Formation of N-nitrosamines from secondary amines andnitrite in human and animal gastric juice

Sen, Nrisinha P.; Smith, Dorothy C.; Schwinghamer, L.

doi:10.1016/s0015-6264(69)80366-4

Cited by 163 publications

(43 citation statements)

References 9 publications

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“…Secondary and tertiary amines react with nitrous acid to form N-nitroso compounds in vitro and in the stomach in vivo (1)(2)(3). Numerous animal studies have demonstrated the carcinogenicity of nitroso compounds (4)(5)(6)(7).…”

Section: Introductionmentioning

confidence: 99%

Genotoxic effects of N-nitrosoketamine and ketamine as assessed by in vitro micronucleus test in Chinese hamster lung fibroblast cell line

Toyama

Shimizu

Suzuki

et al. 2006

Environ. Health Prev. Med.

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Objectives: Ketamine hydrochloride (KT) is a secondary amine that has been safely used as an injectable anesthetic and analgesic to avoid the production of nitroso compounds in the stomach. However, ketamine in the tablet form has recently become an abused, recreational drug. The aim of this study was to investigate the genotoxic effects of N-nitrosoketamine (NKT) and KT on the basis of an in vitro micronucleus (MN) test using a Chinese hamster lung fibroblast cell line (CHL/IU).Methods: NKT was synthesized from KT in our laboratory. In the MN tests, CHL/IU cells were continuously treated with either NKT or KT for 24, 48, or 72 hours without the S9 mix. The cells were also treated with NKT or KT with or without the S9 mix for 6 hours, followed by a recovery period of 18, 42, or 66 hours (short-term treatment). The results were considered to be statistically significant when the p-values of both Fisher's exact test and the trend test were less than 0.05.Results: After the short-term treatment with either NKT or KT with and without the S9 mix, the frequency of micronuclei significantly increased. However, the frequency of micronuclei did not significantly increase after the continuous treatment with either NKT or KT. Both NKT and KT were determined to be genotoxic in the short-term treatment with or without the S9 mix, but they were determined to be nongenotoxic in continuous treatment.Conclusion: Our findings suggest that NKT has a stronger genotoxic effect than KT.

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Section: Introductionmentioning

confidence: 99%

Genotoxic effects of N-nitrosoketamine and ketamine as assessed by in vitro micronucleus test in Chinese hamster lung fibroblast cell line

Toyama

Shimizu

Suzuki

et al. 2006

Environ. Health Prev. Med.

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“…There have also been reports of in vivo nitrosamine formation (Sen et al, 1969;Alam et al, 1971;Sander and Seif, 1969). In these studies, however, analysis was carried out at one time only after feeding reactants.…”

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confidence: 98%

“…Nitrosamines have been shown to be formed in vitro by the reaction of various secondary amines and nitrite in human and animal gastric juice (Lane and Bailey, 1973;Sen, Smith and Schwinghamer, 1969;Sander, 1967;Alam, Saporoschetz and Epstein, 1971). There have also been reports of in vivo nitrosamine formation (Sen et al, 1969;Alam et al, 1971;Sander and Seif, 1969).…”

mentioning

confidence: 99%

Formation of N-Nitrosopyrrolidine in a Dog's Stomach

Mysliwy¹,

Wick²,

Archer³

et al. 1974

Br J Cancer

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“…Nitrosamines have been found in a limited number of foods for human consumption (International Agency for Research on Cancer, 1972), and have been shown to be produced by bacteria that occur in food (CollinsThompson et al, 1972;Fong and Chan, 1973). They may be produced in vivo from nitrites and either secondary amines (Sander, Schweinsberg and Menz, 1968;Sen, Smith and Schwinghamer, 1969;Lijinsky and Epstein, 1970;Mirvish, 1970) or tertiary amines (Lijinsky, 1974) at thepH of the stomach.The possibility of bacterial production of nitrosamines from secondary amines in the presence of nitrate or nitrite in vivo at sites with a pH closer to neutrality has been raised. Production in vitro has been shown with single strains of four nitrate-reducing members of the enterobacteriaceae, Escherichia coli, E. dispar, Proteus vuEgaris and Serratia marcescens, from secondary amines at neutral p H (Sander, 1968).…”

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confidence: 99%

The importance of prolonged incubation for the synthesis of dimethylnitrosamine by enterobacteria

Coloe

Hayward

1976

Journal of Medical Microbiology

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THE experimental demonstration that nitrosamines are carcinogenic, mutagenic and teratogenic (Magee, 1969) has raised the question of their potential danger to man, and prompted studies of the circumstances that might expose him to them. Nitrosamines have been found in a limited number of foods for human consumption (International Agency for Research on Cancer, 1972), and have been shown to be produced by bacteria that occur in food (CollinsThompson et al., 1972;Fong and Chan, 1973). They may be produced in vivo from nitrites and either secondary amines (Sander, Schweinsberg and Menz, 1968;Sen, Smith and Schwinghamer, 1969;Lijinsky and Epstein, 1970;Mirvish, 1970) or tertiary amines (Lijinsky, 1974) at thepH of the stomach.The possibility of bacterial production of nitrosamines from secondary amines in the presence of nitrate or nitrite in vivo at sites with a pH closer to neutrality has been raised. Production in vitro has been shown with single strains of four nitrate-reducing members of the enterobacteriaceae, Escherichia coli, E. dispar, Proteus vuEgaris and Serratia marcescens, from secondary amines at neutral p H (Sander, 1968). Hawksworth and Hill (1971) found that 27% of 37 strains of E. coli and a proportion of strains of other faecal aerobes and anaerobes were able to produce nitrosamines from nitrate and diphenylamine at a pH above 6.5. These authors (Hill and Hawksworth, 1972) consider that the most likely site of in-vivo bacterial production of nitrosamines is the urinary tract, because the substrates, nitrate and secondary amines (principally dimethylamine, DMA), are found in urine-and bacteria with both nitrate-reducing and nitrosamine-forming enzymes may be present during infection. The in-vitro production of dimethylnitrosamine (DMN) by three strains each of P. mirabilis, P. morganii and P. rettgeri from urine, and the detection of DMN in the urine of two patients with urinary-tract infections caused by P. mirabilis, supports this suggestion (Brooks et al., 1972;Thacker and Brooks, 1974). Nitrosamines produced by bacteria during urinary-tract infections may cause cancer in distant anatomical sites (Hill, Hawksworth and Tattersall, 1973; Hawksworth and Hill, 1974).The present survey was undertaken to define which of the bacteria commonly associated with urinary-tract infection are able to produce DMN. The survey of faecal bacteria by Hawksworth and Hill (1971) appears to show that production of diphenylnitrosamine is not a constant feature of all strains of any species. Similarly, we have found wide variation among strains when we tested bacteria that may cause urinary-tract infections for their ability to produce

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Formation of N-nitrosamines from secondary amines andnitrite in human and animal gastric juice

Cited by 163 publications

References 9 publications

Genotoxic effects of N-nitrosoketamine and ketamine as assessed by in vitro micronucleus test in Chinese hamster lung fibroblast cell line

Genotoxic effects of N-nitrosoketamine and ketamine as assessed by in vitro micronucleus test in Chinese hamster lung fibroblast cell line

Formation of N-Nitrosopyrrolidine in a Dog's Stomach

The importance of prolonged incubation for the synthesis of dimethylnitrosamine by enterobacteria

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