[2-(6-methoxy-indol-3-yl)-ethyl]-methyl-amine | 329703-35-7

• 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-(6-methoxy-indol-3-yl)-ethyl]-methyl-amine
• 英文别名: <2-(6-Methoxy-indol-3-yl)-ethyl>-methyl-amin；6-Methoxy-N-methyl-tryptamin；2-(6-methoxy-1H-indol-3-yl)-N-methylethanamine
• CAS: 329703-35-7
• 化学式: C₁₂H₁₆N₂O
• 分子量: 204.272
• InChiKey: AIWADACJVVHAPN-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)：
  2.3
• 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-(6-methoxy-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-(6-methoxy-1H-indol-3-yl)ethyl]-N-methylpropan-2-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：

  benzyl N-[2-(6-methoxy-1H-indol-3-yl)ethyl]carbamate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 [2-(6-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

文献信息

• Novel Heterocyclic Substituted Carbonyl Derivatives and Their Use as Dopamine D3 Receptor Ligands
  申请人：Hendrix James A.

  公开号：US20090247509A1

  公开（公告）日：2009-10-01

  The invention relates to heterocyclic substituted carbonyl derivatives that display selective binding to dopamine D 3 receptors. In another aspect, the invention relates to a method for treating central nervous system disorders associated with the dopamine D 3 receptor activity in a patient in need of such treatment comprising administering to the subject a therapeutically effective amount of said compounds for alleviation of such disorder. The central nervous system disorders that may be treated with these compounds include Psychotic Disorders, Substance Dependence, Substance Abuse, Dyskinetic Disorders (e.g. Parkinson's Disease, Parkinsonism, Neuroleptic-Induced Tardive Dyskinesia, Gilles de la Tourette Syndrome and Huntington's Disease), Dementia, Anxiety Disorders, Sleep Disorders, Circadian Rhythm Disorders and Mood Disorders. The subject invention is also directed towards processes for the preparation of the compounds described herein as well as methods for making and using the compounds as imaging agents for dopamine D 3 receptors.

  本发明涉及杂环取代羰基衍生物，其表现出对多巴胺D3受体的选择性结合。另一方面，本发明涉及一种治疗与多巴胺D3受体活性相关的中枢神经系统疾病的方法，该方法包括向需要此类治疗的患者施用所述化合物的治疗有效量，以缓解此类疾病。这些化合物可以治疗的中枢神经系统疾病包括精神疾病、物质依赖、物质滥用、运动障碍（例如帕金森病、帕金森综合症、神经阻滞引起的迟发性运动障碍、吉尔斯-德-拉-图雷综合症和亨廷顿病）、痴呆、焦虑症、睡眠障碍、昼夜节律紊乱和情绪障碍。本发明还涉及制备所述化合物的方法以及将所述化合物作为多巴胺D3受体成像剂的制备和使用方法。
• Novel heterocyclic substituted carbonyl derivatives and their use as dopamine D3 receptor ligands
  申请人：Hendrix A. James

  公开号：US20070161641A1

  公开（公告）日：2007-07-12

  The invention relates to heterocyclic substituted carbonyl derivatives that display selective binding to dopamine D 3 receptors. In another aspect, the invention relates is to a method for treating central nervous system disorders associated with the dopamine D 3 receptor activity in a patient in need of such treatment comprising administering to the subject a therapeutically effective amount of said compounds for alleviation of such disorder. The central nervous system disorders that may be treated with these compounds include Psychotic Disorders, Substance Dependence, Substance Abuse, Dyskinetic Disorders (e.g. Parkinson's Disease, Parkinsonism, Neuroleptic-Induced Tardive Dyskinesia, Gilles de la Tourette Syndrome and Huntington's Disease), Dementia, Anxiety Disorders, Sleep Disorders, Circadian Rhythm Disorders and Mood Disorders. The subject invention is also directed towards processes for the preparation of the compounds described herein as well as methods for making and using the compounds as imaging agents for dopamine D 3 receptors.

  本发明涉及杂环取代羰基衍生物，其具有选择性地与多巴胺D3受体结合。另一方面，本发明涉及一种治疗中枢神经系统疾病的方法，该疾病与多巴胺D3受体活性有关，包括对患者进行治疗，向患者施用所述化合物的治疗有效量，以缓解此类疾病。这些化合物可以治疗的中枢神经系统疾病包括精神病性障碍、物质依赖、物质滥用、运动障碍（例如帕金森病、帕金森综合症、神经阻滞剂引起的迟发性运动障碍、吉尔·德·拉·图雷特综合症和亨廷顿病）、痴呆、焦虑症、睡眠障碍、昼夜节律紊乱和情绪障碍。本发明还涉及所述化合物的制备过程，以及将所述化合物作为多巴胺D3受体成像剂的制备和使用方法。
• Pyrimidine derivatives as alk-5 Inhibitors
  申请人：Leblanc Catherine

  公开号：US20090209539A1

  公开（公告）日：2009-08-20

  Compounds of formula (I) in free or salt or solvate form, where T 1 , T 2 , R a and R b have the meanings as indicated in the specification, are useful for treating inflammatory or obstructive airways, pulmonary hypertension, pulmonary fibrosis, liver fibrosis, muscle diseases and systemic skeletal disorders. Pharmaceutical compositions that contain the compounds and processes for preparing the compounds are also described.

  式(I)的化合物以自由形式、盐形式或溶剂合形式存在，其中T1、T2、Ra和Rb的含义如说明书中所示，可用于治疗炎症或阻塞性呼吸道、肺动脉高压、肺纤维化、肝纤维化、肌肉疾病和系统性骨骼疾病。还描述了含有该化合物的制药组合物和制备该化合物的方法。
• US7186724B2
  申请人：——

  公开号：US7186724B2

  公开（公告）日：2007-03-06
• US7521445B2
  申请人：——

  公开号：US7521445B2

  公开（公告）日：2009-04-21