N-methyl-2-isopropyltryptamine hydrochloride | 1338383-22-4

• 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-methyl-2-isopropyltryptamine hydrochloride
• 英文别名: N-methyl-2-(2-propan-2-yl-1H-indol-3-yl)ethanamine;hydrochloride
• CAS: 1338383-22-4
• 化学式: C₁₄H₂₀N₂*ClH
• 分子量: 252.787
• InChiKey: HUNORTSEFPMBGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  27.8
• 氢给体数：
  3
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-isopropyltryptamine 在 盐酸 、 lithium aluminium tetrahydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 氯仿 、 水 、 乙酸乙酯 为溶剂， 生成 N-methyl-2-isopropyltryptamine hydrochloride
  参考文献：
  名称：

  Deconstruction of the α4β2 Nicotinic Acetylcholine Receptor Positive Allosteric Modulator Desformylflustrabromine

  摘要：

  Desformylflustrabromine (dFBr; 1), perhaps the first selective positive allosteric modulator of alpha 4 beta 2 neuronal nicotinic acetylcholine (nACh) receptors, was deconstructed to determine which structural features contribute to its actions on receptors expressed in Xenopus ooycytes using two-electrode voltage clamp techniques. Although the intact structure of 1 was found to be optimal, several deconstructed analogs retained activity. Neither the 6-bromo substituent nor the entire 2-position chain is required for activity. In particular, reduction of the olefinic side chain of 1, as seen with 6, not only resulted in retention of activity/potency but in enhanced selectivity for alpha 4 beta 2 versus alpha 7 nACh receptors. Pharmacophoric features for the allosteric modulation of alpha 4 beta 2 nACh receptors by 1 were identified.

  DOI：

  10.1021/jm200834x

文献信息

• Deconstruction of the α4β2 Nicotinic Acetylcholine Receptor Positive Allosteric Modulator Desformylflustrabromine
  作者：Nadezhda German、Jin-Sung Kim、Atul Jain、Malgorzata Dukat、Anshul Pandya、Yilong Ma、Maegan Weltzin、Marvin K. Schulte、Richard A. Glennon

  DOI：10.1021/jm200834x

  日期：2011.10.27

  Desformylflustrabromine (dFBr; 1), perhaps the first selective positive allosteric modulator of alpha 4 beta 2 neuronal nicotinic acetylcholine (nACh) receptors, was deconstructed to determine which structural features contribute to its actions on receptors expressed in Xenopus ooycytes using two-electrode voltage clamp techniques. Although the intact structure of 1 was found to be optimal, several deconstructed analogs retained activity. Neither the 6-bromo substituent nor the entire 2-position chain is required for activity. In particular, reduction of the olefinic side chain of 1, as seen with 6, not only resulted in retention of activity/potency but in enhanced selectivity for alpha 4 beta 2 versus alpha 7 nACh receptors. Pharmacophoric features for the allosteric modulation of alpha 4 beta 2 nACh receptors by 1 were identified.