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N-nitroso-2-hydroxymorpholine, a mutagenic metabolite of n-nitrosodiethanolamine

Research output: Contribution to journal › Article › peer-review

Abstract

N-Nitroso-2-hydroxymorpholine was synthesized from N-(2-hydroxyethyl)aminoacetaldehyde diethylacetal by nitrosation and hydrolysis. It was detected as a metabolite of N-nitrosodiethanolamine in rat hepatic 9000 g supernatant. It was mutagenic toward Salmonella typhimurium TA 1535, with and without activation. The results suggest that N-nitroso-2-hydroxymorpholine, which is formed by metabolic β-oxidation of N-nitrosodiethanolamine, could be involved in carcinogenesis by N-nitrosodiethanolamine.

Original languageEnglish (US)
Pages (from-to)1745-1747
Number of pages3
JournalCarcinogenesis
Volume5
Issue number12
DOIs
StatePublished - Dec 1984

Bibliographical note

Funding Information:
spectra were obtained using the 7T spectrometer at The Rockefeller University, purchased in part with funds from The National Science Foundation (PCM-7912083), The Camille and Henry Dreyfus Foundation, and The Fleischmann Foundation. This is paper No. 76 in the series 'A Study of Chemical Carcinogenesis'.

Funding Information:
This study was supported by NCI Grant CA-23901. I thank George Palladino for the gift of N-(2-hydroxyethyl)aminoacetaldehyde diethy! acetal, Steven Carmella for help with capillary GC, John Adams for help with GC-TEA, Shantu Amin for the liver 9000 g supernatant, Ed LaVoie and Albertina Swanson for mutagenicity assays, J.L.Wiebers for mass spectral determinations, and Dorothy Lin for running 90 MHz n.m.r. spectra. 300 MHz n.m.r.

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