anhydroecgonine (1,1,1-2H3)methyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: anhydroecgonine (1,1,1-2H3)methyl ester
• 英文别名: anhydroecgonine-CD3 ester；Ecgonidine Methyl Ester-d3；trideuteriomethyl (1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate
• 化学式: C₁₀H₁₅NO₂
• 分子量: 184.211
• InChiKey: MPSNEAHFGOEKBI-CWYCHJBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  脱水芽子碱盐酸盐 在 盐酸 、 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 2.0h， 生成 anhydroecgonine (1,1,1-2H3)methyl ester
  参考文献：
  名称：

  The synthesis of deuterium-labelled cocaine, cocaethylene and metabolites

  摘要：

  We describe the syntheses of benzoylecgonine (1,1,1-H-2(3))methyl ester [(H-2(3)) cocaine], (H-2(5))benzoylecgonine, (H-2(5))benzoylecgonine methyl ester [(H-2(5))cocaine], benzoylecgonine (2,2,2-H-2(3))ethyl ester [(H-2(3))cocaethylene], (H-2(5))benzoylecgonine ethyl ester [(H-2(5))cocaethylene], (H-2(5))benzoylecgonine (2,2,2-H-2(3))ethyl ester [(H-2(8))cocaethylene], ecgonine(1,1,1 -H-2(3))methyl ester, ecgonine (2,2,2-H-2(3))ethyl ester, ecgonine(1,1,2,2,2-H-2(5))ethyl ester and anhydroecgonine( 1,1,1-H-2(3))methyl ester. -(H-2(5))Cocaine and (H-2(3))cocaethylene have been administered to human subjects to study the interactions of cocaine and ethanol. The other eight compounds were utilized as analytical standards or internal standards for GC-MS quantitation of cocaine and its metabolites in biological fluids.

  DOI：

  10.1002/(sici)1099-1344(19991230)42:13<1265::aid-jlcr283>3.0.co;2-y

文献信息

• Identification of anhydroecgonine methyl ester<i>N</i>-oxide, a new metabolite of anhydroecgonine methyl ester, using electrospray mass spectrometry
  作者：Anabel S. Fandiño、Michael Karas、Stefan W. Toennes、Gerold Kauert

  DOI：10.1002/jms.310

  日期：2002.5

  hepatotoxic metabolites through oxidative pathways. For anhydroecgonine methyl ester (AEME), the main constituent in crack smoke, the oxidative metabolism has not been studied. Therefore, incubation of AEME with rat liver microsomes was performed and a metabolite of AEME, anhydroecgonine methyl ester N-oxide (AEMENO), was identified. The chemical structure of this new metabolite was confirmed by synthesis

  可卡因通过氧化途径转化为肝毒性代谢产物。对于裂纹烟雾中的主要成分-脱水芽子碱甲酯（AEME），尚未研究其氧化代谢。因此，进行了AEME与大鼠肝微粒体的温育，并鉴定了AEME的代谢产物脱水芽子碱甲酯N-氧化物（AEMENO）。通过合成和通过电喷雾多级质谱的比较解释证实了这种新代谢产物的化学结构，这些质谱是在阳离子模式下获得的。裂纹使用者的全血，血清和尿液样本中也检测到了这种代谢产物。液相色谱/电喷雾质谱或纳米电喷雾质谱的应用是必要的，因为AEMENO在气相色谱/质谱分析过程中容易发生热降解。这项研究表明，AEMENO是由大鼠肝微粒体代谢在体外产生的，存在于裂纹使用者的体液中。
• The synthesis of deuterium-labelled cocaine, cocaethylene and metabolites
  作者：E. Thomas Everhart、Peyton Jacob、John Mendelson、Reese T. Jones

  DOI：10.1002/(sici)1099-1344(19991230)42:13<1265::aid-jlcr283>3.0.co;2-y

  日期：1999.12.30

  We describe the syntheses of benzoylecgonine (1,1,1-H-2(3))methyl ester [(H-2(3)) cocaine], (H-2(5))benzoylecgonine, (H-2(5))benzoylecgonine methyl ester [(H-2(5))cocaine], benzoylecgonine (2,2,2-H-2(3))ethyl ester [(H-2(3))cocaethylene], (H-2(5))benzoylecgonine ethyl ester [(H-2(5))cocaethylene], (H-2(5))benzoylecgonine (2,2,2-H-2(3))ethyl ester [(H-2(8))cocaethylene], ecgonine(1,1,1 -H-2(3))methyl ester, ecgonine (2,2,2-H-2(3))ethyl ester, ecgonine(1,1,2,2,2-H-2(5))ethyl ester and anhydroecgonine( 1,1,1-H-2(3))methyl ester. -(H-2(5))Cocaine and (H-2(3))cocaethylene have been administered to human subjects to study the interactions of cocaine and ethanol. The other eight compounds were utilized as analytical standards or internal standards for GC-MS quantitation of cocaine and its metabolites in biological fluids.