CHEBI:36420 - acridine

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ChEBI Name acridine
ChEBI ID CHEBI:36420
Definition A polycyclic heteroarene that is anthracene in which one of the central CH groups is replaced by a nitrogen atom.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB9232165, eMolecules:35876150, ZINC000256015129
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Acridine is an organic compound and a nitrogen heterocycle with the formula C13H9N. Acridines are substituted derivatives of the parent ring. It is a planar molecule that is structurally related to anthracene with one of the central CH groups replaced by nitrogen. Like the related molecules pyridine and quinoline, acridine is mildly basic. It is an almost colorless solid, which crystallizes in needles. There are few commercial applications of acridines; at one time acridine dyes were popular, but they are now relegated to niche applications, such as with acridine orange. The name is a reference to the acrid odour and acrid skin-irritating effect of the compound.
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Formula C13H9N
Net Charge 0
Average Mass 179.21730
Monoisotopic Mass 179.07350
InChI InChI=1S/C13H9N/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-9H
InChIKey DZBUGLKDJFMEHC-UHFFFAOYSA-N
SMILES c1ccc2nc3ccccc3cc2c1
Roles Classification
Biological Role(s): genotoxin
A role played by a chemical compound to induce direct or indirect DNA damage. Such damage can potentially lead to the formation of a malignant tumour, but DNA damage does not lead inevitably to the creation of cancerous cells.
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ChEBI Ontology
Outgoing acridine (CHEBI:36420) has role genotoxin (CHEBI:50902)
acridine (CHEBI:36420) is a acridines (CHEBI:22213)
acridine (CHEBI:36420) is a mancude organic heterotricyclic parent (CHEBI:36416)
acridine (CHEBI:36420) is a polycyclic heteroarene (CHEBI:38180)
Incoming quinacrine (CHEBI:8711) has parent hydride acridine (CHEBI:36420)
IUPAC Name
acridine
Synonyms Sources
10-azaanthracene ChemIDplus
2,3,5,6-dibenzopyridine ChemIDplus
2,3-benzoquinoline ChemIDplus
9-azaanthracene ChemIDplus
acrydine NIST Chemistry WebBook
Akridin NIST Chemistry WebBook
benzo[b]quinoline NIST Chemistry WebBook
dibenzo[b,e]pyridine NIST Chemistry WebBook
Manual Xref Database
Acridine Wikipedia
View more database links
Registry Numbers Types Sources
120200 Reaxys Registry Number Reaxys
143403 Gmelin Registry Number Gmelin
260-94-6 CAS Registry Number ChemIDplus
260-94-6 CAS Registry Number NIST Chemistry WebBook
Citations Types Sources
11924543 PubMed citation Europe PMC
24416442 PubMed citation Europe PMC
Last Modified
24 March 2014