N-(N-甲基哌啶基)甲基吲哚 | 137641-68-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: N-(N-甲基哌啶基)甲基吲哚
• 英文名称: 1-(1-methylpiperidin-2-ylmethyl)-1H-indole
• 英文别名: 1-(N-methylpiperidin-2-ylmethyl)indole；1-[(1-methyl-2piperidinyl)methyl]-1H-indole；1-[(1-Methylpiperidin-2-yl)methyl]-1H-indole；1-[(1-methylpiperidin-2-yl)methyl]indole
• CAS: 137641-68-0
• 化学式: C₁₅H₂₀N₂
• 分子量: 228.337
• InChiKey: XVOUFWJFSTTZOA-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  8.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(N-甲基哌啶基)甲基吲哚 在 氯化亚砜 、 三乙胺 作用下， 以 氯仿 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship of a Novel Series of Aminoalkylindoles with Potential for Imaging the Neuronal Cannabinoid Receptor by Positron Emission Tomography

  摘要：

  A new series of CB1 ligands with high binding affinity (K-i = 0.7-100 nM) and moderate lipophilicity (cLogD(7.4)) in the range of 2.1-4.5 has been synthesized. A structure-activity relationship study demonstrated that for the studied set of aminoalkylindoles, the molecular dipole of the ground state conformation within the series was inversely related to the affinity. The racemic ligand with highest affinity (0.7 nM), 3-(4-fluoronaphthoyl)-1-(N-methylpiperidin-2-ylmethyl)indole, was radiolabeled with F-18. This radioligand specifically labeled CB, receptors in mouse brain and accumulated in regions of high versus low CB1 receptor density in a ratio of 1.6. The displaceable radioactivity of one enantiomer in the brains of mice determined in a pretreatment study using the CB, antagonist N-(piperidinyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (SR141716) was nearly double that of the racemate for the same determination; therefore, the active enantiomer is a candidate for PET studies in animals. A pretreatement study for the other enantiomer found no displaceable radioactivity in the same group of mice; this result suggested the enantiomer was inactive.

  DOI：

  10.1021/jm0502743
• 作为产物：
  描述：

  吲哚 、 2-(氯甲基)-1-甲基哌啶 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 生成 N-(N-甲基哌啶基)甲基吲哚 、 1-[(1-methyl-3-piperidinyl)methyl]-5-fluoro-1H-indole
  参考文献：
  名称：

  3-arylcarbonyl-1-(C-attached-N-heteryl)-1H-indoles

  摘要：

  2-R.sub.2 -R.sub.4 -取代的-3-R.sub.3 -CO-1-[(C-连接的-N-杂环)-(Alk).sub.n ]-1H-吲哚可用作镇痛、抗风湿、抗炎或抗青光眼药剂。

  公开号：

  US05068234A1

文献信息

• Compounds for Treating Cannabinoid Toxicity and Acute Cannabinoid Overdose
  申请人：MAKScientific, LLC

  公开号：US20220033393A1

  公开（公告）日：2022-02-03

  The present invention relates to novel compounds that can act as antidotes for treating “Acute Cannabinoid Overdose” produced by classical cannabinoids such as Δ 9 -tetrahydrocannabinol (THC) and several synthetic psychoactive cannabinoids (SPCs). The cannabis constituent THC exerts its psychotropic effects via CB1 receptor activation and SPCs mimic the effects of THC with higher potency and severe neurotoxicity. Compounds disclosed in this invention, their enantiomers, diastereomers, geometric isomers, racemates, tautomers, rotamers, atropisomers, metabolites, N-oxides, salts, solvates, hydrates, isotopic variations and their polymorphic forms can be therapeutically useful in an emergency setting for counteracting the intoxicating effects of acute THC ingestion and SPC overdose. Also, aspects of the invention are concerned with pyrazoles, imidazoles, triazoles, thiazoles, oxazoles, dihydropyrazoles, pyrrolidinones, azetidines, oxyazetidines and azaspiro[3.3]heptanes with unique pharmacokinetic and pharmacodynamic properties for treating “Acute Cannabinoid Overdose”.

