Formation of N-Nitrosodimethylamine from Naturally Occurring Quaternary Ammonium Compounds and Tertiary Amines

Fiddler, Walter; Pensabene, John W.; Doerr, Robert C; Wasserman, Aaron E.

doi:10.1038/236307a0

Cited by 76 publications

(37 citation statements)

References 4 publications

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“…Not surprisingly, dimethylamine has been demonstrated to be the most effective organic nitrogen precursor of NDMA formation by both the nitrosation pathway (Fiddler et al, 1972) and the UDMH pathway (Mitch and Sedlak, 2002b). Both pathways also can produce NDMA from tertiary amines containing dimethylamine functional groups (e.g., trimethylamine and dimethylethanolamine) but at lower yields.…”

Section: Organic Nitrogen Precursors: Sources and Occurrencementioning

confidence: 99%

“…Both pathways also can produce NDMA from tertiary amines containing dimethylamine functional groups (e.g., trimethylamine and dimethylethanolamine) but at lower yields. Nitrosation of trimethylamine-N-oxide, a common constituent of urine (Zuppi et al, 1997), resulted in some NDMA formation, but much less than did trimethylamine (Fiddler et al, 1972). Many other organic nitrogen-containing molecules, including the primary amine monomethylamine, the quaternary amine tetramethylamine, and amino acids or proteins, did not form significant concentrations of NDMA after chloramination (Mitch and Sedlak, 2002b).…”

Section: Organic Nitrogen Precursors: Sources and Occurrencementioning

confidence: 99%

“…Many other organic nitrogen-containing molecules, including the primary amine monomethylamine, the quaternary amine tetramethylamine, and amino acids or proteins, did not form significant concentrations of NDMA after chloramination (Mitch and Sedlak, 2002b). Fiddler et al (1972) found that nitrosation of quaternary amines that contained trimethylamine functional groups resulted in four orders of magnitude lower NDMA concentrations than did trimethylamine. Significant organic nitrogen precursors for NDMA formation therefore appear to be limited to dimethylamine and tertiary amines with dimethylamine functional groups.…”

Section: Organic Nitrogen Precursors: Sources and Occurrencementioning

confidence: 99%

“…NDMA precursors can leach from functional groups on quaternary amine-containing exchange resins (Cohen and Bachman, 1978;Kimoto et al, 1980;Najm and Trussell, 2001). At elevated temperatures (i.e., 78°C), some of the quaternary amine functional groups on resins demethylate to form trimethylamine (Fiddler et al, 1972).…”

Section: Organic Nitrogen Precursors: Sources and Occurrencementioning

confidence: 99%

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N-Nitrosodimethylamine (NDMA) as a Drinking Water Contaminant: A Review

Mitch¹,

Sharp²,

Trussell³

et al. 2003

Environmental Engineering Science

595

428

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N-Nitrosodimethylamine (NDMA) is a member of a family of extremely potent carcinogens, the N-nitrosamines. Until recently, concerns about NDMA mainly focused on the presence of NDMA in food, consumer products, and polluted air. However, current concern focuses on NDMA as a drinking water contaminant resulting from reactions occurring during chlorination or via direct industrial contamination. Because of the relatively high concentrations of NDMA formed during wastewater chlorination, the intentional and unintentional reuse of municipal wastewater is a particularly important area of concern. Although ultraviolet (UV) treatment can effectively remove NDMA, there is considerable interest in the development of less expensive alternative treatment technologies. These alternative technologies include approaches for removing organic nitrogen-containing NDMA precursors prior to chlorination and the use of sunlight photolysis, and in situ bioremediation to remove NDMA and its precursors.

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Section: Organic Nitrogen Precursors: Sources and Occurrencementioning

confidence: 99%

Section: Organic Nitrogen Precursors: Sources and Occurrencementioning

confidence: 99%

Section: Organic Nitrogen Precursors: Sources and Occurrencementioning

confidence: 99%

Section: Organic Nitrogen Precursors: Sources and Occurrencementioning

confidence: 99%

See 2 more Smart Citations

N-Nitrosodimethylamine (NDMA) as a Drinking Water Contaminant: A Review

Mitch¹,

Sharp²,

Trussell³

et al. 2003

Environmental Engineering Science

595

428

View full text Add to dashboard Cite

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“…Moreover, nitroso-compounds may result from the interaction of nitrites and secondary amines. These precursors are produced from nitrosamines by bacterial action in the acidic environment of stomach or alkaline intestinal contents [45,46]. The putative role of nitroso-compounds in the induction of NPC has fascinated many researchers.…”

Section: Nitrosaminesmentioning

confidence: 99%

Chemical Carcinogenesis and Nasopharyngeal Carcinoma

Tang¹,

Tang²,

Tian³

et al. 2012

Carcinogenesis, Diagnosis, and Molecular Targeted Treatment for Nasopharyngeal Carcinoma

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N‐Nitroso Compounds

Green¹

2023

Patty's Toxicology

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N ‐Nitroso compounds are a diverse group of hundreds of potentially toxic and carcinogenic chemicals. Of these, the most well studied are chemically simple nitrosamines, such as dimethylnitrosamine (DMN) and diethylnitrosamine (DEN), both of which are remarkably potent causes of cancer in all animal‐species so far tested; and likely to be carcinogenic to humans as well. This chapter addresses how our exogenous exposures to these and related compounds—both occupationally and environmentally—have changed over the decades. Notably, DMN and some other N ‐nitroso compounds are also formed endogenously, in all animals, including humans: mechanisms of this endogenous nitrosation are discussed herein. The chemistry and metabolism of selected nitrosamines are presented, especially as these relate to the formation in vivo of the proximately toxic and carcinogenic chemical‐species. Nitrosamine exposures via cigarettes are detailed, as are (historical and current) occupational exposures, such as via rubber‐manufacturing, and via some metal lubricating fluids. General environmental exposures via food, beverages, and pharmaceuticals are also discussed.

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Formation of N-Nitrosodimethylamine from Naturally Occurring Quaternary Ammonium Compounds and Tertiary Amines

Cited by 76 publications

References 4 publications

N-Nitrosodimethylamine (NDMA) as a Drinking Water Contaminant: A Review

N-Nitrosodimethylamine (NDMA) as a Drinking Water Contaminant: A Review

Chemical Carcinogenesis and Nasopharyngeal Carcinoma

N‐Nitroso Compounds

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