N-trifluoroacetyl-2-(2,5-dimethoxyphenyl)-1-aminoethane | 187389-19-1

• 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: N-trifluoroacetyl-2-(2,5-dimethoxyphenyl)-1-aminoethane
• 英文别名: N-[2-(2,5-Dimethoxyphenyl)ethyl]-2,2,2-trifluoroacetamide
• CAS: 187389-19-1
• 化学式: C₁₂H₁₄F₃NO₃
• 分子量: 277.243
• InChiKey: VJHIWEPSKXAYAB-UHFFFAOYSA-N

物化性质

• 熔点：
  56-57 °C
• 沸点：
  371.5±42.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于二氯甲烷；乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 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：
  6

反应信息

• 作为反应物：
  描述：

  N-trifluoroacetyl-2-(2,5-dimethoxyphenyl)-1-aminoethane 在 一氯化碘 、 溶剂黄146 作用下， 生成 1-(2,5-dimethoxy-4-iodophenyl)-2-(trifluoroacetamido)ethane
  参考文献：
  名称：

  用于新型迷幻药25I-NBOMe敏感检测的纳米传感器。

  摘要：

  这项工作报告了用于检测强效滥用药物25I-NBOMe的混合纳米器件的合成，表征和传感行为。该系统基于中孔二氧化硅纳米粒子，该纳米粒子负载有荧光染料，以5-羟色胺衍生物官能化并以5-HT2A受体抗体封端。在25 I-NBOMe存在的情况下，封端抗体被置换，导致开孔和罗丹明B释放。该递送归因于5-HT2A受体抗体从表面脱离，因为其与溶液中存在的25I-NBOMe具有更强的配位作用。制备的纳米器件可对25I-NBOMe药物敏感（检测限为0.6μm）和选择性识别（可卡因，海洛因，甲斯卡林，麦角酰二乙胺，麦角酸和吗啡不能诱导开孔和若丹明B释放）。

  DOI：

  10.1002/chem.201905688
• 作为产物：
  描述：

  2,5-dimethoxy-β-nitrostyrene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 N-trifluoroacetyl-2-(2,5-dimethoxyphenyl)-1-aminoethane
  参考文献：
  名称：

  用于新型迷幻药25I-NBOMe敏感检测的纳米传感器。

  摘要：

  这项工作报告了用于检测强效滥用药物25I-NBOMe的混合纳米器件的合成，表征和传感行为。该系统基于中孔二氧化硅纳米粒子，该纳米粒子负载有荧光染料，以5-羟色胺衍生物官能化并以5-HT2A受体抗体封端。在25 I-NBOMe存在的情况下，封端抗体被置换，导致开孔和罗丹明B释放。该递送归因于5-HT2A受体抗体从表面脱离，因为其与溶液中存在的25I-NBOMe具有更强的配位作用。制备的纳米器件可对25I-NBOMe药物敏感（检测限为0.6μm）和选择性识别（可卡因，海洛因，甲斯卡林，麦角酰二乙胺，麦角酸和吗啡不能诱导开孔和若丹明B释放）。

  DOI：

  10.1002/chem.201905688

文献信息

• 5-HT_2A/5-HT_2C Receptor Pharmacology and Intrinsic Clearance of <i>N</i>-Benzylphenethylamines Modified at the Primary Site of Metabolism
  作者：Sebastian Leth-Petersen、Ida N. Petersen、Anders A. Jensen、Christoffer Bundgaard、Mathias Bæk、Jan Kehler、Jesper L. Kristensen

  DOI：10.1021/acschemneuro.6b00265

  日期：2016.11.16

  The toxic hallucinogen 25B-NBOMe is very rapidly degraded by human liver microsomes and has low oral bioavailability. Herein we report on the synthesis, microsomal stability, and S-HT2A/5-HT2C receptor profile of novel analogues of 25B-NBOMe modified at the primary site of metabolism. Although microsomal stability could be increased while maintaining potent 5-HT2 receptor agonist properties, all analogues had an intrinsic clearance above 1.3 L/kg/h predictive of high first-pass metabolism.
• 1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT_2A Partial Agonists
  作者：Cynthia S. Dowd、Katharine Herrick-Davis、Christina Egan、Ann DuPre、Carol Smith、Milt Teitler、Richard A. Glennon

  DOI：10.1021/jm9906062

  日期：2000.8.1

  Phenylalkylamines such as 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane (DOB; Pa) and its corresponding iodo derivative DOI (2) are commonly used 5-HT2 serotonin agonists. Previous studies have established that the 2,5-dimethoxy substitution pattern found in these compounds is optimal for high affinity at 5-HT2A receptors and that substituents at the 4-position can modulate affinity over a wide range. We have previously shown, however, that when the 4-position is substituted with a 3-phenylpropyl substituent (i.e., 3), the compound binds with an affinity comparable to that of Pa but that it possesses 5-HT2A antagonist character. The present study examined the structure-affinity relationships of 3, and the results were very much unexpected. That is, the 2,5-dimethoxy substitution pattern of 3 is not required for high affinity. Either of the two methoxy groups can be removed without untoward effect on affinity, and relocation of the methoxy substituents actually enhances affinity by as much as an order of magnitude. None of the compounds displayed more than 20-fold selectivity for 5-HT2A over 5-HT2C receptors. In addition, several were demonstrated to act as 5-HT2A partial agonists. As such, the results of this study suggest that the structure-affinity relationships of phenylalkylamines as 5-HT2A ligands now be reinvestigated in greater detail.
• Nanosensor for Sensitive Detection of the New Psychedelic Drug 25I‐NBOMe
  作者：Eva Garrido、María Alfonso、Borja Díaz de Greñu、Beatriz Lozano‐Torres、Margarita Parra、Pablo Gaviña、M. Dolores Marcos、Ramón Martínez‐Máñez、Félix Sancenón

  DOI：10.1002/chem.201905688

  日期：2020.3.2

  the synthesis, characterization, and sensing behavior of a hybrid nanodevice for the detection of the potent abuse drug 25I-NBOMe. The system is based on mesoporous silica nanoparticles, loaded with a fluorescent dye, functionalized with a serotonin derivative and capped with the 5-HT2A receptor antibody. In the presence of 25I-NBOMe the capping antibody is displaced, leading to pore opening and rhodamine B

  这项工作报告了用于检测强效滥用药物25I-NBOMe的混合纳米器件的合成，表征和传感行为。该系统基于中孔二氧化硅纳米粒子，该纳米粒子负载有荧光染料，以5-羟色胺衍生物官能化并以5-HT2A受体抗体封端。在25 I-NBOMe存在的情况下，封端抗体被置换，导致开孔和罗丹明B释放。该递送归因于5-HT2A受体抗体从表面脱离，因为其与溶液中存在的25I-NBOMe具有更强的配位作用。制备的纳米器件可对25I-NBOMe药物敏感（检测限为0.6μm）和选择性识别（可卡因，海洛因，甲斯卡林，麦角酰二乙胺，麦角酸和吗啡不能诱导开孔和若丹明B释放）。