Norhydromorphone hydrochloride | 14140-35-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: Norhydromorphone hydrochloride
• 英文别名: 4,5α-epoxy-3-hydroxy-morphinan-6-one; hydrochloride；4,5α-Epoxy-3-hydroxy-morphinan-6-on; Hydrochlorid
• CAS: 14140-35-3
• 化学式: C₁₆H₁₇NO₃*ClH
• 分子量: 307.777
• InChiKey: RNAMLZNDHHXDEP-VUICDJBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  21.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  58.56
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Norhydromorphone hydrochloride 在 3 A molecular sieve 、 HOAc-MeOH-buffer 、 potassium acetate 、 sodium cyanoborohydride 作用下， 以 溶剂黄146 为溶剂， 反应 16.0h， 生成 17-(2-phenylethyl)-6,7-dehydro-4,5α-epoxy-3-hydroxy-6,7-2',3'-indolomorphinan
  参考文献：
  名称：

  Opioid agonist and antagonist activities of morphindoles related to naltrindole

  摘要：

  A series of naltrindole-related ligands (4-10) with an N-methyl, N-phenethyl, N-cinnamyl, or an unsubstituted basic nitrogen were synthesized and tested for opioid agonist and antagonist activity in smooth muscle preparations and in mice. The nor compounds (4 and 6) and the phenethyl derivatives (5 and 8) displayed full agonist activity (IC50 = 85-179 nM) in the mouse vas deferens preparation (MVD) while the other members of the series exhibited partial agonist or weak antagonist activity. In the guinea pig ileum preparation (GPI), all compounds except 8 were partial agonists. The ligands that were evaluated in mice were found to produce antinociception that was not selectively mediated via delta opioid receptors. However, two of these ligands (4 and 5) appeared to be delta-selective opioid receptor antagonists at subthreshold doses for antinociception. The finding that all of the compounds bind selectively to delta opioid receptors in guinea pig brain membranes together with the in vitro pharmacology and in vivo antagonist studies suggests that the lack of delta agonist selectivity in vivo may be due to a number of factors, including a basic difference between the delta receptor system in the MVD and in the mouse brain. Further, it is suggested that the constellation of message and address components in the morphindole nucleus may tend to stabilize delta receptors in the brain in an antagonist state.

  DOI：

  10.1021/jm00101a009
• 作为产物：
  描述：

  氢吗啡酮 在 氢氧化钾 、 potassium hydrogencarbonate 、 溶剂黄146 、 锌 作用下， 反应 3.5h， 生成 Norhydromorphone hydrochloride
  参考文献：
  名称：

  氧化吗啡的结构-活性关系。七。4-羟基和3,4-二加氧的6-吗啡酮系列的5-甲基化和14-羟基取代的激动剂和拮抗剂

  摘要：

  通过常规化学方法制备了几种在C（3），C（4），C（5）和C（14）处不同取代的吗啡酮激动剂以及4-羟基和3,4-二甲氧基系列的拮抗剂。事实证明，海湾区域的氧化模式非常重要，包括C（3）和C（4）。C（5）处的烷基化或C（14）处的羟基化降低了化合物的效力。发现最有效的激动剂是N-苯乙基取代的酮27，其在热板测定中的效力是吗啡的六倍。3，4-亚甲基二氧基取代的酮9的效力比其3，4-二甲氧基同类物低约20倍。X射线分析9 且有代表性的激动剂表明，海湾地区的立体化学特征相似，因此不能用来解释这种差异。

  DOI：

  10.1002/hlca.19820650804

文献信息

• [EN] CONJUGATES FOR ASSAYS FOR OXYCODONE AND OXYMORPHONE<br/>[FR] CONJUGUÉS UTILISABLES EN VUE DU DOSAGE DE L'OXYCODONE ET DE L'OXYMORPHONE
  申请人：SIEMENS HEALTHCARE DIAGNOSTICS INC

  公开号：WO2016100113A3

  公开（公告）日：2016-08-18