β-pyrrolidino-2-nitro-3-methoxystyrene | 96096-68-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: β-pyrrolidino-2-nitro-3-methoxystyrene
• 英文别名: 1-[2-(3-Methoxy-2-nitrophenyl)ethenyl]pyrrolidine
• CAS: 96096-68-3
• 化学式: C₁₃H₁₆N₂O₃
• 分子量: 248.282
• InChiKey: MVLONDZYHRQJTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 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：
  58.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  β-pyrrolidino-2-nitro-3-methoxystyrene 在 palladium on activated charcoal 、 镍 lithium aluminium tetrahydride 、 叔丁基邻苯二酚 、 氢气 、 potassium carbonate 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 甲苯 、 xylene 为溶剂， 25.0~60.0 ℃ 、344.73 kPa 条件下， 反应 31.5h， 生成 [2-(7-methoxy-indol-3-yl)-ethyl]-methyl-amine
  参考文献：
  名称：

  Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents

  摘要：

  Eight N-methyl-N-isopropyltryptamines (MIPTs) possessing various aromatic oxygen substituents were prepared, characterized, and evaluated for hallucinogenic activity in man. In at least two instances (the Ar H and the Ar 5-OCH3, 1 and 4) the unsymmetrical nitrogen substitution led to a substantial increase in potency as well as oral activity when compared to the symmetrical dimethyl homologues. Qualitatively, 4-hydroxy-N-methyl-N-isopropyltryptamine (2) was the most interesting in overall effect, producing a classic hallucinogenic profile. The 5-methoxy congener 4 resulted in a state characterized by heightened conceptual stimulation lacking in visual phenomena. Other members of the series exhibited diminished effects.

  DOI：

  10.1021/jm00145a007
• 作为产物：
  描述：

  四氢吡咯 、 3-甲基-2-硝基苯甲醚 、 N,N-二甲基甲酰胺二甲基缩醛 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以54%的产率得到β-pyrrolidino-2-nitro-3-methoxystyrene
  参考文献：
  名称：

  Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents

  摘要：

  Eight N-methyl-N-isopropyltryptamines (MIPTs) possessing various aromatic oxygen substituents were prepared, characterized, and evaluated for hallucinogenic activity in man. In at least two instances (the Ar H and the Ar 5-OCH3, 1 and 4) the unsymmetrical nitrogen substitution led to a substantial increase in potency as well as oral activity when compared to the symmetrical dimethyl homologues. Qualitatively, 4-hydroxy-N-methyl-N-isopropyltryptamine (2) was the most interesting in overall effect, producing a classic hallucinogenic profile. The 5-methoxy congener 4 resulted in a state characterized by heightened conceptual stimulation lacking in visual phenomena. Other members of the series exhibited diminished effects.

  DOI：

  10.1021/jm00145a007

文献信息

• Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents
  作者：David B. Repke、Douglas B. Grotjahn、Alexander T. Shulgin

  DOI：10.1021/jm00145a007

  日期：1985.7

  Eight N-methyl-N-isopropyltryptamines (MIPTs) possessing various aromatic oxygen substituents were prepared, characterized, and evaluated for hallucinogenic activity in man. In at least two instances (the Ar H and the Ar 5-OCH3, 1 and 4) the unsymmetrical nitrogen substitution led to a substantial increase in potency as well as oral activity when compared to the symmetrical dimethyl homologues. Qualitatively, 4-hydroxy-N-methyl-N-isopropyltryptamine (2) was the most interesting in overall effect, producing a classic hallucinogenic profile. The 5-methoxy congener 4 resulted in a state characterized by heightened conceptual stimulation lacking in visual phenomena. Other members of the series exhibited diminished effects.