Abstract
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.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 139-147 |
| Number of pages | 9 |
| Journal | Critical Reviews in Toxicology |
| Volume | 26 |
| Issue number | 2 |
| DOIs | |
| State | Published - Jan 1 1996 |
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All Science Journal Classification (ASJC) codes
- Toxicology
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Synthesis of tobacco-specific N-nitrosamines and their metabolites and results of related bioassays. / Amin, Shantu; Desai, Dhimant; Hecht, Stephen S.; Hoffmann, Dietrich.
In: Critical Reviews in Toxicology, Vol. 26, No. 2, 01.01.1996, p. 139-147.Research output: Contribution to journal › Review article
TY - JOUR
T1 - Synthesis of tobacco-specific N-nitrosamines and their metabolites and results of related bioassays
AU - Amin, Shantu
AU - Desai, Dhimant
AU - Hecht, Stephen S.
AU - Hoffmann, Dietrich
PY - 1996/1/1
Y1 - 1996/1/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0029968631&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0029968631&partnerID=8YFLogxK
U2 - 10.3109/10408449609017927
DO - 10.3109/10408449609017927
M3 - Review article
C2 - 8688157
AN - SCOPUS:0029968631
VL - 26
SP - 139
EP - 147
JO - Critical Reviews in Toxicology
JF - Critical Reviews in Toxicology
SN - 1040-8444
IS - 2
ER -