2-(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-ylmethyl)-4,5-dimethoxy-aniline | 59444-58-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-ylmethyl)-4,5-dimethoxy-aniline
• 英文别名: (+/-)-1-(2-amino-4,5-dimethoxy-benzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydro-isoquinoline；2-(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydro-[1]isoquinolylmethyl)-4,5-dimethoxy-aniline；(+/-)-1-(2-Amino-4,5-dimethoxy-benzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydro-isochinolin；2-(6,7-Dimethoxy-2-methyl-1,2,3,4-tetrahydro-[1]isochinolylmethyl)-4,5-dimethoxy-anilin；2-[(6,7-Dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]-4,5-dimethoxyaniline；2-[(6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl)methyl]-4,5-dimethoxyaniline
• CAS: 59444-58-5
• 化学式: C₂₁H₂₈N₂O₄
• 分子量: 372.464
• InChiKey: PFBZCEPADMMGRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  66.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  硫酸 、 2-(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-ylmethyl)-4,5-dimethoxy-aniline 、 alkaline earth salt of/the/ methylsulfuric acid 生成 海罂粟碱 、 劳丹素
  参考文献：
  名称：

  Gadamer, Archiv der Pharmazie, 1911, vol. 249, p. 664

  摘要：

  DOI：
• 作为产物：
  描述：

  4,5,3',4'-tetramethoxy-2-vinyl-stilbene 在 盐酸 、 硝酸 、 溶剂黄146 、 tin(ll) chloride 作用下， 生成 2-(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-ylmethyl)-4,5-dimethoxy-aniline
  参考文献：
  名称：

  Effects of L-dopa treatment on methylation in mouse brain: Implications for the side effects of L-dopa

  摘要：

  The effects of L-dopa on methylation process in the mouse brain were investigated. The study is based on recent findings that methylation may play an important role in Parkinson's disease (PD) and in the actions of L-dopa. The methyl donor, S-adenosylmethionine (SAM) and a product of SAM, methyl beta-carboline, were shown to cause PD-like symptoms, when injected into the brain of animals. Furthermore, large amounts of 3-O-methyl dopa, the methyl product of L-dopa, are produced in PD patients receiving L-dopa treatment, and L-dopa induces methionine adenosyl transferase, the enzyme that produces SAM. The results show that, at 0.5 hr, L-dopa (100 mg/kg) decreased the methyl donor, S-adenosylmethionine (SAM) by 36%, increased its metabolite S-adenosylhomocysteine (SAH) by 89% and increased methylation (SAH/SAM) by about 200%. All parameters returned to control values within 4 hr. But 2, 3 and 4 consecutive injections of L-dopa, given at 45 min intervals, depleted SAM by 60, 64 and 76% and increased SAM/SAH to 818, 896, and 1524%. L-dopa (50, 100 and 200 mg/kg) dose-dependently depleted SAM from 24.9 +/- 1.7 nmol/g to 13.0 +/- 0.8, 14.7 +/- 0.8 and 7.7 +/- 0.7 nmol/g, and increased SAH from 1.88 +/- 0.14 to 3.43 +/- 0.26, 4.22 +/- 0.32 and 6.21 +/- 0.40 nmol/g. Brain L-dopa was increased to 326, 335 and 779%, dopamine to 138, 116 and 217% and SAH/SAM to 354, 392 and 1101%. The data show that L-dopa depletes SAM, and increases methylation 4-5 times more than dopamine, therefore, methylation may play a role in the actions of L-dopa. This and other studies suggest that the high level of utilization of methyl group by L-dopa leads to the induction of enzymes to replenish SAM and to increase the methylation of L-dopa as well as DA. These changes may be involved in the side effects of L-dopa.

  DOI：

  10.1016/s0024-3205(00)00557-9

文献信息

• Schoepf; Thierfelder, Justus Liebigs Annalen der Chemie, 1932, vol. 497, p. 22,33
  作者：Schoepf、Thierfelder

  DOI：——

  日期：——
• Pschorr; Staehlin; Silberbach, Chemische Berichte, 1904, vol. 37, p. 1939
  作者：Pschorr、Staehlin、Silberbach

  DOI：——

  日期：——
• Effects of L-dopa treatment on methylation in mouse brain: Implications for the side effects of L-dopa
  作者：X.X. Liu、K. Wilson、C.G. Charlton

  DOI：10.1016/s0024-3205(00)00557-9

  日期：2000.4

  The effects of L-dopa on methylation process in the mouse brain were investigated. The study is based on recent findings that methylation may play an important role in Parkinson's disease (PD) and in the actions of L-dopa. The methyl donor, S-adenosylmethionine (SAM) and a product of SAM, methyl beta-carboline, were shown to cause PD-like symptoms, when injected into the brain of animals. Furthermore, large amounts of 3-O-methyl dopa, the methyl product of L-dopa, are produced in PD patients receiving L-dopa treatment, and L-dopa induces methionine adenosyl transferase, the enzyme that produces SAM. The results show that, at 0.5 hr, L-dopa (100 mg/kg) decreased the methyl donor, S-adenosylmethionine (SAM) by 36%, increased its metabolite S-adenosylhomocysteine (SAH) by 89% and increased methylation (SAH/SAM) by about 200%. All parameters returned to control values within 4 hr. But 2, 3 and 4 consecutive injections of L-dopa, given at 45 min intervals, depleted SAM by 60, 64 and 76% and increased SAM/SAH to 818, 896, and 1524%. L-dopa (50, 100 and 200 mg/kg) dose-dependently depleted SAM from 24.9 +/- 1.7 nmol/g to 13.0 +/- 0.8, 14.7 +/- 0.8 and 7.7 +/- 0.7 nmol/g, and increased SAH from 1.88 +/- 0.14 to 3.43 +/- 0.26, 4.22 +/- 0.32 and 6.21 +/- 0.40 nmol/g. Brain L-dopa was increased to 326, 335 and 779%, dopamine to 138, 116 and 217% and SAH/SAM to 354, 392 and 1101%. The data show that L-dopa depletes SAM, and increases methylation 4-5 times more than dopamine, therefore, methylation may play a role in the actions of L-dopa. This and other studies suggest that the high level of utilization of methyl group by L-dopa leads to the induction of enzymes to replenish SAM and to increase the methylation of L-dopa as well as DA. These changes may be involved in the side effects of L-dopa.
• Gadamer, Archiv der Pharmazie, 1911, vol. 249, p. 664
  作者：Gadamer

  DOI：——

  日期：——