PMID: 10691645Feb 26, 2000

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

Journal of Agricultural and Food Chemistry
W Zwickenpflug


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.


Jun 18, 2002·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·J WilpE Richter
Feb 13, 2007·Chemical Research in Toxicology·S S HechtPramod Upadhyaya
Mar 28, 2012·Arhiv za higijenu rada i toksikologiju·Rumyana SimeonovaMitka Mitcheva
Mar 10, 2010·Critical Reviews in Toxicology·Kumar A Shah, H Thomas Karnes
May 30, 2009·Biomarkers : Biochemical Indicators of Exposure, Response, and Susceptibility to Chemicals·Katharina Schütte-BorkovecElmar Richter
Dec 18, 2015·Journal of Agricultural and Food Chemistry·W ZwickenpflugThomas Gudermann
Mar 9, 2011·Regulatory Toxicology and Pharmacology : RTP·Robert Nilsson
Dec 2, 2008·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·J B HavlaE Richter
Aug 5, 2005·Drug Metabolism and Disposition : the Biological Fate of Chemicals·W ZwickenpflugE Richter

Related Concepts

N'-nitrosonornicotine, (+-)-isomer
Plant alkaloid
High Pressure Liquid Chromatography Procedure
Gastric Juice

Trending Feeds


Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Systemic Juvenile Idiopathic Arthritis

Systemic juvenile idiopathic arthritis is a rare rheumatic disease that affects children. Symptoms include joint pain, but also fevers and skin rashes. Here is the latest on this disease.

Chromatin Regulation and Circadian Clocks

The circadian clock plays an important role in regulating transcriptional dynamics through changes in chromatin folding and remodelling. Discover the latest research on Chromatin Regulation and Circadian Clocks here.

Central Pontine Myelinolysis

Central Pontine Myelinolysis is a neurologic disorder caused most frequently by rapid correction of hyponatremia and is characterized by demyelination that affects the central portion of the base of the pons. Here is the latest research on this disease.

Myocardial Stunning

Myocardial stunning is a mechanical dysfunction that persists after reperfusion of previously ischemic tissue in the absence of irreversible damage including myocardial necrosis. Here is the latest research.

Pontocerebellar Hypoplasia

Pontocerebellar hypoplasias are a group of neurodegenerative autosomal recessive disorders with prenatal onset, atrophy or hypoplasia of the cerebellum, hypoplasia of the ventral pons, microcephaly, variable neocortical atrophy and severe mental and motor impairments. Here is the latest research on pontocerebellar hypoplasia.

Cell Atlas Along the Gut-Brain Axis

Profiling cells along the gut-brain axis at the single cell level will provide unique information for each cell type, a three-dimensional map of how cell types work together to form tissues, and insights into how changes in the map underlie health and disease of the GI system and its crosstalk with the brain. Disocver the latest research on single cell analysis of the gut-brain axis here.

Chronic Traumatic Encephalopathy

Chronic Traumatic Encephalopathy (CTE) is a progressive degenerative disease that occurs in individuals that suffer repetitive brain trauma. Discover the latest research on traumatic encephalopathy here.

Related Papers

Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association
J WilpE Richter
Chemical Research in Toxicology
W Zwickenpflug, Stefan Tyroller
Journal of Agricultural and Food Chemistry
Stefan TyrollerElmar Richter
© 2021 Meta ULC. All rights reserved