3-(2,5-dimethoxyphenyl)piperidine | 767264-65-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-(2,5-dimethoxyphenyl)piperidine
• CAS: 767264-65-3
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: MPOSBTBOIRHAEE-UHFFFAOYSA-N

物化性质

• 沸点：
  337.0±42.0 °C(Predicted)
• 密度：
  1.030±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2,5-dimethoxyphenyl)piperidine 在 碘 、 silver nitrate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  作为选择性血清素 5-HT2A 受体激动剂的 2,5-二甲氧基苯基哌啶的发现及其构效关系

  摘要：

  裸盖菇素、麦角酰二乙酰胺 (LSD) 和N,N-二甲基色胺 (DMT) 等经典迷幻药在针对一系列精神疾病（包括抑郁症、焦虑症和药物滥用障碍）的临床试验中显示出良好的结果。这些化合物的特点是具有广泛的药理活性，虽然急性改变思维作用可归因于它们对血清素 2A 受体 (5-HT 2A R) 的共同激动剂活性，但它们明显的持久治疗作用尚未明确联系起来。对该受体的活性。我们在此报告了 2,5-二甲氧基苯基哌啶作为一类新型选择性 5-HT 2A R 激动剂的发现，并详细介绍了导致鉴定 LPH-5 [类似物 ( S ) -11 ] 作为选择性 5-HT 2A R 激动剂的结构-活性研究。 -HT 2A R 激动剂，具有理想的药物样特性。

  DOI：

  10.1021/acs.jmedchem.4c00082
• 作为产物：
  描述：

  (+/-)-ethyl (2-cyanoethyl)(2,5-dimethoxyphenyl)acetate 在 platinum(IV) oxide 、 palladium on activated charcoal lithium aluminium tetrahydride 、 氨 、 氢气 作用下， 以 乙醚 、 乙醇 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 30.0h， 生成 3-(2,5-dimethoxyphenyl)piperidine
  参考文献：
  名称：

  2,5-Dimethoxy congeners of (+)- and (-)-3-(3-hydroxyphenyl)-N-n-propylpiperidine

  摘要：

  p-Dimethoxyaryl analogs of certain potent catechol-derived dopaminergic agonists show dopaminergic properties for which no structure-activity relationship has yet been defined. (S)-3-(3-Hydroxyphenyl)-N-n-propylpiperidine (1, S-''3-PPP'') is a dopaminergic autoreceptor agonist, and at high doses it also exhibits postsynaptic antagonism. (R)-1 is a postsynaptic agonist. In a continuation of studies of effects of the p-dimethoxy moiety at dopamine receptors, synthesis and resolution of the 2,5-dimethoxy analog 3 of 3-PPP was undertaken. The two enantiomers and the racemic modification showed cardiovascular effects consistent with actions at DA-2 receptors. The potency of all three compounds was much lower than that of 3-PPP, although they displayed approximately the same duration of action. Absolute configuration does not seem to be a major determinant of these compounds' ability to interact with DA-2 receptors.

  DOI：

  10.1021/jm00068a021

文献信息

• 5-HT2A AGONISTS FOR USE IN TREATMENT OF DEPRESSION
  申请人：Lophora ApS

  公开号：US20210137908A1

  公开（公告）日：2021-05-13

  The present invention relates to agonists of the 5-HT 2A serotonin receptors and their medical uses. In one aspect the invention relates to 5-HT 2A agonists of formula (I). In second aspect, the invention relates to selective 5-HT 2A agonists of formula (II). In another aspect, the invention relates to mixed 5-HT 2A /5-HT 2C agonists of formula (III). In yet another aspect, the invention relates to 5-HT 2A agonists for use in the treatment of a depressive disorder, more particular a 5-HT 2A agonist for the use in the treatment of treatment-resistant depression.

