[2-(4-Methoxy-1H-indol-3-yl)-ethyl]-methyl-amine | 329703-33-5

• 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: [2-(4-Methoxy-1H-indol-3-yl)-ethyl]-methyl-amine
• 英文别名: 2-(4-methoxy-1H-indol-3-yl)-N-methylethanamine
• CAS: 329703-33-5
• 化学式: C₁₂H₁₆N₂O
• 分子量: 204.272
• InChiKey: PLNZCXIDJPYSHZ-UHFFFAOYSA-N

物化性质

• 沸点：
  374.5±27.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  37
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [2-(4-Methoxy-1H-indol-3-yl)-ethyl]-methyl-amine 、 丙酮 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 15.0h， 生成 N-[2-(4-甲氧基-1H-吲哚-3-基)乙基]-N-甲基-2-丙胺
  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：

  4-甲氧基吲哚 在 palladium on activated charcoal lithium aluminium tetrahydride 、 叔丁基邻苯二酚 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 、 xylene 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 30.5h， 生成 [2-(4-Methoxy-1H-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

文献信息

• TRYPTAMINE COMPOSITIONS FOR ENHANCING NEURITE OUTGROWTH
  申请人：STAMETS Paul Edward

  公开号：US20210069170A1

  公开（公告）日：2021-03-11

  Described herein are neurotrophic and nootropic compositions and methods for treating subjects with such compositions. In one aspect the composition comprises one or more tryptamines or in pure form or extracts from psilocybin containing mushrooms, or combinations thereof optionally combined with one or more phenethylamines or amphetamines in pure form or extracts from a plant or mushroom, or combinations thereof, optionally one or more erinacines or hericenones in pure form, extracts from Hericium mushroom species (e.g., H. erinaceus, H. coralloides, H. ramosum ) or combinations thereof, optionally one or more cannabinoids in pure form or extracts from Cannabis sativa, Cannabis sativa, Cannabis indica , or Cannabis ruderalis , optionally, one or more adversive compounds, and optionally one or more pharmaceutically acceptable excipients.
• [EN] TRYPTAMINE COMPOSITIONS FOR ENHANCING NEURITE OUTGROWTH<br/>[FR] COMPOSITIONS DE TRYPTAMINES DESTINÉES À AMÉLIORER L'EXCROISSANCE DES NEURITES
  申请人：STAMETS PAUL EDWARD

  公开号：WO2021101926A1

  公开（公告）日：2021-05-27

  Described herein are neurotrophic and nootropic compositions and methods for treating subjects with such compositions. In one aspect the composition comprises one or more tryptamines or in pure form or extracts from psilocybin containing mushrooms, or combinations thereof optionally combined with one or more phenethylamines or amphetamines in pure form or extracts from a plant or mushroom, or combinations thereof, optionally one or more erinacines or hericenones in pure form, extracts from Hericium mushroom species (e.g., H. erinaceus, H. coralloides, H. ramosum) or combinations thereof, optionally one or more cannabinoids in pure form or extracts from Cannabis sativa, Cannabis sativa, Cannabis indica, or Cannabis ruderalis, optionally, one or more adversive compounds, and optionally one or more pharmaceutically acceptable excipients.
• 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.