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Key Documents

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:
Molecular Weight:
472.88
Beilstein:
4834013
EC Number:
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.77

Product Name

Quinacrine dihydrochloride, ≥90%

biological source

synthetic

Quality Level

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

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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.

Storage and Stability

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

Signal Word

Warning

Hazard Statements

Precautionary Statements

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

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Certificates of Analysis (COA)

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  4. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  5. Can Product Q3251, Quinacrine dihydrochloride be used for staining platelets?

    We have not tested Product Q3251, Quinacrine dihydrochloride for staining platelets. The reference link indicates that platelets can be visualized with the fluorescent dye mepacrine (quinacrine dihydrochloride) at a final concentration of 10 μM.  Brian Savage, et al., PNAS, 99 (1): 425-430, (2002).

  6. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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)
The role of monoamine metabolism in oxidative glutamate toxicity
Maher P and Davis JB
The Journal of Neuroscience, 16(20), 6394-6401 (1996)
Abnormal differentiation of B cells and megakaryocytes in patients with Roifman syndrome
Heremans J, et al.
The Journal of Allergy and Clinical Immunology, 142(2), 630-646 (2018)
Purinergic signaling in the pulmonary neuroepithelial body microenvironment unraveled by live cell imaging
De Proost I, et al.
Faseb Journal, 23(4), 1153-1160 (2009)

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