4-氨基-5-氯-N-[2-(二乙基氨基)乙基]-2-甲氧基苯甲酰胺 N-氧化物; 甲氧氯普胺 N-氧化物 | 171367-22-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氨基-5-氯-N-[2-(二乙基氨基)乙基]-2-甲氧基苯甲酰胺 N-氧化物; 甲氧氯普胺 N-氧化物
• 中文别名: 4-氨基-5-氯-N-[2-(二乙基氨基)乙基]-2-甲氧基苯甲酰胺N-氧化物;甲氧氯普胺N-氧化物；甲氧氯普安N氧化物
• 英文名称: metoclopramide N-oxide
• 英文别名: 2-[(4-amino-5-chloro-2-methoxybenzoyl)amino]-N,N-diethylethanamine oxide
• CAS: 171367-22-9
• 化学式: C₁₄H₂₂ClN₃O₃
• 分子量: 315.8
• InChiKey: ZEJQXOWYPGUAMD-UHFFFAOYSA-N

物化性质

• 熔点：
  >130°C (dec.)
• 溶解度：
  可溶于氯仿（轻微、加热）、DMSO（轻微）、甲醇（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  82.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-氨基-5-氯-N-[2-(二乙基氨基)乙基]-2-甲氧基苯甲酰胺 N-氧化物; 甲氧氯普胺 N-氧化物 在 iron(II) chloride 作用下， 以 二氯甲烷 为溶剂， 生成 N-去乙基甲氧氯普胺
  参考文献：
  名称：

  Secondary Amines from the lron(II) Ion-Catalyzed Reaction of Amine Oxides: A General Method for the Dealkylation of Tertiary Amines

  摘要：

  DOI：

  10.1055/s-1985-31342
• 作为产物：
  描述：

  甲氧氯普胺 在 双氧水 作用下， 以77%的产率得到4-氨基-5-氯-N-[2-(二乙基氨基)乙基]-2-甲氧基苯甲酰胺 N-氧化物; 甲氧氯普胺 N-氧化物
  参考文献：
  名称：

  Identification and full characterization of a new metabolite of metoclopramide

  摘要：

  The metabolism of metoclopramide 1 has been reinvestigated by HPLC coupled with mass spectrometry. The urine of healthy volunteers showed the presence of a new metabolite 2 derived from the enzymatic oxidation of the primary aromatic amino group of 1 to the hydroxylamino moiety. The structure of the new metabolite was ascertained by its fragmentation pattern in the mass spectrometer and unambiguously secured by an independent synthesis. In addition, the tertiary amine group of 1 was selectively oxidized to the corresponding N-oxide. This compound and its ring oxidation metabolites were not detected in the urine of the tested volunteers.

  DOI：

  10.1016/0223-5234(96)88294-8

文献信息

• Identification and full characterization of a new metabolite of metoclopramide
  作者：V Maurich、M De Amici、C De Micheli、P Rossato

  DOI：10.1016/0223-5234(96)88294-8

  日期：1995.1

  The metabolism of metoclopramide 1 has been reinvestigated by HPLC coupled with mass spectrometry. The urine of healthy volunteers showed the presence of a new metabolite 2 derived from the enzymatic oxidation of the primary aromatic amino group of 1 to the hydroxylamino moiety. The structure of the new metabolite was ascertained by its fragmentation pattern in the mass spectrometer and unambiguously secured by an independent synthesis. In addition, the tertiary amine group of 1 was selectively oxidized to the corresponding N-oxide. This compound and its ring oxidation metabolites were not detected in the urine of the tested volunteers.
• Secondary Amines from the lron(II) Ion-Catalyzed Reaction of Amine Oxides: A General Method for the Dealkylation of Tertiary Amines
  作者：Ivo Monković、Henry Wong、Carol Bachand

  DOI：10.1055/s-1985-31342

  日期：——