伊菠加因盐酸盐 | 5934-55-4

• 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
• 中文名称: 伊菠加因盐酸盐
• 中文别名: 中文名称暂缺
• 英文名称: ibogaine hydrochloride
• 英文别名: (1R,15R,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene;hydrochloride
• CAS: 5934-55-4
• 化学式: C₂₀H₂₆N₂O*ClH
• 分子量: 346.9
• InChiKey: IKJFDJLQPHDRTD-ISYVNWANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  28.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  伊菠加因盐酸盐 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以93.15%的产率得到伊博格碱
  参考文献：
  名称：

  [EN] NORIBOGAINE COMPOSITIONS
  [FR] COMPOSITIONS DE NORIBOGAÏNE

  摘要：

  公开的是含有非常高水平的2（R），4（S），5（S），6（S）和18（R）对映体的诺利波甲酸组合物，相对于诺利波甲酸的总量不超过0.5重量％的伊波甲酸。

  公开号：

  WO2012012764A1
• 作为产物：
  描述：

  伏康京碱 在 盐酸 、 potassium hydroxide 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 0.08h， 生成 伊菠加因盐酸盐
  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] IBOGAMINE CONGENERS<br/>[FR] CONGENERES D'IBOGAMINE
  申请人：ALBANY MEDICAL COLLEGE

  公开号：WO1997005869A1

  公开（公告）日：1997-02-20

  (EN) The present invention is directed to compounds having formula (1), wherein n is from 0 to 8; R1 is CH2OH, CH(OH)R5, CH2OR5, CO2R5, C(O)NH2, C(O)NHR5, C(O)NR5R6, C(O)NHNH2, C(O)NHNHR5, C(O)NHNR5R6, C(O)NR5NH2, C(O)NR5NHR6, C(O)NR5NR6R7, C(O)NHNH(C(O)R5), C(O)NHNR5(C(O)R6), C(O)NR5NH(C(O)R6), C(O)NR5NR6(C(O)R7), CN, or C(O)R5; R2 is H, unsubstituted or substituted alkyl, YH, YR8, YC(O)R8, C(O)YR8, C(O)NH2, C(O)NHR8, C(O)NR8R9, NH2, NHR8, NR8R9, NHC(O)R8, or NR8C(O)R9; R3 and R4 are the same or different and are selected from the group consisting of H, halogens, unsubstituted or substituted alkyl, OH, OR10, NH2, NHR10, NR10R11, NHC(O)R10, or NR10C(O)R11; R5, R6, R7, R8, R9, R10, and R11 are the same or different and are selected from the group consisting of unsubstituted alkyl and substituted alkyl; R12 is selected from the group consisting of H, unsubstituted alkyl, and substituted alkyl; and Y is O or S; provided that when n is O, R2 is selected from the group consisting of H, substituted alkyl, and unsubstituted alkyl; and pharmaceutically acceptable salts thereof. The compounds are useful in the treatment of subjects addicted to opiates and stimulants and have reduced side effects relative to other ibogamine congeners.(FR) L'invention concerne des composés représentés par la formule, dans laquelle, n vaut 0 à 8; R1 représente CH2OH, CH(OH)R5, CH2OR5, CO2R5, C(O)NH2, C(O)NHR5, C(O)NR5R6, C(O)NHNH2, C(O)NHNHR5, C(O)NHNR5R6, C(O)NR5NH2, C(O)NR5NHR6, C(O)NR5NR6R7, C(O)NHNH(C(O)R5), C(O)NHNR5(C(O)R6), C(O)NR5NH(C(O)R6) C(O)NR5NR6(C(O)R7), CN ou C(O)R5; R2 représente H, alkyle substitué ou non, YH, YR8, YC(O)R8, C(O)YR8, C(O)NH2, C(O)NHR8, C(O)NR8R9, NH2, NHR8, NR8R9, NHC(O)R8 ou NR8C(O)R9; R3 et R4 sont semblables ou différents et sont sélectionnés dans le groupe constitué par H, halogènes, alkyle substitué ou non, OH, OR10, NH2, NHR10, NR10R11, NHC(O)R10 ou NR10C(O)R11; R5, R6; R7, R8, R9, R10 et R11 sont semblables ou différents et sont sélectionnés dans le groupe constitué par alkyle non substitué et alkyle substitué; R12 est sélectionné dans le groupe constitué par H, alkyle non substitué et alkyle substitué; Y représente O ou S; à savoir que, quand n vaut 0, R2 est sélectionné dans le groupe constitué par H, alkyle substitué et alkyle non substitué; ainsi que leurs sels acceptables sur le plan pharmaceutique. Ces composés sont utiles pour traiter des sujets dépendants des opiacés et des stimulants et présentent des effets secondaires limités par rapport à d'autres congénères d'ibogamine.

