Encyclopedia of Cancer

Living Edition
| Editors: Manfred Schwab

Aromatic Amine

  • Denis M. Grant
Living reference work entry
DOI: https://doi.org/10.1007/978-3-642-27841-9_396-2

Definition

A primary aromatic amine is a homocyclic (strictly carbon-based) or heterocyclic (usually both carbon and nitrogen-based) conjugated ring structure that contains a primary amine (-NH2) substituent directly attached to the ring. As many as 12 % of all of the substances listed by the U.S. National Toxicology Program as being a known or probable human carcinogen is a primary aromatic amine or a compound that can be converted into one. The simplest aromatic amine is aniline. N-acetylation of primary aromatic amines by arylamine N-acetyltransferase (NAT) enzymes is considered to be detoxifying since the product of the reaction is chemically stable. On the other hand, aromatic amines can be bioactivated to DNA-damaging electrophiles by a metabolic sequence of N-oxidation of the primary amino group by cytochrome P450 enzymes followed by O-acetylation either by NAT or by other O-conjugating enzymes such as sulfotransferases and UDP-glucuronosyltransferases. Examples of aromatic...

Keywords

Cancer Research Ring Structure Primary Amine Aromatic Amine Cytochrome P450 Enzyme 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
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Copyright information

© Springer-Verlag Berlin Heidelberg 2015

Authors and Affiliations

  1. 1.Department of Pharmacology and Toxicology, Faculty of MedicineUniversity of TorontoTorontoCanada