| Synthesis of tobacco-specific N-nitrosamines and their metabolites and results of related bioassays. | |
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MedLine Citation:
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PMID: 8688157 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Tobacco-specific N-nitrosamines (TSNA) are the most abundant, strong carcinogens in tobacco smoke. Seven TSNA have been identified in tobacco products: N'-nitrosonornicotine (NNN), N'-nitrosoanabasine (NAB), N'-nitrosoanatabine (NAT), 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL), 4-(methylnitrosamino)-4-(3-pyridyl)-1-butanol (iso-NNAL), and 4-(methylnitrosamino)-4-3-pyridyl)butyric acid (iso-NNAC). The syntheses of these compounds are reviewed. The syntheses of 14C- and 3H-labeled NNK as well as metabolites of NNK and NNN are also discussed. Comparative assays for lung tumorigenesis in female A/J mice were carried out for six of the TSNA and for two related compounds, N-nitrosodimethylamine (NDMA) and N-nitrosopyrrolidine (NPYR). They yielded the following ranking of potency: NDMA > NNK > NNAL > NPYR > NNN > NAB. Iso-NNAL and iso-NNAC were inactive. These results are also compared with previous assays of TSNA carcinogenicity in rats and hamsters. |
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Authors:
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S Amin; D Desai; S S Hecht; D Hoffmann |
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Publication Detail:
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Type: Journal Article; Research Support, U.S. Gov't, P.H.S.; Review |
Journal Detail:
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Title: Critical reviews in toxicology Volume: 26 ISSN: 1040-8444 ISO Abbreviation: Crit. Rev. Toxicol. Publication Date: 1996 |
Date Detail:
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Created Date: 1996-08-27 Completed Date: 1996-08-27 Revised Date: 2007-11-14 |
Medline Journal Info:
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Nlm Unique ID: 8914275 Medline TA: Crit Rev Toxicol Country: UNITED STATES |
Other Details:
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Languages: eng Pagination: 139-47 Citation Subset: IM |
Affiliation:
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American Health Foundation, Valhalla, NY 10595, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Adenoma
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chemically induced* Animals Carcinogenicity Tests Carcinogens / chemistry, metabolism Chromatography, High Pressure Liquid Cricetinae Female Lung Neoplasms / chemically induced* Mice Nitrosamines / chemistry, metabolism, toxicity* Plants, Toxic* Rats Tobacco / chemistry* |
| Grant Support | |
ID/Acronym/Agency:
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CA-29580/CA/NCI NIH HHS; CA-44377/CA/NCI NIH HHS; N01-CP-21115/CP/NCI NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Carcinogens; 0/Nitrosamines |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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