4-bromo-2,5-dimethoxyphenethylamine hydrochloride

• 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: 4-bromo-2,5-dimethoxyphenethylamine hydrochloride
• 英文别名: 2-(4-bromo-2,5-dimethoxyphenyl)ethan-1-amine hydrochloride；2-(4-bromo-2,5-dimethoxy-phenyl)ethanamine; hydrochloride；2-(4-bromo-2,5-dimethoxyphenyl)ethanamine;hydron;chloride
• 化学式: C₁₀H₁₄BrNO₂*ClH
• 分子量: 296.592
• InChiKey: UJTWHDAMHSIRDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-bromo-2,5-dimethoxyphenethylamine hydrochloride 在 苯酐 、 三乙胺 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 0.75h， 生成 4-(2-((2-fluorobenzyl)amino)ethyl)-2,5-dimethoxybenzonitrile hydrochloride
  参考文献：
  名称：

  Discovery of β-Arrestin-Biased 25CN-NBOH-Derived 5-HT_2A Receptor Agonists

  摘要：

  DOI：

  10.1021/acs.jmedchem.2c00702
• 作为产物：
  描述：

  2,5-二甲氧基苯甲醛 在 ammonium acetate 、 溴 、 溶剂黄146 作用下， 生成 4-bromo-2,5-dimethoxyphenethylamine hydrochloride
  参考文献：
  名称：

  Discovery of β-Arrestin-Biased 25CN-NBOH-Derived 5-HT_2A Receptor Agonists

  摘要：

  DOI：

  10.1021/acs.jmedchem.2c00702

文献信息

• Synthesis and pharmacological evaluation of N-benzyl substituted 4-bromo-2,5-dimethoxyphenethylamines as 5-HT2A/2C partial agonists
  作者：Martin Hansen、Stine Engesgaard Jacobsen、Shane Plunkett、Gudrun Eckhard Liebscher、John D. McCorvy、Hans Bräuner-Osborne、Jesper Langgaard Kristensen

  DOI：10.1016/j.bmc.2014.12.011

  日期：2015.7

  N-Benzyl substitution of phenethylamine 5-HT2A receptor agonists has dramatic effects on binding affinity, receptor selectivity and agonist activity. In this paper we examine how affinity for the 5-HT2A/2C receptors are influenced by N-benzyl substitution of 4-bromo-2,5-dimethoxyphenethylamine derivatives. Special attention is given to the 2' and 3'-position of the N-benzyl as such compounds are known to be very potent. We found that substitutions in these positions are generally well tolerated. The 2'-position was further examined using a range of substituents to probe the hydrogen bonding requirements for optimal affinity and selectivity, and it was found that small changes in the ligands in this area had a profound effect on their affinities. Furthermore, two ligands that lack a 2'-benzyl substituent were also found to have high affinity contradicting previous held notions. Several high-affinity ligands were identified and assayed for functional activity at the 5-HT2A and 5-HT2C receptor, and they were generally found to be less efficacious agonists than previously reported N-benzyl phenethylamines. (C) 2014 Elsevier Ltd. All rights reserved.
• Convergent 18F-labeling and evaluation of N-benzyl-phenethylamines as 5-HT2A receptor PET ligands
  作者：Ida Nymann Petersen、Jonas Villadsen、Hanne Demant Hansen、Anders A. Jensen、Szabolcs Lehel、Nic Gillings、Matthias M. Herth、Gitte M. Knudsen、Jesper L. Kristensen

