noribogaine | 481-88-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 依波格型生物碱
• 英文名称: noribogaine
• 英文别名: (1R,15R,17S,18S)-17-ethyl-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraen-7-ol
• CAS: 481-88-9
• 化学式: C₁₉H₂₄N₂O
• 分子量: 296.412
• InChiKey: RAUCDOKTMDOIPF-RYRUWHOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  39.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  noribogaine 在 硫酸 作用下， 以 异丙醇 为溶剂， 以89%的产率得到noribogaine sulfate
  参考文献：
  名称：

  NORIBOGAINE SALT ANSOLVATES

  摘要：

  稳定的无溶剂盐态诺比冈可用于制备药物组合物并缓解患者的疼痛。这样的无溶剂盐态可以通过在EtOH /水中搅拌溶剂化形式，最好是MeOH溶剂化的诺比冈盐酸盐制备而成。

  公开号：

  US20130072472A1
• 作为产物：
  描述：

  伏康京碱 在 碘 、 氢化铝 、 potassium hydroxide 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 3.08h， 生成 noribogaine
  参考文献：
  名称：

  A Single Administration of the Atypical Psychedelic Ibogaine or Its Metabolite Noribogaine Induces an Antidepressant-Like Effect in Rats

  摘要：

  Anecdotal reports and open-label case studies in humans indicated that the psychedelic alkaloid ibogaine exerts profound antiaddictive effects. Ample preclinical evidence demonstrated the efficacy of ibogaine, and its main metabolite, noribogaine, in substance-use-disorder rodent models. In contrast to addiction research, depression-relevant effects of ibogaine or noribogaine in rodents have not been previously examined. We have recently reported that the acute ibogaine administration induced a long-term increase of brain-derived neurotrophic factor mRNA levels in the rat prefrontal cortex, which led us to hypothesize that ibogaine may elicit antidepressant-like effects in rats. Accordingly, we characterized behavioral effects (dose- and time-dependence) induced by the acute ibogaine and noribogaine administration in rats using the forced swim test (FST, 20 and 40 mg/kg i.p., single injection for each dose). We also examined the correlation between plasma and brain concentrations of ibogaine and noribogaine and the elicited behavioral response. We found that ibogaine and noribogaine induced a dose- and time-dependent antidepressant-like effect without significant changes of animal locomotor activity. Noribogaine's FST effect was short-lived (30 min) and correlated with high brain concentrations (estimated >8 mu M of free drug), while the ibogaine's antidepressant-like effect was significant at 3 h. At this time point, both ibogaine and noribogaine were present in rat brain at concentrations that cannot produce the same behavioral outcome on their own (ibogaine similar to 0.5 mu M, noribogaine similar to 2.5 mu M). Our data suggests a polypharmacological mechanism underpinning the antidepressant-like effects of ibogaine and noribogaine.

  DOI：

  10.1021/acschemneuro.0c00152

文献信息

• [EN] A NEW CLASS OF MU-OPIOID RECEPTOR AGONISTS<br/>[FR] NOUVELLE CLASSE D'AGONISTES DU RÉCEPTEUR MU-OPIOÏDE
  申请人：UNIV COLUMBIA

  公开号：WO2015138791A1

  公开（公告）日：2015-09-17

  The present invention provides a compound having the structure (I) or a pharmaceutically acceptable salt or ester thereof.

  本发明提供了一种具有结构（I）的化合物或其药用可接受的盐或酯。
• [EN] SMALL MOLECULE INDUCERS OF GDNF AS POTENTIAL NEW THERAPEUTICS FOR NEUROPSYCHIATRIC DISORDERS<br/>[FR] PETITES MOLÉCULES INDUCTRICES DE GDNF COMME NOUVELLE THÉRAPEUTIQUE POSSIBLE DES TROUBLES NEUROPSYCHIATRIQUES
  申请人：UNIV COLUMBIA

  公开号：WO2013028999A1

  公开（公告）日：2013-02-28

  The invention provides a compound having the structure (I), wherein A is a substituted or unsubstituted ring; Z is present or absent and when present is (II), wherein n is 0, 1, 2, 3, or 4; Y is -(CR11R12)-, -NH(CR11R12)- or -O(CR11R12)- wherein R11 and R12 are each hydrogen or combine to form a carbonyl; and wherein R1 to R10 are herein as described.

  本发明提供了一种具有结构（I）的化合物，其中A是取代的或未取代的环；Z是否存在，如果存在则为（II），其中n为0，1，2，3或4；Y是-(CR11R12)-，-NH(CR11R12)-或-O(CR11R12)-，其中R11和R12分别是氢或结合形成一个羰基；以及其中R1至R10如本文所述。
• [EN] MITRAGYNINE ALKALOIDS AS OPIOID RECEPTOR MODULATORS<br/>[FR] ALCALOÏDES DE TYPE MITRAGYNINE UTILISÉS COMME MODULATEURS DE RÉCEPTEURS OPIOÏDES
  申请人：UNIV COLUMBIA

  公开号：WO2017165738A1

  公开（公告）日：2017-09-28

  The present invention provides a compound having the structure: or a pharmaceutically acceptable salt or ester thereof, and a method of treating a subject afflicted with pain, a depressive disorder, a mood disorder or an anxiety disorder by administering the compound to the subject.

  本发明提供一种具有以下结构的化合物：或其药用可接受的盐或酯，并通过向受痛苦、抑郁症、情绪障碍或焦虑障碍的对象施用该化合物的方法来治疗患者。
• Compositions comprising noribogaine and an excipient to facilitate transport across the blood brain barrier
  申请人：Mash Deborah C.

  公开号：US08637648B1

  公开（公告）日：2014-01-28

  This invention relates generally to compositions comprising noribogaine and an excipient to facilitate transport across the blood brain barrier.

  这项发明通常涉及包含诺利波甲碱和辅助剂以促进穿越血脑屏障的组合物。
• [EN] N-SUBSTITUTED NORIBOGAINE PRODRUGS<br/>[FR] PROMÉDICAMENTS DE NORIBOGAÏNE N-SUBSTITUÉ
  申请人：DEMERX INC

  公开号：WO2015163844A1

  公开（公告）日：2015-10-29

  This invention relates generally to prodrugs of noribogaine. This invention also relates to pharmaceutical compositions comprising the prodrugs of noribogaine as well as method of treating pain, addiction and/or stress using such compounds and/or pharmaceutical compositions.

  这项发明通常涉及诺伊波甲醇的前药。这项发明还涉及包含诺伊波甲醇前药的药物组合物，以及使用这些化合物和/或药物组合物治疗疼痛、成瘾和/或压力的方法。