1-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane | 733720-95-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane
• 英文别名: 8-bromo-2,3,6,7-tetrahydro-benzo[1,2-b:4,5-b]difuran-4-ethanamine；8-bromo-2,3,6,7-benzodihydrodifuranethylamine；2C-B-Fly；2-(4-bromo-2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-8-yl)ethanamine
• CAS: 733720-95-1
• 化学式: C₁₂H₁₄BrNO₂
• 分子量: 284.153
• InChiKey: YZDFADGMVOSVIX-UHFFFAOYSA-N

物化性质

• 沸点：
  418.4±45.0 °C(Predicted)
• 密度：
  1.557±0.06 g/cm3(Predicted)
• 保留指数：
  2133

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-羟基-6-甲氧基苯甲醛 、 1-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  大鼠尿液、人肝微粒体和秀丽隐杆线虫中的 2C-B-Fly-NBOMe 代谢物：使用合成分析标准进行确认

  摘要：

  从化合物Ñ -benzylphenethylamine（NBPEA）类的新颖的精神活性物质在神经生物学和临床研究正在越来越多地利用，作为诊断工具或用于娱乐目的。因此，要了解这些物质的药理学、安全性或潜在毒性，阐明它们的代谢命运是最重要的。一些关于 NBPEA 代谢的研究已经出现，但关于具有四氢苯并二呋喃（“苍蝇”）部分的物质的信息很少。在这里，我们研究了 2-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl) -N- (2-methoxybenzyl ) 的代谢)ethan-1-amine (2C-B-Fly-NBOMe) 在三种不同的系统中：分离的人肝微粒体、Cunninghamella elegans菌丝体，并在大鼠体内。2C-B-Fly-NBOMe 的 I 和 II 相代谢物首先在非靶向筛选中检测到，并通过液相色谱-串联质谱

  DOI：

  10.3390/metabo11110775
• 作为产物：
  描述：

  1-(2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane 在 溴 、 溶剂黄146 作用下， 反应 2.25h， 以73%的产率得到1-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane
  参考文献：
  名称：

  Dihydrobenzofuran Analogues of Hallucinogens. 3. Models of 4-Substituted (2,5-Dimethoxyphenyl)alkylamine Derivatives with Rigidified Methoxy Groups

  摘要：

  Tetrahydrobenzodifuran functionalities were employed as conformationally restricted bioisosteres of the aromatic methoxy groups in prototypical hallucinogenic phenylalkylamines 1 and 2. Thus, a series of 8-substituted 1-(2,3,6,7-tetrahydrobenzo[ 1,2-b:4,5-b']difuran-4-yl)-2-aminoalkanes (7a-e) were prepared and evaluated for activity in the two-lever drug discrimination paradigm in rats trained to discriminate saline from LSD tartrate (0.08 mg/kg) and for the ability to displace [H-3]ketanserin from rat cortical homogenate 5-HT2A receptors and [(3)H3-8-OH-DPAT from rat hippocampal homogenate 5-HT1A receptors. In addition, 1-(8-(bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5- (7b), which was found to be extremely potent in the rat in vivo assays, was evaluated for its ability to compete with [I-125][DOI and [H-3]ketanserin binding to cells expressing cloned human 5-HT2A, 5-H-2B, and 5-HT2C receptors. All of the dihydrofuranyl compounds having a hydrophobic substituent para to the alkylamine side chain had activities in both the in vitro and in vivo assays that equaled or surpassed the activity of the analogous conformationally flexible parent compounds. For example, 7b substituted for LSD in the drug discrimination assay with an ED(50) Of 61 nmol/kg and had K-i values in the nanomolar to subnanomolar range for the displacement of radioligand from rat and human 5-HT2 receptors, making it one of the most potent hallucinogen-like phenylalkylamine derivatives reported to date. The results suggest that the dihydrofuran rings in these pew analogues effectively model the active binding conformations of the methoxy groups of the parent compounds 1 and 2. In addition, the results provide information about the topography and relative orientation of residues involved in agonist binding in the serotonin 5-HT2 receptors.

  DOI：

  10.1021/jm960199j

文献信息

• [EN] METHODS OF TREATING PSYCHOLOGICAL CONDITIONS<br/>[FR] PROCÉDÉS DE TRAITEMENT DE TROUBLES PSYCHOLOGIQUES
  申请人：UNIV OKLAHOMA STATE

  公开号：WO2010151258A1

  公开（公告）日：2010-12-29

  A method and composition for inducing in a subject a tolerance to a psychoactive substance or for treating an abnormal mental condition in a subject. The composition used in the method comprises in one embodiment a 5-HT2B receptor agonist disposed within a pharmaceutically-acceptable vehicle or carrier.

  一种用于诱导受试者对精神活性物质产生耐受性或用于治疗受试者异常精神状况的方法和组合物。该方法中使用的组合物在一个实施例中包括一个5-HT2B受体激动剂，该激动剂被置于药学上可接受的载体或载体中。
• [EN] PHENALKYLAMINES AND METHODS OF TREATING MOOD DISORDERS<br/>[FR] PHÉNALKYLAMINES ET PROCÉDÉS DE TRAITEMENT DE TROUBLES DE L'HUMEUR
  申请人：GILGAMESH PHARMACEUTICALS INC

  公开号：WO2022006186A1

  公开（公告）日：2022-01-06

  Phenalkylamines and methods of treating mood disorders with phenalkylamines. Also provided are pharmaceutical compositions that include phenalkylamines.

  Phenalkylamines和使用Phenalkylamines治疗情绪障碍的方法。还提供了包含Phenalkylamines的制药组合物。