去甲肾上腺素杂质 | 24159-36-2

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 去甲肾上腺素杂质
• 英文名称: dopamine β-sulfonate
• 英文别名: Norepinephrine Sulfonic Acid；2-amino-1-(3,4-dihydroxyphenyl)ethanesulfonic acid
• CAS: 24159-36-2；78995-76-3
• 化学式: C₈H₁₁NO₅S
• 分子量: 233.245
• InChiKey: WJIJWGIAHLTTFH-UHFFFAOYSA-N

物化性质

• 溶解度：
  DMSO（稍微加热）、水（稍微加热）

计算性质

• 辛醇/水分配系数(LogP)：
  -4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  DL-正肾上腺素盐酸盐 在 sodium disulfite 作用下， 以 水 为溶剂， 以55%的产率得到去甲肾上腺素杂质
  参考文献：
  名称：

  Synthesis and adrenoceptor affinity of some highly polar .beta.-substituted catecholamines

  摘要：

  In order to assess the potential for sympathomimetic or sympatholytic activity within the series of catecholamine beta-sulfonates 3a-c, alpha- and beta-adrenoceptor binding affinities were determined using rat brain homogenate preparations. Furthermore, their potential for indirect activity was assessed by measurement of blockade of norepinephrine uptake into rat synaptosomal preparations. Activity was uniformly low or nonexistent throughout the series. The possibility of unfavorable solution conformational distribution within the series was investigated by examination of the side chain vicinal 1H NMR coupling constants, but no differences that could account for the lack of affinity were found. The observed behavior may be due to receptor intolerance of the bulky beta-sulfonate substituent or an electronic mismatch in which normal H bonding is significantly altered.

  DOI：

  10.1021/jm00142a026

文献信息

• Synthesis and adrenoceptor affinity of some highly polar .beta.-substituted catecholamines
  作者：James G. Henkel、Neil Sikand、Alexandros Makriyannis、Gerald Gianutsos

  DOI：10.1021/jm00142a026

  日期：1981.10

  In order to assess the potential for sympathomimetic or sympatholytic activity within the series of catecholamine beta-sulfonates 3a-c, alpha- and beta-adrenoceptor binding affinities were determined using rat brain homogenate preparations. Furthermore, their potential for indirect activity was assessed by measurement of blockade of norepinephrine uptake into rat synaptosomal preparations. Activity was uniformly low or nonexistent throughout the series. The possibility of unfavorable solution conformational distribution within the series was investigated by examination of the side chain vicinal 1H NMR coupling constants, but no differences that could account for the lack of affinity were found. The observed behavior may be due to receptor intolerance of the bulky beta-sulfonate substituent or an electronic mismatch in which normal H bonding is significantly altered.