AMINACRINE HYDROCHLORIDE

US Previously Marketed

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H10N2.ClH
Molecular Weight	230.693
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.NC1=C2C=CC=CC2=NC3=CC=CC=C13

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

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C13H10N2
Molecular Weight	194.2319
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.pnas.org/content/74/1/188.full.pdf
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).

Originator

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Mycoses 12 Sources: https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=012470	Curative	Approved 8583	AKRINOL Approved Use Antifungal agent
Vaginal trichomoniasis 9 Sources: http://www.ncbi.nlm.nih.gov/pubmed/9132982	Curative	Phase I 438	Unknown Approved Use Unknown
Adult T-cell leukemia/lymphoma 5 Sources: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4060757/pdf/1742-4690-11-43.pdf	Primary	Basic research	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse 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 Sources: https://pubmed.ncbi.nlm.nih.gov/9132982/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/9132982/	Other AEs: Vulvovaginal discomfort... Other AEs: Vulvovaginal discomfort (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/9132982/

AEs

AE	Significance	Dose	Population
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 Sources: https://pubmed.ncbi.nlm.nih.gov/9132982/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/9132982/

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY454464	https://www.001chemical.com/chem/90-45-9
3B Scientific (Wuhan) Corp	3B3-019151	http://www.3bsc.com/index/pro_info.php?id=41675
AA Blocks	AA00GRHV	http://www.aablocks.com/goods/Goods/detail?id=AA00GRHV
Aaron Chemicals	AR00GS9N	http://www.aaronchem.com/90-45-9
abcr GmbH	AB336861	http://www.abcr.com/shop/en/AB336861
AbMole Bioscience	M3179	http://www.abmole.com/products/9-aminoacridine.html
Acadechem	ACDS-033467	http://www.acadechemical.com/product/108166
Accela ChemBio Inc	SY039786	http://www.accelachem.com/cn/search.html?keyword=SY039786&attname=GoodsCode
Achemica	ACMC-20mczt	http://www.achemica.com/prodinfo/?id=198255
Achemo Scientific Limited	AC-81344	http://www.achemo.com/search/?Keyword= 90-45-9
Achemtek	0104-017002	http://www.achemtek.com/90-45-9
AEchem Scientific Corp., USA	AE021949	http://www.aechemsc.com/info_products/AE021949.php
AHH Chemical co.,ltd	MT-46290	http://www.ahhchemical.com/product/MT-46290.html
AK Scientific, Inc. (AKSCI)	U978	http://www.aksci.com/item_detail.php?cat=U978
Alfa Chemistry	ACM90459	https://materials.alfachemic.com/cas_90-45-9.htm
Alfa Chemistry	AP90459	https://reagents.alfa-chemistry.com/product/9-aminoacridine-cas-90-45-9-18378.html
Alichem	449041850	http://www.alichem.com/en/products/90-45-9.html
Alinda	ALBB-020726	http://alinda.ru/finechem_en_.html?i=ALBB-020726
Ambinter	Amb1150362	http://www.ambinter.com/reference/1150362
Angel Pharmatech	AG109244	http://www.angelpharmatech.com/90-45-9.html
Angene	AGN-PC-0JK7VC	http://www.angenechemical.com/productshow/AGN-PC-0JK7VC.html
Anward	ANW-75188	http://www.anward.com/pro_result/61639
Ark Pharm	AK109135	http://www.arkpharminc.com/products/90-45-9.html
Aurum Pharmatech LLC	M-2337	http://www.Aurumpharmatech.com/Product/ProductDetails/M_2337
Avantor Inc	200010-864	https://us.vwr.com/store/product/18599285/9-aminoacridine-hemihydrate
BioChemPartner	BCP25849	http://www.biochempartner.com/90-45-9-BCP25849
BLD Pharm	BD14518	http://www.bldpharm.com/products/90-45-9.html
Chem Scene	CS-4915	http://www.chemscene.com/90-45-9.html
Chemenu	CM119179	http://www.chemenu.com/products/CM119179
ChemFish Tokyo co.,ltd	7019	http://www.chemfish.co.jp/index.php?id=2464&project=product
Chemspace	CSSB00000183055	https://chem-space.com/CSSB00000183055
CSNpharm	CSN11568	https://www.csnpharm.com/products/9-aminoacridine.html
DC Chemicals	DC37402	http://www.dcchemicals.com//product_show-Aminoacridine.html
Debye Scientific	DB-026983	http://www.debyesci.com/DB-026983.html
Finetech	FT-0621612	http://www.finetechnology-ind.com/prod/detail/pub/90-45-9.html
Hairui	HR134673	http://www.hairuichem.com/en/product/90-45-9.html
Hefei Hirisun Pharmatech Co., Ltd	HR120307	http://www.hirisunpharm.com/90-45-9.html
Lab Network	LN00178594	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00178594
Matrix Scientific	79751	https://www.matrixscientific.com/079751.html
mcule	MCULE-4734217474	https://mcule.com/MCULE-4734217474/
MedChem Express	HY-B1422	https://www.medchemexpress.com/9-Aminoacridine.html
Molcore	MC454464	https://www.molcore.com/product/90-45-9
MuseChem	R053827	https://www.musechem.com/product/R053827.html
Oakwood	235796	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=116795&ExtHyperLink=1
Otava	1311314	https://search.otavachemicals.com/#!/search?query=1311314&type=code&base=dbb
Sigma-Aldrich	92817_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/92817?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S017810	http://www.sinfoobiotech.com/product/1021208
Smolecule	S518501	http://www.smolecule.com/products/s518501
Smolecule	S793384	https://www.smolecule.com/products/s793384
TCI (Tokyo Chemical Industry)	A2905	http://www.tcichemicals.com/eshop/en/us/commodity/A2905/index.html
THE BioTek	bt-259339	https://www.thebiotek.com/product/inhibitors/bt-259339
Vitas-M Laboratory	BBL011755	http://www.request.vitasmlab.biz/index.php?option=com_search_stk&Itemid=22&stk=BBL011755&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink
VladaChem	VL260686-1G	https://www.vladachem.com/product.php?products=90-45-9
Yuhao Chemical	RT2025	http://www.chemyuhao.com/90-45-9.html

