80508-23-2

Usage

Uses

Used in Tobacco Products:
rac N'-Nitrosonornicotine is used in tobacco products as a naturally occurring alkaloid. It contributes to the addictive properties of tobacco and is associated with the development of esophageal and oral cavity cancer in smokers and snuff dippers.
Used in Research and Toxicology Studies:
rac N'-Nitrosonornicotine is also used as a research compound in toxicology and cancer research. It serves as a model compound to study the mechanisms of carcinogenesis and the effects of tobacco-related chemicals on human health. The study of rac N'-Nitrosonornicotine helps researchers understand the role of specific enantiomers in the development of cancer and the potential for enantioselective detoxification strategies.
Used in Public Health and Regulatory Efforts:
The identification and characterization of rac N'-Nitrosonornicotine in tobacco products have led to increased awareness of the health risks associated with tobacco use. This knowledge has informed public health campaigns, smoking cessation programs, and regulatory efforts to reduce the levels of harmful chemicals in tobacco products and promote the development of safer alternatives.

Upstream product

• 22083-74-5 3-(1-methyl-pyrrolidin-2-yl)-pyridine 
• 532-12-7 Myosmine 
• 73130-52-6 ethyl N-methyl-N-<4-chloro-4-(3-pyridyl)butnyl>carbamate 

Downstream Products

• 75195-76-5 N'-Nitrosonornicotine 1-N-oxide 
• 864071-82-9 pyridyl-N-β-D-glucopyranuronosyl-N'-nitrosonornicotinium inner salt 

Relevant academic research and scientific papers

N-nitrosation of myosmine yields HPB (4-hydroxy-1-(3-pyridyl)-1- butanone) and NNN (N-nitrosonornicotine)

N-Nitrosonornicotine (NNN) is formed by synthetic or biological N- nitrosation of the tobacco alkaloid nornicotine. Following metabolic activation of NNN, DNA and protein adducts are formed releasing 4-hydroxy-1- (3-pyridyl)-1-butanone (HPB), an actual biomarker to differentiate between tobacco smokers and passive smokers, NNN and HPB can be prepared in a new one-step reaction by N-nitrosation of the nicotinoid myosmine which has been found not only in tobacco but also in nut products. The reaction was tested also in human gastric juice. The formation rate of NNN and HPB depends on the pH value in the reaction solutions. This is important under the aspect of myosmine uptake by humans from other biological sources and subsequent biological activation. The new reaction pathway indicates that human exposure to nicotinoid nitrosation products seems to be not restricted exclusively to tobacco.

Transformations involving the Pyrrolidine Ring of Nicotine

Nicotine was oxidised to cotinine and this successively alkylated and reduced to a series of 4'-mono- and 4',4'-di-alkylnicotines, the mass spectra of which are discussed.The pyrrolidine ring has been opened with ethyl chloroformate and the product both recyclised to S-nicotine without loss of optical activity and converted to metanicotine.The dihydrochloride of the last, on successive treatment with bromine and sodium hydrogencarbonate, yielded 3'-bromonicotine.Cotinine has been converted into various derivatives, and the demethylation of nicotine has been investigated.