Auramine O


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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
340

Solid Auramine O

Auramine O in aqueous solution

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 InfoCard 100.017.789 Edit this at Wikidata
EC 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 check

    Key: KSCQDDRPFHTIRL-UHFFFAOYSA-N check

  • 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
C17H22ClN3
Molar mass 303.83 g·mol−1
Melting point 267 °C (513 °F; 540 K)
Hazards
GHS labelling:
GHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H302, H311, H319, H351, H411
P201, P202, P264, P270, P273, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P312, P322, P330, P337+P313, P361, P363, P391, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code

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 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.[1] It can also be used as a fluorescent version of the Schiff reagent.[2]

Auramine O can be used together with Rhodamine B as the Truant auramine-rhodamine stain for Mycobacterium tuberculosis.[3][4] It can be also used as an antiseptic agent.

  1. ^ Kommareddi S, Abramowsky C, Swinehart G, Hrabak L (1984). "Nontuberculous mycobacterial infections: comparison of the fluorescent auramine-O and Ziehl–Neelsen techniques in tissue diagnosis". Hum Pathol. 15 (11): 1085–9. doi:10.1016/S0046-8177(84)80253-1. PMID 6208117.
  2. ^ Khavkin T, Kudryavtseva M, Dragunskaya E, et al. (1980). "Fluorescent PAS-reaction study of the epithelium of normal rabbit ileum and after challenge with enterotoxigenic Escherichia coli". Gastroenterology. 78 (4): 782–90. doi:10.1016/0016-5085(80)90684-8. PMID 6986320.
  3. ^ Truant J, Brett W, Thomas W (1962). "Fluorescence microscopy of tubercle bacilli stained with auramine and rhodamine". Henry Ford Hosp Med Bull. 10: 287–96. PMID 13922644.
  4. ^ Arrowood M, Sterling C (1989). "Comparison of conventional staining methods and monoclonal antibody-based methods for Cryptosporidium oocyst detection". J Clin Microbiol. 27 (7): 1490–5. doi:10.1128/JCM.27.7.1490-1495.1989. PMC 267601. PMID 2475523.