Document Detail

Biotransformation of 1-(4-chlorophenyl)-3,3-dimethyltriazene into 3-chloro-4-hydroxyaniline: intramolecular hydroxylation-induced chlorine migration during a catabolic degradation of a chemical carcinogen.
MedLine Citation:
PMID:  1235058     Owner:  NLM     Status:  MEDLINE    
Five modified anilines were identified in ethyl acetate extract from hydrolysed urine of rats which had been injected with the carcinogenic 1-(4-chlorophenyl)-3,3-dimethyltriazene. 4-Chloro-2-hydroxyaniline (15.1%) and 4-chloroaniline (5.2%) were the most abundant metabolites arising by in vivo fission of the diazoamino group. The structures and distribution of 4-hydroxyaniline (less than 0.1%), 4-chloro-3-hydroxyaniline (0.7%) and of 3-chloro-4-hydroxyaniline (8.2%) suggest that these metabolites are derived from a common 3,4-epoxy intermediate and arise either by elimination of chlorine, by opening of the epoxide ring or by an intramolecular hydroxylation-induced chlorine migration, respectively.
G F Kolar; J Schlesiger
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Cancer letters     Volume:  1     ISSN:  0304-3835     ISO Abbreviation:  Cancer Lett.     Publication Date:  1975 Sep 
Date Detail:
Created Date:  1977-04-25     Completed Date:  1977-04-25     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  7600053     Medline TA:  Cancer Lett     Country:  NETHERLANDS    
Other Details:
Languages:  eng     Pagination:  43-7     Citation Subset:  IM    
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MeSH Terms
Aniline Compounds / metabolism*,  urine
Chemical Phenomena
Triazenes / metabolism*
Reg. No./Substance:
0/Aniline Compounds; 0/Triazenes

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