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)

ChemSpider

16254^Y

ECHA InfoCard

100.017.789

PubChem CID

17170

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

R-phrases (outdated)

R22 R24 R40

S-phrases (outdated)

S36/37 S45

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 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.

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 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

↑ 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. PMID 6208117. doi:10.1016/S0046-8177(84)80253-1.
↑ 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. 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. PMC 267601 . PMID 2475523.

External links

Auramine O spectra data

Microbial and histological stains
Iron/hemosiderin	Prussian blue
Lipids	Sudan stain Sudan II Sudan III Sudan IV Oil Red O Sudan Black B
Carbohydrates	Periodic acid–Schiff stain
Amyloid	Congo red
Bacteria	Gram staining Methyl violet/Gentian violet Safranin Ziehl–Neelsen stain/acid-fast Carbol fuchsin/Fuchsine Methylene blue Auramine-rhodamine stain Auramine O Rhodamine B
Connective tissue	trichrome stain: Masson's trichrome stain/Lillie's trichrome Light Green SF yellowish Biebrich scarlet Phosphomolybdic acid Fast Green FCF Van Gieson's stain
Other	H&E stain Haematoxylin Eosin Y Silver stain Grocott's methenamine silver stain Warthin–Starry stain Methyl blue Wright's stain Giemsa stain Gömöri trichrome stain Neutral red Janus Green B Alcian blue stain Movat's stain
Tissue stainability	Acidophilic Basophilic Chromophobic

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