Amsacrine: A DNA Intercalator with the Inhibition of Topoisomerase IIAmsacrine (known as m-AMSA) hydrochloride is an acridine derivative that has a potent antitumor activity against leukemic cells. Amsacrine inhibits topoisomerase II which is a group of essential enzymes for DNA replication with important functions for DNA function and cell survival. Topoisomerase II is now viewed as an important cellular target of antitumor drugs including both DNA intercalators (amsacrine and doxorubicin [D4193]) and the nonintercalator epipodophyllotoxin derivatives (etoposide [E0675] and teniposide [T3109]). Amsacrine is often used in combination with other chemotherapy drugs to treat types of adult leukemia, particularly acute myeloid leukemia (AML). (The product is for research purpose only.)

Specifications

Sinónimos

Especificaciones y pureza

≥98%(HPLC)

Condiciones de almacenamiento de almacenamiento

Room temperature

Enviado en

Normal

Pureza

≥98%(HPLC)

Nombres e identificadores

Pubchem Sid	488188212
Pubchem Sid Url	https://pubchem.ncbi.nlm.nih.gov/substance/488188212
Sonrisas canónicas	COC1=C(C=CC(=C1)NS(=O)(=O)C)NC2=C3C=CC=CC3=NC4=CC=CC=C42.Cl
IUPAC Name	N-[4-(acridin-9-ylamino)-3-methoxyphenyl]methanesulfonamide;hydrochloride
InChIKey	WDISRLXRMMTXEV-UHFFFAOYSA-N
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
Isómeros SMILES	COC1=C(C=CC(=C1)NS(=O)(=O)C)NC2=C3C=CC=CC3=NC4=CC=CC=C42.Cl
WGK Alemania	3
RTECS	PB1081000
Número ONU	2811
Peso molecular	429.92
Reaxy-Rn	5692112
Reaxys-RN_link_address	https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=5692112&ln=

Documentation

📋 Safety Data Sheet (SDS)

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Advanced Data

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
- Superclass Organoheterocyclic compounds
  - Clase Quinolines and derivatives
    - Subclass Benzoquinolines

Kingdom	Organic compounds
Superclass	Organoheterocyclic compounds
Clase	Quinolines and derivatives
Subclass	Benzoquinolines
Intermediate Tree Nodes	Not available
Direct Parent	Acridines
Alternative Parents	4-aminoquinolines Sulfanilides Aminophenyl ethers Methoxyanilines Phenoxy compounds Methoxybenzenes Anisoles Alkyl aryl ethers Aminopyridines and derivatives Organosulfonamides Organic sulfonamides Aminosulfonyl compounds Heteroaromatic compounds Secondary amines Azacyclic compounds Hydrocarbon derivatives Hydrochlorides Organic oxides Organopnictogen compounds
Molecular Framework	Aromatic heteropolycyclic compounds
Substituents	Acridine - Aminoquinoline - 4-aminoquinoline - Sulfanilide - Methoxyaniline - Aminophenyl ether - Phenoxy compound - Anisole - Methoxybenzene - Phenol ether - Aniline or substituted anilines - Aminopyridine - Alkyl aryl ether - Monocyclic benzene moiety - Organic sulfonic acid amide - Organosulfonic acid amide - Benzenoid - Pyridine - Organic sulfonic acid or derivatives - Sulfonyl - Aminosulfonyl compound - Heteroaromatic compound - Organosulfonic acid or derivatives - Azacycle - Ether - Secondary amine - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organosulfur compound - Hydrochloride - Amine - Aromatic heteropolycyclic compound
Descripción	This compound belongs to the class of organic compounds known as acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocycle which consists of two benzene rings joined by a pyridine ring.
External Descriptors	Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61. DOI: 10.1186/s13321-016-0174-y

Estructura 3D

Objetivos asociados (humanos)

VDR Tclin Vitamin D receptor (26531 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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GLA Tclin Alpha-galactosidase A (5444 Activities)

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GBA1 Tclin Beta-glucocerebrosidase (14647 Activities)

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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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SMPD1 Tchem Sphingomyelin phosphodiesterase (13561 Activities)

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GLP1R Tclin Glucagon-like peptide 1 receptor (111429 Activities)

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HEK293 (82097 Activities)

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HepG2 (196354 Activities)

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FEN1 Tchem Flap endonuclease 1 (12055 Activities)

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GNAS Tbio Guanine nucleotide-binding protein G(s), subunit alpha (103405 Activities)

