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Details

Stereochemistry ACHIRAL
Molecular Formula C13H10N2.ClH
Molecular Weight 230.6933
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMINACRINE HYDROCHLORIDE

SMILES

c1ccc2c(c1)c(=N)c3ccccc3[nH]2.Cl

InChI

InChIKey=FTGPOQQGJVJDCT-UHFFFAOYSA-N
InChI=1S/C13H10N2.ClH/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13;/h1-8H,(H2,14,15);1H

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/23841224

Aminacrine has long been known to be a potent frameshift mutagen in viruses and bacteria. It is one in a general class of aminoacridine dyes that bind to DNA and possess mutagenic activity. Aminacrine is used clinically as a topical antiseptic. A part from therapeutic use, aminacrine is also introduced as a matrix for negative mode matrix-assisted laser desorption/ionization (MALDI).

Approval Year

Conditions

Conditions

Doses

Doses

DosePopulationAdverse events​
14 mg 2 times / day multiple, vaginal
Recommended
Dose: 14 mg, 2 times / day
Route: vaginal
Route: multiple
Dose: 14 mg, 2 times / day
Co-administed with::
sulfanilamide(1.05 g; 2/day)
allantoin(140 mg; 2/day)
Sources:
unhealthy, adult
n = 51
Health Status: unhealthy
Condition: trichomoniasis
Age Group: adult
Sex: F
Population Size: 51
Sources:
Other AEs: Vulvovaginal discomfort...
Other AEs:
Vulvovaginal discomfort (2 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Vulvovaginal discomfort 2 patients
14 mg 2 times / day multiple, vaginal
Recommended
Dose: 14 mg, 2 times / day
Route: vaginal
Route: multiple
Dose: 14 mg, 2 times / day
Co-administed with::
sulfanilamide(1.05 g; 2/day)
allantoin(140 mg; 2/day)
Sources:
unhealthy, adult
n = 51
Health Status: unhealthy
Condition: trichomoniasis
Age Group: adult
Sex: F
Population Size: 51
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Acridin-9-yl exchange: a proposal for the action of some 9-aminoacridine drugs.
2006
Complexes of Pd(II) and Pt(II) with 9-aminoacridine: reactions with DNA and study of their antiproliferative activity.
2007
Analysis of low molecular weight acids by negative mode matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.
2007
Quantitative detection of metabolites using matrix-assisted laser desorption/ionization mass spectrometry with 9-aminoacridine as the matrix.
2007
Imaging Matrix Assisted Laser Desorption Ionization Mass Spectrometry: a technique to map plant metabolites within tissues at high spatial resolution.
2007
Discriminating between cellular and misfolded prion protein by using affinity to 9-aminoacridine compounds.
2007 Apr
A real-time fluorescence assay for measuring N-dealkylation.
2007 Jan
Preparation of magnetite nanocrystals with surface reactive moieties by one-pot reaction.
2007 Jul 15
Unexpected reactivity of the 9-aminoacridine chromophore in guanidylation reactions.
2007 Jul 6
A binary matrix for background suppression in MALDI-MS of small molecules.
2007 Mar
Molecular recognition of DNA by rigid [N]-polynorbornane-derived bifunctional intercalators: synthesis and evaluation of their binding properties.
2007 May 17
The electrochemical behavior and direct determination of tyrosine at a glassy carbon electrode modified with poly (9-aminoacridine).
2007 Oct
A role of the 9-aminoacridines and their conjugates in a life science.
2007 Oct
Modulation of the genotoxicity of bleomycin by amines through noncovalent DNA interactions and alteration of physiological conditions in yeast.
2007 Oct 1
Ultrasonic trapping of microparticles in suspension and reaction monitoring using Raman microspectroscopy.
2007 Oct 15
Frameshift mutations produced by 9-aminoacridine in wild-type, uvrA and recA strains of Escherichia coli; specificity within a hotspot.
2007 Sep
In silico chemical library screening and experimental validation of a novel 9-aminoacridine based lead-inhibitor of human S-adenosylmethionine decarboxylase.
2007 Sep-Oct
Negative ion mode matrix-assisted laser desorption/ionisation time-of-flight mass spectrometric analysis of oligosaccharides using halide adducts and 9-aminoacridine matrix.
