5-氯安非他酮富马酸盐 | 1193779-50-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-氯安非他酮富马酸盐
• 英文名称: 2-(tert-butylamino)-3',5'-dichloropropiophenone fumarate
• 英文别名: 5-Chloro Bupropion Fumarate；(E)-but-2-enedioic acid;2-(tert-butylamino)-1-(3,5-dichlorophenyl)propan-1-one
• CAS: 1193779-50-8
• 化学式: C₄H₄O₄*C₁₃H₁₇Cl₂NO
• 分子量: 390.263
• InChiKey: MGHPTSVYSLXGEG-WLHGVMLRSA-N

物化性质

• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  安非他酮杂质 、 富马酸 以 甲醇 为溶剂， 反应 0.25h， 以1.69 g的产率得到5-氯安非他酮富马酸盐
  参考文献：
  名称：

  [EN] MONOAMINE REUPTAKE INHIBITORS
  [FR] INHIBITEURS DE LA RECAPTURE DES MONOAMINES

  摘要：

  该发明提供了一种能够抑制一种或多种单胺再摄取的丁丙吡胺类似化合物。这些化合物可以选择性地结合到一种或多种单胺转运体上，包括多巴胺、去甲肾上腺素和5-羟色胺的转运体。这些化合物可用于治疗对单胺再摄取抑制有响应的疾病，包括成瘾、抑郁和肥胖症。

  公开号：

  WO2010121022A1

文献信息

• Synthesis and Biological Evaluation of Bupropion Analogues as Potential Pharmacotherapies for Cocaine Addiction
  作者：F. Ivy Carroll、Bruce E. Blough、Philip Abraham、Andrew C. Mills、J. Ashley Holleman、Scott A. Wolckenhauer、Ann M. Decker、Antonio Landavazo、K. Timothy McElroy、Hernán A. Navarro、Michael B. Gatch、Michael J. Forster

  DOI：10.1021/jm901189z

  日期：2009.11.12

  A series of bupropion (1a) analogues (1b-1ff) were synthesized, and their in vitro and in vivo pharmacological properties evaluated with the goal of developing a la analogue that had better properties for treating addictions. Their in vitro pharmacological properties were examined by [H-3]dopamine ([H-3]DA), [H-3]serotonin ([H-3](HT)-H-5), and [H-3]norepinephrine ([H-3]NE) uptake inhibition studies, and by binding studies at the dopamine, serotonin, and norepinephrine transporters using [I-125]RTI-55 in cloned transporters. Several analogues showed increased [H-3]DA uptake inhibition with reduced or little change in [H-3](HT)-H-5 and [H-3]NE uptake inhibition relative to bupropion. Thirty-five analogues were evaluated in a 1 h locomotor activity observation test and 32 in an 8 h locomotor activity observation test and compared to the locomotor activity of cocaine. Twenty-four analogues were evaluated for generalization to cocaine drug discrimination after i.p. administration, and twelve analogues were tested in a tithe course cocaine discrimination study using oral administration. 2-(N-Cyclopropylamino)-3-chloropropiophenone (1x) had the most favorable in vitro efficacy and in vivo pharmacological profile for an indirect dopamine agonist pharmacotherapy for treating cocaine, methamphetamine, nicotine, and other drugs of abuse addiction.