TY - JOUR
T1 - Kinetics of nornicotine and anabasine nitrosation in relation to N′-nitrosonornicotine occurrence in tobacco and to tobacco-induced cancer
AU - Mirvish, Sidney S.
AU - Sams, James
AU - Hecht, Stephen S.
PY - 1977/10
Y1 - 1977/10
N2 - The kinetics of nornicotine and anabasine nitrosa-tion, studied in aqueous solution, obeyed equations typical for the nitrosation of aliphatic secondary amines, with third-order stoichiometric rate constants of 1.15 (nornicotine) and 0.86 (anabasine) m–2 sec–1. The similarity of the two rate constants suggested that the nitrosonornicotine occurring in tobacco arises from nicotine rather than nornicotine, because tobacco contains anabasine but apparently does not contain nitro-soanabasine. The high rate constants suggested that in vivo nitrosation of these secondary amines may constitute a hazard to tobacco smokers and chewers, in addition to that presented by preformed nitrosonornicotine.
AB - The kinetics of nornicotine and anabasine nitrosa-tion, studied in aqueous solution, obeyed equations typical for the nitrosation of aliphatic secondary amines, with third-order stoichiometric rate constants of 1.15 (nornicotine) and 0.86 (anabasine) m–2 sec–1. The similarity of the two rate constants suggested that the nitrosonornicotine occurring in tobacco arises from nicotine rather than nornicotine, because tobacco contains anabasine but apparently does not contain nitro-soanabasine. The high rate constants suggested that in vivo nitrosation of these secondary amines may constitute a hazard to tobacco smokers and chewers, in addition to that presented by preformed nitrosonornicotine.
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U2 - 10.1093/jnci/59.4.1211
DO - 10.1093/jnci/59.4.1211
M3 - Article
C2 - 561854
AN - SCOPUS:0017693211
SN - 0027-8874
VL - 59
SP - 1211
EP - 1213
JO - Journal of the National Cancer Institute
JF - Journal of the National Cancer Institute
IS - 4
ER -