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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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S Fabbri et al.
Carcinogenesis, 14(9), 1963-1967 (1993-09-01)
Nitrogen mustard (HN2) and quinacrine mustard (QM) both inhibited the binding of NF kappa B to the GC-rich consensus sequence in the HIV long terminal repeat (LTR), as assessed by gel-shift assays. QM also inhibited the binding of OTF-1 to
J A Hartley et al.
Nucleic acids research, 20(12), 3175-3178 (1992-06-25)
Nitrogen mustard alkylating agents react with isolated DNA in a sequence selective manner, and the substituent attached to the drug reactive group can impose a distinct sequence preference. It is not clear however to what extent the observed DNA sequence
W B Mattes
Analytical biochemistry, 206(1), 161-167 (1992-10-01)
Alkylation at the N7 position of guanine in DNA renders the C8-hydrogen acidic. This serves as the basis for an assay of guanine N7 alkylation using [8-3H]-guanine-labeled DNA. I modified the assay by preparing a high specific activity substrate in
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
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