17-methyl-4,5α-epoxy-6-one-3-methoxy-8-[thioacetic acid]morphinan | 1418280-96-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: 17-methyl-4,5α-epoxy-6-one-3-methoxy-8-[thioacetic acid]morphinan
• 英文别名: 8-thioacetic acid hydrocodone；2-[[(4R,4aR,7aR,12bS)-9-methoxy-3-methyl-7-oxo-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-5-yl]sulfanyl]acetic acid
• CAS: 1418280-96-2
• 化学式: C₂₀H₂₃NO₅S
• 分子量: 389.472
• InChiKey: BMMSKJQLOQHZMI-PSTOXSJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  17-methyl-4,5α-epoxy-6-one-3-methoxy-8-[thioacetic acid]morphinan 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 17-methyl-4,5α-epoxy-6-one-3-methoxy-8-[thio-N-(2-mercaptoethyl)acetamido]morphinan
  参考文献：
  名称：

  Reduced Antinociception of Opioids in Rats and Mice by Vaccination with Immunogens Containing Oxycodone and Hydrocodone Haptens

  摘要：

  Prescription opioids abuse and associated deaths are an emerging concern in the USA. Vaccination against prescription opioids may provide an alternative to pharmacotherapy. An oxycodone hapten containing a tetraglycine linker at the C6 position (60XY(Gly)(4)OH) conjugated to keyhole limpet hemocyanin (KLH) has shown early proof-of-efficacy in rodents as a candidate immunogen (60XY(Gly)(4)-KLH) for the treatment of oxycodone abuse. In this study, oxycodone-based and hydrocodone-based haptens were conjugated to KLH to generate immunogens that would recognize both oxycodone and hydrocodone. Vaccination with 60XY(Gly)(4)-KLH increased drug binding in serum, reduced drug distribution to brain, and blunted analgesia for both oxycodone and hydrocodone. An analogous C6-linked hydrocodone vaccine blocked hydrocodone effects but less so than 60XY(Gly)(4)-KLH. C8-Linked hydrocodone immunogens had only limited efficacy. Amide conjugation showed higher haptenation ratios and greater efficacy than thioether conjugation to maleimide activated KLH (mKLH). The 60XY(Gly)(4)-KLH vaccine may be used for treatment of prescription opioid abuse.

  DOI：

  10.1021/jm3013745
• 作为产物：
  描述：

  巯基乙酸 、 可待因酮 以 四氢呋喃 为溶剂， 反应 20.0h， 以87%的产率得到17-methyl-4,5α-epoxy-6-one-3-methoxy-8-[thioacetic acid]morphinan
  参考文献：
  名称：

  COMPOSITIONS AND METHODS OF TREATING OPIOID ADDICTION

  摘要：

  本发明涉及用于治疗阿片类药物成瘾的结合物和疫苗组合物，以及这些结合物和组合物的使用方法。

  公开号：

  US20140093525A1