The reaction of tertiary amines with nitrous acid

Hein, George E.

doi:10.1021/ed040p181

Cited by 37 publications

(13 citation statements)

References 9 publications

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“…A number of studies have confirmed the formation of Nnitrosodimethylamine from TMA and TMNO in vitro [145,146,153,174,175]. Whilst intricate mechanisms have been proposed, some involving dimethylamine as an intermediate [153], varying the reaction conditions (temperature and pH) can influence the amount of N-nitrosodimethylamine produced [153].…”

Section: N-nitrosodimethylamine Can Originate In the Body Via A Numbementioning

confidence: 98%

“…A range of toxic effects have been implicated with TMA from in vivo and in vitro studies including psychosocial reactions such as depression [19,20], abnormal neurological symptoms [141], teratogenic effects [142,143], altered rRNA synthesis [144] as well as the potential to form the carcinogen N-nitrosodimethylamine [145,146] (Fig. 2).…”

Section: Potential Toxicity Of Trimethylamine and Trimethylamine-n-oxidementioning

confidence: 99%

“…The endogenous formation of N-nitrosodimethylamine can occur via a number of reaction mechanisms with factors such as pH [145,146,169], and bacteria [151,152,155] determining which mechanism is most likely. In the presence of acid, sodium nitrite can react with amines such as dimethylamine to form N-nitrosodimethylamine [36,155,170,171] meaning that the acidic conditions of the stomach, particularly in the presence of dimethylamine and nitrite, are conducive to the formation of N-nitrosodimethylamine.…”

Section: N-nitrosodimethylamine Can Originate In the Body Via A Numbementioning

confidence: 99%

“…Whilst intricate mechanisms have been proposed, some involving dimethylamine as an intermediate [153], varying the reaction conditions (temperature and pH) can influence the amount of N-nitrosodimethylamine produced [153]. For instance, an acidic pH favours the protonation of nitrite and a shift in equilibrium to form the nitrosating nitrosyl cation [146]. However, a lower fraction of the reactive deprotonated species of TMA would also exist under these highly acidic conditions and hence, a pH of 3.6 is optimum for the formation of N-nitrosodimethylamine from TMA [146].…”

Section: N-nitrosodimethylamine Can Originate In the Body Via A Numbementioning

confidence: 99%

“…For instance, an acidic pH favours the protonation of nitrite and a shift in equilibrium to form the nitrosating nitrosyl cation [146]. However, a lower fraction of the reactive deprotonated species of TMA would also exist under these highly acidic conditions and hence, a pH of 3.6 is optimum for the formation of N-nitrosodimethylamine from TMA [146].…”

Section: N-nitrosodimethylamine Can Originate In the Body Via A Numbementioning

confidence: 99%

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Trimethylamine: Metabolic, Pharmacokinetic and Safety Aspects

Bain¹,

Fornasini²,

Evans

2005

CDM

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Trimethylamine (TMA) is a volatile tertiary aliphatic amine that is derived from the diet either directly from the consumption of foods containing TMA, or by the intake of food containing precursors to TMA such as trimethylamine-N-oxide (TMNO), choline and L-carnitine. Following oral absorption in humans, TMA undergoes efficient N-oxidation to TMNO, a reaction catalyzed by the flavin-containing monooxygenase (FMO) isoform 3 enzyme. TMNO subsequently undergoes excretion in the urine, although, evidence also suggests that metabolic retro-reduction of TMNO can occur. Whilst the pharmacokinetics of TMA and TMNO has not been fully elucidated in humans, a number of studies provide information on the likely fate of dietary derived TMA. Trimethylaminuria is a condition that is characterized by a deficiency in FMO3 enzyme activity, resulting in the excretion of increased amounts of TMA in bodily fluids such as urine and sweat, and breath. A human FMO3 database has been established and currently twenty-eight variants of the FMO3 gene have been reported including twenty-four missense, three nonsense, and one gross deletion mutation. Whilst TMA and TMNO are generally regarded as non-toxic substances, they are of clinical interest because of their potential to form the carcinogen N-nitrosodimethylamine.

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