N—2—甲基丙基N—1—甲基丙酮基亚硝胺的合成及物理性质

在林县食物和自然霉变的食品中,本研究组首次发现一种亚硝胺:N-2-甲基丙基-N-1-甲基丙酮基亚硝胺(N-2-methylpropyl-N-1-methylacetonylnitrosamine,简称NMAMPA),并确定了它的结构。 NMAMPA是一种挥发性亚硝胺,已证实其对细菌和哺乳类动物细胞有致突变作用。为进一步研究

Synthesis of N-2-methylpropyl-N-1'-methylacetonylnitrosamine and its physical properties

N-2-methylpropyl-N-1'-methylacetonylnitrosamine (NMAMPA) is a new N-nitroso compound found in natural moldy millet and wheat flour from Linxian county, Henan Province. The volatile nitrosamine is mutagenic in several short-term biological assays, and so we proceeded to synthesize larger amounts for the study of carcinogenesis. The main steps were as follows: 1) preparation of 3-bromobutanone (I) by bromination of butanone, 2) alkylation of 3-bromobutanone (I) with isobutylamine to give the secondary amine (II), and 3) nitrosaton of secondary amine (II) with sodium nitrite to yield NMAMPA (III). NMAMPA is a pale yellow liquid which is slightly soluble in water and freely soluble in ether, chloroform and dichloromethane. At room temperature, NMAMPA slowly turns brown, and decomposition takes place after prolonged exposure to UV light. A dilute solution of NMAMPA may be degraded in a freezer at 4 degrees to 6 degrees C.