(S,S)-N-α-methylbenzyl-3-methoxyamphetamine | 892500-55-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S,S)-N-α-methylbenzyl-3-methoxyamphetamine
• 英文别名: [(S)-2-(3-methoxy-phenyl)-1-methyl-ethyl]-((S)-1-phenyl-ethyl)-amine；(2S)-1-(3-methoxyphenyl)-N-[(1S)-1-phenylethyl]propan-2-amine
• CAS: 892500-55-9
• 化学式: C₁₈H₂₃NO
• 分子量: 269.387
• InChiKey: YSUBRSFEHMECJZ-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S,S)-N-α-methylbenzyl-3-methoxyamphetamine 在 盐酸 作用下， 以 乙醚 、 水 为溶剂， 以65%的产率得到(S,S)-N-α-Methylbenzyl-3-methoxyamphetamine hydrochloride
  参考文献：
  名称：

  The Synthesis of Haptens and Their Use for the Development of Monoclonal Antibodies for Treating Methamphetamine Abuse

  摘要：

  In addition to addiction, the repeated use of (+)-methamphetamine [(+)-METH], (+)-amphetamine [(+)-AMP], or (+/-)-3,4-methylenedioxymethamphetamine ((+/-)-MDMA, commonly called ecstasy) can lead to life-threatening medical problems including cardiovascular injury, severe depression, and psychosis. Currently, there are no specific pharmacotherapies to treat these medical problems. In this study, we report the design and synthesis of two haptens, (S)-(+)-3-(9-carboxynonyloxy)methamphetamine (3a, (+)-METH MO10) and (S)-(+)-3-(5-carboxypentyloxy)methamphetamine (3b, (+)-METH MO6), and their use in generating high affinity (low K-D value) monoclonal antibodies (mAbs) against (+)METH, (+)-AMP, and/or (+)-MDMA. On the basis of results from the determination of mAb K-D values and ligand specificity, the mAbs generated from hapten 3a showed the greatest promise for generating active and passive immunotherapies for treating overdose or addiction from (+)-METH-like stimulants.

  DOI：

  10.1021/jm901134w
• 作为产物：
  描述：

  3-甲氧基苯基丙酮 、 (S)-(-)- α-甲基苄胺 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 以99%的产率得到(S,S)-N-α-methylbenzyl-3-methoxyamphetamine
  参考文献：
  名称：

  The Synthesis of Haptens and Their Use for the Development of Monoclonal Antibodies for Treating Methamphetamine Abuse

  摘要：

  In addition to addiction, the repeated use of (+)-methamphetamine [(+)-METH], (+)-amphetamine [(+)-AMP], or (+/-)-3,4-methylenedioxymethamphetamine ((+/-)-MDMA, commonly called ecstasy) can lead to life-threatening medical problems including cardiovascular injury, severe depression, and psychosis. Currently, there are no specific pharmacotherapies to treat these medical problems. In this study, we report the design and synthesis of two haptens, (S)-(+)-3-(9-carboxynonyloxy)methamphetamine (3a, (+)-METH MO10) and (S)-(+)-3-(5-carboxypentyloxy)methamphetamine (3b, (+)-METH MO6), and their use in generating high affinity (low K-D value) monoclonal antibodies (mAbs) against (+)METH, (+)-AMP, and/or (+)-MDMA. On the basis of results from the determination of mAb K-D values and ligand specificity, the mAbs generated from hapten 3a showed the greatest promise for generating active and passive immunotherapies for treating overdose or addiction from (+)-METH-like stimulants.

  DOI：

  10.1021/jm901134w

文献信息

• Methamphetamine derivatives and conjugates for immunoassay
  申请人：Hui A. Raymond

  公开号：US20060134711A1

  公开（公告）日：2006-06-22

  Compounds of methamphetamine derivatives having a meta-substituted alkyl linker on the benzene ring and a protective group on the nitrogen of the methamphetamine hapten. Such compounds have the structure wherein R 1 is an alkyl linker comprising 2-15 carbon atoms and 0-6 heteroatoms, R 2 is a leaving group, and R 3 is a protecting group.

  在苯环上具有元取代烷基连接的甲基苯丙胺衍生物化合物，并且在甲基苯丙胺半抗原的氮上具有保护基。这些化合物具有以下结构：其中R1是由2-15个碳原子和0-6个杂原子组成的烷基连接，R2是离去基团，而R3是保护基。
• METHAMPHETAMINE DERIVATIVES AND CONJUGATES FOR IMMUNOASSAY
  申请人：Hui A. Raymond

  公开号：US20080050843A1

  公开（公告）日：2008-02-28

  Compounds of methamphetamine derivatives having a meta-substituted alkyl linker on the benzene ring and a protective group on the nitrogen of the methamphetamine hapten. Such compounds have the structure. wherein R 1 is an alkyl linker comprising 2-15 carbon atoms and 0-6 heteroatoms, R 2 is a leaving group, and R 3 is a protecting group.

  具有苯环上的甲基苯丙胺衍生物的间位取代烷基连接剂和甲基苯丙胺半抗原氮上的保护基的化合物。这些化合物具有以下结构，其中R1是由2-15个碳原子和0-6个杂原子组成的烷基连接剂，R2是离去基团，而R3是保护基。
• US7294649B2
  申请人：——

  公开号：US7294649B2

  公开（公告）日：2007-11-13
• US7732160B2
  申请人：——

  公开号：US7732160B2

  公开（公告）日：2010-06-08
• The Synthesis of Haptens and Their Use for the Development of Monoclonal Antibodies for Treating Methamphetamine Abuse
  作者：F. Ivy Carroll、Philip Abraham、Paul K. Gong、Ramakrishna R. Pidaparthi、Bruce E. Blough、Yingni Che、Amber Hampton、Melinda Gunnell、Jackson O. Lay、Eric C. Peterson、S. Michael Owens

  DOI：10.1021/jm901134w

  日期：2009.11.26

  In addition to addiction, the repeated use of (+)-methamphetamine [(+)-METH], (+)-amphetamine [(+)-AMP], or (+/-)-3,4-methylenedioxymethamphetamine ((+/-)-MDMA, commonly called ecstasy) can lead to life-threatening medical problems including cardiovascular injury, severe depression, and psychosis. Currently, there are no specific pharmacotherapies to treat these medical problems. In this study, we report the design and synthesis of two haptens, (S)-(+)-3-(9-carboxynonyloxy)methamphetamine (3a, (+)-METH MO10) and (S)-(+)-3-(5-carboxypentyloxy)methamphetamine (3b, (+)-METH MO6), and their use in generating high affinity (low K-D value) monoclonal antibodies (mAbs) against (+)METH, (+)-AMP, and/or (+)-MDMA. On the basis of results from the determination of mAb K-D values and ligand specificity, the mAbs generated from hapten 3a showed the greatest promise for generating active and passive immunotherapies for treating overdose or addiction from (+)-METH-like stimulants.