Auramine O

Auramine O is a diarylmethane dye used as a fluorescent stain. In its pure form, Auramine O appears as yellow needle crystals. It is very soluble in water and soluble in ethanol.

"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 pictograms
GHS Signal word	Danger
GHS hazard statements	H302, H311, H319, H351, H411
GHS precautionary statements	P201, P202, P264, P270, P273, P280, P281, P301+312, P302+352, P305+351+338, P308+313, P312, P322, P330, P337+313, P361, P363, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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

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, Polotsky Y, Kudryavtsev B (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