  本发明涉及具有式（1）的化合物，其中n为0至8; R1为CH2OH，CH（OH）R5，CH2OR5，CO2R5，C（O）NH2，C（O）NHR5，C（O）NR5R6，C（O）NHNH2，C（O）NHNHR5，C（O）NHNR5R6，C（O）NR5NH2，C（O）NR5NHR6，C（O）NR5NR6R7，C（O）NHNH（C（O）R5），C（O）NHNR5（C（O）R6），C（O）NR5NH（C（O）R6），C（O）NR5NR6（C（O）R7），CN或C（O）R5; R2为H，未取代或取代的烷基，YH，YR8，YC（O）R8，C（O）YR8，C（O）NH2，C（O）NHR8，C（O）NR8R9，NH2，NHR8，NR8R9，NHC（O）R8或NR8C（O）R9; R3和R4相同或不同，选择自H，卤素，未取代或取代的烷基，OH，OR10，NH2，NHR10，NR10R11，NHC（O）R10或NR10C（O）R11的群; R5，R6，R7，R8，R9，R10和R11相同或不同，选择自未取代的烷基和取代的烷基的群; R12选择自H，未取代的烷基和取代的烷基的群; Y为O或S; 假设当n为O时，R2选择自H，取代的烷基和未取代的烷基的群; 以及其在药学上可接受的盐。这些化合物对治疗对阿片类和兴奋剂上瘾的受试者有用，并且相对于其他伊博加曼同系物具有较少的副作用。
• Noribogaine in the treatment of pain and drug addiction
  申请人：Mash C. Deborah

  公开号：US20070185085A1

  公开（公告）日：2007-08-09

  The present invention is directed to methods of treating patients for pain by administering noribogaine. Noribogaine may also be used to treat patients for the symptoms associated with withdrawal from drug dependency. In the latter case, the noribogaine treatment should be supplemented with the administration of an opioid antagonist such as naloxone.

  本发明涉及使用诺比盖因治疗疼痛的方法。诺比盖因也可用于治疗戒断症状的患者。在后一种情况下，诺比盖因治疗应辅以给予阿片类拮抗剂如纳洛酮。
• NORIBOGAINE IN THE TREATMENT OF PAIN AND DRUG ADDICTION
  申请人：Mash Deborah C.

  公开号：US20120083485A1

  公开（公告）日：2012-04-05

  The present invention is directed to methods of treating patients for pain by administering noribogaine. Noribogaine may also be used to treat patients for the symptoms associated with withdrawal from drug dependency. In the latter case, the noribogaine treatment should be supplemented with the administration of an opioid antagonist such as naloxone.

  本发明涉及通过给予诺比高因治疗患者疼痛的方法。诺比高因也可用于治疗戒断症状的患者。在后一种情况下，应该辅以给予阿片类拮抗剂如纳洛酮的治疗。
• NORIBOGAINE COMPOSITIONS
  申请人：Moriarty Robert M.

  公开号：US20130131046A1

  公开（公告）日：2013-05-23

  Disclosed are noribogaine compositions comprising a very high level of the 2(R), 4(S), 5(S), 6(S) and 18(R) enantiomer and not more than 0.5 wt % of ibogaine relative to the total amount of noribogaine.

  本发明涉及一种诺利波甘组合物，其包含非常高水平的2(R)，4(S)，5(S)，6(S)和18(R)对映体，相对于诺利波甘的总量，伊博甘的含量不超过0.5重量%。
• Method of treating chemical dependency in mammals and a composition therefor
  申请人：——

  公开号：US20030153552A1

  公开（公告）日：2003-08-14

  An essentially pure noribogaine compound having the formula: 1 wherein R is hydrogen or a hydrolyzable group of the formula: 2 wherein X is an unsubstituted C 1 -C 12 group or a C 1 -C 12 group substituted by lower alkyl or lower alkoxy groups, wherein the noribogaine compound having the hydrolyzable group hydrolyzes in vivo to form 12-hydroxy ibogamine.

  一种基本纯净的去甲乌头碱化合物，其化学式为 1 其中 R 是氢或式中的可水解基团： 2 其中 X 是未取代的 C 1 -C 12 基团或 C 1 -C 12 12基团或被低级烷基或低级烷氧基取代的C 1 -C 12基团，其中具有可水解基团的去甲乌头碱化合物在体内水解形成12-羟基伊博格明。