Acridine orange

Acridine orange
IUPAC name	N,N,N',N'-tetramethylacridine- 3,6-diamine
Other names	Euchrysine 3,6-Acridinediamine Waxoline Orange A Acridine Orange Base Solvent Orange 15 Rhoduline Orange Rhoduline Orange N Acridine Orange NO Rhoduline Orange NO Basic Orange 14
Identifiers
CAS number	494-38-2 Y, 65-61-2 (hydrochloride)
PubChem	62344
RTECS number	AR7601000
SMILES	n1c3c(cc2c1cc(N(C)C)cc2)ccc(c3)N(C)C
InChI	1/C17H19N3/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
InChI key	DPKHZNPWBDQZCN-UHFFFAOYAJ
ChemSpider ID	56136
Properties
Molecular formula	C17H19N3
Molar mass	265.35 g mol−1
Appearance	Orange powder
Hazards
EU classification	Xi N
S-phrases	S26 S28 S37 S45
NFPA 704	0 2 0
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Acridine orange is a nucleic acid selective fluorescent cationic dye useful for cell cycle determination. It is cell-permeable, and interacts with DNA and RNA by intercalation or electrostatic attractions respectively. When bound to DNA, it is very similar spectrally to fluorescein, with an excitation maximum at 502 nm and an emission maximum at 525 nm (green). When it associates with RNA, the excitation maximum shifts to 460 nm (blue) and the emission maximum shifts to 650 nm (red). Acridine orange will also enter acidic compartments such as lysosomes and become protonated and sequestered. In these low pH conditions, the dye will emit orange light when exited by blue light. The dye is often used in epifluorescence microscopy.

Acridine orange is prepared from coal tar and creosote oil.

Acridine orange can be used in conjunction with ethidium bromide to differentiate between live and apoptotic cells.

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