(R)-dehydronorketamine | 153381-93-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-dehydronorketamine
• 英文别名: Dehydronorketamine, (R)-；(6R)-6-amino-6-(2-chlorophenyl)cyclohex-2-en-1-one
• CAS: 153381-93-2
• 化学式: C₁₂H₁₂ClNO
• 分子量: 221.686
• InChiKey: BXBPJMHHWPXBJL-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-dehydronorketamine 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 四氯化碳 、 乙酸乙酯 、 甲苯 为溶剂， 23.0~80.0 ℃ 、101.33 kPa 条件下， 反应 23.0h， 生成 (1S,5R)-5-(2-chlorophenyl)-2-oxa-4-azabicyclo[3.3.1]nonane-3,6-dione
  参考文献：
  名称：

  氯胺酮代谢物的合成和N-甲基-d-天冬氨酸（NMDA）受体活性

  摘要：

  氯胺酮在人体内迅速代谢为多种代谢物，包括羟基去甲酮胺。至少两个hydroxynorketamines具有在啮齿动物模型显著抗抑郁作用，与针对有限的行动Ñ甲基d天冬氨酸（NMDA）受体。这里介绍了12种羟基降甲酮胺的合成及其与NMDA受体的结合亲和力。

  DOI：

  10.1021/acs.orglett.7b02177
• 作为产物：
  描述：

  邻氯苯基环戊基酮 在 ammonium hydroxide 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 pyridinium hydrobromide perbromide 、 sodium hydroxide 、 copper(ll) bromide 作用下， 以 乙醇 、 水 、 乙酸乙酯 、 异丙醇 、 乙腈 为溶剂， 反应 2.5h， 生成 (R)-dehydronorketamine
  参考文献：
  名称：

  氯胺酮代谢物的合成和N-甲基-d-天冬氨酸（NMDA）受体活性

  摘要：

  氯胺酮在人体内迅速代谢为多种代谢物，包括羟基去甲酮胺。至少两个hydroxynorketamines具有在啮齿动物模型显著抗抑郁作用，与针对有限的行动Ñ甲基d天冬氨酸（NMDA）受体。这里介绍了12种羟基降甲酮胺的合成及其与NMDA受体的结合亲和力。

  DOI：

  10.1021/acs.orglett.7b02177

文献信息

• THE USE OF (2R, 6R)-HYDROXYNORKETAMINE, (S)-DEHYDRONORKETAMINE AND OTHER STEREOISOMERIC DEHYDRO AND HYDROXYLATED METABOLITES OF (R,S)- KETAMINE IN THE TREATMENT OF DEPRESSION AND NEUROPATHIC PAIN
  申请人：The United State of America, as Represented by the Secretary, Department od Health and Human Service

  公开号：US20140296241A1

  公开（公告）日：2014-10-02

  The disclosure provides pharmaceutical preparations containing (2R,6R)-hydroxynorketamine, or (R)- or (S)-dehydronorketamine, or other stereoisomeric dehydro or hydroxylated ketamine metabolite. (2R,6R)-hydroxynorketamine The disclosure also provides novel ketamine metabolite prodrugs. The disclosure provides methods of treating, bipolar depression, major depressive disorder, neuropathic and chronic pain, including complex regional pain disorder (CRPS) by administering a purified ketamine metabolite or a ketamine metabolite prodrug directly to patients in need of such treatment.
• USE OF (2R, 6R)-HYDROXYNORKETAMINE, (S)-DEHYDRONORKETAMINE AND OTHER STEREOISOMERIC DEHYDRO AND HYDROXYLATED METABOLITES OF (R,S)- KETAMINE IN THE TREATMENT OF DEPRESSION AND NEUROPATHIC PAIN
  申请人：THE USA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：US20170049780A1

  公开（公告）日：2017-02-23

  The disclosure provides pharmaceutical preparations containing (2R,6R)-hydroxynorketamine, or (R)- or (S)-dehydronorketamine, or other stereoisomeric dehydro or hydroxylated ketamine metabolite. (2R,6R)-hydroxynorketamine The disclosure also provides novel ketamine metabolite prodrugs. The disclosure provides methods of treating, bipolar depression, major depressive disorder, neuropathic and chronic pain, including complex regional pain synthetic pain disorder (CRPD) by administering a purified ketamine metabolite or a ketamine metabolite prodrug directly to patients in need of such treatment.
• USE OF (2R, 6R)-HYDROXYNORKETAMINE, (S)-DEHYDRONORKETAMINE AND OTHER STEREOISOMERIC DEHYDRO AND HYDROXYLATED METABOLITES OF (R,S)-KETAMINE IN THE TREATMENT OF DEPRESSION AND NEUROPATHIC PAIN
  申请人：THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVIC

  公开号：US20200360393A1

  公开（公告）日：2020-11-19

  The disclosure provides pharmaceutical preparations containing (2R,6R)-hydroxynorketamine, or (R)- or (S)-dehydronorketamine , or other stereoisomeric dehydro or hydroxylated ketamine metabolite. (2R,6R)-Hydroxynorketamine The disclosure also provides novel ketamine metabolite prodrugs. The disclosure provides methods of treating, bipolar depression, major depressive disorder, neuropathic and chronic pain, including complex regional pain synthetic pain disorder (CRPD) by administering a purified ketamine metabolite or a ketamine metabolite prodrug directly to patients in need of such treatment.
• US8912201B2
  申请人：——

  公开号：US8912201B2

  公开（公告）日：2014-12-16
• US9650352B2
  申请人：——

  公开号：US9650352B2

  公开（公告）日：2017-05-16