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Topic summary

Auramine O

Auramine O
Names IUPAC name
bis[4-(dimethylamino)phenyl]methaniminium chloride
Other names
auramine hydrochloride, basic yellow 2, pyocatanium aureum, aizen auramine, pyoktanin yellow, canary yellow, pyoktanin, or C.I. 41000
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard100.017.789EC Number
  • 219-567-2
UNII
  • InChI=1S/C17H21N3.ClH/c1-19(2)15-9-5-13(6-10-15)17(18)14-7-11-16(12-8-14)20(3)4;/h5-12,18H,1-4H3;1H
    Key: KSCQDDRPFHTIRL-UHFFFAOYSA-N
  • InChI=1/C17H21N3/c1-19(2)15-9-5-13(6-10-15)17(18)14-7-11-16(12-8-14)20(3)4/h5-12,18H,1-4H3
    Key: JPIYZTWMUGTEHX-UHFFFAOYAY
  • InChI=1/C17H21N3.ClH/c1-19(2)15-9-5-13(6-10-15)17(18)14-7-11-16(12-8-14)20(3)4;/h5-12,18H,1-4H3;1H
    Key: KSCQDDRPFHTIRL-UHFFFAOYAK
  • [N@H]=C(c1ccc(N(C)C)cc1)c2ccc(N(C)C)cc2
  • Cl.[N@H]=C(c1ccc(N(C)C)cc1)c2ccc(N(C)C)cc2
Properties C17H22ClN3Molar mass303.83 g·mol Melting point267 °C (513 °F; 540 K) Hazards GHS labelling: DangerH302, H311, H319, H351, H411P201, P202, P264, P270, P273, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P312, P322, P330, P337+P313, P361, P363, P391, P405, P501NFPA 704 (fire diamond)
3
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Auramine O is a diarylmethane dye used as a fluorescent stain. In its pure form, Auramine O appears as yellow needle crystals. It is insoluble in water and soluble in ethanol and DMSO.

Auramine O can be used to stain acid-fast bacteria (e.g. Mycobacterium, where it binds to the mycolic acid in its cell wall) in a way similar to Ziehl–Neelsen stain. It can also be used as a fluorescent version of the Schiff reagent.

Auramine O can be used together with Rhodamine B as the Truant auramine-rhodamine stain for Mycobacterium tuberculosis. It can be also used as an antiseptic agent.

Wikipedia source