2,5-二甲氧基-4-硝基苯乙胺 | 261789-00-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,5-二甲氧基-4-硝基苯乙胺
• 英文名称: 2-(2,5-dimethoxy-4-nitrophenyl)ethanamine
• 英文别名: 2,5-Dimethoxy-4-nitrophenethylamine
• CAS: 261789-00-8
• 化学式: C₁₀H₁₄N₂O₄
• 分子量: 226.232
• InChiKey: ZMUSDZGRRJGRAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 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：
  90.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-二甲氧基-4-硝基苯乙胺 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 生成 2,5-Dimethoxy-4-nitro-phenethylamine HCl
  参考文献：
  名称：

  [EN] SELECTIVE, PARTIAL, AND ARRESTIN-BIASED 5-HT2A AGONISTS WITH UTILITY IN VARIOUS DISORDERS
  [FR] AGONISTES SÉLECTIFS, PARTIELS ET POLARISÉS DE 5-HT2A AVEC UTILITÉ DANS DIVERS TROUBLES

  摘要：

  本文披露了一些新型的血清素5-HT2A受体激动剂，具有对其他血清素受体亚型的选择性。其中一些5-HT2A激动剂表现出功能选择性，优先激活阿雷斯汀信号转导而非G蛋白介导的信号转导。此外，还披露了这些化合物的制药组合物和治疗某些疾病或病症的方法。

  公开号：

  WO2022241006A1
• 作为产物：
  描述：

  2,5-二甲氧基苯乙胺 在 硝酸 、 溶剂黄146 作用下， 以 水 为溶剂， 生成 2,5-二甲氧基-4-硝基苯乙胺
  参考文献：
  名称：

  一组苯烷基胺 5-HT2A 受体激动剂的偏向激动的结构-活性评估和深入分析

  摘要：

  据描述，血清素能致幻剂的主要药理作用是激活血清素 2A 受体 (5-HT 2A )。尽管它们具有相关性，但某些 5-HT 2A激动剂引起迷幻作用的分子机制仍然难以捉摸。提出的假设之一是偏向激动的发生，其定义为某些信号通路相对于其他信号通路的优先激活。这项研究比较监测了一组不同的 4 位取代（和N-苄基衍生的）苯基烷基胺诱导 β-arrestin2 (βarr2) 或 miniGα q募集到 5-HT 2A的效率，使我们能够评估结构–活动关系和偏激性。所有测试化合物均表现出激动剂特性，EC 50和E max值范围相对较大。有趣的是，2C-X 苯乙胺的亲脂性与其在两种测定中的功效相关，但在 miniGα q中产生的相关性比在 βarr2 测定中更强。分子对接表明，2C-X 类似物的 4-取代基容纳在 5-HT 2A 跨膜螺旋 4 和 5 之间的疏水袋中可能有助于这种差异效应。除了以前使用的标准条件（麦角酸二乙酰胺

  DOI：

  10.1021/acschemneuro.3c00267

文献信息

• [EN] 5-HT2C RECEPTOR AGONISTS AND COMPOSITIONS AND METHODS OF USE<br/>[FR] AGONISTES DE RÉCEPTEUR 5-HT2C ET COMPOSITIONS ET PROCÉDÉS D'UTILISATION
  申请人：ARENA PHARM INC

  公开号：WO2017023679A1

  公开（公告）日：2017-02-09

  Provided in some embodiments are compounds of Formula A, as defined herein, that modulate the activity of 5-HT2C receptor. Also provided in some embodiments are methods, such as, for weight management, inducing satiety, and decreasing food intake, and for preventing and treating obesity, antipsychotic-induced weight gain, type 2 diabetes, Prader-Willi syndrome, tobacco/nicotine dependence, drug addiction, alcohol addiction, pathological gambling, reward deficiency syndrome, and sex addiction), obsessive-compulsive spectrum disorders and impulse control disorders (including nail-biting and onychophagia), sleep disorders (including insomnia, fragmented sleep architecture, and disturbances of slow-wave sleep), urinary incontinence, psychiatric disorders (including schizophrenia, anorexia nervosa, and bulimia nervosa), Alzheimer disease, sexual dysfunction, erectile dysfunction, epilepsy, movement disorders (including parkinsonism and antipsychotic-induced movement disorder), hypertension, dyslipidemia, nonalcoholic fatty liver disease, obesity-related renal disease, and sleep apnea.

