Auramine O

"Canary yellow" redirects here. For the color, see Yellow. For the bird, see Yellow canary.

Auramine O

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
CAS Number	2465-27-2^Y
3D model (JSmol)	Interactive image Interactive 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^Y Key: KSCQDDRPFHTIRL-UHFFFAOYSA-N^Y 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
SMILES [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
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 ^YN ?) Infobox references

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.

References

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

• Auramine O spectra data