2-methyl-2-methylamino-1-phenyl-propan-1-one; hydrochloride | 14611-65-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-2-methylamino-1-phenyl-propan-1-one; hydrochloride
• 英文别名: α-methylaminoisobutyrophenone hydrochloride；α-methylmethcathinone hydrochloride；2-Methyl-2-methylamino-1-phenyl-propan-1-on; Hydrochlorid
• CAS: 14611-65-5
• 化学式: C₁₁H₁₅NO*ClH
• 分子量: 213.707
• InChiKey: FLKGZYLLLBYOMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-methyl-2-methylamino-1-phenyl-propan-1-one; hydrochloride 在 镍 氢气 作用下， 以 甲醇 为溶剂， 生成 β-Hydroxymephentermin
  参考文献：
  名称：

  Schulz,H., Pharmazie, 1967, vol. 22, p. 19 - 22

  摘要：

  DOI：
• 作为产物：
  描述：

  2-溴-2-甲基苯丙酮 在 盐酸 、 potassium carbonate 作用下， 以 甲醇 、 乙醚 、 乙酸乙酯 为溶剂， 反应 7.0h， 生成 2-methyl-2-methylamino-1-phenyl-propan-1-one; hydrochloride
  参考文献：
  名称：

  Investigation of the Optical Isomers of Methcathinone, and Two Achiral Analogs, at Monoamine Transporters and in Intracranial Self-Stimulation Studies in Rats

  摘要：

  Methcathinone (MCAT; 1), the progenitor of numerous and widely abused "synthetic cathinone" central stimulants, exists as a pair of optical isomers. Although S(-)MCAT is several-fold more potent than R(+)MCAT in rodent locomotor stimulation and in stimulus generalization studies in rat drug discrimination assays, the individual optical isomers of MCAT have never been directly compared for their actions at monoamine transporters that seem to underlie their actions and have never been examined for their relative abuse potential. Here, we found that the isomers of MCAT are nearly equieffective at dopamine and norepinephrine transporters (DAT and NET, respectively) as transporter substrates (i.e., as releasing agents) and are >= 63-fold less potent at the serotonin transporter (SERT). In intracranial self-stimulation (ICSS) studies to evaluate abuse-related drug effects in rats, S(-)MCAT was approximately twice as potent as its R-enantiomer. Achiral analogs, alpha-methyl MCAT (3) and alpha-des-methyl MCAT (4), also were DAT/NET substrates and also produced abuse-related ICSS effects, indicating that they retain abuse potential and that they might be useful for the further study of the stereochemistry of synthetic cathinone analogs with chiral beta- (or other) substituents.

  DOI：

  10.1021/acschemneuro.9b00617