alpha-甲基-N-丙基-1,3-苯并二氧戊环-5-乙胺 | 74698-36-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 中文名称: alpha-甲基-N-丙基-1,3-苯并二氧戊环-5-乙胺
• 中文别名: 异噻唑,4,5-二氢-3-(1-甲基乙基)-5-噁丙环基-,(R*,S*)-(9CI)
• 英文名称: (+)-N-propyl-3,4-methylendioxyamphetamine
• 英文别名: 3,4-Methylenedioxy-N-propylamphetamine；1-(1,3-benzodioxol-5-yl)-N-propylpropan-2-amine
• CAS: 74698-36-5
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: LBXMQBTXOLBCCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  alpha-甲基-N-丙基-1,3-苯并二氧戊环-5-乙胺 在 cytochrome P₄₅₀ 2D₆ wild-type 作用下， 生成 、 替苯丙胺 、 4-[2-(丙基氨基)丙基]-1,2-苯二醇
  参考文献：
  名称：

  Metabolic Regio- and Stereoselectivity of Cytochrome P450 2D6 towards 3,4-Methylenedioxy-N-alkylamphetamines:  in Silico Predictions and Experimental Validation

  摘要：

  A series of 3,4-methylenedioxy-N-alkylamphetamines (MDAAs) were automatically docked and subjected to molecular dynamics (MD) simulations in a cytochrome P450 2D6 (CYP2D6) protein model. The predicted substrate binding orientations, sites of oxidation, and relative reactivities were compared to the experimental data of wild-type and Phe(120)Ala mutant CYP2D6. Automated docking results were not sufficient to accurately rationalize experimental binding orientations of 3,4-methylenedioxy-N-methylamphetamine (MDMA) in the two enzymes as measured with spin lattice relaxation NMR. Nevertheless, the docking results could be used as starting structures for MD simulations. Predicted binding orientations of MDMA and sites of oxidation of the MDAAs derived from MD simulations matched well with the experimental data. It appeared the experimental results were best described in MD simulations considering the nitrogen atoms of the MDAAs in neutral form. Differences in regioselectivity and stereoselectivity in the oxidative metabolism of the MDAAs by the Phe(120)Ala mutant CYP2D6 were correctly predicted, and the effects of the Phe(120)Ala mutation could be rationalized as well.

  DOI：

  10.1021/jm050338+
• 作为产物：
  描述：

  胡椒基丙酮 、 盐酸丙胺 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 36.0h， 生成 alpha-甲基-N-丙基-1,3-苯并二氧戊环-5-乙胺
  参考文献：
  名称：

  3,4-亚甲基二氧基苯基异丙胺（3,4-亚甲基二氧基苯丙胺）的中枢活性N-取代类似物。

  摘要：

  3，4-亚甲基二氧基苯基异丙基胺及其N-甲基同系物的已知中枢神经系统活性促使合成一系列在氮原子上具有取代基的类似物。这些类似物的大多数（R =烷基，烯基，羟基，烷氧基和烷氧基烷基）是通过3,4-亚甲基二氧基苯基丙酮与适当的胺和氰基硼氢化钠进行还原性烷基化反应制备的。受阻异构体是间接合成的。在几种动物试验和人类受试者中对它们的药理活性的测量表明，中央活性随N取代基体积的增加而降低。

  DOI：

  10.1002/jps.2600690220

文献信息

• Derivatives of amphetamine, antibodies against said derivatives, reagent kits, methods of producing said antibodies, and methods of detecting said derivatives
  申请人：Roche Diagnostics GmbH

  公开号：EP1340980A1

  公开（公告）日：2003-09-03

  Compounds including haptens, intermediates, and immunogens that are useful in the production of antibodies specific for the methylenedioxy class of amphetamine derivatives are described. Antibodies specific for the methylenedioxy class of amphetamine derivatives, reagent kits containing antibodies specific for the methylenedioxy class of amphetamine derivatives, methods of producing antibodies specific for the methylenedioxy class of amphetamine derivatives, and methods of detecting analytes including members of the methylenedioxy class of amphetamine derivatives are also described.

