N-{4-[(acridin-9-yl)amino]-3-methoxyphenyl}methanesulfonamide hydrochloride

• ChemBase ID: 134337
• Molecular Formular: C21H20ClN3O3S
• Molecular Mass: 429.9198
• Monoisotopic Mass: 429.0913902
• SMILES: COc1cc(ccc1Nc1c2ccccc2nc2c1cccc2)NS(=O)(=O)C.Cl
• Canonical SMILES: COc1cc(ccc1Nc1c2ccccc2nc2c1cccc2)NS(=O)(=O)C.Cl
• InChI: 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
• InChIKey: WDISRLXRMMTXEV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{4-[(acridin-9-yl)amino]-3-methoxyphenyl}methanesulfonamide hydrochloride
• IUPAC Traditional name: amsacrine hydrochloride
• Synonyms: 4-(9-Acridinylamino)-N-(methanesulfonyl)-m-anisidine hydrochloride; m-AMSA; Amsacrine hydrochloride

Database IDs

• CAS Number: 54301-15-4
• MDL Number: MFCD07799963
• PubChem SID: 24278248; 162228613
• PubChem CID: 148673

CALCULATED PROPERTIES

• Acid pKa: 10.824813
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.4867606
• LogD (pH = 7.4): 2.164806
• Log P: 3.1616213
• Molar Refractivity: 107.6901 cm^3
• Polarizability: 44.860916 Å^3
• Polar Surface Area: 80.32 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 30% ethanol: soluble4 mg/mL; DMSO: soluble10 mg/mL (with heat and sonication)
• Apperance: red to brown powder
• Melting Point: 197-199 °C(lit.)

Safety Information

• RTECS: PB1081000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25-36/37/38
• Safety Statements: 26-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Gene Information: human ... TOP2A(7153), TOP2B(7155)

Product Information

• Purity: ≥98% (TLC)

DETAILS

Sigma Aldrich - A9809

Biochem/physiol Actions
Amsacrine hydrochloride is a DNA topoisomerase II inhibitor.