Nitrosation of the antimicrobial drug hexetidine: Nitrosamines derived from a triamine decomposition product

Five new nitrosamines were identified as nitrosation products of N 1, N 3-bis(2-ethylhexyl)-2-methyl-1,2,3-propantriamine, a hydrolysis product usually found in preparations of the antimicrobial drug hexetidine. All nitrosamines are formed after deamination of the primary amino group by nitrosation...

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Published inFood and chemical toxicology Vol. 31; no. 1; pp. 53 - 58
Main Authors Mende, P., Wacker, C.-D., Preussmann, R., Spiegelhalder, B.
Format Journal Article
LanguageEnglish
Published Oxford Elsevier Ltd 1993
New York, NY Elsevier Science
Subjects
Antibiotics. Antiinfectious agents. Antiparasitic agents
antimicrobial agents
Antiseptics
Biological and medical sciences
Chromatography, High Pressure Liquid
degradation
Drug Stability
Hexetidine - chemistry
Magnetic Resonance Spectroscopy
Mass Spectrometry
Medical sciences
Nitrites - chemistry
nitrosamines
Nitrosamines - chemistry
Nitrosation
Pharmacology. Drug treatments
Polyamines - chemistry
Spectrophotometry, Infrared
NMR
NA
TMS
PTA
4J
MS
Hydrolysis
Oral cavity
Toxicity
Nitrosamine
Antiseptic
Triamine
Metabolism
Nitrosation
Formation
In vitro
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Summary:Five new nitrosamines were identified as nitrosation products of N 1, N 3-bis(2-ethylhexyl)-2-methyl-1,2,3-propantriamine, a hydrolysis product usually found in preparations of the antimicrobial drug hexetidine. All nitrosamines are formed after deamination of the primary amino group by nitrosation of one of the two secondary amino groups. The propantriamine derivative is very easily nitrosatable, with total nitrosamine yields in the upper range of a comparative scale of drug nitrosatability.
Bibliography:ObjectType-Article-2
SourceType-Scholarly Journals-1
ObjectType-Feature-1
content type line 23
ISSN:0278-6915
1873-6351
DOI:10.1016/0278-6915(93)90179-3