rac-N-methylanatabine | 91180-47-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: rac-N-methylanatabine
• 英文别名: 1-methyl-1,2,3,6-tetrahydro-[2,3']bipyridinyl；(+/-)-1'-methyl-anatabine；(+/-)-1-Methyl-1,2,3,6-tetrahydro-2,3'-bipyridin, dl-N-Methylanatabin；dl-N-Methyl-anatabin；3-(1-methyl-3,6-dihydro-2H-pyridin-2-yl)pyridine
• CAS: 91180-47-1
• 化学式: C₁₁H₁₄N₂
• 分子量: 174.246
• InChiKey: ATWWUVUOWMJMTM-UHFFFAOYSA-N

物化性质

• 沸点：
  262.7±28.0 °C(Predicted)
• 密度：
  1.035±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  rac-N-methylanatabine 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以88%的产率得到(+/-)-N-methylanatabine-N-oxide
  参考文献：
  名称：

  两种同分异构的四氢吡啶基生物碱的便捷外消旋合成：异那他滨和他那滨

  摘要：

  Anatabine是烟草的主要生物碱，其异构体isoanatabine最近在海洋蠕虫中被发现。用硼氢化钠还原1-甲基碘化碘，得到1-甲基-3-哌啶，然后用过氧化氢转化成N-氧化物。N氧化物先后与三氟乙酸酐和氰化钾反应，生成2氰基1甲基3哌啶。它与3-吡啶基氯化镁反应生成（±）-N-甲基-异他他滨。这与转化的米氯过苯甲酸入Ñ氧化物这是Ñ用硫酸铁（II）脱甲基，得到（±）-异anatabatin。通过N氧化物分解进行N脱甲基化的文献方法的连续应用，有助于人们了解这种氧化重排的机理。另一方面，自两层醚-水系统中反应开始以来，用硼氢化钠和氰化钾还原1-甲基吡啶碘化物，得到2-氰基-1-甲基-4-哌啶。通过合成（±）-异anatabine的相同反应顺序，将其转化为（±）-anatabine。J.杂环化​​学。（2010）。

  DOI：

  10.1002/jhet.359
• 作为产物：
  描述：

  3-溴吡啶 、 1-甲基-1,2,3,6-四氢-2-吡啶甲腈 在 异丙基氯化镁 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 以83%的产率得到rac-N-methylanatabine
  参考文献：
  名称：

  两种同分异构的四氢吡啶基生物碱的便捷外消旋合成：异那他滨和他那滨

  摘要：

  Anatabine是烟草的主要生物碱，其异构体isoanatabine最近在海洋蠕虫中被发现。用硼氢化钠还原1-甲基碘化碘，得到1-甲基-3-哌啶，然后用过氧化氢转化成N-氧化物。N氧化物先后与三氟乙酸酐和氰化钾反应，生成2氰基1甲基3哌啶。它与3-吡啶基氯化镁反应生成（±）-N-甲基-异他他滨。这与转化的米氯过苯甲酸入Ñ氧化物这是Ñ用硫酸铁（II）脱甲基，得到（±）-异anatabatin。通过N氧化物分解进行N脱甲基化的文献方法的连续应用，有助于人们了解这种氧化重排的机理。另一方面，自两层醚-水系统中反应开始以来，用硼氢化钠和氰化钾还原1-甲基吡啶碘化物，得到2-氰基-1-甲基-4-哌啶。通过合成（±）-异anatabine的相同反应顺序，将其转化为（±）-anatabine。J.杂环化​​学。（2010）。

  DOI：

  10.1002/jhet.359

文献信息

• Stereoselectivity of the demethylation of nicotine piperidine homologues by Nicotiana plumbaginifolia cell suspension cultures
  作者：Trixie Ann Bartholomeusz、Roland Molinié、Albrecht Roscher、François-Xavier Felpin、Françoise Gillet、Jacques Lebreton、François Mesnard、Richard J. Robins

  DOI：10.1016/j.phytochem.2005.07.012

  日期：2005.8

  The metabolism of (R,S)-N-methylanabasine and (R,S)-N-methylanatabine has been studied in a cell suspension culture of Nicotiana plumbaginifolia. Both substrates are effectively demethylated, anabasine or anatabine, respectively, accumulating in the medium. Similarly, there is strong stereoselectivity for the (R)-isomers of both substrates. The kinetics of metabolism of (R,S)-N-methylanabasine differ significantly from those of nicotine in that no further degradation of the initial demethylation product occurs. (R,S)-N-Methylanatabine, however, shows kinetics closer to those of nicotine, with loss of alkaloid from the system. Furthermore, (R,S)-N-methylanabasine does not diminish (S)-nicotine demethylation, indicating a lack of competition. However, the metabolism of (S)-nicotine is affected by the presence of (R,S)-N-methylanabasine. Hence, the demethylation of the piperidine homologues of nicotine is seen to be similar but not identical to that of the pyridine analogues. The implications of these different metabolic profiles in relation to the demethylation activity are discussed. (c) 2005 Elsevier Ltd. All rights reserved.
• LIPOPHILIC ACTIVE AGENT INFUSED COMPOSITIONS WITH REDUCED FOOD EFFECT
  申请人：POVIVA TEA, LLC

  公开号：US20210145036A1

  公开（公告）日：2021-05-20

  Aspects described herein relate to improved methods for infusing compositions with lipophilic active agents, particularly methods for reducing food effect in lipophilic active agent infused compositions, such as food and beverage compositions.
• COMPOSITIONS INFUSED WITH NICOTINE COMPOUNDS AND METHODS OF USE THEREOF
  申请人：POVIVA TEA, LLC

  公开号：US20210145818A1

  公开（公告）日：2021-05-20

  Aspects described herein relate to compositions, including edible compositions, infused with nicotine compounds and methods of use for the treatment of a nicotine-related disorders. More particularly, aspects described herein relate to compositions, including edible compositions, infused with nicotine compounds that provide enhanced bioavailability of the nicotine compounds in a subject, and that mask unpleasant tastes of the nicotine compounds.
• ENHANCEMENT OF DELIVERY OF LIPOPHILIC ACTIVE AGENTS ACROSS THE BLOOD-BRAIN BARRIER AND METHODS FOR TREATING CENTRAL NERVOUS SYSTEM DISORDERS
  申请人：POVIVA CORP.

  公开号：US20210145841A1

  公开（公告）日：2021-05-20

  Aspects described herein relate to edible compositions and methods for the enhancement of delivery of lipophilic active agents across the blood-brain barrier, particularly wherein the lipophilic active agent infused edible compositions produce greater concentrations of lipophilic active agents in subjects' central nervous system tissues as compared to control compositions. Further provided are methods for treating central nervous system disorders comprising administering the edible compositions to subjects in need thereof.
• LIPOPHILIC ACTIVE AGENT INFUSED TOBACCO LEAVES AND/OR TOBACCO MATERIALS AND METHODS OF USE THEREOF
  申请人：POVIVA CORP.

  公开号：US20210213091A1

  公开（公告）日：2021-07-15

  Aspects described herein relate to lipophilic active agent infused tobacco leaves and/or tobacco materials and methods of use thereof. More particularly, aspects described herein relate to tobacco leaves and/or tobacco materials infused with lipophilic active agents that provide enhanced bioavailability of the lipophilic active agents in a subject, and that mask unpleasant tastes.