N-[2-(4-bromo-2,5-dimethoxyphenyl)ethyl]acetamide | 155639-33-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[2-(4-bromo-2,5-dimethoxyphenyl)ethyl]acetamide
• CAS: 155639-33-1
• 化学式: C₁₂H₁₆BrNO₃
• 分子量: 302.168
• InChiKey: FPJLSDPZIUNKGU-UHFFFAOYSA-N

物化性质

• 沸点：
  456.9±45.0 °C(predicted)
• 密度：
  1.340±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[2-(4-bromo-2,5-dimethoxyphenyl)ethyl]acetamide 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 N-ethyl-2-(4-bromo-2,5-dimethoxyphenyl)-1-aminoethane
  参考文献：
  名称：

  Influence of Amine Substituents on 5-HT2A versus 5-HT2C Binding of Phenylalkyl- and Indolylalkylamines

  摘要：

  The effect of 15 different amine substituents on 5-HT2A and 5-HT2C serotonin receptor binding was investigated for two series of compounds (i.e., phenylalkylamine and indolylalkylamine derivatives). In general, amine substitution decreases receptor affinity; however, N-(4-bromobenzyl) substitution results in compounds that bind at 5-HT2A receptors with high affinity (K-i < 1 nM) and with >100-fold selectivity. Although parallel structural modifications in the two series result in parallel shifts in 5-HT2C binding, these same modifications alter 5-HT2A binding in a less consistent manner.

  DOI：

  10.1021/jm00039a004
• 作为产物：
  描述：

  4-溴-2,5二甲氧基苯乙胺 、 乙酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到N-[2-(4-bromo-2,5-dimethoxyphenyl)ethyl]acetamide
  参考文献：
  名称：

  Influence of Amine Substituents on 5-HT2A versus 5-HT2C Binding of Phenylalkyl- and Indolylalkylamines

  摘要：

  The effect of 15 different amine substituents on 5-HT2A and 5-HT2C serotonin receptor binding was investigated for two series of compounds (i.e., phenylalkylamine and indolylalkylamine derivatives). In general, amine substitution decreases receptor affinity; however, N-(4-bromobenzyl) substitution results in compounds that bind at 5-HT2A receptors with high affinity (K-i < 1 nM) and with >100-fold selectivity. Although parallel structural modifications in the two series result in parallel shifts in 5-HT2C binding, these same modifications alter 5-HT2A binding in a less consistent manner.

  DOI：

  10.1021/jm00039a004

文献信息

• 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.
• WO2023/115002
  申请人：——

  公开号：——

  公开（公告）日：——
• Influence of Amine Substituents on 5-HT2A versus 5-HT2C Binding of Phenylalkyl- and Indolylalkylamines
  作者：Richard A. Glennon、Malgorzata Dukat、Mohamed El-Bermawy、Ho Law、Joseph De Los Angeles、Milt Teitler、Allison King、Katharine Herrick-Davis

  DOI：10.1021/jm00039a004

  日期：1994.6

  The effect of 15 different amine substituents on 5-HT2A and 5-HT2C serotonin receptor binding was investigated for two series of compounds (i.e., phenylalkylamine and indolylalkylamine derivatives). In general, amine substitution decreases receptor affinity; however, N-(4-bromobenzyl) substitution results in compounds that bind at 5-HT2A receptors with high affinity (K-i < 1 nM) and with >100-fold selectivity. Although parallel structural modifications in the two series result in parallel shifts in 5-HT2C binding, these same modifications alter 5-HT2A binding in a less consistent manner.