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A9809

Amsacrine hydrochloride

≥98% (TLC), DNA topoisomerase II inhibitor, powder

Synonym(s):

4-(9-Acridinylamino)-N-(methanesulfonyl)-m-anisidine hydrochloride, m-AMSA

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10 mg

Available to ship TODAYfromMILWAUKEE

$370.00
50 mg

Available to ship TODAYfromMILWAUKEE

$1,350.00

About This Item

Empirical Formula (Hill Notation):
C21H19N3O3S · HCl
CAS Number:
54301-15-4
Molecular Weight:
429.92
UNSPSC Code:
51111800
PubChem Substance ID:
24278248
NACRES:
NA.77
MDL number:
MFCD07799963

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Product Name

Amsacrine hydrochloride, ≥98% (TLC), powder

Quality Level

200

assay

≥98% (TLC)

form

powder

color

red to brown

mp

197-199 °C (lit.)

solubility

DMSO: 10 mg/mL (with heat and sonication), 30% ethanol: 4 mg/mL

storage temp.

room temp

SMILES string

Cl.COc1cc(NS(C)(=O)=O)ccc1Nc2c3ccccc3nc4ccccc24

InChI

1S/C21H19N3O3S.ClH/c1-27-20-13-14(24-28(2,25)26)11-12-19(20)23-21-15-7-3-5-9-17(15)22-18-10-6-4-8-16(18)21;/h3-13,24H,1-2H3,(H,22,23);1H

InChI key

WDISRLXRMMTXEV-UHFFFAOYSA-N

Gene Information

human ... TOP2A(7153), TOP2B(7155)

Application

Amsacrine hydrochloride has been used:
  • as a topoisomerase poison in bacteriophage T4 topoisomerase assay[1]
  • as a topoisomerase inhibitor in Drosophila cell line, Kc167 [2]
  • as an antileukemia drug to test its effect on p53 transcriptional activity in tumor xenografts[3]
  • as a topoisomerase II poison in dose-response assays in C elegans[4]

Biochem/physiol Actions

Amsacrine (m-AMSA) is a derivative of acridine[5] and an antileukemia drug.[3] It is an anticancer drug with antineoplastic activity that targets topoisomerase II.[5] AMSA is an apoptosis inducer[6] and favors the accumulation of double-stranded breaks (DSBs).[2] It also inhibits the expression of matrix metallopeptidase 2 (MMP-2) and MMP-9 expression in leukemia cells by generating reactive oxygen species (ROS). AMSA serves as an adjuvant in trabeculectomy surgery.[6]
Amsacrine hydrochloride is a DNA topoisomerase II inhibitor.

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This Item
PZ0365G3796M3449
Amsacrine hydrochloride ≥98% (TLC), powder

Sigma-Aldrich

A9809

Amsacrine hydrochloride

CP-376395 hydrochloride ≥98% (HPLC)

Sigma-Aldrich

PZ0365

CP-376395 hydrochloride

Granisetron hydrochloride ≥98% (HPLC), solid

Sigma-Aldrich

G3796

Granisetron hydrochloride

Mephedrone hydrochloride

Sigma-Aldrich

M3449

Mephedrone hydrochloride

assay

≥98% (TLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

Gene Information

human ... TOP2A(7153), TOP2B(7155)

Gene Information

-

Gene Information

-

Gene Information

-

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

100

form

powder

form

powder

form

solid

form

powder

storage temp.

room temp

storage temp.

room temp

storage temp.

room temp

storage temp.

room temp

solubility

DMSO: 10 mg/mL (with heat and sonication), 30% ethanol: 4 mg/mL

solubility

DMSO: 2 mg/mL, clear

solubility

H2O: >10 mg/mL

solubility

DMSO: >20 mg/mL

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Carc. 2 - Muta. 2 - Repr. 2 - Skin Sens. 1

Storage Class

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

wgk

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000404427
0000404427
0000375877
0000360738
0000360738

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E M Nelson et al.
Proceedings of the National Academy of Sciences of the United States of America, 81(5), 1361-1365 (1984-03-01)
The intercalative acridine derivative 4'-(9-acridinylamino)methanesulfon-m-anisidide (m-AMSA), but not its isomer o-AMSA, is a potent antitumor drug that in mammalian cells stimulates the formation of DNA strand breaks that are characterized by tightly bound proteins. Using purified mammalian DNA topoisomerases, we
Adrien Marchand et al.
Journal of the American Chemical Society, 140(39), 12553-12565 (2018-09-06)
Designing ligands targeting G-quadruplex nucleic acid structures and affecting cellular processes is complicated because there are multiple target sequences and some are polymorphic. Further, structure alone does not reveal the driving forces for ligand binding. To know why a ligand
R A Davey et al.
Cancer chemotherapy and pharmacology, 39(5), 424-430 (1997-01-01)
The effectiveness of N-[2-(dimethylamino)ethyl]acridine-4-carboxamide (DACA) relative to that of amsacrine, idarubicin, daunorubicin and paclitaxel against three different forms of multidrug resistance (MDR) was determined using two sublines of the CCRF-CEM human leukaemia cell line, the P-glyco-protein-expressing CEM/VLB100 subline and the
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Global Trade Item Number

SKUGTIN
A9809-50MG04061833020616
A9809-10MG04061833412558

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