2008 Apr
Effect of spermine conjugation on the interaction of acridine with alternating purine-pyrimidine oligodeoxyribonucleotides studied by CD, fluorescence and absorption spectroscopies.
2008 Apr
New palladium(II) and platinum(II) complexes with 9-aminoacridine: structures, luminiscence, theoretical calculations, and antitumor activity.
2008 Aug 4
Drug 9AA reactivates p21/Waf1 and Inhibits HIV-1 progeny formation.
2008 Mar 18
Synthesis and biological activity of stable and potent antitumor agents, aniline nitrogen mustards linked to 9-anilinoacridines via a urea linkage.
2008 May 15
Matrix-assisted laser desorption/ionization time-of-flight mass spectrometric analysis of cellular glycerophospholipids enabled by multiplexed solvent dependent analyte-matrix interactions.
2008 Oct 1
Biological safety of liposome-fullerene consisting of hydrogenated lecithin, glycine soja sterols, and fullerene-C60 upon photocytotoxicity and bacterial reverse mutagenicity.
2009 Apr
Semi-synthetic and synthetic 1,2,4-trioxaquines and 1,2,4-trioxolaquines: synthesis, preliminary SAR and comparison with acridine endoperoxide conjugates.
2009 Apr 1
Phosphatidylcholines and -ethanolamines can be easily mistaken in phospholipid mixtures: a negative ion MALDI-TOF MS study with 9-aminoacridine as matrix and egg yolk as selected example.
2009 Dec
Blockade of NMDA receptor channels by 9-aminoacridine and its derivatives.
2009 Feb 13
9-Aminoacridine-based anticancer drugs target the PI3K/AKT/mTOR, NF-kappaB and p53 pathways.
2009 Feb 26
Novel acridine-based compounds that exhibit an anti-pancreatic cancer activity are catalytic inhibitors of human topoisomerase II.
2009 Jan 14
Combining 4-aminoquinoline- and clotrimazole-based pharmacophores toward innovative and potent hybrid antimalarials.
2009 Jan 22
In situ primary metabolites localization on a rat brain section by chemical mass spectrometry imaging.
2009 Jul 1
9-Aminoacridine inhibition of HIV-1 Tat dependent transcription.
2009 Jul 24
Biological safety of LipoFullerene composed of squalane and fullerene-C60 upon mutagenesis, photocytotoxicity, and permeability into the human skin tissue.
2009 Jun
Identification of chemical compounds that induce HIF-1alpha activity.
2009 Nov
Binding of TCA to the prion protein: mechanism, implication for therapy, and application as probe for complex formation of bio-macromolecules.
2009 Oct
A kinetic and structural investigation of DNA-based asymmetric catalysis using first-generation ligands.
2009 Sep 21
Investigation on the Interactions of NiCR and NiCR-2H with DNA.
2010
Alveolar osteitis: a comprehensive review of concepts and controversies.
2010
Host hindrance to HIV-1 replication in monocytes and macrophages.
2010 Apr 7
The intact muscle lipid composition of bulls: an investigation by MALDI-TOF MS and 31P NMR.
2010 Feb
Genotoxicity and antigenotoxicity evaluation of non-photoactivated hypericin.
2010 Jan
Lipidomic analysis of porcine olfactory epithelial membranes and cilia.
2010 Jul
Mutagenic and antimutagenic effects of hexane extract of some Astragalus species grown in the eastern Anatolia region of Turkey.
2010 Jul
Significant sensitivity improvements by matrix optimization: a MALDI-TOF mass spectrometric study of lipids from hen egg yolk.
2010 Jun
Selective desorption/ionization of sulfatides by MALDI-MS facilitated using 9-aminoacridine as matrix.
2010 Jun
Modulation of mdm2 pre-mRNA splicing by 9-aminoacridine-PNA (peptide nucleic acid) conjugates targeting intron-exon junctions.
2010 Jun 30
The surface charge density of plant cell membranes (sigma): an attempt to resolve conflicting values for intrinsic sigma.
2010 May
Molecular docking studies of selected tricyclic and quinone derivatives on trypanothione reductase of Leishmania infantum.
2010 Oct
MALDI-TOF/MS analysis of archaebacterial lipids in lyophilized membranes dry-mixed with 9-aminoacridine.
2010 Sep
Mononuclear Fe(II)-N4Py complexes in oxidative DNA cleavage: structure, activity and mechanism.
2010 Sep 14
Patents

