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Q2876

Sigma-Aldrich

Quinacrine mustard dihydrochloride

≥85% (HPLC)

Synonym(s):

2-Methoxy-6-chloro-9-(4-bis[β-chloroethyl]amino-1-methylbutylamino)acridine dihydrochloride, 9-[4-(Bis(2-chloroethyl)amino)-1-methylbutylamino]-6-chloro-2-methoxyacridine dihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C23H28Cl3N3O · 2HCl
CAS Number:
4213-45-0
Molecular Weight:
541.77
Beilstein:
3819822
EC Number:
224-140-9
MDL number:
MFCD00043254
UNSPSC Code:
12352101
PubChem Substance ID:
24899329
NACRES:
NA.32

Assay

≥85% (HPLC)

storage temp.

−20°C

SMILES string

Cl[H].Cl[H].COc1ccc2nc3cc(Cl)ccc3c(NC(C)CCCN(CCCl)CCCl)c2c1

InChI

1S/C23H28Cl3N3O.2ClH/c1-16(4-3-11-29(12-9-24)13-10-25)27-23-19-7-5-17(26)14-22(19)28-21-8-6-18(30-2)15-20(21)23;;/h5-8,14-16H,3-4,9-13H2,1-2H3,(H,27,28);2*1H

InChI key

JETDZFFCRPFPDH-UHFFFAOYSA-N

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General description

Quinacrine mustard dihydrochloride is a fluorescent acridine dye, also abbreviated as QM. In an aqueous solution, the chloroethyl groups rapidly lose chloride ions yielding aziridinium cations. These readily react with the carboxyl, thiol, and heterocyclic ring nitrogen groups of proteins and nucleic acids, or with other nucleophiles.

Application

Quinacrine mustard dihydrochloride is used to stain metaphase chromosomes. Recent applications include the Q-banding of maize and karyotyping of fish. The dye is also used as a vital stain for trypanosomes.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Repr. 2 - Resp. Sens. 1 - Skin Sens. 1

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Monika Pietrzak et al.
Biophysical chemistry, 104(1), 305-313 (2003-07-02)
The present study was designed to estimate the ability of chlorophyllin (CHL) to interact with two acridine mutagens, quinacrine mustard (QM) and acridine orange (AO), and with the antitumor anthracycline doxorubicin (Dox). To this end, aqueous solutions of QM, AO
B Ardelt et al.
International journal of oncology, 18(4), 849-853 (2001-03-17)
Chlorophyllin (CHL), the sodium and copper salt of chlorophyll, is capable of inhibiting the mutagenic activity of many chemical compounds. Several mechanisms have been advanced to explain the antimutagenic activity of CHL, including its antioxidant properties and its ability to
Jan Kapuscinski et al.
Biochemical pharmacology, 63(4), 625-634 (2002-05-07)
Recently, accumulated statistical data indicate the protective effect of caffeine consumption against several types of cancer diseases. There are also reports about protective effect of caffeine and other xanthines against tumors induced by polycyclic aromatic hydrocarbons. One of the explanations
Michiko Inuma et al.
Zoological science, 26(5), 344-348 (2009-09-01)
Chromosomes stained with fluorochromes, including quinacrine mustard (QM), emit the brightest fluorescence immediately after exposure to excitation light, and the fluorescence gradually fades with an increase in exposure time. However, in the QM-stained chromosomes of the small Japanese field mouse
M L Check et al.
Archives of andrology, 44(1), 47-50 (2000-02-26)
Previous methods of enriching sperm with a higher percentage of Y-bearing sperm have been questioned because the claims that Y enrichment was present were based on quinacrine staining of the Y chromosome, and the enrichment was not confirmed by polymerase
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