N-{1-[2-(4-羟基-苯基)-乙基]-哌啶-4-基}-N-苯基-丙酰胺 | 76107-53-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: N-{1-[2-(4-羟基-苯基)-乙基]-哌啶-4-基}-N-苯基-丙酰胺
• 英文名称: N-phenyl-N-[1-[2-(4-hydroxyphenyl)ethyl]-4-piperidinyl]propanamide
• 英文别名: 1-(p-hydroxyphenethyl)-4-(N-propionylanilino)piperidine；4'-hydroxy-fentanyl；N-{1-[2-(4-Hydroxy-phenyl)-ethyl]-piperidin-4-yl}-N-phenyl-propionamide；N-[1-[2-(4-hydroxyphenyl)ethyl]piperidin-4-yl]-N-phenylpropanamide
• CAS: 76107-53-4
• 化学式: C₂₂H₂₈N₂O₂
• 分子量: 352.477
• InChiKey: LCMFYINHURKMTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为产物：
  描述：

  N-苯基-N-(4-哌啶)丙胺 混合盐酸 在 盐酸小檗碱 、 sodium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 N-{1-[2-(4-羟基-苯基)-乙基]-哌啶-4-基}-N-苯基-丙酰胺
  参考文献：
  名称：

  Lobbezoo; Soudijn; Van Wijngaarden, European Journal of Medicinal Chemistry, 1980, vol. 15, # 4, p. 357 - 361

  摘要：

  DOI：

文献信息

• Metabolism of fentanyl in isolated hepatocytes from rat and guinea pig.
  作者：TSUYOSHI GOROMARU、MASATAKA KATASHIMA、HIROSHI MATSUURA、NOZOMU YOSHIMURA

  DOI：10.1248/cpb.33.3922

  日期：——

  The metabolites of fentanyl (FT) were identified in isolated rat and guinea pig hepatocytes by gas chromatography-mass spectrum (GC-MS) combined with the stable isotope tracer technique. Isolated hepatocytes were prepared by the collagenase perfusion method and were incubated with a 0.3mM equimolar mixture of FT and FT-d5 citrate in a rotating round-bottomed flask at 37°C. The metabolites were extracted with chloroform. The extracts were subjected to GC and GC-MS after trimethylsilylation. Characteristic doublet peaks in the mass spectra indicated the presence of 6 and 7 metabolites in rat and guinea pig hepatocytes, respectively. 4-(N-Propionylanilino) piperidine was identified as the main metabolite in both species. Other metabolites were oxidation products of the phenethyl, piperidine and propionyl groups of FT. Oxidation of the anilino ring and hydrolysis of the amide bond were not found in hepatocytes.

  通过气相色谱-质谱（GC-MS）结合稳定同位素示踪技术，鉴定了大鼠和豚鼠离体肝细胞中芬太尼（FT）的代谢物。离体肝细胞采用胶原酶灌注法制备，并与 0.3mM 等摩尔 FT 和柠檬酸 FT-d5 混合物在 37°C 旋转圆底烧瓶中培养。代谢物用氯仿提取。提取物经三甲基硅烷化后进行气相色谱和气相色谱-质谱分析。质谱中的特征性双峰表明，在大鼠和豚鼠肝细胞中分别存在 6 种和 7 种代谢物。在这两个物种中，4-（N-丙酰基苯胺基）哌啶被确定为主要代谢物。其他代谢物是 FT 的苯乙基、哌啶基和丙酰基的氧化产物。在肝细胞中未发现苯胺基环的氧化和酰胺键的水解。
• Hydrophilic fentanyl derivatives
  申请人：Allegheny-Singer Research Institute

  公开号：US11066366B2

  公开（公告）日：2021-07-20

  Various fentanyl derivatives are described. The derivatives exhibit high binding affinity to opioid receptors, but also have decreased blood brain permeability as compared to standard fentanyl. This, the resulting derivatives can be less addictive than standard fentanyl. Methods of making such derivatives are also disclosed in this document.

  介绍了各种芬太尼衍生物。这些衍生物与阿片受体的结合亲和力很高，但与标准芬太尼相比，其脑血渗透性也有所降低。因此，与标准芬太尼相比，这些衍生物的成瘾性较低。本文件还公开了制造这种衍生物的方法。