutics for neurological and psychiatric disorders. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2008.12.015
• 作为产物：
  描述：

  C₂₅H₃₄⁽²⁾H₄O₈ 在 β-glucuronidase from Escherichia coli 作用下， 以 aq. phosphate buffer 为溶剂， 反应 1.5h， 生成 雄甾酮-[D4]
  参考文献：
  名称：

  合成代谢类固醇的气相色谱/化学电离三重四极杆质谱分析：电离和碰撞诱导的解离行为

  摘要：

  新的合成代谢类固醇代谢物和新设计的类固醇的检测在掺杂分析中是一项艰巨的任务。从电子电离气相色谱三重四极杆质谱（GC / EI-MS / MS）切换到化学电离（CI）是提高GC / MS / MS分析灵敏度并促进合成代谢类固醇检测的有效方法。CI还扩展了GC / MS / MS分析的可能性，因为分子离子由于较软的电离而保留为其质子化形式。在EI中，由于分子离子的丰度低或不存在以及广泛的（很大程度上是不可预测的）碎片，很难找到以前未知但预期的代谢物。这项工作的主要目的是研究大量合成代谢雄激素类固醇（AAS）作为其三甲基甲硅烷基衍生物的CI和碰撞诱导解离（CID）行为，以确定结构与CID片段化之间的相关性。需要澄清这些相关性，以阐明未知类固醇和新代谢产物的结构。

  DOI：

  10.1002/rcm.7472