  本发明涉及一种新型化合物，可以作为治疗由经典大麻素（如Δ9-四氢大麻酚（THC））和几种合成精神活性大麻素（SPCs）产生的“急性大麻素过量”的解毒剂。大麻成分THC通过CB1受体激活发挥其精神活性作用，而SPCs则模拟THC的效果，具有更高的效力和严重的神经毒性。本发明披露的化合物及其对映体、二对映体、几何异构体、拉克酸盐、互变异构体、转型异构体、异构异构体、代谢物、N-氧化物、盐、溶剂合物、水合物、同位素变体及其多态形式在急诊情况下可以在对抗急性THC摄入和SPC过量的中毒作用方面具有治疗用途。此外，本发明涉及吡唑烷、咪唑烷、三唑烷、噻唑烷、噁唑烷、二氢吡唑烷、吡咯烷酮、氮杂环丁烷、氧杂环丁烷和氮杂螺[3.3]庚烷等具有独特药代动力学性能的化合物，用于治疗“急性大麻素过量”。
• Receptor selective cannabimimetic aminoalkylindoles
  申请人：——

  公开号：US20040077851A1

  公开（公告）日：2004-04-22

  Disclosed are cannabimimetic aminoalkylindole compounds and methos for their manufacture. The disclosed compounds are surprisingly potent and selective cannabinoinds. Also disclosed are methods of using the disclosed compounds, including use of the disclosed compounds to stimulate a cannabinoid receptor, to provide a physiological effect in an animal or individual and to treat a condition in an animal or individual.

  本发明涉及大麻样氨基烷基吲哚化合物及其制备方法。所披露的化合物具有惊人的强大和选择性的大麻素作用。本发明还涉及使用所披露的化合物的方法，包括使用所披露的化合物刺激大麻素受体，在动物或个体中产生生理效应以及治疗动物或个体的疾病的使用方法。
• Receptor Selective Cannabimimetic Aminoalkylindoles
  申请人：Makriyannis Alexandros

  公开号：US20070243134A1

  公开（公告）日：2007-10-18

  Disclosed are cannabimimetic aminoalkylindole compounds and methods for their manufacture. The disclosed compounds are surprisingly potent and selective cannabinoids. The disclosed compounds may include radioactive atoms. Also disclosed are methods of using the disclosed compounds, including use of the disclosed compounds to stimulate a cannabinoid receptor, to provide a physiological effect in an animal or individual, to treat a condition in an animal or individual and for use in radioimaging.

  本发明涉及大麻类氨基烷基吲哚化合物及其制备方法。所述化合物具有惊人的强效和选择性大麻素。所述化合物可能包括放射性原子。本发明还涉及使用所述化合物的方法，包括使用所述化合物刺激大麻素受体，在动物或个体中产生生理效应，治疗动物或个体的疾病以及用于放射性成像。
• CANNABINERGIC NITRATE ESTERS AND RELATED ANALOGS
  申请人：Northeastern University

  公开号：US20160002195A1

  公开（公告）日：2016-01-07

  The present technology relates to novel cannabinergic nitrate esters and related analogs, process of preparation, pharmaceutical compositions and their methods of use as medicaments, pharmacological tools and/or biomarkers. The novel cannabinergic nitrate ester compounds provide medicaments useful in treating a variety of diseases and medical disorders.

  本技术涉及新型大麻素硝酸酯及其类似物、制备方法、制药组合物及其作为药物、药理工具和/或生物标志物的使用方法。这些新型大麻素硝酸酯化合物提供了治疗各种疾病和医学障碍的有用药物。
• Novel Cannabinergic Nitrate Esters and Related Analogs
  申请人：Makriyannis Alexandros

  公开号：US20160096822A1

  公开（公告）日：2016-04-07

  Biologically active cannabinergic nitrate esters and related analogs, process of preparation, pharmaceutical compositions and their methods of use as medicaments, pharmacological tools or biomarkers. Pharmaceutical compositions may include one or more of the nitrate ester compounds. Medicaments include one or more of the cannabinergic nitrate ester compounds and are useful in treating a variety of diseases. A method of treating, preventing or reducing the severity of a condition includes administering at least one of the disclosed nitrate ester compounds to an individual or animal in need thereof.

  具有生物活性的大麻素硝酸酯及其类似物、制备方法、制药组合物及其作为药物、药理工具或生物标志物的使用方法。制药组合物可以包括一个或多个硝酸酯化合物。药物包括一个或多个大麻素硝酸酯化合物，可用于治疗各种疾病。一种治疗、预防或减轻症状的方法包括向需要的个体或动物中至少给予所披露的硝酸酯化合物之一。