dextromethorphan | 510-53-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: dextromethorphan
• 英文别名: 3-Methoxy-N-methylmorphinan；Racemethorphan；4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene
• CAS: 510-53-2
• 化学式: C₁₈H₂₅NO
• 分子量: 271.403
• InChiKey: MKXZASYAUGDDCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  dextromethorphan 在 溴 、 [¹²³I]iodide 、 双氧水 作用下， 生成 2-[123I]iododextrorphan
  参考文献：
  名称：

  Gildehaus, F. J.; Li, H. F.; Linke, R., Journal of Labelled Compounds and Radiopharmaceuticals, 2001, vol. 44, p. S292 - S295

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(4-Methoxybenzyl)-2-methyl-5,6,7,8-tetrahydroisochinoliniumiodide 在 sodium hydroxide 、 sodium tetrahydroborate 、 氢溴酸 作用下， 以 甲醇 、 乙醇 、 氯仿 、 水 为溶剂， 反应 70.0h， 生成 dextromethorphan
  参考文献：
  名称：

  选择性催化氢化和氢解，第 6 版。1-苄基-2-甲基八氢异喹啉的改进合成

  摘要：

  标题化合物 3 可以方便地由相应的 Bz-四氢异喹啉 1 的甲碘化物 2 通过 NaBH4 还原制备。

  DOI：

  10.1002/ardp.19853180804

文献信息

• 3,4,6-Substituted pyridazines for treating neuropathic pain and associated syndromes
  申请人：Sultzbaugh Lance

  公开号：US20070191365A1

  公开（公告）日：2007-08-16

  The present invention is directed to the use of 3,4,6-substituted pyridazines such as those characterized by structure I for treating conditions such as neuropathic pain among others.

  本发明涉及使用3,4,6-取代吡啶嗪，如结构I所示的化合物，用于治疗神经病痛等疾病。
• [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] HETEROARYL AMIDE ANALOGUES<br/>[FR] ANALOGUES D'HÉTÉROARYLAMIDES
  申请人：NEUROGEN CORP

  公开号：WO2009023623A1

  公开（公告）日：2009-02-19

  Compounds, pharmaceutical compositions, and methods of use are disclosed for heteroaryl amide analogues of formula Ia and/or Ib: . In certain embodiments, the heteroaryl amide analogues are agonists and/or ligands of dopamine receptors and may be useful, inter alia, for the treatment of a condition responsive to P2X7 receptor modulation, for example, pain, inflammation, a neurological or neurodegenerative disorder, a cardiovascular disorder, an ocular disorder or an immune system disorder.

  公开了公式Ia和/或Ib的杂环酰胺类似物的化合物、药物组合物和使用方法。在某些实施例中，这些杂环酰胺类似物是多巴胺受体的激动剂和/或配体，可能有助于治疗对P2X7受体调节敏感的疾病，例如疼痛、炎症、神经系统或神经退行性疾病、心血管疾病、眼部疾病或免疫系统疾病。
• [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。
• ENANTIOMERIC COMPOSITIONS OF 2-AMINO-1-(2-ISOPROPYLPYRAZOLO[1,5-a]PYRIDIN-3-YL)PROPAN-1-ONE AND RELATED METHODS
  申请人：Johnson Kirk W.

  公开号：US20100324082A1

  公开（公告）日：2010-12-23

  Enantiomerically pure (S)-2-amino-1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one, (S)-AV1013, is a candidate therapeutic for treating neuroathic pain, addiction behavior and drug withdrawal symptoms. Also described are methods for preparing and using (S)-AV1013, its pharmaceutically acceptable salts as well as pharmaceutically acceptable formulations of the same.

  (S)-2-氨基-1-(2-异丙基吡唑并[1,5-a]吡啶-3-基)丙酮，即(S)-AV1013，是一种治疗神经痛、成瘾行为和药物戒断症状的候选治疗药物。还描述了制备和使用(S)-AV1013及其药用可接受盐以及相同药用可接受配方的方法。

表征谱图