  在某些实施例中提供了一些符合本文所定义的A式化合物，其调节5-HT2C受体的活性。在某些实施例中还提供了一些方法，例如用于体重管理、诱导饱腹感、减少食物摄入，以及预防和治疗肥胖、抗精神病药物引起的体重增加、2型糖尿病、普拉德-威利综合征、烟草/尼古丁依赖、药物成瘾、酒精成瘾、病理性赌博、奖赏缺乏综合征和性成瘾，强迫症谱系障碍和冲动控制障碍（包括咬指甲和咬甲症），睡眠障碍（包括失眠、睡眠结构碎裂和慢波睡眠紊乱），尿失禁，精神障碍（包括精神分裂症、厌食症和暴食症），阿尔茨海默病，性功能障碍，勃起功能障碍，癫痫，运动障碍（包括帕金森病和抗精神病药物引起的运动障碍），高血压，血脂异常，非酒精性脂肪肝病，肥胖相关肾脏疾病和睡眠呼吸暂停症。
• [EN] 5-HT2C RECEPTOR AGONISTS AND COMPOSITIONS AND METHODS OF USE<br/>[FR] AGONISTES DU RÉCEPTEUR 5-HT2C ET COMPOSITIONS ET PROCÉDÉS D'UTILISATION
  申请人：ARENA PHARM INC

  公开号：WO2015066344A1

  公开（公告）日：2015-05-07

  Provided are 5-HT2C receptor agonists. Also provided are methods for weight management, inducing satiety, and decreasing food intake, and for preventing and treating obesity, antipsychotic-induced weight gain, type 2 diabetes, Prader-Willi syndrome, tobacco/nicotine dependence, drug addiction, alcohol addiction, pathological gambling, reward deficiency syndrome, and sex addiction), obsessive-compulsive spectrum disorders and impulse control disorders (including nail-biting and onychophagia), sleep disorders (including insomnia, fragmented sleep architecture, and disturbances of slow-wave sleep), urinary incontinence, psychiatric disorders (including schizophrenia, anorexia nervosa, and bulimia nervosa), Alzheimer disease, sexual dysfunction, erectile dysfunction, epilepsy, movement disorders (including parkinsonism and antipsychotic-induced movement disorder), hypertension, dyslipidemia, nonalcoholic fatty liver disease, obesity-related renal disease, and sleep apnea. Also provided are compositions comprising a selective 5-HT2C receptor agonist, optionally in combination with a supplemental agent, and methods for reducing the frequency of smoking tobacco in an individual attempting to reduce frequency of smoking tobacco; aiding in the cessation or lessening of use of a tobacco product in an individual attempting to cease or lessen use of a tobacco product; aiding in smoking cessation and preventing associated weight gain; controlling weight gain associated with smoking cessation by an individual attempting to cease smoking tobacco; reducing weight gain associated with smoking cessation by an individual attempting to cease smoking tobacco; treating nicotine dependency, addiction and/or withdrawal in an individual attempting to treat nicotine dependency, addiction and/or withdrawal; or reducing the likelihood of relapse use of nicotine by an individual attempting to cease nicotine use comprising administering a selective 5-HT2C receptor agonist, optionally in combination with a supplemental agent.

