+ Site Statistics
References:
52,654,530
Abstracts:
29,560,856
PMIDs:
28,072,755
+ Search Articles
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ PDF Full Text
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Translate
+ Recently Requested

Intragastric nitrosation of nicotine is not a significant contributor to nitrosamine exposure



Intragastric nitrosation of nicotine is not a significant contributor to nitrosamine exposure



Annals of the New York Academy of Sciences 686: 213-27; Discussion 227-8



To determine the potential for intragastric nicotine nitrosation, we carried out a kinetic study of the reaction of nicotine with nitrous acid in aqueous solution. The reaction of nicotine with nitrous acid resulted in the formation of three products, NNA, NNN, and NNK. The three parallel reactions were first order of 10-6 L/mol/s. The optimum pH range for formation of NNA, NNN, and NNK was 2.4 to 3.1. Thiocyanate (100 mM) slightly increased the rate of formation of NNN and NNK but tripled the rate of formation of NNA at pH 3.5 at 37 degrees C. We have also studied the nitrosation of pseudooxynicotine, a bacterial and fungal metabolite of nicotine. This secondary amine nitrosated rapidly to produce NNK. Our proposed mechanism for the conversion of nicotine to NNK includes nine kinetically distinct steps and is in agreement with our experimental results. The rate limiting step involves the formation of nicotine-1',2'-iminium ion. This ion hydrolyzes to form pseudooxynicotine which undergoes rapid, irreversible nitrosation to NNK. Given the very slow rate of nicotine nitrosation, it is unlikely that nicotine itself contributes to exposure to nitroso compounds due to chemically mediated intragastric nitrosation.

(PDF emailed within 0-6 h: $19.90)

Accession: 032015074

Download citation: RISBibTeXText

PMID: 8512249

DOI: 10.1111/j.1749-6632.1993.tb39178.x


Related references

Some effects of phenol nitrosation and thiol nitrosation reactions on n nitrosamine formation. Walker, E A , M Castegnaro, L Griciute And R E Lyle (Ed ) Iarc (International Agency For Research on Cancer) Scientific Publications, No 19 Environmental Aspects Of N-Nitroso Compounds Proceedings Of A Working Conference Durham, N H , Usa, Aug 22-24, 1977 Xxiv+561p Illus World Health Organization: Geneva, Switzerland ISBN 92-832-1119-7: 183-197, 1978

Identification of gamma-butenyl-(beta-propenyl)nitrosamine, the principal volatile nitrosamine formed in the nitrosation of spermidine or spermine. Journal of agricultural and food chemistry: 23 (1) 34-37, 1975

Hypothesis on the relationship between gastric cancer and intragastric nitrosation: N-nitrosamines in gastric juice of subjects from a high-risk area for gastric cancer and the inhibition of N-nitrosamine formation by fruit juices. European Journal of Cancer Prevention 2(1): 25-36, 1993

Is indirect exposure a significant contributor to the burden of perfluorinated acids observed in humans?. Environmental Science and Technology 45(19): 7974-7984, 2012

On the carcinogenic action of n nitroso compounds part 7 methyl nitrosamine tri deutero methyl nitrosamine ethyl nitrosamine n propyl nitrosamine n butyl nitrosamine acetoxymethyl nitrosamine and methylbutyroxymethyl nitrosamine. Zeitschrift fuer Krebsforschung und Klinische Onkologie 91(3): 317-322, 1978

Mutagenicity in salmonella typhimurium of n 3 methylbutyl n 1 methylacetonyl nitrosamine and n methyl n benzyl nitrosamine n nitrosation products isolated from corn bread contaminated with commonly occurring molds in linshien county a high incidence area for esophageal cancer in northern china. Carcinogenesis 1(10): 867-870, 1980

Tobacco Product Use Patterns, and Nicotine and Tobacco-Specific Nitrosamine Exposure: NHANES 1999-2012. Cancer Epidemiology, Biomarkers and Prevention 26(10): 1525-1530, 2017

Studies on the nicotine exposure of individual smokers. I. Changes in mouth-level exposure to nicotine on switching to lower nicotine cigarettes. International Journal of the Addictions 11(6): 933-950, 1976

Kinetics of dimethylamine nitrosation in relation to nitrosamine carcinogenesis. Journal of the National Cancer Institute 44(3): 633-639, 1970

C nitrosation of sesamol and its effects on n nitrosamine formation in vitro. Chemical & Pharmaceutical Bulletin 27(10): 2442-2449, 1979

Nitrosation of phenol and 2 6 dimethoxyphenol and its effect on nitrosamine formation. Journal of Agricultural & Food Chemistry 33(6): 1082-1085, 1985

Some effects of phenol- and thiol-nitrosation reactions on N-nitrosamine formation. Iarc Scientific Publications 1978(19): 183-197, 1978

Accelerating effect of ascorbic acid on N-nitrosamine formation and nitrosation by oxyhyponitrite. Cancer Research 39(10): 3871-3874, 1979

Intragastric bacterial activity and nitrosation before, during, and after treatment with omeprazole. British Medical Journal 289(6447): 717-719, 1984

Chronic nitrosamine ingestion in 1040 rodents: the effect of the choice of nitrosamine, the species studied, and the age of starting exposure. Cancer Research 51(23 Pt 2): 6470-6491, 1991