N,N-dimethyl-2-(2-methyl-1H-indol-1-yl)ethan-1-amine | 1128165-36-5

• 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-(2-methyl-1H-indol-1-yl)ethan-1-amine
• 英文别名: N,N-dimethyl-2-(2-methylindol-1-yl)ethanamine
• CAS: 1128165-36-5
• 化学式: C₁₃H₁₈N₂
• 分子量: 202.299
• InChiKey: CMJUSCMKELZWJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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

• 作为反应物：
  描述：

  N,N-dimethyl-2-(2-methyl-1H-indol-1-yl)ethan-1-amine 、 富马酸 以 丙酮 为溶剂， 以172 mg的产率得到N,N-dimethyl-2-(2-methyl-1H-indol-1-yl)ethan-1-amine fumarate
  参考文献：
  名称：

  Identification of Psychoplastogenic N,N-Dimethylaminoisotryptamine (isoDMT) Analogues through Structure–Activity Relationship Studies

  摘要：

  Ketamine, N,N-dimethyltryptamine (DMT), and other psychoplastogens possess enormous potential as neurotherapeutics due to their ability to potently promote neuronal growth. Here, we report the first-ever structure activity relationship study with the explicit goal of identifying novel psychoplastogens. We have discovered several key features of the psychoplastogenic pharmacophore and used this information to develop N,N-dimethylaminoisotryptamine (isoDMT) psychoplastogens that are easier to synthesize, have improved physicochemical properties, and possess reduced hallucinogenic potential as compared to their DMT counterparts.

  DOI：

  10.1021/acs.jmedchem.9b01404
• 作为产物：
  描述：

  2-甲基吲哚 、 2-氯-N,N-二甲基乙胺 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 以75%的产率得到N,N-dimethyl-2-(2-methyl-1H-indol-1-yl)ethan-1-amine
  参考文献：
  名称：

  Inhibition of Dynamin Mediated Endocytosis by the Dynoles—Synthesis and Functional Activity of a Family of Indoles

  摘要：

  Screening identified two bisindolylmaleimides as 100 mu M inhibitors of the GTPase activity of dynamin I. Focused library approaches allowed development of indole-based dynamin inhibitors called dynoles. 100-Fold in vitro enhancement of potency was noted with the best inhibitor, 2-cyano-3-(1-(2-(dimethylamino)ethyl)- 1H-indol-3-yl)-N-octylacrylamide (dynole 34-2), a 1.3 +/- 0.3 mu M dynamin I inhibitor. Dynole 34-2 potently inhibited receptor mediated endocytosis (RME) internalization of Texas red-transferrin. The rank order of potency for a variety of dynole analogues on RME in U2OS cells matched their rank order for dynamin inhibition, suggesting that the mechanism of inhibition is via dynamin. Dynoles are the most active dynamin I inhibitors reported for in vitro or RME evaluations. Dynole 34-2 is 15-fold more active than dynasore against dynamin I and 6-fold more active against dynamin mediated RME (IC50 similar to 15 mu M; RME IC50 similar to 80 mu M). The dynoles represent a new series of tools to better probe endocytosis and dynamin-mediated trafficking events in a variety of cells.

  DOI：

  10.1021/jm900036m

文献信息

• N-substituted indoles and other heterocycles for treating brain disorders
  申请人：The Regents of the University of California

  公开号：US11254640B2

  公开（公告）日：2022-02-22

  The present invention provides N-substituted indoles and other heterocycles and methods of using the compounds for treating brain disorders.

  本发明提供了 N-取代吲哚和其他杂环化合物以及使用这些化合物治疗脑部疾病的方法。
• N-SUBSTITUTED INDOLES AND OTHER HETEROCYCLES FOR TREATING BRAIN DISORDERS
  申请人：The Regents of the University of California

  公开号：US20210332012A1

  公开（公告）日：2021-10-28

  The present invention provides N-substituted indoles and other heterocycles and methods of using the compounds for treating brain disorders.
• Inhibition of Dynamin Mediated Endocytosis by the <i>Dynoles</i>—Synthesis and Functional Activity of a Family of Indoles
  作者：Timothy A. Hill、Christopher P. Gordon、Andrew B. McGeachie、Barbara Venn-Brown、Luke R. Odell、Ngoc Chau、Annie Quan、Anna Mariana、Jennette A. Sakoff、Megan Chircop (nee Fabbro)、Phillip J. Robinson、Adam McCluskey

  DOI：10.1021/jm900036m

  日期：2009.6.25

  Screening identified two bisindolylmaleimides as 100 mu M inhibitors of the GTPase activity of dynamin I. Focused library approaches allowed development of indole-based dynamin inhibitors called dynoles. 100-Fold in vitro enhancement of potency was noted with the best inhibitor, 2-cyano-3-(1-(2-(dimethylamino)ethyl)- 1H-indol-3-yl)-N-octylacrylamide (dynole 34-2), a 1.3 +/- 0.3 mu M dynamin I inhibitor. Dynole 34-2 potently inhibited receptor mediated endocytosis (RME) internalization of Texas red-transferrin. The rank order of potency for a variety of dynole analogues on RME in U2OS cells matched their rank order for dynamin inhibition, suggesting that the mechanism of inhibition is via dynamin. Dynoles are the most active dynamin I inhibitors reported for in vitro or RME evaluations. Dynole 34-2 is 15-fold more active than dynasore against dynamin I and 6-fold more active against dynamin mediated RME (IC50 similar to 15 mu M; RME IC50 similar to 80 mu M). The dynoles represent a new series of tools to better probe endocytosis and dynamin-mediated trafficking events in a variety of cells.
• Identification of Psychoplastogenic <i>N</i>,<i>N</i>-Dimethylaminoisotryptamine (isoDMT) Analogues through Structure–Activity Relationship Studies
  作者：Lee E. Dunlap、Arya Azinfar、Calvin Ly、Lindsay P. Cameron、Jayashri Viswanathan、Robert J. Tombari、Douglas Myers-Turnbull、Jack C. Taylor、Ana Cristina Grodzki、Pamela J. Lein、David Kokel、David E. Olson

  DOI：10.1021/acs.jmedchem.9b01404

  日期：2020.2.13

  Ketamine, N,N-dimethyltryptamine (DMT), and other psychoplastogens possess enormous potential as neurotherapeutics due to their ability to potently promote neuronal growth. Here, we report the first-ever structure activity relationship study with the explicit goal of identifying novel psychoplastogens. We have discovered several key features of the psychoplastogenic pharmacophore and used this information to develop N,N-dimethylaminoisotryptamine (isoDMT) psychoplastogens that are easier to synthesize, have improved physicochemical properties, and possess reduced hallucinogenic potential as compared to their DMT counterparts.