2-(5-methoxy-1H-indol-1-yl)-N,N-dimethylethan-1-amine | 87482-13-1

• 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-(5-methoxy-1H-indol-1-yl)-N,N-dimethylethan-1-amine
• 英文别名: [2-(5-Methoxy-indol-1-yl)-ethyl]-dimethyl-amine；2-(5-methoxyindol-1-yl)-N,N-dimethylethanamine
• CAS: 87482-13-1
• 化学式: C₁₃H₁₈N₂O
• 分子量: 218.299
• InChiKey: HRCTXPIFQNOZCQ-UHFFFAOYSA-N

物化性质

• 沸点：
  340.6±22.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  17.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(5-methoxy-1H-indol-1-yl)-N,N-dimethylethan-1-amine 、 富马酸 以 丙酮 为溶剂， 以111 mg的产率得到2-(5-methoxy-1H-indol-1-yl)-N,N-dimethylethan-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：

  5-甲氧基吲哚 、 2-氯-N,N-二甲基乙胺 在 sodium hydride 作用下， 以 六甲基磷酰三胺 、 甲苯 为溶剂， 反应 2.0h， 以65%的产率得到2-(5-methoxy-1H-indol-1-yl)-N,N-dimethylethan-1-amine
  参考文献：
  名称：

  NOVEL INDOLIC DERIVATIVES, THEIR PREPARATION PROCESSES AND THEIR USES IN PARTICULAR AS ANTIBACTERIALS

  摘要：

  该发明涉及使用至少一种具有以下式（I）的化合物，其中R和R3特别是氢原子，R1特别是氢原子或甲基、乙基或异丁基mi基团，R4、R5、R6和R7独立地是氢原子、具有1至7个碳原子的烷氧基团或卤原子，R2是氢原子、O−基团或OH基团，B是N-GP1或NRc基团，GP1是Boc或Cbz基团，Rc是氢原子或甲基或叔丁基基团，用于制备用于治疗与细菌感染相关的疾病症状的药物，特别是用于治疗细菌性疾病。

  公开号：

  US20100144726A1

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。
• [EN] N-SUBSTITUTED INDOLES AND OTHER HETEROCYCLES FOR TREATING BRAIN DISORDERS<br/>[FR] INDOLES N-SUBSTITUÉS ET AUTRES HÉTÉROCYCLES DESTINÉS AU TRAITEMENT DES TROUBLES DU CERVEAU
  申请人：UNIV CALIFORNIA

  公开号：WO2020176597A9

  公开（公告）日：2021-08-05
• 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.
• NOUVEAUX DERIVES INDOLIQUES, LEURS PROCEDES DE PREPARATION ET LEURS UTILISATIONS NOTAMMENT EN TANT QU'ANTIBACTERIENS
  申请人：Université Joseph Fourier

  公开号：EP2121601B1

  公开（公告）日：2016-06-15
• 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.