Sample Use Guides

In Vivo Use Guide
Vaginal suppositories containing 1.05 g of sulfanilamide, 14 mg of aminacrine hydrochloride, and 140 mg of allantoin (AVC suppositories) were given twice a day for 7 days.
Route of Administration: Vaginal
In Vitro Use Guide
S. typhimurium cells were treated with aminacrine at concentration of 2-250 ug/ml and incubated during 60 min.
Name Type Language
AMINACRINE HYDROCHLORIDE
HSDB   MI   USAN   VANDF  
USAN  
Official Name English
AMINACRINE HYDROCHLORIDE [VANDF]
Common Name English
MONACRIN
Brand Name English
AMINOACRIDINE HYDROCHLORIDE
MART.   WHO-DD  
Systematic Name English
NSC-7571
Code English
AMINACRINE HYDROCHLORIDE [MI]
Common Name English
AMINOACRIDINE HYDROCHLORIDE [WHO-DD]
Common Name English
AMINACRINE HYDROCHLORIDE [USAN]
Common Name English
AMINOACRIDINE HCL
Common Name English
AMINOACRIDINE HYDROCHLORIDE [MART.]
Common Name English
9-ACRIDINAMINE MONOHYDROCHLORIDE
Systematic Name English
AMINACRINE HYDROCHLORIDE [HSDB]
Common Name English
AMINACRINE HCL
Common Name English
Classification Tree Code System Code
CFR 21 CFR 310.531
Created by admin on Sat Jun 26 13:13:43 UTC 2021 , Edited by admin on Sat Jun 26 13:13:43 UTC 2021
NCI_THESAURUS C28394
Created by admin on Sat Jun 26 13:13:43 UTC 2021 , Edited by admin on Sat Jun 26 13:13:43 UTC 2021
EPA PESTICIDE CODE 55503
Created by admin on Sat Jun 26 13:13:43 UTC 2021 , Edited by admin on Sat Jun 26 13:13:43 UTC 2021
Code System Code Type Description
EVMPD
SUB00450MIG
Created by admin on Sat Jun 26 13:13:43 UTC 2021 , Edited by admin on Sat Jun 26 13:13:43 UTC 2021
PRIMARY
PUBCHEM
8643
Created by admin on Sat Jun 26 13:13:44 UTC 2021 , Edited by admin on Sat Jun 26 13:13:44 UTC 2021
PRIMARY
CAS
134-50-9
Created by admin on Sat Jun 26 13:13:43 UTC 2021 , Edited by admin on Sat Jun 26 13:13:43 UTC 2021
PRIMARY
ECHA (EC/EINECS)
205-145-5
Created by admin on Sat Jun 26 13:13:43 UTC 2021 , Edited by admin on Sat Jun 26 13:13:43 UTC 2021
PRIMARY
MERCK INDEX
M1672
Created by admin on Sat Jun 26 13:13:43 UTC 2021 , Edited by admin on Sat Jun 26 13:13:43 UTC 2021
PRIMARY Merck Index
RXCUI
81949
Created by admin on Sat Jun 26 13:13:44 UTC 2021 , Edited by admin on Sat Jun 26 13:13:44 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C77024
Created by admin on Sat Jun 26 13:13:44 UTC 2021 , Edited by admin on Sat Jun 26 13:13:44 UTC 2021
PRIMARY
ChEMBL
CHEMBL43184
Created by admin on Sat Jun 26 13:13:43 UTC 2021 , Edited by admin on Sat Jun 26 13:13:43 UTC 2021
PRIMARY
FDA UNII
OR5RM3Q5QL
Created by admin on Sat Jun 26 13:13:43 UTC 2021 , Edited by admin on Sat Jun 26 13:13:43 UTC 2021
PRIMARY
EPA CompTox
134-50-9
Created by admin on Sat Jun 26 13:13:43 UTC 2021 , Edited by admin on Sat Jun 26 13:13:43 UTC 2021
PRIMARY
HSDB
4505
Created by admin on Sat Jun 26 13:13:43 UTC 2021 , Edited by admin on Sat Jun 26 13:13:43 UTC 2021
PRIMARY