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Nicotine-derived nitrosamine ketone (NNK), also known as 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone is one of the key tobacco-specific nitrosamines which play an important role in carcinogenesis. == Synthesis == NNK is a compound that is naturally synthesized in tobacco leaves that are exposed to light: the pyrrolidine ring in the nicotine opens and turns the nicotine into NNK. It can also be formed synthetically by taking the following steps: “The potent carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) is present in tobacco and tobacco smoke. ()NNK (6) was synthesized in 27% overall yield. () nicotinic acid was esterified with benzyl alcohol and the ester was alkylated by 3-lithio-N-methylpyrrolidin-2-one. The resulting keto-lactam was hydrolyzed and decarboxylated by treatment with boiling hydrochloric acid. Nitrosation at pH 4.0 gave ()NNK. Carbonyl reduction of ()NNK with either sodium borohydride or cultured rat liver slices gave () 4-(methylnitrosamino)-1-(3-pyridyl) butan-1-ol.” 〔Castonguay, A., & Hecht, S. S. (1985). Synthesis of carbon-14 labeled 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Journal of Labelled Compounds and Radiopharmaceuticals, 22(1), 23-28. doi: 10.1002/jlcr.2580220104〕 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「NNK」の詳細全文を読む スポンサード リンク
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