7-bromo-N,N-dimethyltryptamine | 74798-68-8

• 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: 7-bromo-N,N-dimethyltryptamine
• 英文别名: 2-(7-bromo-1H-indol-3-yl)-N,N-dimethylethanamine
• CAS: 74798-68-8
• 化学式: C₁₂H₁₅BrN₂
• 分子量: 267.168
• InChiKey: AIGRKPCJNQCZCI-UHFFFAOYSA-N

物化性质

• 熔点：
  86-88 °C
• 沸点：
  75-85 °C(Press: 0.1 Torr)
• 密度：
  1.397±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-bromo-N,N-dimethyltryptamine 在 四(三苯基膦)钯 、 18-冠醚-6 、 potassium tert-butylate 、 potassium acetate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-[2-(dimethylamino)ethyl]-1,2-benzothiazino[2,3,4-ab]indole S,S-dioxide
  参考文献：
  名称：

  Interaction of N1-unsubstituted and N1-benzenesulfonyltryptamines at h5-HT6 receptors

  摘要：

  Despite possessing a common tryptaminergic scaffold, examination of 28 (i.e., 14 pairs of) compounds suggests that N-1-unsubstituted and N-1-benzenesulfonyltryptamines likely bind at h5-HT6 receptors in a dissimilar manner (r(2) = 0.201). Additionally, an examination of two rotationally constrained N-1-benzenesulfonyltryptamine analogs indicates that a non-coplanar relationship between the two aryl groups might be preferred for interaction with the receptors. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.068
• 作为产物：
  描述：

  2-(7-bromo-1H-indol-3-yl)-2-oxoacetyl chloride 在 aluminium hydride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 20.0h， 生成 7-bromo-N,N-dimethyltryptamine
  参考文献：
  名称：

  Studies on several 7-substituted N,N-dimethyltryptamines

  摘要：

  Several 7-substituted derivatives of N,N-dimethyltryptamine (DMT) were prepared and evaluated in the rat fundus serotonin receptor assay and in a behavioral (discriminative stimulus) assay in rats. Both 7-Me- and 5-OMe-7-Me-DMT possess a higher pA2, and 5,7-(OMe)2-DMT a lower pA2, than that of DMT itself. Like DMT, all three of these compounds produce behavioral effects in rats which are similar to those of the hallucinogen 5-OMe-DMT. Although 7-ET- and 7-Br-DMT possess a higher serotonin receptor affinity than DMT, neither produce behavioral effects which parallel those of 5-OMe-DMT. In contrast, 6-Me-DMT and its 5-OMe derivative do not interact with the serotonin receptors in a competitive manner and are inactive in the discriminative stimulus assay.

  DOI：

  10.1021/jm00185a014

文献信息

• Marine AChE inhibitors isolated from Geodia barretti: natural compounds and their synthetic analogs
  作者：Elisabeth K. Olsen、Espen Hansen、Lindon W. K. Moodie、Johan Isaksson、Kristina Sepčić、Marija Cergolj、Johan Svenson、Jeanette H. Andersen

  DOI：10.1039/c5ob02416a

  日期：——

  Based on the inhibitory activity, a library of 22 simplified synthetic analogs was designed and prepared to probe the role of the brominated indole, common to all the isolated compounds. From the structure–activity investigation it was shown that the brominated indole motif is not sufficient to generate a high acetylcholinesterase inhibitory activity, even when combined with natural cationic ligands

  从收集自挪威沿海的海绵海绵Geodia barretti中分离出Barettin，8,9-dihydrobarettin，bromoconicamin和一种新型的溴化海洋吲哚。将该化合物评估为鳗鳗乙酰胆碱酯酶的抑制剂。Barettin和8,9-dihydrobarettin表现出对该酶的显着抑制作用，对乙酰胆碱酯酶的抑制常数（K i）分别为29和19μM 。可逆的非竞争机制。这些活性与海洋来源的几种其他天然乙酰胆碱酯酶抑制剂的活性相当。溴康那敏对乙酰胆碱酯酶的效力较弱，该新型化合物无活性。基于抑制活性，设计并制备了22种简化的合成类似物库，以探测所有分离的化合物共有的溴化吲哚的作用。从结构活性研究表明，即使与天然的阳离子配体结合用于乙酰胆碱酯酶活性位点，溴化的吲哚基团也不足以产生高的乙酰胆碱酯酶抑制活性。此外，还分析了这四种天然化合物的丁酰胆碱酯酶抑制活性，并显示出可比的活性。这项研究说明了巴瑞汀和8
• Synthesis of Novel Rigid Analogs of Tryptamine as Potential Serotonin Ligands through Pd(0)-Catalyzed Diaryl Coupling Reactions
  作者：Ramasastri Kambhampati、Prabhakar Kothmirkar、Amol D. Deshpande、Sobhanadri Arepalli、Kameswara Rao Karturi、Narasimha Reddy G. Pamuleti、Anil K. Shinde、Ramakrishna V. S. Nirogi

  DOI：10.1080/00397910802139205

  日期：2008.6.27

  A series of novel tetracyclic 6-thia-5a-aza-acephenanthrylene derivatives 7 were synthesized by rigidization of the arylsulfonyl/carbonyl/methyl moiety through C7 of indole, which was achieved under Heck conditions. The strategy of altering the palladium-bromine exchange site produced target products.
• GLENNON R. A.; SCHUBERT E.; JACYNO J. M.; ROSECRANS J. A., J. MED. CHEM., 1980, 23, NO 11, 1222-1226
  作者：GLENNON R. A.、 SCHUBERT E.、 JACYNO J. M.、 ROSECRANS J. A.

  DOI：——

  日期：——
• Studies on several 7-substituted N,N-dimethyltryptamines
  作者：R. A. Glennon、E. Schubert、J. M. Jacyno、J. A. Rosecrans

  DOI：10.1021/jm00185a014

  日期：1980.11

  Several 7-substituted derivatives of N,N-dimethyltryptamine (DMT) were prepared and evaluated in the rat fundus serotonin receptor assay and in a behavioral (discriminative stimulus) assay in rats. Both 7-Me- and 5-OMe-7-Me-DMT possess a higher pA2, and 5,7-(OMe)2-DMT a lower pA2, than that of DMT itself. Like DMT, all three of these compounds produce behavioral effects in rats which are similar to those of the hallucinogen 5-OMe-DMT. Although 7-ET- and 7-Br-DMT possess a higher serotonin receptor affinity than DMT, neither produce behavioral effects which parallel those of 5-OMe-DMT. In contrast, 6-Me-DMT and its 5-OMe derivative do not interact with the serotonin receptors in a competitive manner and are inactive in the discriminative stimulus assay.
• Interaction of N1-unsubstituted and N1-benzenesulfonyltryptamines at h5-HT6 receptors
  作者：Renata Kolanos、Małgorzata Dukat、Bryan L. Roth、Richard A. Glennon

  DOI：10.1016/j.bmcl.2006.08.068

  日期：2006.11

  Despite possessing a common tryptaminergic scaffold, examination of 28 (i.e., 14 pairs of) compounds suggests that N-1-unsubstituted and N-1-benzenesulfonyltryptamines likely bind at h5-HT6 receptors in a dissimilar manner (r(2) = 0.201). Additionally, an examination of two rotationally constrained N-1-benzenesulfonyltryptamine analogs indicates that a non-coplanar relationship between the two aryl groups might be preferred for interaction with the receptors. (c) 2006 Elsevier Ltd. All rights reserved.