PubMed

Title	Date	PubMed
Molecular docking studies of selected tricyclic and quinone derivatives on trypanothione reductase of Leishmania infantum.	2010-10	20340105
Mononuclear Fe(II)-N4Py complexes in oxidative DNA cleavage: structure, activity and mechanism.	2010-09-14	20657939
MALDI-TOF/MS analysis of archaebacterial lipids in lyophilized membranes dry-mixed with 9-aminoacridine.	2010-09	20538644
Lipidomic analysis of porcine olfactory epithelial membranes and cilia.	2010-07	20512424
Mutagenic and antimutagenic effects of hexane extract of some Astragalus species grown in the eastern Anatolia region of Turkey.	2010-07	19957249
Modulation of mdm2 pre-mRNA splicing by 9-aminoacridine-PNA (peptide nucleic acid) conjugates targeting intron-exon junctions.	2010-06-30	20591158
Significant sensitivity improvements by matrix optimization: a MALDI-TOF mass spectrometric study of lipids from hen egg yolk.	2010-06	20420816
Selective desorption/ionization of sulfatides by MALDI-MS facilitated using 9-aminoacridine as matrix.	2010-06	20124011
The surface charge density of plant cell membranes (sigma): an attempt to resolve conflicting values for intrinsic sigma.	2010-05	20435694
Host hindrance to HIV-1 replication in monocytes and macrophages.	2010-04-07	20374633
The intact muscle lipid composition of bulls: an investigation by MALDI-TOF MS and 31P NMR.	2010-02	19900429
Genotoxicity and antigenotoxicity evaluation of non-photoactivated hypericin.	2010-01	19585477
Investigation on the Interactions of NiCR and NiCR-2H with DNA.	2010	20671951
Alveolar osteitis: a comprehensive review of concepts and controversies.	2010	20652078
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.	2009-12	19690837
Identification of chemical compounds that induce HIF-1alpha activity.	2009-11	19502547
Binding of TCA to the prion protein: mechanism, implication for therapy, and application as probe for complex formation of bio-macromolecules.	2009-10	19583442
A kinetic and structural investigation of DNA-based asymmetric catalysis using first-generation ligands.	2009-09-21	19579236
9-Aminoacridine inhibition of HIV-1 Tat dependent transcription.	2009-07-24	19630958
In situ primary metabolites localization on a rat brain section by chemical mass spectrometry imaging.	2009-07-01	19514699
Biological safety of LipoFullerene composed of squalane and fullerene-C60 upon mutagenesis, photocytotoxicity, and permeability into the human skin tissue.	2009-06	19371265
Semi-synthetic and synthetic 1,2,4-trioxaquines and 1,2,4-trioxolaquines: synthesis, preliminary SAR and comparison with acridine endoperoxide conjugates.	2009-04-01	19251414
Biological safety of liposome-fullerene consisting of hydrogenated lecithin, glycine soja sterols, and fullerene-C60 upon photocytotoxicity and bacterial reverse mutagenicity.	2009-04	19482914
9-Aminoacridine-based anticancer drugs target the PI3K/AKT/mTOR, NF-kappaB and p53 pathways.	2009-02-26	19137016
Blockade of NMDA receptor channels by 9-aminoacridine and its derivatives.	2009-02-13	19111901
Combining 4-aminoquinoline- and clotrimazole-based pharmacophores toward innovative and potent hybrid antimalarials.	2009-01-22	19113955
Novel acridine-based compounds that exhibit an anti-pancreatic cancer activity are catalytic inhibitors of human topoisomerase II.	2009-01-14	19071108
Matrix-assisted laser desorption/ionization time-of-flight mass spectrometric analysis of cellular glycerophospholipids enabled by multiplexed solvent dependent analyte-matrix interactions.	2008-10-01	18767869
