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Q3251

Sigma-Aldrich

Quinacrine dihydrochloride

≥90% (TLC), powder, MAO-A/B inhibitor

Synonym(s):

6-Chloro-9-(4-diethylamino-1-methylbutylamino)-2-methoxyacridine dihydrochloride, Atebrin dihydrochloride, Mepacrine dihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C23H30ClN3O · 2HCl
CAS Number:
69-05-6
Molecular Weight:
472.88
Beilstein:
4834013
EC Number:
200-700-8
MDL number:
MFCD00012659
UNSPSC Code:
12352101
PubChem Substance ID:
24278192
NACRES:
NA.77

product name

Quinacrine dihydrochloride, ≥90%

biological source

synthetic

Quality Level

100

Assay

≥90%

form

powder

mp

257 °C

solubility

H2O: soluble, clear to hazy

originator

Bayer

SMILES string

Cl[H].Cl[H].CCN(CC)CCCC(C)Nc1c2ccc(Cl)cc2nc3ccc(OC)cc13

InChI

1S/C23H30ClN3O.2ClH/c1-5-27(6-2)13-7-8-16(3)25-23-19-11-9-17(24)14-22(19)26-21-12-10-18(28-4)15-20(21)23;;/h9-12,14-16H,5-8,13H2,1-4H3,(H,25,26);2*1H

InChI key

UDKVBVICMUEIKS-UHFFFAOYSA-N

Gene Information

human ... MAOA(4128) , MAOB(4129)

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General description

Quinacrine is an acridine derivative and a potent antimalarial agent.

Application

Quinacrine dihydrochloride has been used:
  • in its uptake and accumulation studies in mouse lung slices using fluorescence microscope
  • in the staining of ATP vesicles in mesenchymal stem cells (MSCs)
  • in uptake-release assay for characterization of dense granule functionality of platelets

Biochem/physiol Actions

Quinacrine has anthelmintic functionality and used in the female sterilization. It is used to treat systemic lupus erythematosus and rheumatic diseases. Apart from malaria, Quinacrine is effective for treating giardia and tapeworm infections. It inhibits nicotinamide adenine dinucleotide phosphate (NADPH) oxidase activity in addition to monoamine oxidase inhibition.
Non-selective MAO-A/B inhibitor.

Features and Benefits

This compound was developed by Bayer. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The role of monoamine metabolism in oxidative glutamate toxicity
Maher P and Davis JB
The Journal of Neuroscience, 16(20), 6394-6401 (1996)
Quinacrine sterilization (QS): time for reconsideration
Lippes J
Contraception, 92(2), 91-95 (2015)
Mechanically induced chromatin condensation requires cellular contractility in mesenchymal stem cells
Heo SJ, et al.
Biophysical Journal, 111(4), 864-874 (2016)
Genotoxic potential of some commonly used antimalarials: A review
Sahu Rand Kashyap P
International Journal of Pharmaceutical Sciences and Research, 3(6), 1569-1569 (2012)
Denise De Zanet et al.
PloS one, 12(9), e0184941-e0184941 (2017-09-19)
A new biosensor for the real-time analysis of thrombus formation is reported. The fast and accurate monitoring of the individual thrombotic risk represents a challenge in cardiovascular diagnostics and in treatment of hemostatic diseases. Thrombus volume, as representative index of
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