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Merck

Q3251

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
NACRES:
NA.77
PubChem Substance ID:
24278192
UNSPSC Code:
12352101
EC Number:
200-700-8
MDL number:
MFCD00012659
Beilstein/REAXYS Number:
4834013
Assay:
≥90%
Form:
powder
Quality level:
100

Key Documents

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Product Name

Quinacrine dihydrochloride, ≥90%

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

SMILES string

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

biological source

synthetic

assay

≥90%

form

powder

mp

257 °C

solubility

H2O: soluble, clear to hazy

originator

Bayer

Quality Level

100

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

Non-selective MAO-A/B inhibitor.
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.

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.

Preparation Note

Stock solutions are stable for up to 60 h at 20°C.

Other Notes

This product is not assigned an expiration date or recommended retest date.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG8201
BCCD8591
BCCB2922
BCBV6879
BCBR3327V

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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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