Document Detail

The synthesis and mutagenicity of the N-formyl analog of N-hydroxyphenacetin.
MedLine Citation:
PMID:  6360408     Owner:  NLM     Status:  MEDLINE    
The synthesis and purification of N-hydroxy-N-formyl-p-phenetidine (N-OH-FP) is described. This new compound was subjected to mutagenicity testing using Salmonella typhimurium strains TA98, TA100, TA1535, TA1537 and TA1538 both in the presence and absence of the post-mitochondrial fraction of rat liver homogenate. Simultaneous mutagenicity testing of the known phenacetin metabolite, N-hydroxyphenacetin (N-OH-AP), was conducted with the same tester strains. The N-formyl derived hydroxamic acid (N-OH-FP) was found to be a much stronger mutagen than N-hydroxy-phenacetin (N-OH-AP). Furthermore, N-OH-FP also behaved as a direct-acting mutagen unlike N-OH-AP. The chemical stabilities of N-OH-AP and N-OH-FP were studied in phosphate buffer in the pH range of 3-8; and both the hydroxamic acids were found to be stable to the conditions employed. The results of this study support the hypothesis that enzymatic deacylation is an activation process for the expression of mutagenicity by hydroxamic acids.
M D Corbett; C I Wei; S Y Fernando; D R Doerge; B R Corbett
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Carcinogenesis     Volume:  4     ISSN:  0143-3334     ISO Abbreviation:  Carcinogenesis     Publication Date:  1983 Dec 
Date Detail:
Created Date:  1984-02-14     Completed Date:  1984-02-14     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  8008055     Medline TA:  Carcinogenesis     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  1615-8     Citation Subset:  IM    
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MeSH Terms
Aminophenols / chemical synthesis*
Indicators and Reagents
Magnetic Resonance Spectroscopy
Mass Spectrometry
Mutagenicity Tests
Mutagens / chemical synthesis*
Phenetidine / analogs & derivatives,  chemical synthesis*,  toxicity
Salmonella typhimurium / drug effects
Structure-Activity Relationship
Grant Support
Reg. No./Substance:
0/Aminophenols; 0/Indicators and Reagents; 0/Mutagens; 156-43-4/Phenetidine; 88751-11-5/N-hydroxy-N-formyl-4-phenetidine

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