4,5-亚甲基二氧基吲哚 | 17367-93-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 中文名称: 4,5-亚甲基二氧基吲哚
• 英文名称: 4,5-(methylenedioxy)indole
• 英文别名: 6H-[1,3]Dioxolo[4,5-e]indole
• CAS: 17367-93-0
• 化学式: C₉H₇NO₂
• mdl: MFCD08458984
• 分子量: 161.16
• InChiKey: KWRKIMIEEYHFCG-UHFFFAOYSA-N

物化性质

• 熔点：
  90-92 °C
• 沸点：
  334.7±11.0 °C(Predicted)
• 密度：
  1.425±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  4,5-亚甲基二氧基吲哚 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.5h， 生成 4,5-(methylenedioxy)-N,N-dimethyltryptamine
  参考文献：
  名称：

  Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety

  摘要：

  A series of N,N-dialkyltryptamines with methylthio or methylenedioxy substituents in the 4, 5, and 6 positions and methyl or isopropyl on the side-chain nitrogen has been synthesized. The behavioral pharmacology of these compounds showed them to possess Bovet-Gatti profiles characteristic of hallucinogens, and the 5-methylthio congener was the most potent. Binding studies at [3H]LSD and [3H]5-HT sites demonstrated that no single structural feature correlated with binding or behavioral changes and suggest a complex mode of action for these potential hallucinogenic agents.

  DOI：

  10.1021/jm00350a005
• 作为产物：
  描述：

  4-甲基-1,3-苯并二氧戊环 在 palladium on activated charcoal mercury(II) diacetate 、 氢气 、 硝酸 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 80.0 ℃ 、303.98 kPa 条件下， 反应 13.0h， 生成 4,5-亚甲基二氧基吲哚
  参考文献：
  名称：

  Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety

  摘要：

  A series of N,N-dialkyltryptamines with methylthio or methylenedioxy substituents in the 4, 5, and 6 positions and methyl or isopropyl on the side-chain nitrogen has been synthesized. The behavioral pharmacology of these compounds showed them to possess Bovet-Gatti profiles characteristic of hallucinogens, and the 5-methylthio congener was the most potent. Binding studies at [3H]LSD and [3H]5-HT sites demonstrated that no single structural feature correlated with binding or behavioral changes and suggest a complex mode of action for these potential hallucinogenic agents.

  DOI：

  10.1021/jm00350a005

文献信息

• Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety
  作者：Toni B. Kline、Frederick Benington、Richard D. Morin、John M. Beaton

  DOI：10.1021/jm00350a005

  日期：1982.8

  A series of N,N-dialkyltryptamines with methylthio or methylenedioxy substituents in the 4, 5, and 6 positions and methyl or isopropyl on the side-chain nitrogen has been synthesized. The behavioral pharmacology of these compounds showed them to possess Bovet-Gatti profiles characteristic of hallucinogens, and the 5-methylthio congener was the most potent. Binding studies at [3H]LSD and [3H]5-HT sites demonstrated that no single structural feature correlated with binding or behavioral changes and suggest a complex mode of action for these potential hallucinogenic agents.