N'-Nitrosonornicotine 1-N-oxide | 78246-24-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N'-Nitrosonornicotine 1-N-oxide
• 英文别名: 3-(1-Nitrosopyrrolidin-2-yl)-1-oxidopyridin-1-ium
• CAS: 78246-24-9
• 化学式: C₉H₁₁N₃O₂
• mdl: MFCD09879997
• 分子量: 193.205
• InChiKey: ZQELURDMDMQXQV-UHFFFAOYSA-N

物化性质

• 沸点：
  329.41°C (rough estimate)
• 密度：
  1.2371 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  58.1
• 氢给体数：
  0
• 氢受体数：
  4

ADMET

代谢

NNN N-氧化物是N'-硝基索尼金（NNN）的一个已知的第三手烟雾代谢物。

NNN N-Oxide is a known thirdhand smoke metabolite of N'-Nitrosonornicotine (NNN).

来源:NORMAN Suspect List Exchange

反应信息

• 作为产物：
  描述：

  去甲基烟碱亚硝胺 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以70%的产率得到N'-Nitrosonornicotine 1-N-oxide
  参考文献：
  名称：

  Metabolic .beta.-hydroxylation and N-oxidation of n'-nitrosonornicotine

  摘要：

  3'-Hydroxy-N'-nitrosonornicotine (2), 4'-hydroxy-N'-nitrosonornicotine (3), N'-nitrosonornicotine 1-N-oxide (4) were synthesized and identified as metabolites in the F-344 rat of the tobacco-specific carcinogen N'-nitrosonornicotine (1). For the synthesis of 2, myosmine (5) was converted to 3'-bromomyosmine (6). Displacement by acetate and hydrolysis gave 3'-hydroxymyosmine (7), which was reduced and nitrosated to give 2. 4'-Hydroxymyosmine (13), the precursor to 3, was prepared by ammonolysis of 1,2-epoxy-4-(N-morpholino)-4-(3-pyridyl)-4-cyanobutane (10). N'-Nitrosonornicotine 1-N-oxide (4) was prepared by m-chloroperbenzoic acid oxidation of 1. When 1 was incubated with liver microsomes from Aroclor-pretreated F-344 rats, trace amounts of 2 and 3 were produced and 4 was a major metabolite. The urine from rats treated with N'-nitrosonornicotine-2'-14C contained only trace amounts of 2 and 3, whereas 4 accounted for 6.7-9.4% of the dose.

  DOI：

  10.1021/jm00185a005

文献信息

• HECHT S. S.; CHEN CHI-HONG B.; HOFFMANN D., J. MED. CHEM., 1980, 23, NO 11, 1175-1178
  作者：HECHT S. S.、 CHEN CHI-HONG B.、 HOFFMANN D.

  DOI：——

  日期：——
• Metabolic .beta.-hydroxylation and N-oxidation of n'-nitrosonornicotine
  作者：Stephen S. Hecht、Chi-Hong B. Chen、Dietrich Hoffmann

  DOI：10.1021/jm00185a005

  日期：1980.11

  3'-Hydroxy-N'-nitrosonornicotine (2), 4'-hydroxy-N'-nitrosonornicotine (3), N'-nitrosonornicotine 1-N-oxide (4) were synthesized and identified as metabolites in the F-344 rat of the tobacco-specific carcinogen N'-nitrosonornicotine (1). For the synthesis of 2, myosmine (5) was converted to 3'-bromomyosmine (6). Displacement by acetate and hydrolysis gave 3'-hydroxymyosmine (7), which was reduced and nitrosated to give 2. 4'-Hydroxymyosmine (13), the precursor to 3, was prepared by ammonolysis of 1,2-epoxy-4-(N-morpholino)-4-(3-pyridyl)-4-cyanobutane (10). N'-Nitrosonornicotine 1-N-oxide (4) was prepared by m-chloroperbenzoic acid oxidation of 1. When 1 was incubated with liver microsomes from Aroclor-pretreated F-344 rats, trace amounts of 2 and 3 were produced and 4 was a major metabolite. The urine from rats treated with N'-nitrosonornicotine-2'-14C contained only trace amounts of 2 and 3, whereas 4 accounted for 6.7-9.4% of the dose.