New palladium(II) and platinum(II) complexes with 9-aminoacridine: structures, luminiscence, theoretical calculations, and antitumor activity.	2008-08-04	18593114
Synthesis and biological activity of stable and potent antitumor agents, aniline nitrogen mustards linked to 9-anilinoacridines via a urea linkage.	2008-05-15	18450456
Negative ion mode matrix-assisted laser desorption/ionisation time-of-flight mass spectrometric analysis of oligosaccharides using halide adducts and 9-aminoacridine matrix.	2008-04	18338375
Effect of spermine conjugation on the interaction of acridine with alternating purine-pyrimidine oligodeoxyribonucleotides studied by CD, fluorescence and absorption spectroscopies.	2008-04	17644401
Drug 9AA reactivates p21/Waf1 and Inhibits HIV-1 progeny formation.	2008-03-18	18348731
Ultrasonic trapping of microparticles in suspension and reaction monitoring using Raman microspectroscopy.	2007-10-15	17874849
Modulation of the genotoxicity of bleomycin by amines through noncovalent DNA interactions and alteration of physiological conditions in yeast.	2007-10-01	17428504
The electrochemical behavior and direct determination of tyrosine at a glassy carbon electrode modified with poly (9-aminoacridine).	2007-10	18153995
A role of the 9-aminoacridines and their conjugates in a life science.	2007-10	17979762
Frameshift mutations produced by 9-aminoacridine in wild-type, uvrA and recA strains of Escherichia coli; specificity within a hotspot.	2007-09	17611351
In silico chemical library screening and experimental validation of a novel 9-aminoacridine based lead-inhibitor of human S-adenosylmethionine decarboxylase.	2007-08-07	17676832
Preparation of magnetite nanocrystals with surface reactive moieties by one-pot reaction.	2007-07-15	17433352
Unexpected reactivity of the 9-aminoacridine chromophore in guanidylation reactions.	2007-07-06	17552568
Molecular recognition of DNA by rigid [N]-polynorbornane-derived bifunctional intercalators: synthesis and evaluation of their binding properties.	2007-05-17	17429957
Discriminating between cellular and misfolded prion protein by using affinity to 9-aminoacridine compounds.	2007-04	17374787
A binary matrix for background suppression in MALDI-MS of small molecules.	2007-03	17260136
A real-time fluorescence assay for measuring N-dealkylation.	2007-01	17035601
Complexes of Pd(II) and Pt(II) with 9-aminoacridine: reactions with DNA and study of their antiproliferative activity.	2007	18364995
Analysis of low molecular weight acids by negative mode matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.	2007	17880046
Quantitative detection of metabolites using matrix-assisted laser desorption/ionization mass spectrometry with 9-aminoacridine as the matrix.	2007	17546650
Imaging Matrix Assisted Laser Desorption Ionization Mass Spectrometry: a technique to map plant metabolites within tissues at high spatial resolution.	2007	17005924
Acridin-9-yl exchange: a proposal for the action of some 9-aminoacridine drugs.	2006	16933221

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:58:41 GMT 2025` Edited by `admin` on `Mon Mar 31 17:58:41 GMT 2025`
Record UNII	OR5RM3Q5QL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AMINOACRIDINE HYDROCHLORIDE

Preferred Name

English

AMINACRINE HYDROCHLORIDE

Official Name

English

Aminoacridine hydrochloride [WHO-DD]

Common Name

English

AMINACRINE HYDROCHLORIDE [VANDF]

Common Name

English

MONACRIN

Brand Name

English

NSC-7571

Code

English

AMINACRINE HYDROCHLORIDE [MI]

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