Base-catalyzed decomposition of N-nitrosobis(2-oxopropyl)amine.
نویسندگان
چکیده
N-Nitrosobis(2-oxopropyl)amine, a potent carcinogen for the pancreas in Syrian hamsters, undergoes a facile, base-catalyzed, intramolecular aldol condensation to yield N-nitroso-5-hydroxy-5-methyl-3-piperidone. This cyclic nitrosamine then decomposes to yield 3-hydroxy-5-methylpyridine.
منابع مشابه
Carcinogenic effect of N-nitroso(2-hydroxypropyl)(2-oxopropyl)amine, a postulated proximate pancreatic carcinogen in Syrian hamsters.
N-Nitroso(2-hydroxypropyl)(2-oxopropyl)amine (HPOP) proved to be a potent carcinogen in Syrian golden hamsters. The compound is an in vivo metabolite of N-nitrosobis(2-hydroxypropyl)amine, N-nitrosobis(2-oxopropyl)amine (BOP), and N-nitroso-2,6-dimethylmorpholine and a postulated proximate pancreatic carcinogen in hamsters. As with BOP, HPOP induced a higher incidence of pancreatic ductular ade...
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Ovarian and testicular tumors were induced in the offspring (F1 generation) of MRC rats that received single or multiple doses of N-nitrosobis(2-oxopropyl)amine on the 14th, 18th, and/or 20th days of pregnancy. The ovarian tumor incidence was significantly higher (46%) in the F1 generation exposed to the carcinogen a single time at the 18th day of gestation, when compared to those exposed at th...
متن کاملThe metabolism of the pancreas carcinogen N-nitrosobis(2-oxopropyl)amine by hamster pancreas duct epithelial cell clones; evidence for different metabolic efficiencies and response to cytochrome P450 inducers.
CONTEXT We have isolated five stable clones from a primary culture of Syrian golden hamster pancreatic duct epithelial cells and have designated them as CK1 through CK5. DESIGN Here we describe the ability of two of these, CK1 and CK5, to metabolize the pancreas carcinogen N-nitrosobis(2-oxopropyl)amine. The metabolism was assessed as the production of mutated V79 cells in a CK cell/V79 co-cu...
متن کاملMetabolism of pancreatic carcinogens N-nitroso-2,6-dimethylmorpholine and N-nitrosobis(2-oxopropyl)amine by microsomes and cytosol of hamster pancreas and liver.
Liver preparations from Syrian golden hamsters catalyze the metabolism of the pancreatic carcinogen N-nitroso-2,6-dimethylmorpholine largely to N-nitroso(2-hydroxypropyl)(2-oxopropyl)amine (HPOP). This reaction is catalyzed by a mixed-function oxidase in the presence of reduced nicotinamide adenine dinucleotide phosphate and oxygen at a rate of 3.8 nmol/min/mg of protein, and it is inhibited by...
متن کاملMetabolism of the pancreatic carcinogen N-nitroso-2,6-dimethylmorpholine by hamster liver and component cells of pancreas.
/v-Nitroso-2,6-dimethylmorpholine (NNDM) is an indirect nitrosamine carcinogen which induces ductal adenocarcinoma of the pancreas in the Syrian golden hamster. NNDM is oxidized by normal male hamster pancreas postmitochondrial supernatants (S-9) in the presence of reduced nicotinamide adenine dinucleotide phosphate and oxygen to give three major identi fiable metabolites as measured by high-pr...
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ورودعنوان ژورنال:
- Chemical research in toxicology
دوره 1 1 شماره
صفحات -
تاریخ انتشار 1988