dextromethorphan

• 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: (1S,9S)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene
• 化学式: C₁₈H₂₅NO
• 分子量: 271.403
• InChiKey: MKXZASYAUGDDCJ-BEEDKBRMSA-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 DAP⁽²⁺⁾*2BF₄⁽¹⁺⁾ 、 氧气 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以95%的产率得到(1S,9S)-4-methoxy-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene
  参考文献：
  名称：

  Electron-transfer activation. Photochemical N-demethylation of tertiary amines

  摘要：

  DOI：

  10.1016/s0040-4039(00)99160-3

文献信息

• Singlet oxygen mediated alkaloid tertiary amines oxidation by single electron transfer
  作者：Clotilde Ferroud、Patrice Rool、Jean Santamaria

  DOI：10.1016/s0040-4039(98)02184-4

  日期：1998.12

  A chemical study of the oxidation of tertiary amines and alkaloids through monoelectronic transfer is presented and allows us to assign to singlet oxygen a new behavior as electron acceptor during the oxidation process.

  提出了通过单电子转移氧化叔胺和生物碱的化学研究，它使我们能够在氧化过程中为单重态氧赋予新的行为作为电子受体。
• OPIOID AND OPIOID-LIKE COMPOUNDS AND USES THEREOF
  申请人：Wu Edwin S.C.

  公开号：US20090169508A1

  公开（公告）日：2009-07-02

  The present invention relates to opioid and opioid-like compounds, and pharmaceutical formulations thereof, and use thereof for prevention and treatment of disorders such as septic shock and organ damage.

  本发明涉及阿片类和类阿片化合物，以及其制药配方和用于预防和治疗败血性休克和器官损伤等疾病的用途。
• Methods for treating depressive symptoms
  申请人：Alkermes Pharma Ireland Limited

  公开号：US10231963B2

  公开（公告）日：2019-03-19

  The present application relates methods for treating a depressive symptom comprising administering an effective amount of a μ opioid receptor agonist or a pharmaceutically acceptable salt thereof to a subject in need thereof. Non-limiting examples of such agonist include the compounds of Formulas I, II, III, and IV, as well as the compounds of Table A.

  本申请涉及治疗抑郁症状的方法，包括向有需要的受试者施用有效量的μ阿片受体激动剂或其药学上可接受的盐。此类激动剂的非限制性实例包括式I、II、III和IV化合物以及表A化合物。
• Morphan and morphinan analogues, and methods of use
  申请人：Alkermes Pharma Ireland Limited

  公开号：US10287250B2

  公开（公告）日：2019-05-14

  The present application relates to analogs of morphan and morphinan, compositions thereof, and methods for treating a disease or condition comprising administering an effective amount of the compounds or compositions to a subject in need thereof.

  本申请涉及吗啡烷和吗啡烷的类似物、其组合物以及治疗疾病或病症的方法，其中包括向有需要的受试者施用有效量的化合物或组合物。
• Analogs of dextromethorphan with balanced receptor activities
  申请人：The Center for Neurologic Study

  公开号：US11535596B2

  公开（公告）日：2022-12-27

  Substituted analogs of dextromethorphan (DM) are disclosed, which are shown to have substantial binding affinity at both NMDA and sigma-1 receptors, and which are degraded by human liver enzymes more slowly than dextromethorphan. The analogs are useful as alternatives to dextromethorphan, and can provide the same benefits without requiring co-administration of a cytochrome P-450 enzyme inhibitor.

  本研究公开了右美沙芬（DM）的替代类似物，这些类似物在 NMDA 和 sigma-1 受体上都有很强的结合亲和力，而且被人体肝脏酶降解的速度比右美沙芬慢。 这些类似物可作为右美沙芬的替代品，而且无需同时服用细胞色素 P-450 酶抑制剂就能获得同样的疗效。