  提供了5-HT2C受体激动剂。还提供了用于体重管理、诱导饱腹感、减少食物摄入量、预防和治疗肥胖、抗精神病药物引起的体重增加、2型糖尿病、普拉德-威利综合征、烟草/尼古丁依赖、药物成瘾、酒精成瘾、病态赌博、奖赏缺乏综合征和性成瘾）、强迫症谱系障碍和冲动控制障碍（包括咬指甲和咬甲）、睡眠障碍（包括失眠、睡眠结构碎裂和慢波睡眠紊乱）、尿失禁、精神障碍（包括精神分裂症、厌食症和暴食症）、阿尔茨海默病、性功能障碍、勃起功能障碍、癫痫、运动障碍（包括帕金森病和抗精神病药物引起的运动障碍）、高血压、血脂异常、非酒精性脂肪肝病、肥胖相关肾脏疾病和睡眠呼吸暂停。还提供了包含选择性5-HT2C受体激动剂的组合物，可选地与辅助剂结合，以及用于减少个体尝试减少吸烟频率的吸烟频率；帮助个体戒除或减少使用烟草制品的个体戒除或减少使用烟草制品；帮助戒烟并预防相关体重增加；通过个体尝试戒烟来控制与戒烟相关的体重增加；通过个体尝试戒烟来减少与戒烟相关的体重增加；治疗尼古丁依赖、成瘾和/或戒断的个体尝试治疗尼古丁依赖、成瘾和/或戒断；或减少个体尝试戒除尼古丁使用的复发可能性，包括给予选择性5-HT2C受体激动剂，可选地与辅助剂结合。
• [EN] 5-HT2C RECEPTOR AGONISTS AND COMPOSITIONS AND METHODS OF USE<br/>[FR] AGONISTES DES RÉCEPTEURS 5-HT2C ET COMPOSITIONS ET MÉTHODES D'UTILISATION
  申请人：ARENA PHARM INC

  公开号：WO2016176177A1

  公开（公告）日：2016-11-03

  Provided in some embodiments are compounds herein. Also provided in some embodiments are methods for weight management, inducing satiety, and decreasing food intake, and for preventing and treating obesity, antipsychotic-induced weight gain, type 2 diabetes, Prader-Willi syndrome, tobacco/nicotine dependence, drug addiction, alcohol addiction, pathological gambling, reward deficiency syndrome, and sex addiction), obsessive-compulsive spectrum disorders and impulse control disorders (including nail-biting and onychophagia), sleep disorders (including insomnia, fragmented sleep architecture, and disturbances of slow-wave sleep), urinary incontinence, psychiatric disorders (including schizophrenia, anorexia nervosa, and bulimia nervosa), Alzheimer disease, sexual dysfunction, erectile dysfunction, epilepsy, movement disorders (including parkinsonism and antipsychotic-induced movement disorder), hypertension, dyslipidemia, nonalcoholic fatty liver disease, obesity-related renal disease, and sleep apnea. Also provided in some embodiments are compositions comprising a compound herein, optionally in combination with a supplemental agent, and methods for reducing the frequency of smoking tobacco in an individual attempting to reduce frequency of smoking tobacco; aiding in the cessation or lessening of use of a tobacco product in an individual attempting to cease or lessen use of a tobacco product; aiding in smoking cessation and preventing associated weight gain; controlling weight gain associated with smoking cessation by an individual attempting to cease smoking tobacco; reducing weight gain associated with smoking cessation by an individual attempting to cease smoking tobacco; treating nicotine dependency, addiction and/or withdrawal in an individual attempting to treat nicotine dependency, addiction and/or withdrawal; or reducing the likelihood of relapse use of nicotine by an individual attempting to cease nicotine use comprising administering a compound herein, optionally in combination with a supplemental agent.

