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Auramine O

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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)

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

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.

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. 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.

External links

Auramine O spectra data

v t e Microbial and histological stains
Iron/hemosiderin	Perls Prussian blue
Lipids	Sudan stain Sudan II Sudan III Sudan IV Oil Red O Sudan Black B
Carbohydrates	Alcian blue Mucicarmine Periodic acid–Schiff stain
Amyloid	Congo red Thioflavin
Bacteria	Gram stain Methyl violet/Gentian violet Safranin Acid-fast Ziehl–Neelsen stain/Kinyoun stain Carbol fuchsin/Fuchsine Methylene blue Auramine–rhodamine stain Auramine O Rhodamine B Auramine phenol stain
Connective tissue	trichrome stain: Masson's trichrome stain/Lillie's trichrome Light Green SF yellowish Biebrich scarlet Phosphomolybdic acid Fast Green FCF Sirius Red Van Gieson's stain
Other	Cresyl violet Cyanine Jaswant Singh–Bhattacharji (JSB) stain H&E stain Haematoxylin Eosin Y Janus Green B Giemsa stain Gömöri trichrome stain Luxol fast blue stain Methyl blue Moeller stain Movat's stain Neutral red Schaeffer–Fulton stain Silver stain Bielschowsky stain Grocott's methenamine silver stain Warthin–Starry stain Wright's stain
Tissue stainability	Acidophilic Basophilic Chromophobic

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