  DOI：10.1016/j.bmc.2016.08.056

  日期：2016.11

  Positron emission tomography (PET) investigations of the 5-HT2A receptor (5-HT2AR) system can be used as a research tool in diseases such as depression, Alzheimer's disease and schizophrenia. We have previously developed a C-11-labeled agonist PET ligand ([C-11]Cimbi-36), and the aim of this study was to identify a F-18-labeled analogue of this PET-ligand. Thus, we developed a convergent radiochemical approach giving easy access to 5 different F-18-labeled ligands structurally related to Cimbi-36 from a common F-18-labeled intermediate. After intravenous injection, all ligands entered the pig brain. However, since within-scan intervention with ketanserin, a known orthosteric 5-HT2A receptor antagonist, did not result in significant blocking, the radioligands seem unsuitable for neuroimaging of the 5-HT2AR in vivo. (C) 2016 Elsevier Ltd. All rights reserved.
• Synthesis and Structure–Activity Relationships of <i>N</i>-Benzyl Phenethylamines as 5-HT_2A/2C Agonists
  作者：Martin Hansen、Karina Phonekeo、James S. Paine、Sebastian Leth-Petersen、Mikael Begtrup、Hans Bräuner-Osborne、Jesper L. Kristensen

  DOI：10.1021/cn400216u

  日期：2014.3.19

  N-Benzyl substitution of 5-HT2A receptor agonists of the phenethylamine structural class of psychedelics (such as 4-bromo-2,5-dimethoxyphenethylamine, often referred to as 2C-B) confer a significant increase in binding affinity as well as functional activity of the receptor. We have prepared a series of 48 compounds with structural variations in both the phenethylamine and N-benzyl part of the molecule to determine the effects on receptor binding affinity and functional activity at 5-HT2A and 5-HT2c receptors. The compounds generally had high affinity for the 5-HT2A receptor with 8b having the highest affinity at 0.29 nM but with several other compounds also exhibiting subnanomolar binding affinities. The functional activity of the compounds was distributed over a wider range with lb being the most potent at 0.074 nM. Most of the compounds exhibited low to moderate selectivity (1- to 40-fold) for the 5-HT2A receptor in the binding assays, although one compound 6b showed an impressive 100-fold selectivity for the 5-HT2A receptor. In the functional assay, selectivity was generally higher with lb being more than 400-fold selective for the 5-HT2A receptor.
• SWENTON, JOHN. S.;SHIH, CHUAN;CHEN, CHUNG-PIN;CHOU, CHUN-TZER, J. ORG. CHEM., 55,(1990) N, C. 2019-2026
  作者：SWENTON, JOHN. S.、SHIH, CHUAN、CHEN, CHUNG-PIN、CHOU, CHUN-TZER

  DOI：——

  日期：——
• Disposition of 4-bromo-2,5-dimethoxyphenethylamine (2C-B) and its metabolite 4-bromo-2-hydroxy-5-methoxyphenethylamine in rats after subcutaneous administration
  作者：Miroslava Rohanová、Tomáš Páleníček、Marie Balíková

  DOI：10.1016/j.toxlet.2008.01.017

  日期：2008.4

  The psychedelic compound 4-bromo-2,5-dimethoxyphenethylamine (2C-B) has appeared as an agent in drug abuse or overdose cases in humans. The human pharmacokinetics of this drug is unknown and only partial information is available on its metabolites. Our experimental study was focused on the disposition and kinetic profile of 2C-B in rats after subcutaneous administration using a GC-MS validated method. One of the major metabolites 4-bromo-2-hydroxy-5-methoxyphenethylarnine (2H5M-BPEA) was confirmed in rat tissues of lung, brain, liver and was quantitatively evaluated as well. The disposition of 2C-B was characterized by its estimated half-life 1.1 h and estimated volume of distribution 16 L/kg. The lung susceptibility for drug retention and gradual temporal release parallel to the brain were ascertained. The drug penetrating the blood/brain barrier was without significant delay. 2C-B brain to serum ratio attained a maximum value of 13.9 and remained over the value of 6.5 to the end of our observation (6 h after the dose). The distribution of the hydroxylated metabolite 2H5M-BPEA into the lipophilic brain tissue was less efficient in relation to the parent compound. The kinetics of the drug partitioning between blood to brain may be important for the subsequent assessment of its psychotropic or toxic effects. (C) 2008 Elsevier Ireland Ltd. All rights reserved.