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POLI Tchem DNA polymerase iota (116820 Activities)

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POLH Tchem DNA polymerase eta (21678 Activities)

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KDM4A Tchem Lysine-specific demethylase 4A (52245 Activities)

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APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

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EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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ERG Tbio Transcriptional regulator ERG (5589 Activities)

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KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)

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SMN1 Tchem Survival motor neuron protein (34246 Activities)

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LMNA Tbio Prelamin-A/C (36751 Activities)

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RECQL Tbio ATP-dependent DNA helicase Q1 (5575 Activities)

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BLM Tchem Bloom syndrome protein (4248 Activities)

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HPGD Tchem 15-hydroxyprostaglandin dehydrogenase [NAD+] (24926 Activities)

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SMAD3 Tchem Mothers against decapentaplegic homolog 3 (68039 Activities)

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GMNN Tbio Geminin (128009 Activities)

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PMP22 Tbio Peripheral myelin protein 22 (699 Activities)

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KMT2A Tchem Histone-lysine N-methyltransferase MLL (17327 Activities)

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MBNL1 Tbio Muscleblind-like protein 1 (34431 Activities)

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GFER Tchem FAD-linked sulfhydryl oxidase ALR (1466 Activities)

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ATAD5 Tbio ATPase family AAA domain-containing protein 5 (122566 Activities)

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MPHOSPH8 Tbio M-phase phosphoprotein 8 (656 Activities)

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BAZ2B Tchem Bromodomain adjacent to zinc finger domain protein 2B (56204 Activities)

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ATXN2 Tbio Ataxin-2 (54410 Activities)

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USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)

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IDH1 Tclin Isocitrate dehydrogenase [NADP] cytoplasmic (40980 Activities)

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RAD54L Tbio DNA repair and recombination protein RAD54-like (409 Activities)

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GLS Tchem Glutaminase kidney isoform, mitochondrial (16997 Activities)

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RAD52 Tchem DNA repair protein RAD52 homolog (856 Activities)

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TARDBP Tchem TAR DNA-binding protein 43 (40113 Activities)

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RAN Tchem GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1 (21853 Activities)

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Objetivos asociados (no humanos)

Plasmodium falciparum (966862 Activities)

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Npsr1 Neuropeptide S receptor (260 Activities)

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Luciferin 4-monooxygenase (66902 Activities)

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Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

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Mapt Microtubule-associated protein tau (6 Activities)

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Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

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Impa1 Inositol monophosphatase 1 (16203 Activities)

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nfo Endonuclease 4 (425 Activities)

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NS1 Nonstructural protein 1 (33327 Activities)

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Mecanismos de acción

Certificados (CoA, COO, BSE/TSE y tabla de análisis)

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8 results found

Lot Number	Certificate Type	Fecha	Articulo
G2214053	Certificate of Analysis	Apr 07, 2026	A107930
G2214091	Certificate of Analysis	Apr 07, 2026	A107930
G2214092	Certificate of Analysis	Apr 07, 2026	A107930
G2214093	Certificate of Analysis	Apr 07, 2026	A107930
I1213012	Certificate of Analysis	Jul 15, 2024	A107930
B2324332	Certificate of Analysis	Feb 12, 2022	A107930
E2311111	Certificate of Analysis	Feb 12, 2022	A107930
E2311113	Certificate of Analysis	Feb 12, 2022	A107930

Propiedades químicas y físicas

Sensibilidad	Light Sensitive
Punto de fusión (°C)	197-199°C
Peso molecular	429.900 g/mol
XLogP3
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	5
Exact Mass	429.091 Da
Monoisotopic Mass	429.091 Da
Topological Polar Surface Area	88.700 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	601.000
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
The total count of all stereochemical bonds	0
Covalently-Bonded Unit Count	2

Preguntas frecuentes y artículos

Why Acridine Can Turn “Trace Molecules” into a Measurable Light Signal: A Mechanistic, Selection, and Troubleshooting Guide to Acridinium Ester Chemiluminescent Immunoassays (Including Product Tables 1–4)

Categories: Technical articles

Tags:

Nitrogen-containing heterocycles Polycyclic aromatic compounds aromatic compounds Chemiluminescence immunoassay

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Amsacrine hydrochloride - ≥98%(HPLC) , CAS No.54301-15-4

Why this grade

Storage & shipping

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Literature proof

Descripción general

Specifications

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📋 Safety Data Sheet (SDS)

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