  本发明涉及5-HT2A 5-羟色胺受体的激动剂及其医疗用途。在一个方面，本发明涉及式(I)的5-HT2A激动剂。在第二个方面，本发明涉及式(II)的选择性5-HT2A激动剂。在另一个方面，本发明涉及式(III)的混合5-HT2A/5-HT2C激动剂。在另一个方面，本发明涉及用于治疗抑郁症的5-HT2A激动剂，更具体地说是用于治疗难治性抑郁症的5-HT2A激动剂。
• 5-HT2A agonists for use in treatment of depression
  申请人：Lophora ApS

  公开号：US11246860B2

  公开（公告）日：2022-02-15

  The present invention relates to agonists of the 5-HT2A serotonin receptors and their medical uses. In one aspect the invention relates to 5-HT2A agonists of formula (I). In second aspect, the invention relates to selective 5-HT2A agonists of formula (II). In another aspect, the invention relates to mixed 5-HT2A/5-HT2C agonists of formula (III). In yet another aspect, the invention relates to 5-HT2A agonists for use in the treatment of a depressive disorder, more particular a 5-HT2A agonist for the use in the treatment of treatment-resistant depression.

  本发明涉及 5-HT2A 血清素受体的激动剂及其医疗用途。一方面，本发明涉及式（I）的 5-HT2A 激动剂。第二方面，本发明涉及式（II）的选择性 5-HT2A 激动剂。另一方面，本发明涉及式（III）的 5-HT2A/5-HT2C 混合激动剂。再一方面，本发明涉及用于治疗抑郁障碍的5-HT2A激动剂，尤其是用于治疗耐药抑郁症的5-HT2A激动剂。
• 2,5-Dimethoxy congeners of (+)- and (-)-3-(3-hydroxyphenyl)-N-n-propylpiperidine
  作者：Joseph G. Cannon、Karen S. Kirschbaum、Victor E. D. Amoo、Alan K. Johnson、John Paul Long

  DOI：10.1021/jm00068a021

  日期：1993.8

  p-Dimethoxyaryl analogs of certain potent catechol-derived dopaminergic agonists show dopaminergic properties for which no structure-activity relationship has yet been defined. (S)-3-(3-Hydroxyphenyl)-N-n-propylpiperidine (1, S-''3-PPP'') is a dopaminergic autoreceptor agonist, and at high doses it also exhibits postsynaptic antagonism. (R)-1 is a postsynaptic agonist. In a continuation of studies of effects of the p-dimethoxy moiety at dopamine receptors, synthesis and resolution of the 2,5-dimethoxy analog 3 of 3-PPP was undertaken. The two enantiomers and the racemic modification showed cardiovascular effects consistent with actions at DA-2 receptors. The potency of all three compounds was much lower than that of 3-PPP, although they displayed approximately the same duration of action. Absolute configuration does not seem to be a major determinant of these compounds' ability to interact with DA-2 receptors.
• Discovery and Structure–Activity Relationships of 2,5-Dimethoxyphenylpiperidines as Selective Serotonin 5-HT_2A Receptor Agonists
  作者：Emil M. Ro̷rsted、Anders A. Jensen、Gints Smits、Karla Frydenvang、Jesper L. Kristensen

  DOI：10.1021/acs.jmedchem.4c00082

  日期：——

  Classical psychedelics such as psilocybin, lysergic acid diethylamide (LSD), and N,N-dimethyltryptamine (DMT) are showing promising results in clinical trials for a range of psychiatric indications, including depression, anxiety, and substance abuse disorder. These compounds are characterized by broad pharmacological activity profiles, and while the acute mind-altering effects can be ascribed to their

  裸盖菇素、麦角酰二乙酰胺 (LSD) 和N,N-二甲基色胺 (DMT) 等经典迷幻药在针对一系列精神疾病（包括抑郁症、焦虑症和药物滥用障碍）的临床试验中显示出良好的结果。这些化合物的特点是具有广泛的药理活性，虽然急性改变思维作用可归因于它们对血清素 2A 受体 (5-HT 2A R) 的共同激动剂活性，但它们明显的持久治疗作用尚未明确联系起来。对该受体的活性。我们在此报告了 2,5-二甲氧基苯基哌啶作为一类新型选择性 5-HT 2A R 激动剂的发现，并详细介绍了导致鉴定 LPH-5 [类似物 ( S ) -11 ] 作为选择性 5-HT 2A R 激动剂的结构-活性研究。 -HT 2A R 激动剂，具有理想的药物样特性。