1-(5-methyl-1H-imidazol-4-yl)-2-propanamine | 82977-50-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(5-methyl-1H-imidazol-4-yl)-2-propanamine
• 英文别名: (+/-)-4-(2-Aminopropyl)-5-methyl-imidazol；1H-Imidazole-4-ethanamine, alpha,5-dimethyl-；1-(5-methyl-1H-imidazol-4-yl)propan-2-amine
• CAS: 82977-50-2
• 化学式: C₇H₁₃N₃
• 分子量: 139.2
• InChiKey: VULHNWNHMRINQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  54.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-chloro-3-(5-methyl-1H-imidazol-4-yl)-2-propanamine dihydrochloride 在 palladium on activated charcoal 氢气 、 sodium acetate 、 溶剂黄146 作用下， 反应 240.0h， 生成 1-(5-methyl-1H-imidazol-4-yl)-2-propanamine
  参考文献：
  名称：

  Synthesis and histamine H3-receptor agonist activity of mono- and dialkyl-substituted histamine derivatives

  摘要：

  In search for potential histamine H-3-receptor agonists a series of mono- and dialkyl-substituted histamine derivatives was synthesized. All target compounds were tested in vitro for their agonist activity at H-3-, H-2-, and H-1-receptors. Introduction of one ethyl or two methyl residues into histamine led to compounds with decreased histamine H-3-agonist potency in most cases. However, the non-chiral alpha,alpha-dimethylhistamine (15) was identified to be three times as active as histamine itself at H-3-receptors. In addition 15 Dimethylhistamine 23, which is a potential metabolite of (alpha R)-alpha-methylhistamine 1, proved to be inactive at all three histamine receptor subtypes.

  DOI：

  10.1016/0223-5234(96)88228-6

文献信息

• Struktur-Wirkungs-Beziehungen bei Histaminanaloga, 24. Mitt. Absolute Konfiguration und histaminartige Wirkung der Enantiomere von 4-(2-Aminopropyl)-5-methyl-imidazol
  作者：Siegfried Schwarz、Walter Schunack

  DOI：10.1002/ardp.19823150804

  日期：——

  Es werden die Racematspaltung von 4‐(2‐Aminopropyl)‐5‐methyl‐imidazol (1), die Bestimmung der absoluten Konfiguration sowie die histaminartige Wirksamkeit der Enantiomere am Ileum (H1) und Atrium (H2) des Meerschweinchens beschrieben.

  4-（2-氨基丙基）-5-甲基-咪唑（1）的拆分，豚鼠回肠（H1）和心房（H2）对映异构体的绝对构型和类组胺活性的测定被描述。
• Sarasin, Helvetica Chimica Acta, 1923, vol. 6, p. 380
  作者：Sarasin

  DOI：——

  日期：——
• PLAZZI, P. V.;BORDI, F.;VITTO, M.;IMPICCIATORE, M., FARMACO. ED. SCI., 1981, 36, N 11, 921-931
  作者：PLAZZI, P. V.、BORDI, F.、VITTO, M.、IMPICCIATORE, M.

  DOI：——

  日期：——
• Synthesis and histamine H3-receptor agonist activity of mono- and dialkyl-substituted histamine derivatives
  作者：R Lipp、H Stark、JM Arrang、M Garbarg、JC Schwartz、W Schunack

  DOI：10.1016/0223-5234(96)88228-6

  日期：1995.1

  In search for potential histamine H-3-receptor agonists a series of mono- and dialkyl-substituted histamine derivatives was synthesized. All target compounds were tested in vitro for their agonist activity at H-3-, H-2-, and H-1-receptors. Introduction of one ethyl or two methyl residues into histamine led to compounds with decreased histamine H-3-agonist potency in most cases. However, the non-chiral alpha,alpha-dimethylhistamine (15) was identified to be three times as active as histamine itself at H-3-receptors. In addition 15 Dimethylhistamine 23, which is a potential metabolite of (alpha R)-alpha-methylhistamine 1, proved to be inactive at all three histamine receptor subtypes.