N,N-di-n-propylserotonin hydrochloride | 113111-11-8

• 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-di-n-propylserotonin hydrochloride
• 英文别名: 3-(2-dipropylamino-ethyl)-indol-5-ol; hydrochloride；3-(2-Dipropylamino-aethyl)-indol-5-ol; Hydrochlorid；3-[2-(dipropylamino)ethyl]-1H-indol-5-ol;hydrochloride
• CAS: 113111-11-8
• 化学式: C₁₆H₂₄N₂O*ClH
• 分子量: 296.84
• InChiKey: YEMVBUVCFVKGTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  39.26
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  5-苄氧基吲哚 在 palladium on activated charcoal 盐酸 、 lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 40.0 ℃ 、289.58 kPa 条件下， 反应 116.5h， 生成 N,N-di-n-propylserotonin hydrochloride
  参考文献：
  名称：

  N,N-Di-n-propylserotonin: binding at serotonin binding sites and a comparison with 8-hydroxy-2-(di-n-propylamino)tetralin

  摘要：

  8-Hydroxy-2-(di-n-propylamino)tetralin (8-OH-DPAT) is a serotonergic agonist with high affinity and selectivity for a particular population of central serotonin (5-HT) binding sites (i.e., 5-HT1A sites). Because the selectivity of 8-OH-DPAT may be due to the terminal amine substituents, the di-n-propyl analogue of 5-HT (i.e., 4) and of 5-methoxytryptamine (i.e., 5) were prepared and compared with 8-OH-DPAT with respect to their binding profile. Unlike 8-OH-DPAT, neither compound 4 nor 5 displays selectivity for 5-HT1A vs 5-HT2 sites. Consistent with these results, stimulus generalization occurs with 5 both in rats trained to discriminate 8-OH-DPAT from saline and in rats trained to discriminate the 5-HT2 agonist DOM from saline. The results of this study suggest that it is not the N,N-dipropyl groups that account for selectivity, but, rather, it is some feature associated with the pyrrole portion of the indolylalkanamines that is important.

  DOI：

  10.1021/jm00399a031

文献信息

• N,N-Di-n-propylserotonin: binding at serotonin binding sites and a comparison with 8-hydroxy-2-(di-n-propylamino)tetralin
  作者：Richard A. Glennon、Milt Titeler、Robert A. Lyon、R. M. Slusher

  DOI：10.1021/jm00399a031

  日期：1988.4

  8-Hydroxy-2-(di-n-propylamino)tetralin (8-OH-DPAT) is a serotonergic agonist with high affinity and selectivity for a particular population of central serotonin (5-HT) binding sites (i.e., 5-HT1A sites). Because the selectivity of 8-OH-DPAT may be due to the terminal amine substituents, the di-n-propyl analogue of 5-HT (i.e., 4) and of 5-methoxytryptamine (i.e., 5) were prepared and compared with 8-OH-DPAT with respect to their binding profile. Unlike 8-OH-DPAT, neither compound 4 nor 5 displays selectivity for 5-HT1A vs 5-HT2 sites. Consistent with these results, stimulus generalization occurs with 5 both in rats trained to discriminate 8-OH-DPAT from saline and in rats trained to discriminate the 5-HT2 agonist DOM from saline. The results of this study suggest that it is not the N,N-dipropyl groups that account for selectivity, but, rather, it is some feature associated with the pyrrole portion of the indolylalkanamines that is important.