  本文描述了在生产特异性针对亚甲二氧基类安非他命衍生物的抗体中有用的包括半抗原、中间体和免疫原的化合物。还描述了特异性针对亚甲二氧基类安非他命衍生物的抗体、含有特异性针对亚甲二氧基类安非他命衍生物的抗体的试剂盒、制备特异性针对亚甲二氧基类安非他命衍生物的抗体的方法以及检测包括亚甲二氧基类安非他命衍生物成员的分析物的方法。
• Antibodies for detecting ecstasy-class analytes
  申请人：Roche Diagnostics GmbH

  公开号：EP1498428A1

  公开（公告）日：2005-01-19

  Compounds including haptens, intermediates, and immunogens that are useful in the production of antibodies specific for the methylenedioxy class of amphetamine derivatives are described. Antibodies specific for the methylenedioxy class of amphetamine derivatives, reagent kits containing antibodies specific for the methylenedioxy class of amphetamine derivatives, methods of producing antibodies specific for the methylenedioxy class of amphetamine derivatives, and methods of detecting analytes including members of the methylenedioxy class of amphetamine derivatives are also described.

  本文描述了包括半抗原、中间体和免疫原在内的化合物，这些化合物对于生产特异性针对亚甲二氧基类安非他命衍生物的抗体是有用的。本文还描述了特异性针对亚甲二氧基类安非他命衍生物的抗体、包含特异性针对亚甲二氧基类安非他命衍生物的抗体的试剂盒、生产特异性针对亚甲二氧基类安非他命衍生物的抗体的方法以及检测分析物，包括亚甲二氧基类安非他命衍生物成员的方法。
• Compounds, antibodies, reagent kits, methods of producing antibodies, and methods of detecting analytes
  申请人：Roche Diagnostics Corporation

  公开号：US20030170917A1

  公开（公告）日：2003-09-11

  Compounds including haptens, intermediates, and immunogens that are useful in the production of antibodies specific for the methylenedioxy class of amphetamine derivatives are described. Antibodies specific for the methylenedioxy class of amphetamine derivatives, reagent kits containing antibodies specific for the methylenedioxy class of amphetamine derivatives, methods of producing antibodies specific for the methylenedioxy class of amphetamine derivatives, and methods of detecting analytes including members of the methylenedioxy class of amphetamine derivatives are also described.

  本文介绍了一些有用的化合物，包括半抗原、中间体和免疫原，这些化合物可用于生产特异性针对甲基二氧苯丙胺衍生物的抗体。本文还介绍了特异性针对甲基二氧苯丙胺衍生物的抗体、含有特异性针对甲基二氧苯丙胺衍生物的抗体的试剂盒、制备特异性针对甲基二氧苯丙胺衍生物的抗体的方法以及检测包括甲基二氧苯丙胺衍生物成员的分析物的方法。
• Derivatives, conjugates, and antibodies for detecting ecstasy-class analytes
  申请人：Roche Diagnostics Corporation

  公开号：US20040077021A1

  公开（公告）日：2004-04-22

  Compounds including haptens, intermediates, and immunogens that are useful in the production of antibodies specific for the methylenedioxy class of amphetamine derivatives are described. Antibodies specific for the methylenedioxy class of amphetamine derivatives, reagent kits containing antibodies specific for the methylenedioxy class of amphetamine derivatives, methods of producing antibodies specific for the methylenedioxy class of amphetamine derivatives, and methods of detecting analytes including members of the methylenedioxy class of amphetamine derivatives are also described.

  本文描述了一些化合物，包括半抗原、中间体和免疫原，这些化合物在生产特异性抗甲基二氧基苯丙胺衍生物的抗体方面非常有用。本文还描述了特异性抗甲基二氧基苯丙胺衍生物的抗体、含有特异性抗甲基二氧基苯丙胺衍生物的抗体的试剂盒、制备特异性抗甲基二氧基苯丙胺衍生物的抗体的方法，以及检测分析物，包括甲基二氧基苯丙胺衍生物成员的方法。
• [EN] PHENALKYLAMINES AND METHODS OF TREATING MOOD DISORDERS<br/>[FR] PHÉNALKYLAMINES ET PROCÉDÉS DE TRAITEMENT DE TROUBLES DE L'HUMEUR
  申请人：GILGAMESH PHARMACEUTICALS INC

  公开号：WO2022006186A1

  公开（公告）日：2022-01-06

  Phenalkylamines and methods of treating mood disorders with phenalkylamines. Also provided are pharmaceutical compositions that include phenalkylamines.

  Phenalkylamines和使用Phenalkylamines治疗情绪障碍的方法。还提供了包含Phenalkylamines的制药组合物。