  在某些实施例中提供了本文中的化合物。在某些实施例中还提供了用于体重管理、诱发饱腹感、减少食物摄入、预防和治疗肥胖、抗精神病药物引起的体重增加、2型糖尿病、普拉德-威利综合征、烟草/尼古丁依赖、药物成瘾、酒精成瘾、病理赌博、奖赏缺乏综合征、性成瘾）、强迫症谱系障碍和冲动控制障碍（包括咬指甲和咬甲）、睡眠障碍（包括失眠、睡眠结构紊乱和慢波睡眠障碍）、尿失禁、精神障碍（包括精神分裂症、厌食症和暴食症）、阿尔茨海默病、性功能障碍、勃起功能障碍、癫痫、运动障碍（包括帕金森病和抗精神病药物引起的运动障碍）、高血压、血脂异常、非酒精性脂肪肝病、肥胖相关肾脏疾病和睡眠呼吸暂停。在某些实施例中还提供了包含本文中的化合物的组合物，可选择地与辅助剂结合，并且提供了用于减少个体尝试减少吸烟频率的吸烟频率；帮助个体戒除或减少吸烟产品的使用；帮助戒烟并预防相关体重增加；通过个体试图戒烟来控制与戒烟相关的体重增加；通过个体试图戒烟来减少与戒烟相关的体重增加；治疗个体试图治疗尼古丁依赖、成瘾和/或戒断的尼古丁依赖、成瘾和/或戒断；或减少个体试图停止尼古丁使用的复发尼古丁使用的可能性，包括给予本文中的化合物，可选择地与辅助剂结合。
• Multicyclic aromatic compounds and uses thereof
  申请人：Roche Diagnostics Corporation

  公开号：US06525200B1

  公开（公告）日：2003-02-25

  Multicyclic aromatic compounds useful as complexing agents having the general formula: Methods of complexing and quantitating a component in a sample such as urea or guanidine are also disclosed.

  多环芳香化合物可作为具有一般公式的络合剂：还公开了在样品中络合和定量化尿素或胍嘧啶等成分的方法。
• [EN] 5-HT2C RECEPTOR AGONISTS AND COMPOSITIONS AND METHODS OF USE<br/>[FR] AGONISTES DES RÉCEPTEURS 5-HT2C, COMPOSITIONS ET MÉTHODES D'UTILISATION
  申请人：ARENA PHARM INC

  公开号：WO2018035477A1

  公开（公告）日：2018-02-22

  The present invention relates to compounds of Formula A and pharmaceutical compositions thereof that modulate the activity of the 5-HT2C receptor. Compounds of the present invention and pharmaceutical compositions thereof are directed to methods useful in the treatment of a 5-HT2C receptor-mediated disorder, such as, weight management, inducing satiety, and decreasing food intake, and for preventing and treating obesity, antipsychotic-induced weight gain, type 2 diabetes, Prader-Willi syndrome, tobacco/nicotine dependence, drug addiction, alcohol addiction and the like, obsessive-compulsive spectrum disorders and impulse control disorders (including nail-biting and onychophagia), sleep disorders, urinary incontinence, psychiatric disorders (including schizophrenia, anorexia nervosa, and bulimia nervosa), Alzheimer disease, sexual dysfunction, erectile dysfunction, epilepsy, movement disorders (including parkinsonism and antipsychotic-induced movement disorder), hypertension, dyslipidemia, nonalcoholic fatty liver disease, obesity-related renal disease, and sleep apnea. Also provided are compositions comprising a compound herein, optionally in combination with a supplemental agent.

  本发明涉及式A的化合物及其药物组合物，可调节5-HT2C受体的活性。本发明的化合物及其药物组合物用于治疗5-HT2C受体介导的疾病，如体重管理、诱发饱腹感、减少食物摄入，以及预防和治疗肥胖、抗精神病药物引起的体重增加、2型糖尿病、普拉德-威利综合征、烟草/尼古丁依赖、药物成瘾、酒精成瘾等，强迫症谱系障碍和冲动控制障碍（包括咬指甲和咬甲症），睡眠障碍、尿失禁、精神障碍（包括精神分裂症、厌食症和暴食症）、阿尔茨海默病、性功能障碍、勃起功能障碍、癫痫、运动障碍（包括帕金森病和抗精神病药物引起的运动障碍）、高血压、血脂异常、非酒精性脂肪肝病、肥胖相关肾脏疾病和睡眠呼吸暂停症。还提供含有本文中化合物的组合物，可选择性地与辅助剂组合使用。