Lucigenin

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| verifiedrevid = 400292840

| ImageFile=Lucigenin.svg

| ImageSize=150px

| PIN=10,10{{prime}}-Dimethyl[9,9{{prime}}-biacridine]-10,10{{prime}}-diium dinitrate

| OtherNames=Bis-N-methylacridinium nitrate; N,{{prime|N}}-Dimethyl-9,9'-bisacridinium nitrate

|Section1={{Chembox Identifiers

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

| ChemSpiderID = 58609

| InChI = 1/C28H22N2.2NO3/c1-29-23-15-7-3-11-19(23)27(20-12-4-8-16-24(20)29)28-21-13-5-9-17-25(21)30(2)26-18-10-6-14-22(26)28;2*2-1(3)4/h3-18H,1-2H3;;/q+2;2*-1

| InChIKey = KNJDBYZZKAZQNG-UHFFFAOYAH

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

| StdInChI = 1S/C28H22N2.2NO3/c1-29-23-15-7-3-11-19(23)27(20-12-4-8-16-24(20)29)28-21-13-5-9-17-25(21)30(2)26-18-10-6-14-22(26)28;2*2-1(3)4/h3-18H,1-2H3;;/q+2;2*-1

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

| StdInChIKey = KNJDBYZZKAZQNG-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|??}}

| CASNo=2315-97-1

| PubChem=65099

| SMILES = C[n+]1c2ccccc2c(c3c1cccc3)c4c5ccccc5[n+](c6c4cccc6)C.[N+](=O)([O-])[O-].[N+](=O)([O-])[O-]

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|Section2={{Chembox Properties

| C=28 | H=22 | N=4 | O=6

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Lucigenin is an aromatic compound used in areas which include chemiluminescence. Its chemical name is bis-N-methylacridinium nitrate. It exhibits a bluish-green fluorescence.

It is used as a probe for superoxide anion in biology, for its chemiluminescent properties.

Synthesis

It may be prepared from acridone.

There's also a route from toluene:{{cite journal |last1=Amiet |first1=R. Gary |title=The preparation of lucigenin: An experiment with charm |journal=Journal of Chemical Education |date=February 1982 |volume=59 |issue=2 |pages=163–164 |doi=10.1021/ed059p163 |access-date=20 November 2023 |url=https://dx.doi.org/10.1021/ed059p163|issn=0021-9584|url-access=subscription }}

File: Synthesis of lucigenin starting from toluene.png

References