Compound: Acridine orange
SMILES: n1c2c(cc3c1cc(N(C)C)cc3)ccc(c2)N(C)C
InChIKey: DPKHZNPWBDQZCN-UHFFFAOYSA-N
Synonyms: Acridine orange, Acridine Orange Base, 494-38-2, 3,6-Bis(dimethylamino)acridine, Waxoline Orange A, 3,6-Di(dimethylamino)acridine, Oranz akridinova, Acridine Orange NO, Rhoduline Orange, C.I. No. 46005:1, Oranz rozpoustedlova 15, Basic Orange 14, Rhoduline Orange NO, F30N4O6XVV, DTXSID60197783, NSC-194350, Acridine Orange N, Orange, Acridine, Orange, Rhoduline, CHEBI:51739, Orange 3RN, Basic, Base, Acridine Orange, Orange Base, Acridine, Tetramethyl Acridine Diamine, Acridine Diamine, Tetramethyl, Diamine, Tetramethyl Acridine, RefChem:552697, DTXCID20120274, 3,6-Bis(dimethylamino)acridine hydrochloride, Acridine Orange NS, Acridine Orange R, Sumitomo Acridine Orange NO, Sumitomo Acridine Orange RK conc, YO2175B15I, N3,N3,N6,N6-Tetramethylacridine-3,6-diamine, Euchrysine, Solvent Orange 15, C.I. Solvent Orange 15, Brilliant Acridine Orange E, Acridine Orange Free Base, Acridine Orange Stain, Rhoduline Orange N, C.I. 46005B, Acridine, 3,6-bis(dimethylamino)-, N,N,N',N'-Tetramethyl-3,6-acridinediamine, Acridinorange, NSC 194350, 2,8-Bis(dimethylamino)acridine, 3,6-Bis-(dimethylamino)akridin, 3-N,3-N,6-N,6-N-tetramethylacridine-3,6-diamine, 3,6-ACRIDINEDIAMINE, N,N,N',N'-TETRAMETHYL-, Rhoduline Orange N, Rhoduline Orange NO, Acridinediamine, N,N,N',N'-tetramethyl-, CHEMBL81880, MFCD00005029, NSC194350, Oranz akridinova [Czech], 2,8-Bisdimethylaminoacridine, AO, [6-(dimethylamino)acridin-3-yl]dimethylamine, Oranz rozpoustedlova 15 [Czech], N,N,N',N'-Tetramethylacridinediamine, UNII-F30N4O6XVV, BRN 0020916, 3,6-Bis-(dimethylamino)akridin [Czech], N,N,N(sup 1),N(sup 1)-Tetramethylacridinediamine, Euchrysine (Salt/Mix), Rhoduline Orange (Salt/Mix), 4-22-00-05490 (Beilstein Handbook Reference), 3,6-Bis-dimethylaminoacridine, BIDD:GT0571, SCHEMBL297155, ACRIDINE ORANGE [IARC], Basic Orange 14 (Salt/Mix), Basic Orange 3RN (Salt/Mix), orb1982091, 3, 6-Bis-dimethylaminoacridine, Acridine,6-bis(dimethylamino)-, ACRIDINE ORANGE [MART.], Acridine Orange NO (Salt/Mix), SCHEMBL29361720, CHEBI:87346, Rhoduline Orange NO (Salt/Mix), C.I. 46005 (Salt/Mix), HY-D0952, BDBM50105462, SBB057772, AKOS016009859, FA39736, FS-5125, Acridine Orange base, Dye content 75 %, BP-43789, NCI60_001622, N,N',N'-Tetramethyl-3,6-acridinediamine, DB-051628, CS-0022134, N,N,N',N'-tetramethylacridine-3,6-diamine, NS00015153, ST50306844, WLN: T C666 BNJ EN1&1 MN1&1, C19315, EN300-657194, F19170, [6-(dimethylamino)acridin-3-yl]-dimethyl-amine, N,N,N'',N''-Tetramethyl-acridine-3,6-diamine, F240163, Q342717, N(3),N(3),N(6),N(6)-tetramethylacridine-3,6-diamine, N~3~,N~3~,N~6~,N~6~-Tetramethyl-3,6-acridinediamine, N~3~,N~3~,N~6~,N~6~-Tetramethylacridine-3,6-diamine, N3,N3,N6,N6-Tetramethylacridine-3,6-diamine (Acridine orange)
Theoretical properties:
molecular_formula: C17H19N3
molecular_weight: 265.35 g/mol
exact_mass: 265.157897619 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 2
heavy_atom_count: 20
topological_polar_surface_area: 19.4 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "Acridine orange free base is a member of the class of aminoacridines that is acridine carrying two dimethylamino substituents at positions 3 and 6. The hydrochloride salt is the fluorescent dye 'acridine orange', used for cell cycle determination. It has a role as a fluorochrome and a histological dye. It is an aromatic amine, a tertiary amino compound and a member of aminoacridines.", "chebi": "A member of the class of aminoacridines that is acridine carrying two dimethylamino substituents at positions 3 and 6. The hydrochloride salt is the fluorescent dye 'acridine orange', used for cell cycle determination.", "chembl": "ACRIDINE ORANGE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Acridine orange is an organic compound that serves as a nucleic acid-selective fluorescent dye with cationic properties useful for cell cycle determination. Acridine orange is cell-permeable, which allows it to interact with DNA by intercalation, or RNA via electrostatic attractions. When bound to DNA, acridine orange is very similar spectrally to an organic compound known as fluorescein sodium.\nAcridine orange is used in epifluorescence microscopy and flow cytometry. The ability to penetrate the cell membranes of acidic organelles and cationic properties of acridine orange allows it to differentiate between various types of cells (i.e., bacterial cells and white blood cells).\nAcridine orange and fluorescein have a maximum excitation at 502nm and 525 nm (green). When acridine orange associates with RNA, the fluorescent dye experiences a maximum excitation shift from 525 nm (green) to 460 nm (blue). The shift in maximum excitation also produces a maximum emission of 650 nm (red). Acridine orange is able to withstand low pH environments, allowing the fluorescent dye to penetrate acidic organelles such as lysosomes and phagolysosomes that are membrane-bound organelles essential for acid hydrolysis or for producing products of phagocytosis of apoptotic cells. The shift in maximum excitation and emission wavelengths provides a foundation to predict the wavelength at which the cells will stain."}