[3-(5-Methoxy-1H-indol-3-yl)-propyl]-dimethyl-amine | 709028-93-3

• 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: [3-(5-Methoxy-1H-indol-3-yl)-propyl]-dimethyl-amine
• 英文别名: 3-(3-(Dimethylamino)propyl)-5-methoxy-1H-indole；3-(5-methoxy-1H-indol-3-yl)-N,N-dimethylpropan-1-amine
• CAS: 709028-93-3
• 化学式: C₁₄H₂₀N₂O
• 分子量: 232.326
• InChiKey: AAVYCYAMAJRINF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  28.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-甲氧基吲哚 在 cis-2-methylfuryl-3-N-methyl-5-benzyl-4-imidazolidone 、 三乙酰氧基硼氢化钠 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 异丙醇 为溶剂， 反应 3.0h， 生成 [3-(5-Methoxy-1H-indol-3-yl)-propyl]-dimethyl-amine
  参考文献：
  名称：

  One-pot synthesis of homotryptamines from indoles

  摘要：

  A method is presented for the one-pot synthesis of homotryptamines by the MacMillan reaction of indoles with acrolein followed by reductive amination. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.070

文献信息

• Homotryptamines as potent and selective serotonin reuptake inhibitors (SSRIs)
  作者：William D. Schmitz、Derek J. Denhart、Allison B. Brenner、Jonathan L. Ditta、Ronald J. Mattson、Gail K. Mattson、Thaddeus F. Molski、John E. Macor

  DOI：10.1016/j.bmcl.2005.01.059

  日期：2005.3

  A series of N,N-dimethylhomotryptamines was prepared and their binding affinities at the serotonin transporter (SERT) were determined. Compounds possessing an electron withdrawing substituent at the C5-position of the indole nucleus were found to be potent SSRIs. Initial attempts at conformational restriction of the propylamine sidechain by incorporation of a quinuclidine bicyclic structure did not improve binding affinity at SERT. (c) 2005 Elsevier Ltd. All rights reserved.
• [EN] DEUTERATED OR PARTIALLY DEUTERATED N,N-DIMETHYLTRYPTAMINE COMPOUNDS<br/>[FR] COMPOSÉS DE N,N-DIMÉTHYLTRYPTAMINE DEUTÉRÉS OU PARTIELLEMENT DEUTÉRÉS
  申请人：[en]SMALL PHARMA LTD

  公开号：WO2022117359A1

  公开（公告）日：2022-06-09

  The present invention relates to compounds of formula (I) as defined herein, which comprise a greater proportion of deuterium to protium than naturally found in hydrogen; and compositions, including pharmaceutical compositions, comprising these compounds and optionally analogous compounds of formula (I), which are not deuterium-enriched. These compounds and compositions are of use in therapy, in particular in the treatment of psychiatric or neurological disorders. Varying the amounts of the different compounds within the compositions of the invention allows tailoring of the compositions' therapeutic effects. A particularly efficient synthetic method which enables compounds of formula (I) and related compounds of formula (I') is also provided.