10-酮基纳曲酮 | 96445-14-6

• 物质功能分类: 有机原料 - 酮类化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 10-酮基纳曲酮
• 中文别名: 纳曲酮EP杂质I
• 英文名称: 10-Ketonaltrexone
• 英文别名: 10-oxonaltrexone；(4S,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-1,2,4,5,6,7a-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-7,13-dione
• CAS: 96445-14-6
• 化学式: C₂₀H₂₁NO₅
• 分子量: 355.39
• InChiKey: MLHMRULRADVYER-FUMNGEBKSA-N

物化性质

• 熔点：
  160-165°C
• 沸点：
  633.6±55.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)
• 闪点：
  9℃
• 溶解度：
  乙腈（少量溶解）、氯仿（少量溶解）、DMSO（少量溶解）、甲醇（少量溶解）

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  26
• 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：
  87.1
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• WGK Germany：
  1

反应信息

• 作为产物：
  描述：

  纳曲酮EP杂质J 在 chromium(VI) oxide 、 硫酸 、 三溴化硼 作用下， 以 氯仿 为溶剂， 反应 71.0h， 生成 10-酮基纳曲酮
  参考文献：
  名称：

  10-Ketonaltrexone and 10-ketooxymorphone

  摘要：

  Ethylketocyclazocine (1) has greater kappa/mu selectivity than cyclazocine in brain binding assays. 10-Ketonaltrexone (11) and 10-ketooxymorphone (10) were prepared from naltrexone 3-methyl ether and oxycodone, respectively. Bioassays in the myenteric plexus longitudinal muscle preparation of the guinea pig ileum and in the mouse vas deferens, in addition to brain binding assays, demonstrated that 10 and 11 were far less potent than naltrexone (2) and oxymorphone (3) at mu sites and also had little affinity for kappa and delta sites. It is concluded that introduction of the 10-keto group in naltrexone and oxymorphone diminished opioid effects at all binding sites.

  DOI：

  10.1021/jm00145a024

文献信息

• 10-Ketonaltrexone and 10-ketooxymorphone
  作者：Sydney Archer、Ahmad Seyed-Mozaffari、Susan Ward、Hans W. Kosterlitz、Stewart J. Paterson、Alexander T. McKnight、Alistair D. Corbett

  DOI：10.1021/jm00145a024

  日期：1985.7

  Ethylketocyclazocine (1) has greater kappa/mu selectivity than cyclazocine in brain binding assays. 10-Ketonaltrexone (11) and 10-ketooxymorphone (10) were prepared from naltrexone 3-methyl ether and oxycodone, respectively. Bioassays in the myenteric plexus longitudinal muscle preparation of the guinea pig ileum and in the mouse vas deferens, in addition to brain binding assays, demonstrated that 10 and 11 were far less potent than naltrexone (2) and oxymorphone (3) at mu sites and also had little affinity for kappa and delta sites. It is concluded that introduction of the 10-keto group in naltrexone and oxymorphone diminished opioid effects at all binding sites.