Lucigenin
Names
Preferred IUPAC name
10,10′-Dimethyl[9,9′-biacridine]-10,10′-diium dinitrate
Other names
Bis-N-methylacridinium nitrate; N,N′-Dimethyl-9,9'-bisacridinium nitrate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.017.295
  • InChI=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 checkY
    Key: KNJDBYZZKAZQNG-UHFFFAOYSA-N checkY
  • 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
    Key: KNJDBYZZKAZQNG-UHFFFAOYAH
  • C[n+]1c2ccccc2c(c3c1cccc3)c4c5ccccc5[n+](c6c4cccc6)C.[N+](=O)([O-])[O-].[N+](=O)([O-])[O-]
Properties
C28H22N4O6
Molar mass 510.506 g·mol−1
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

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:[1]

Synthesis of Lucigenin from Toluene. References in the image description.
Synthesis of Lucigenin from Toluene. References in the image description.

References

  1. ↑ Amiet, R. Gary (February 1982). "The preparation of lucigenin: An experiment with charm". Journal of Chemical Education. 59 (2): 163–164. doi:10.1021/ed059p163. ISSN 0021-9584. Retrieved 20 November 2023.


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