Auramine O (original) (raw)
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Auramine O
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 Solid Auramine O  Auramine O in aqueous solution |
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| Names | |
| IUPAC name bis[4-(dimethylamino)phenyl]methaniminium chloride | |
| Other namesauramine hydrochloride, basic yellow 2, pyocatanium aureum, aizen auramine, pyoktanin yellow, canary yellow, pyoktanin, or C.I. 41000 | |
| Identifiers | |
| CAS Number | 2465-27-2  Y |
| 3D model (JSmol) | Interactive imageInteractive image |
| ChemSpider | 16254 Y |
| ECHA InfoCard | 100.017.789  |
| EC Number | 219-567-2 |
| PubChem CID | 17170 |
| UNII | DL992L7W39 |
| CompTox Dashboard (EPA) | DTXSID9020114 |
| InChI 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 YKey: KSCQDDRPFHTIRL-UHFFFAOYSA-N YInChI=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,1-4H3Key: JPIYZTWMUGTEHX-UHFFFAOYAYInChI=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;1HKey: KSCQDDRPFHTIRL-UHFFFAOYAK |
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| SMILES [N@H]=C(c1ccc(N(C)C)cc1)c2ccc(N(C)C)cc2Cl.[N@H]=C(c1ccc(N(C)C)cc1)c2ccc(N(C)C)cc2 | |
| Properties | |
| Chemical formula | C17H22ClN3 |
| Molar mass | 303.83 g·mol−1 |
| Melting point | 267 °C (513 °F; 540 K) |
| Hazards | |
| GHS labelling: | |
| Pictograms |     |
| Signal word | Danger |
| Hazard statements | H302, H311, H319, H351, H411 |
| Precautionary statements | 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) |  3 1 0 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is Y N ?) Infobox references |
Chemical compound
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.[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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.