(+/-)-gacyclidine | 68134-81-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (+/-)-gacyclidine
• 英文别名: 1-<1-(2-thienyl)-2-methylcyclohexyl>piperidine；rac-gacyclidine；1-[(1S,2R)-2-Methyl-1-(thiophen-2-yl)cyclohexyl]piperidine；1-[(1S,2R)-2-methyl-1-thiophen-2-ylcyclohexyl]piperidine
• CAS: 68134-81-6
• 化学式: C₁₆H₂₅NS
• 分子量: 263.447
• InChiKey: DKFAAPPUYWQKKF-ZBFHGGJFSA-N

物化性质

• 熔点：
  80-81 °C(Solv: hexane (110-54-3); ethyl ether (60-29-7))
• 沸点：
  352.5±17.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  31.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-gacyclidine 反应 12.0h， 生成 gacyclidine
  参考文献：
  名称：

  Homochiral structures derived from 1-[1-(2-thienyl)cyclohexyl]piperidine (TCP) are potent non-competitive antagonists of glutamate at NMDA receptor sites

  摘要：

  The racemates of cis (pip/Me) 1-[1-(2-thienyl)-2-methylcyclohexyl]pipe and cis (pip/Me) 1-[1-(2-furanyl)-2-methylcyclohexyl]piperidine, 2 derivatives of the noncompetitive N-methyl-D-aspartate (NMDA) antagonist 1-[1-(2-thienyl)cyclohexyl]piperidine (TCP) have been synthesized. The corresponding isomers were resolved by a crystallization procedure, via the diastereoisomeric salts formed with (+)- and (-)-di-O,O'-4-toluoyltartaric acid. The absolute configuration was determined by single-crystal X-ray analysis and by comparison with previously published data in related series. The 4 homochiral structures obtained were tested for their affinity for the PCP receptor sites labelled with [H-3]TCP. Their neuroprotective potency was assessed in primary cultured neuronal cells against neurotoxicity induced by glutamate. The 2(-)-1S, 2R-isomers displayed the highest affinity for the PCP receptor sites and the highest efficacy for neuronal protection in comparison with the (+)-1R, 2S-isomers.

  DOI：

  10.1016/0223-5234(94)90109-0

文献信息

• Novel therapeutic use of a thienylcyclohexylamine derivative
  申请人：Simonnet Guy

  公开号：US20050032840A1

  公开（公告）日：2005-02-10

  The invention concerns the use of a thienylcyclohexylamine, on its own or associated with other substances with pharmaceutical activity, for preparing a medicine designed to prevent and/or treat pain and/or nociception.

  本发明涉及噻吩基环己胺本身或与其他具有药物活性的物质一起用于制备预防和/或治疗疼痛和/或痛觉的药物。
• NOUVELLE APPLICATION THERAPEUTIQUE D'UN DERIVE DE LA THIENYLCYCLOHEXYLAMINE POUR TRAITER LA DOULEUR
  申请人：SOCIETE DE CONSEILS DE RECHERCHES ET D'APPLICATIONS SCIENTIFIQUES (S.C.R.A.S.)

  公开号：EP1359914B1

  公开（公告）日：2006-08-30
• Delivery of modulators of glutamate-mediated neurotransmission to the inner ear
  申请人：Puel Jean-Luc

  公开号：US20070015727A1

  公开（公告）日：2007-01-18

  The invention features methods and devices for local delivery of agents that modify glutamate-mediated neurotransmission to the inner ear for treatment of inner ear disorders caused by glutamate-induced hearing loss and/or tinnitus.
• Therapeutic use of a derivative of thienylcyclohexylamine
  申请人：Simonnet Guy

  公开号：US20090023780A1

  公开（公告）日：2009-01-22

  The invention concerns the use of a thienylcyclohexylamine, on its own or associated with other substances with pharmaceutical activity, for preparing a medicine designed to prevent and/or treat pain and/or nociception.
• US5972952A
  申请人：——

  公开号：US5972952A

  公开（公告）日：1999-10-26