Auramine O

{{redirect|Canary yellow|the color|Yellow|the bird|Yellow canary}}

{{chembox

| Watchedfields = changed

| verifiedrevid = 401809121

| Name = Auramine O

| ImageFile = Auramine O Formula V.1.svg

| ImageName = 340

| ImageFileL1 = Sample of Auramine O.jpg

| ImageSizeL1 = 130

| ImageCaptionL1 = Solid Auramine O

| ImageFileR1 = Auramine O in aqueous solution.jpg

| ImageSizeR1 = 130

| ImageCaptionR1 = Auramine O in aqueous solution

| IUPACName = bis[4-(dimethylamino)phenyl]methaniminium chloride

| OtherNames = auramine hydrochloride, basic yellow 2, pyocatanium aureum, aizen auramine, pyoktanin yellow, canary yellow, pyoktanin, or C.I. 41000

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 16254

| 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

| InChIKey = JPIYZTWMUGTEHX-UHFFFAOYAY

| PubChem = 17170

| EC_number = 219-567-2

| UNII = DL992L7W39

| InChI1 = 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

| InChIKey1 = KSCQDDRPFHTIRL-UHFFFAOYAK

| SMILES1 = Cl.[N@H]=C(c1ccc(N(C)C)cc1)c2ccc(N(C)C)cc2

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = KSCQDDRPFHTIRL-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 2465-27-2

| SMILES = [N@H]=C(c1ccc(N(C)C)cc1)c2ccc(N(C)C)cc2

}}

|Section2={{Chembox Properties

| C=17 | H=22 | N=3 | Cl=1

| Density =

| MeltingPtC = 267

| MeltingPt_notes =

| BoilingPt =

}}

|Section7={{Chembox Hazards

| GHSPictograms = {{GHS06}}{{GHS07}}{{GHS08}}{{GHS09}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|302|311|319|351|411}}

| PPhrases = {{P-phrases|201|202|264|270|273|280|281|301+312|302+352|305+351+338|308+313|312|322|330|337+313|361|363|391|405|501}}

| NFPA-H = 3

| NFPA-F = 1

| NFPA-R = 0

}}

}}

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.{{cite journal |vauthors=Kommareddi S, Abramowsky C, Swinehart G, Hrabak L |title=Nontuberculous mycobacterial infections: comparison of the fluorescent auramine-O and Ziehl–Neelsen techniques in tissue diagnosis |journal=Hum Pathol |volume=15 |issue=11 |pages=1085–9 |year=1984 |pmid=6208117 |doi=10.1016/S0046-8177(84)80253-1}} It can also be used as a fluorescent version of the Schiff reagent.{{cite journal |vauthors=Khavkin T, Kudryavtseva M, Dragunskaya E, Polotsky Y, Kudryavtsev B |display-authors=3|title=Fluorescent PAS-reaction study of the epithelium of normal rabbit ileum and after challenge with enterotoxigenic Escherichia coli |journal=Gastroenterology |volume=78 |issue=4 |pages=782–90 |year=1980 |pmid=6986320|doi=10.1016/0016-5085(80)90684-8 |doi-access=free }}

Auramine O can be used together with Rhodamine B as the Truant auramine-rhodamine stain for Mycobacterium tuberculosis.{{cite journal |vauthors=Truant J, Brett W, Thomas W |title=Fluorescence microscopy of tubercle bacilli stained with auramine and rhodamine |journal=Henry Ford Hosp Med Bull |volume=10 |pages=287–96 |year=1962 |pmid=13922644}}{{cite journal |vauthors=Arrowood M, Sterling C |title=Comparison of conventional staining methods and monoclonal antibody-based methods for Cryptosporidium oocyst detection |journal=J Clin Microbiol |volume=27 |issue=7 |pages=1490–5 |year=1989 |pmid=2475523 |pmc=267601|doi=10.1128/JCM.27.7.1490-1495.1989 }} It can be also used as an antiseptic agent.