CHEBI:74789 - 9-aminoacridine

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ChEBI Name 9-aminoacridine
ChEBI ID CHEBI:74789
Definition An aminoacridine that is acridine in which the hydrogen at position 9 is replaced by an amino group. A fluorescent dyd and topical antiseptic agent, it is used (usually as the hydrochloride salt) in eye drops for the treatment of superficial eye infections.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB4227430, eMolecules:36749948, eMolecules:1938357, eMolecules:529516
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Proflavine, also called proflavin and diaminoacridine, is an acriflavine derivative, a disinfectant bacteriostatic against many gram-positive bacteria. It has been used in the form of the dihydrochloride and hemisulfate salts as a topical antiseptic, and was formerly used as a urinary antiseptic. Proflavine is also known to have a mutagenic effect on DNA by intercalating between nucleic acid base pairs. It differs from most other mutagenic components by causing basepair-deletions or basepair-insertions and not substitutions. In the presence of light, proflavine can induce double-stranded breaks in DNA. Proflavine absorbs strongly in the blue region at 445 nm (in water at pH 7) with molar extinction coefficient of c. 40,000. Proflavin is a fluorescent dye that is sometimes used in microscopic in-vivo imaging due to its intercalation properties. However, there was concern that women exposed to proflavin could develop cervical cancer since they have mutagenesis potential. However, the retrospective analysis performed by Pantano et. al. demonstrated that there is no increased cervical cancer risk after exposure to proflavin.
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Formula C13H10N2
Net Charge 0
Average Mass 194.23190
Monoisotopic Mass 194.08440
InChI InChI=1S/C13H10N2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8H,(H2,14,15)
InChIKey XJGFWWJLMVZSIG-UHFFFAOYSA-N
SMILES Nc1c2ccccc2nc2ccccc12
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): mutagen
An agent that increases the frequency of mutations above the normal background level, usually by interacting directly with DNA and causing it damage, including base substitution.
Application(s): antiinfective agent
A substance used in the prophylaxis or therapy of infectious diseases.
fluorescent dye

MALDI matrix material
A compound used to form the matrix for MALDI (matrix-assisted laser desorption/ionization) mass spectrometry. MALDI matrix materials are crystalline compounds with a fairly low molecular weight, so as to allow facile vaporization, have strong absorption at UV or IR wavelengths (to rapidly and efficiently absorb laser irradiation), generally contain polar groups (enabling them to be used in aqueous solutions) and are frequently acidic (so assisting ionisation of the compound being studied, which is contained within the matrix material).
acid-base indicator
An acid or base which exhibits a colour change on neutralization by the basic or acidic titrant at or near the equivalence point of a titration.
antiseptic drug
A substance used locally on humans and other animals to destroy harmful microorganisms or to inhibit their activity (cf. disinfectants, which destroy microorganisms found on non-living objects, and antibiotics, which can be transported through the lymphatic system to destroy bacteria within the body).
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ChEBI Ontology
Outgoing 9-aminoacridine (CHEBI:74789) has role acid-base indicator (CHEBI:50407)
9-aminoacridine (CHEBI:74789) has role antiinfective agent (CHEBI:35441)
9-aminoacridine (CHEBI:74789) has role antiseptic drug (CHEBI:48218)
9-aminoacridine (CHEBI:74789) has role fluorescent dye (CHEBI:51121)
9-aminoacridine (CHEBI:74789) has role MALDI matrix material (CHEBI:64345)
9-aminoacridine (CHEBI:74789) has role mutagen (CHEBI:25435)
9-aminoacridine (CHEBI:74789) is a aminoacridines (CHEBI:51803)
9-aminoacridine (CHEBI:74789) is a primary amino compound (CHEBI:50994)
9-aminoacridine (CHEBI:74789) is conjugate base of 9-aminoacridine(1+) (CHEBI:74835)
Incoming 9-aminoacridine(1+) (CHEBI:74835) is conjugate acid of 9-aminoacridine (CHEBI:74789)
IUPAC Name
acridin-9-amine
INNs Sources
aminoacridina WHO MedNet
aminoacridine WHO MedNet
aminoacridine WHO MedNet
aminoacridinum WHO MedNet
Synonyms Sources
10-amino-5-azaanthracene NIST Chemistry WebBook
5-aminoacridine ChEBI
9-acridinamine ChemIDplus
9AA NIST Chemistry WebBook
aminacrin NIST Chemistry WebBook
aminacrine NIST Chemistry WebBook
Manual Xrefs Databases
160 DrugCentral
9-Aminoacridine Wikipedia
LSM-15516 LINCS
View more database links
Registry Numbers Types Sources
141171 Reaxys Registry Number Reaxys
90-45-9 CAS Registry Number NIST Chemistry WebBook
90-45-9 CAS Registry Number ChemIDplus
Citations Types Sources
22477060 PubMed citation Europe PMC
23257326 PubMed citation Europe PMC
24341665 PubMed citation Europe PMC
Last Modified
22 February 2017