N,N-Dimethyl-2-(6-methyl-1H-indol-1-yl)ethan-1-amine | 87482-17-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N,N-Dimethyl-2-(6-methyl-1H-indol-1-yl)ethan-1-amine
• 英文别名: N,N-dimethyl-2-(6-methylindol-1-yl)ethanamine
• CAS: 87482-17-5
• 化学式: C₁₃H₁₈N₂
• 分子量: 202.299
• InChiKey: ZAXRPTWZFOWFLD-UHFFFAOYSA-N

物化性质

• 沸点：
  319.9±25.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  8.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  6-甲基吲哚 、 2-氯-N,N-二甲基乙胺 在 sodium hydride 作用下， 生成 N,N-Dimethyl-2-(6-methyl-1H-indol-1-yl)ethan-1-amine
  参考文献：
  名称：

  Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines

  摘要：

  A novel series of N,N-dimethylisotryptamine (isoDMT) derivatives, i.e., derivatives of 1-[2-(dimethylamino)ethyl]indole, was prepared and found to be isosteric with their corresponding N,N-dimethyltryptamine (DMT) counterparts with respect to serotonin receptor (rat fundus) affinity. Whereas the isoDMT derivatives possessed a greater affinity than did their corresponding DMT derivatives, they were relatively ineffective in displacing [3H]-5-HT binding from rat brain (cortex) homogenates. In a drug discrimination paradigm, using rats as subjects, 6-OMe-isoDMT produced effects similar to those of 5-OMe-DMT. Attempts to antagonize the discriminative stimulus effects of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) using two of the isoDMT derivatives proved unsuccessful.

  DOI：

  10.1021/jm00367a008

文献信息

• Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines
  作者：Richard A. Glennon、John M. Jacyno、R. Young、J. D. McKenney、David Nelson

  DOI：10.1021/jm00367a008

  日期：1984.1

  A novel series of N,N-dimethylisotryptamine (isoDMT) derivatives, i.e., derivatives of 1-[2-(dimethylamino)ethyl]indole, was prepared and found to be isosteric with their corresponding N,N-dimethyltryptamine (DMT) counterparts with respect to serotonin receptor (rat fundus) affinity. Whereas the isoDMT derivatives possessed a greater affinity than did their corresponding DMT derivatives, they were relatively ineffective in displacing [3H]-5-HT binding from rat brain (cortex) homogenates. In a drug discrimination paradigm, using rats as subjects, 6-OMe-isoDMT produced effects similar to those of 5-OMe-DMT. Attempts to antagonize the discriminative stimulus effects of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) using two of the isoDMT derivatives proved unsuccessful.