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Chemical Compound Review:

CHEMBL165231 methyl1-nitroso-5,6-dihydro- 2H-pyridine-3...

Synonyms: CCRIS 3050, AG-F-94364, LS-7600, AC1L1WHJ, CTK8G1964, ...

Rivenson, A. et al., Lijinsky, W. et al., Wenke, G. et al., Nair, J. et al., Wenke, G. et al., et al.

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Disease relevance of N-NITROSOGUVACINE

The approximate total doses of the nitrosamines (mmol/kg of body weight) in these groups were: NNK, 0.073, 0.17, and 0.68; NNAL, 0.69; NG, 4.1; NG and NNK, 4.1 and 0.17 [1].
The results seem to suggest that NG may play only a minor role, if any, in the etiology of oral cancer among betel quid chewers [2].

High impact information on N-NITROSOGUVACINE

Two unsaturated derivatives of N-nitrosopiperidine (NP), N-nitroso-1,2,3,6-tetrahydropyridine (NTP) and N-nitrosoguvacoline (NGC), were administered to Sprague-Dawley rats as solutions in drinking water at concentrations equimolar (0.88X10(-3) M) with those used to test NP [3].
N'-Nitrosoanatabine (NAT) and N-nitrosoguvacoline (NGCO) levels decreased significantly in saliva of chewers of BQT in the presence of ascorbic acid, suggesting inhibition of their formation [4].
In model studies, nitrosation of the major areca alkaloid, arecoline, leads to the formation of N-nitrosoguvacoline, 3-(methylnitrosamino)propionitrile (MNPN), 3-(methylnitrosamino)propionaldehyde and two unknown N-nitrosamines [5].

Analytical, diagnostic and therapeutic context of N-NITROSOGUVACINE

Groups of 30 to 80 rats were treated with 0.5 ppm, 1.0 ppm, or 5.0 ppm of NNK; 5.0 ppm of NNAL, 20 ppm of NG, a mixture of 20 ppm of NG and 1 ppm of NNK, and water only in the control group [1].
NG is most likely not carcinogenic, MNPN is suspected to be a relatively strong animal carcinogen based on bioassays with its lower homologue [6].

References

Induction of lung and exocrine pancreas tumors in F344 rats by tobacco-specific and Areca-derived N-nitrosamines. Rivenson, A., Hoffmann, D., Prokopczyk, B., Amin, S., Hecht, S.S. Cancer Res. (1988) [Pubmed]
Oral lesions, genotoxicity and nitrosamines in betel quid chewers with no obvious increase in oral cancer risk. Stich, H.F., Rosin, M.P., Brunnemann, K.D. Cancer Lett. (1986) [Pubmed]
Carcinogenicity test of two unstaurated derivatives of N-nitrosopiperdine in Sprague-Dawley rats. Lijinsky, W., Taylor, H.W. J. Natl. Cancer Inst. (1976) [Pubmed]
Endogenous nitrosation in the oral cavity of chewers while chewing betel quid with or without tobacco. Nair, J., Nair, U.J., Ohshima, H., Bhide, S.V., Bartsch, H. IARC Sci. Publ. (1987) [Pubmed]
A study of betel quid carcinogenesis. II. Formation of N-nitrosamines during betel quid chewing. Wenke, G., Rivenson, A., Brunnemann, K.D., Hoffmann, D., Bhide, S.V. IARC Sci. Publ. (1984) [Pubmed]
A study of betel quid carcinogenesis. 1. On the in vitro N-nitrosation of arecoline. Wenke, G., Hoffmann, D. Carcinogenesis (1983) [Pubmed]

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