N-乙基-N-亚硝基-1-[3-(三氟甲基)苯基]-2-丙胺 | 19023-40-6

• 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: N-乙基-N-亚硝基-1-[3-(三氟甲基)苯基]-2-丙胺
• 中文别名: N-亚硝基芬氟拉明
• 英文名称: (+/-)-1-ethyl-1-{1-methyl-2-[3-(trifluoromethyl)phenyl]ethyl}-2-oxohydrazine
• 英文别名: (+/-)-N-nitrosofenfluramine；N-Nitrosofenfluramine；N-ethyl-N-[1-[3-(trifluoromethyl)phenyl]propan-2-yl]nitrous amide
• CAS: 19023-40-6
• 化学式: C₁₂H₁₅F₃N₂O
• 分子量: 260.259
• InChiKey: JVGWNJLSTCQSCZ-UHFFFAOYSA-N

物化性质

• 沸点：
  331.2±42.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)
• 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)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  芬氟拉明 在 sodium nitrate 作用下， 以 氯仿 、 水 为溶剂， 反应 1.0h， 生成 N-乙基-N-亚硝基-1-[3-(三氟甲基)苯基]-2-丙胺
  参考文献：
  名称：

  Effects of N-nitrosofenfluramine, a component of Chinese dietary supplement for weight loss, on CD-1 mice

  摘要：

  Many cases of hepatopathy including deaths have frequently occurred after ingestion of Chinese dietary supplements for weight loss containing N-nitrosofenfluramine (N-fen), a nitroso derivative of fenfluramine (Fen), which was used for the treatment of obesity in the United States. Since Fen decreases appetite by decreasing the serotonin level and exhibits an antibiotic effect, N-fen may have been added, expecting a similar effect. Thus, we synthesized N-fen and orally administered it to mice, and investigated its effect on the liver as well as on the cerebral serotonin nervous system to investigate whether N-fen exhibits an anorectic effect. Three doses of N-fen were orally administered once daily to mice for 1 week. No significant changes in body weight, food intake, and general condition were noted. The liver and kidney weights were significantly increased. On blood chemistry, alkaline phosphatase, aspartate aminotransferase, and alanine aminotransferase activities were increased, and total bilirubin and albumin were slightly decreased. On histopathological examination, acidophilic changes and mild cellular swelling were noted in the liver. The liver drug-metabolizing enzyme (P-450) level was significantly higher. The effect of N-fen on the serotonin (5HT) nervous system was examined by quantitative autoradiography of the mouse brain, and it was found that N-fen did not decrease the 5HT nerve activity. Effects of reuptake and release of monoamine neurotransmitters [dopamine (DA), 5HT, and norepinephrine (NE)] were investigated. N-fen inhibited a little 5HT reuptake, and did not inhibit reuptakes of DA and NE. Moreover, N-fen did not affect release of the three monoamines. The above findings suggested that N-fen did not exhibit a serotonin nerve fiber-mediated anorectic effect in mice, but induced hepatopathy.

  DOI：

  10.1007/s00204-006-0082-4

文献信息

• Effects of N-nitrosofenfluramine, a component of Chinese dietary supplement for weight loss, on CD-1 mice
  作者：Kanako Satoh、Ryouichi Nonaka、Yukie Tada、Nobutaka Fukumori、Akio Ogata、Arisa Yamada、Tsuyoshi Satoh、Fumiko Nagai

  DOI：10.1007/s00204-006-0082-4

  日期：2006.9

  Many cases of hepatopathy including deaths have frequently occurred after ingestion of Chinese dietary supplements for weight loss containing N-nitrosofenfluramine (N-fen), a nitroso derivative of fenfluramine (Fen), which was used for the treatment of obesity in the United States. Since Fen decreases appetite by decreasing the serotonin level and exhibits an antibiotic effect, N-fen may have been added, expecting a similar effect. Thus, we synthesized N-fen and orally administered it to mice, and investigated its effect on the liver as well as on the cerebral serotonin nervous system to investigate whether N-fen exhibits an anorectic effect. Three doses of N-fen were orally administered once daily to mice for 1 week. No significant changes in body weight, food intake, and general condition were noted. The liver and kidney weights were significantly increased. On blood chemistry, alkaline phosphatase, aspartate aminotransferase, and alanine aminotransferase activities were increased, and total bilirubin and albumin were slightly decreased. On histopathological examination, acidophilic changes and mild cellular swelling were noted in the liver. The liver drug-metabolizing enzyme (P-450) level was significantly higher. The effect of N-fen on the serotonin (5HT) nervous system was examined by quantitative autoradiography of the mouse brain, and it was found that N-fen did not decrease the 5HT nerve activity. Effects of reuptake and release of monoamine neurotransmitters [dopamine (DA), 5HT, and norepinephrine (NE)] were investigated. N-fen inhibited a little 5HT reuptake, and did not inhibit reuptakes of DA and NE. Moreover, N-fen did not affect release of the three monoamines. The above findings suggested that N-fen did not exhibit a serotonin nerve fiber-mediated anorectic effect in mice, but induced hepatopathy.