β-2'-Hydroxy-5,9-dimethyl-benzomorphan | 16603-67-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 6,7-苯并吗啡烷
• 英文名称: β-2'-Hydroxy-5,9-dimethyl-benzomorphan
• 英文别名: β-2'-Hydroxy-5,9-dimethyl-6,7-benzomorphan；(1R,13S)-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-4-ol
• CAS: 16603-67-1；16670-83-0；16670-84-1；16670-86-3；16671-00-4；16808-63-2；25144-77-8；25144-78-9；52079-30-8
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: DXESFJJJWBHLJX-STGJRIPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  β-2'-Hydroxy-5,9-dimethyl-benzomorphan 生成 normetazocine
  参考文献：
  名称：

  Synthesis and biological evaluation of a metazocine-containing enkephalinamide. Evidence for nonidentical roles of the tyramine moiety in opiates and opioid peptides

  摘要：

  In an effort to test the hypothesis that the tyramine moiety present in opiates and in opioid peptides plays an identical functional role at opioid receptors, a hybrid enkephalinamide (3) that contains (-)-metazocine (4a) in place of Tyr was synthesized. It was found that 3 and its congeners are inactive or feebly active in the electrically stimulated guinea pig ileum and mouse vas deferens preparations. The results of these studies suggest that the tyramine moiety in opiates and related structures does not play the same functional role as that in the opioid peptides. It is suggested that the different functional roles of the tyramine moiety in opiates and opioid peptides is a consequence of different modes of interaction with common receptors.

  DOI：

  10.1021/jm00354a006

文献信息

• Synthesis and biological evaluation of a metazocine-containing enkephalinamide. Evidence for nonidentical roles of the tyramine moiety in opiates and opioid peptides
  作者：K. Ramakrishnan、P. S. Portoghese

  DOI：10.1021/jm00354a006

  日期：1982.12

  In an effort to test the hypothesis that the tyramine moiety present in opiates and in opioid peptides plays an identical functional role at opioid receptors, a hybrid enkephalinamide (3) that contains (-)-metazocine (4a) in place of Tyr was synthesized. It was found that 3 and its congeners are inactive or feebly active in the electrically stimulated guinea pig ileum and mouse vas deferens preparations. The results of these studies suggest that the tyramine moiety in opiates and related structures does not play the same functional role as that in the opioid peptides. It is suggested that the different functional roles of the tyramine moiety in opiates and opioid peptides is a consequence of different modes of interaction with common receptors.