碘代N-乙胺(简称) | 1043868-97-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 碘代N-乙胺(简称)
• 中文别名: 正在做；N-(2-甲氧基苄基)-2-(2,5-二甲氧基-4-碘苯基)乙胺盐酸盐
• 英文名称: 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine hydrochloride
• 英文别名: 4-iodo-2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine hydrochloride；N-(2-Methoxybenzyl)-2-(2,5-dimethoxy-4-iodophenyl)ethanamine hydrochloride；2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine;hydrochloride
• CAS: 1043868-97-8
• 化学式: C₁₈H₂₂INO₃*ClH
• 分子量: 463.743
• InChiKey: IPBBLNVKGLDTML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  39.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E)-2-(4-iodo-2,5-dimethoxyphenyl)-N-(2-methoxybenzylidene)ethanamine 在 sodium tetrahydroborate 、 盐酸 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 0.5h， 生成 碘代N-乙胺(简称)
  参考文献：
  名称：

  N-Benzyl-5-methoxytryptamines as Potent Serotonin 5-HT₂Receptor Family Agonists and Comparison with a Series of Phenethylamine Analogues

  摘要：

  A series of N-benzylated-5-methoxytryptarnine analogues was prepared and investigated, with special emphasis on substituents in the meta position of the benzyl group. A parallel series of several N-benzylated analogues of 2,5-dimethoxy-4-iodophenethylamine (2C-I) also was included for comparison of the two major templates (i.e., tryptamine and phenethylamine). A broad affinity screen at serotonin receptors showed that most of the compounds had the highest affinity at the 5-HT2 family receptors. Substitution at the para position of the benzyl group resulted in reduced affinity, whereas substitution in either the ortho or the meta position enhanced affinity. In general, introduction of a large lipophilic group improved affinity, whereas functional activity often followed the opposite trend. Tests of the compounds for functional activity utilized intracellular Ca2+ mobilization. Function was measured at the human 5-HT2A, 5-HT2B, and 5-HT2c receptors, as well as at the rat 5-HT2A and 5-HT2c receptors. There was no general correlation between affinity and function. Several of the tryptamine congeners were very potent functionally (EC50 values from 7.6 to 63 nM), but most were partial agonists. Tests in the mouse head twitch assay revealed that many of the compounds induced the head twitch and that there was a significant correlation between this behavior and functional potency at the rat 5-HT2A receptor.

  DOI：

  10.1021/cn500292d

文献信息

• High specific activity tritium-labeled N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (INBMeO): A high-affinity 5-HT2A receptor-selective agonist radioligand
  作者：David E. Nichols、Stewart P. Frescas、Benjamin R. Chemel、Kenneth S. Rehder、Desong Zhong、Anita H. Lewin

  DOI：10.1016/j.bmc.2008.04.050

  日期：2008.6

  carrier added tritiated iodomethane in DMF with K(2)CO(3). Removal of the t-BOC protecting group and purification by HPLC afforded an overall yield of 43%, with a radiochemical purity of 99% and specific activity of 164Ci/mmol. The new radioligand was suitable for labeling human 5-HT(2A) receptors in two heterologous cell lines and had about 20-fold higher affinity than [(3)H]ketanserin.

  标题化合物 ([3H]INBMeO) 是通过 t-BOC 保护的二酚前体的 O,O-二甲基化反应制备的，不使用载体在 DMF 中添加氚化碘甲烷和 K(2)CO(3)。去除t-BOC保护基并通过HPLC纯化，总产率为43%，放射化学纯度为99%，比活为164Ci/mmol。新的放射性配体适用于标记两个异源细胞系中的人类 5-HT(2A) 受体，并且具有比 [(3)H] ketanserin 高约 20 倍的亲和力。