N-Allylamphetamine | 33236-68-9

• 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: N-Allylamphetamine
• 英文别名: 1-phenyl-N-prop-2-enylpropan-2-amine
• CAS: 33236-68-9
• 化学式: C₁₂H₁₇N
• 分子量: 175.274
• InChiKey: XZFWMYPSKIXPNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  非那明 、 3-溴丙烯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以310 %的产率得到N-Allylamphetamine
  参考文献：
  名称：

  Metabolism of N,N-dialkylated amphetamines, including deprenyl, by CYP2D6 expressed in a human cell line

  摘要：

  1. Five N,N-dialkylated amphetamines, N-methyl-N-propargylamphetamine (deprenyl; DEP), N-benzyl-N-methylamphetamine (benzphetamine; BPA), N-allyl-N-methylamphetamine (AMA), N,N-diallylamphetamine (DAA) and N-methyl-N-propylamphetamine (MPA), were metabolized in vitro with a microsomal preparation from cells expressing human CYP2D6 to determine what influence the N,N-dialkyl substituents had on the extent of N-dealkylation and/or aromatic ring oxidation.2. The results obtained from experiments with the first two substrates, DEP and BPA, were surprisingly different. Whereas DEP was N-demethylated and N-depropargylated by the CYP2D6 enzyme system, no metabolites were formed from BPA. Subsequently, it was determined that AMA, DAA and MPA also underwent CYP2D6-catalysed N-dealkylation. Both N-methyl- and N-allylamphetamine were identified as products of AMA metabolism; similarly, metabolism of MPA produced both N-methyl- and N-propargylamphetamine, and N-allylamphetamine was the sole metabolite of DAA.3. No N,N-didealkylated product (i.e. amphetamine) was isolated from incubates of any of the five substrates, and none of the N,N-dialkylated substrates was metabolized to a ring-hydroxylated product.4. Rates of these CYP2D6-catalysed reactions were dependent on the nature and degree of unsaturation of the N-substituents.

  DOI：

  10.1080/004982500237686

文献信息

• [EN] DEUTERATED MORPHINE DERIVATIVES<br/>[FR] DÉRIVÉS DE MORPHINE DEUTÉRÉS
  申请人：SZEGEDI TUDOMÁNYEGYETEM

  公开号：WO2014170704A1

  公开（公告）日：2014-10-23

  The invention relates to new morphine derivatives deuterated at the 7,8-position of the morphine ring, furthermore to a process for the preparation thereof, and to pharmaceutical compositions comprising them. The new deuterated morphine derivatives show high and selective μ-opioid receptor binding activity leading to the benefit of higher analgesic activity at lower dosages inducing thereby reduced adverse effects compared to the hydrogenated derivatives. The compounds of the invention are useful for example in the treatment of pain or can be used as antitussive agents with a reduced risk of the possibility of drug abuse.

  这项发明涉及新的吗啡衍生物，其在吗啡环的7,8-位置被氘代取，此外还涉及其制备方法以及包含它们的药物组合物。这些新的氘代吗啡衍生物显示出高度和选择性的μ-阿片受体结合活性，从而在较低剂量下产生更高的镇痛活性，因此与氢化衍生物相比，减少了不良反应。该发明的化合物可用于例如治疗疼痛，或可用作镇咳剂，具有较低的药物滥用可能性。
• MARKARYAN EH. A.; AJRAPETYAN G. K.; TSATINYAN A. S.; AVAKYAN O. M.; VOSKA+, AJKAKAN KIMIAKAN AMSAGIR, ARM. XIM. ZH. <AUKZ-AN>, 1976, 29, HO 5, 440-44+
  作者：MARKARYAN EH. A.、 AJRAPETYAN G. K.、 TSATINYAN A. S.、 AVAKYAN O. M.、 VOSKA+

  DOI：——

  日期：——
• DEUTERATED MORPHINE DERIVATIVES
  申请人：Szegedi Tudományegyetem

  公开号：EP2986612A1

  公开（公告）日：2016-02-24
• DEUTERATED MORPHINE DERIVATIVES FOR USE IN ANALGESIA
  申请人：Szegedi Tudományegyetem

  公开号：EP3312183B1

  公开（公告）日：2020-06-17
• US9447108B2
  申请人：——

  公开号：US9447108B2

  公开（公告）日：2016-09-20