3-N,3-N,6-N,6-N-tetramethylacridine-3,6-diamine hydrochloride

• ChemBase ID: 107356
• Molecular Formular: C17H20ClN3
• Molecular Mass: 301.8138
• Monoisotopic Mass: 301.13457534
• SMILES: Cl.CN(C)c1cc2nc3cc(ccc3cc2cc1)N(C)C
• Canonical SMILES: CN(c1ccc2c(c1)nc1c(c2)ccc(c1)N(C)C)C.Cl
• InChI: InChI=1S/C17H19N3.ClH/c1-19(2)14-7-5-12-9-13-6-8-15(20(3)4)11-17(13)18-16(12)10-14;/h5-11H,1-4H3;1H
• InChIKey: VSTHNGLPHBTRMB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-N,3-N,6-N,6-N-tetramethylacridine-3,6-diamine hydrochloride
• IUPAC Traditional name: acridine orange hydrochloride
• Synonyms: ACRIDINE ORANGE; ACRIDINE ORANGE N; ACRIDINE ORANGE (E. GURR); 3,6-Bis(dimethylamino)acridine hydrochloride; Acridine Orange hydrochloride solution

Database IDs

• CAS Number: 65-61-2
• EC Number: 200-614-0
• MDL Number: MFCD00012660
• Beilstein Number: 3575587
• PubChem SID: 24891317; 24844902; 162093378
• PubChem CID: 517204

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.0666623
• LogD (pH = 7.4): 2.9319835
• Log P: 3.7223153
• Molar Refractivity: 84.9147 cm^3
• Polarizability: 34.26807 Å^3
• Polar Surface Area: 19.37 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 284-287°C
• Density: 1.001 g/mL at 20 °C
• Refractive Index: n20/D 1.338
• Fluorescence: λex 495 nm; λem 526 nm in TE buffer pH 8.0 (enhanced fluorescence with DNA)

Safety Information

• RTECS: AR7601000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: R:20/21/22-40
• Safety Statements: S:36/37/39-45
• Personal Protective Equipment: Eyeshields, Gloves; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)

Product Information

• Concentration: ~1% in H2O; 10 mg/mL in H2O
• Grade: for fluorescence
• Empirical Formula (Hill Notation): C17H19N3 · HCl

DETAILS

MP Biomedicals - 05203423

MP Biomedicals Rare Chemical collection

MP Biomedicals - 05205478

MP Biomedicals Rare Chemical collection

MP Biomedicals - 05220129

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 01663

Application
Metachromatic dye useful as a mitochondrial probe in living cells. This dye has been used to analyze mitochondria by flow cytometry, characterize multidrug resistance, and measure changes in mitochondrial mass during apoptosis in rat thymocytes.

Sigma Aldrich - A8097

Application
Metachromatic dye useful as a mitochondrial probe in living cells. This dye has been used to analyze mitochondria by flow cytometry, characterize multidrug resistance, and measure changes in mitochondrial mass during apoptosis in rat thymocytes.