(S)-1-(3-methoxyphenyl)-N-methylpropan-2-amine hydrochloride | 1313762-90-1

• 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)-1-(3-methoxyphenyl)-N-methylpropan-2-amine hydrochloride
• 英文别名: (2S)-1-(3-methoxyphenyl)-N-methylpropan-2-amine;hydrochloride
• CAS: 1313762-90-1
• 化学式: C₁₁H₁₇NO*ClH
• 分子量: 215.723
• InChiKey: UFGUIIUBDSVRFC-FVGYRXGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  21.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S,S)-N-formyl-N-α-methylbenzyl-3-methoxyamphetamine 在 盐酸 、 硼烷四氢呋喃络合物 、 5%-palladium/activated carbon 、 甲酸铵 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 4.0h， 生成 (S)-1-(3-methoxyphenyl)-N-methylpropan-2-amine hydrochloride
  参考文献：
  名称：

  Synthesis of Mercapto-(+)-methamphetamine Haptens and Their Use for Obtaining Improved Epitope Density on (+)-Methamphetamine Conjugate Vaccines

  摘要：

  This study reports the synthesis of the mercapto-hapten (S)-N-(2-(mercaptoethyl)-6-(3-(2-(methylamino)propyl)phenoxy)hexanamide [3, (+)-METH HSMO9] and its use to prepare METH-conjugated vaccines (MCV) from maleimide-activated proteins. MALDI-TOF mass spectrometry analysis of the MCV synthesized using 3 showed there was a high and controllable epitope density on two different carrier proteins. In addition, the MCV produced a substantially greater immunological response in mice than previous METH haptens, and a monoclonal antibody generated from this MCV in mice showed a very high affinity for (+)-METH (K(D) = 6.8 nM). The efficient covalent coupling of (+)-METH HSMO9 to the activated carrier proteins suggests that this approach could be cost-effective for large-scale production of MCV. In addition, the general methods described for the synthesis of (+)-METH HSMO9 (3) and its use to synthesize MCV will be applicable for conjugated vaccines of small molecules and other substances of abuse such as morphine, nicotine, and cocaine.

  DOI：

  10.1021/jm2004943

文献信息

• Synthesis of Mercapto-(+)-methamphetamine Haptens and Their Use for Obtaining Improved Epitope Density on (+)-Methamphetamine Conjugate Vaccines
  作者：F. Ivy Carroll、Bruce E. Blough、Ramakrishna R. Pidaparthi、Philip Abraham、Paul K. Gong、Liu Deng、Xiaodong Huang、Melinda Gunnell、Jackson O. Lay、Eric C. Peterson、S. Michael Owens

  DOI：10.1021/jm2004943

  日期：2011.7.28

  This study reports the synthesis of the mercapto-hapten (S)-N-(2-(mercaptoethyl)-6-(3-(2-(methylamino)propyl)phenoxy)hexanamide [3, (+)-METH HSMO9] and its use to prepare METH-conjugated vaccines (MCV) from maleimide-activated proteins. MALDI-TOF mass spectrometry analysis of the MCV synthesized using 3 showed there was a high and controllable epitope density on two different carrier proteins. In addition, the MCV produced a substantially greater immunological response in mice than previous METH haptens, and a monoclonal antibody generated from this MCV in mice showed a very high affinity for (+)-METH (K(D) = 6.8 nM). The efficient covalent coupling of (+)-METH HSMO9 to the activated carrier proteins suggests that this approach could be cost-effective for large-scale production of MCV. In addition, the general methods described for the synthesis of (+)-METH HSMO9 (3) and its use to synthesize MCV will be applicable for conjugated vaccines of small molecules and other substances of abuse such as morphine, nicotine, and cocaine.