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222992

Sigma-Aldrich

Quinacrine dihydrochloride

98%

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:
12352200

Assay

98%

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

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Biochem/physiol Actions

Non-selective MAO-A/B inhibitor.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Ranjan Preet et al.
Carcinogenesis, 34(2), 277-286 (2012-11-07)
We previously reported that quinacrine (QC) has anticancer activity against breast cancer cells. Here, we examine the mechanism of action of QC and its ability to inhibit Wnt-TCF signaling in two independent breast cancer cell lines. QC altered Wnt-TCF signaling
Vitaliy Kasymov et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 33(2), 435-441 (2013-01-11)
Astrocytes might function as brain interoceptors capable of detecting different (chemo)sensory modalities and transmitting sensory information to the relevant neural networks controlling vital functions. For example, astrocytes that reside near the ventral surface of the brainstem (central respiratory chemosensitive area)
Jifeng Bian et al.
Proceedings of the National Academy of Sciences of the United States of America, 111(16), 6028-6033 (2014-04-09)
Quinacrine's ability to reduce levels of pathogenic prion protein (PrP(Sc)) in mouse cells infected with experimentally adapted prions led to several unsuccessful clinical studies in patients with prion diseases, a 10-y investment to understand its mechanism of action, and the
Tingting Gu et al.
Biosensors & bioelectronics, 33(1), 222-227 (2012-02-07)
A novel strategy of amperometric assay for drug-dsDNA interactions was developed based on an inhibitory effect of antimararial drug (quinacrine) on an electrocatalytic activity of DNA-Cu(II) complex. In this method, a DNA-Cu(II) complex immobilized DNA/polyallylamine(PAA) polyion complex membrane was used
Misol Ahn et al.
PloS one, 7(7), e39112-e39112 (2012-07-07)
The lipophilic cationic compound quinacrine has been used as an antimalarial drug for over 75 years but its pharmacokinetic profile is limited. Here, we report on the pharmacokinetic properties of quinacrine in mice. Following an oral dose of 40 mg/kg/day
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