(R)-nantenine | 1207542-48-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 英文名称: (R)-nantenine
• 英文别名: (R)-1,2-Dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-[1,3]dioxolo[4',5':4,5]benzo[1,2-g]benzo[de]quinoline；(12R)-18,19-dimethoxy-13-methyl-5,7-dioxa-13-azapentacyclo[10.7.1.02,10.04,8.016,20]icosa-1(20),2,4(8),9,16,18-hexaene
• CAS: 1207542-48-0
• 化学式: C₂₀H₂₁NO₄
• 分子量: 339.391
• InChiKey: WSVWKHTVFGTTKJ-CQSZACIVSA-N

物化性质

• 沸点：
  487.5±45.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (+/-)-nantenine 在 D-(+)-二对甲基苯甲酰酒石酸 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以32%的产率得到(R)-nantenine
  参考文献：
  名称：

  Synthetic studies and pharmacological evaluations on the MDMA (‘Ecstasy’) antagonist nantenine

  摘要：

  The naturally occurring aporphine alkaloid nantenine, has been shown to antagonize behavioral and physiological effects of MDMA in mice. We have synthesized (+/-)-nantenine via an oxidative cyclization reaction with PIFA and evaluated its binding profile against a panel of CNS targets. To begin to understand the importance of the chiral center of nantenine with regards to its capacity to antagonize the effects of MDMA in vivo, (R)- and (S)-nantenine were prepared and evaluated in a food-reinforced operant task in rats. Pretreatment with either nantenine enantiomer (0.3 mg/kg ip) completely blocked the behavioral suppression induced upon administration of 3.0 mg/kg MDMA. (+/-)-Nantenine displayed high affinity and selectivity for the alpha(1A) adrenergic receptor among several other receptors suggesting that this alpha(1) subtype may be significantly involved in the anti-MDMA effects of the enantiomers. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.11.053

文献信息

• Evaluation of structural effects on 5-HT2A receptor antagonism by aporphines: Identification of a new aporphine with 5-HT2A antagonist activity
  作者：Shashikanth Ponnala、Junior Gonzales、Nirav Kapadia、Hernan A. Navarro、Wayne W. Harding

  DOI：10.1016/j.bmcl.2014.02.066

  日期：2014.4

  A set of aporphine analogs related to nantenine was evaluated for antagonist activity at 5-HT2A and alpha(1A) adrenergic receptors.With regards to 5-HT2A receptor antagonism, a C2 allyl group is detrimental to activity. The chiral center of nantenine is not important for 5-HT2A antagonist activity, however the N6 nitrogen atom is a critical feature for 5-HT2A antagonism.Compound 12b was the most potent 5-HT2A aporphine antagonist identified in this study and has similar potency to previously identified aporphine antagonists 2 and 3. The ring A and N6 modifications examined were detrimental to alpha(1A) antagonism. A slight eutomeric preference for the R enantiomer of nantenine was observed in relation to alpha(1A) antagonism. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthetic studies and pharmacological evaluations on the MDMA (‘Ecstasy’) antagonist nantenine
  作者：Onica LeGendre、Stevan Pecic、Sandeep Chaudhary、Sarah M. Zimmerman、William E. Fantegrossi、Wayne W. Harding

  DOI：10.1016/j.bmcl.2009.11.053

  日期：2010.1

  The naturally occurring aporphine alkaloid nantenine, has been shown to antagonize behavioral and physiological effects of MDMA in mice. We have synthesized (+/-)-nantenine via an oxidative cyclization reaction with PIFA and evaluated its binding profile against a panel of CNS targets. To begin to understand the importance of the chiral center of nantenine with regards to its capacity to antagonize the effects of MDMA in vivo, (R)- and (S)-nantenine were prepared and evaluated in a food-reinforced operant task in rats. Pretreatment with either nantenine enantiomer (0.3 mg/kg ip) completely blocked the behavioral suppression induced upon administration of 3.0 mg/kg MDMA. (+/-)-Nantenine displayed high affinity and selectivity for the alpha(1A) adrenergic receptor among several other receptors suggesting that this alpha(1) subtype may be significantly involved in the anti-MDMA effects of the enantiomers. Published by Elsevier Ltd.