Document Detail


Synthesis of tobacco-specific N-nitrosamines and their metabolites and results of related bioassays.
MedLine Citation:
PMID:  8688157     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
S Amin; D Desai; S S Hecht; D Hoffmann
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, P.H.S.; Review    
Journal Detail:
Title:  Critical reviews in toxicology     Volume:  26     ISSN:  1040-8444     ISO Abbreviation:  Crit. Rev. Toxicol.     Publication Date:  1996  
Date Detail:
Created Date:  1996-08-27     Completed Date:  1996-08-27     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  8914275     Medline TA:  Crit Rev Toxicol     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  139-47     Citation Subset:  IM    
Affiliation:
American Health Foundation, Valhalla, NY 10595, USA.
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MeSH Terms
Descriptor/Qualifier:
Adenoma / 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:
CA-29580/CA/NCI NIH HHS; CA-44377/CA/NCI NIH HHS; N01-CP-21115/CP/NCI NIH HHS
Chemical
Reg. No./Substance:
0/Carcinogens; 0/Nitrosamines

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