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Auramine O

Summary

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
  • 2465-27-2 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
ChemSpider
  • 16254 checkY
ECHA InfoCard 100.017.789 Edit this at Wikidata
EC Number
  • 219-567-2
  • 17170
UNII
  • DL992L7W39
  • DTXSID9020114 Edit this at Wikidata
  • 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 checkY
    Key: KSCQDDRPFHTIRL-UHFFFAOYSA-N checkY
  • 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).
checkY verify (what is checkY☒N ?)
Infobox references

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.

References edit

  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.

External links edit

  • Auramine O spectra data

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