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Acriflavine

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Acriflavine
Wireframe of acriflavine
Wireframe of acriflavine
Names
IUPAC name 3,6-Diamino-10-methylacridin-10-ium chloride
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.211.047 Edit this at Wikidata
EC Number
  • 201-668-8
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C14H13N3.ClH/c1-17-13-7-11(15)4-2-9(13)6-10-3-5-12(16)8-14(10)17;/h2-8H,1H3,(H3,15,16);1HKey: KKAJSJJFBSOMGS-UHFFFAOYSA-N
  • InChI=1S/C14H13N3.C13H11N3.ClH/c1-17-13-7-11(15)4-2-9(13)6-10-3-5-12(16)8-14(10)17;14-10-3-1-8-5-9-2-4-11(15)7-13(9)16-12(8)6-10;/h2-8H,1H3,(H3,15,16);1-7H,14-15H2;1HKey: PEJLNXHANOHNSU-UHFFFAOYSA-N
  • InChI=1S/C14H13N3.C13H11N3.ClH/c1-17-13-7-11(15)4-2-9(13)6-10-3-5-12(16)8-14(10)17;14-10-3-1-8-5-9-2-4-11(15)7-13(9)16-12(8)6-10;/h2-8H,1H3,(H3,15,16);1-7H,14-15H2;1HKey: PEJLNXHANOHNSU-UHFFFAOYSA-N
SMILES
  • .C1=C2C=C(N)C=CC2=CC2=C1C=C(N)C=C2
  • .n1c3c(cc2c1cc(N)cc2)ccc(c3)N.Nc3cc2(c1cc(N)ccc1cc2cc3)C
Properties
Chemical formula C14H14ClN3
Molar mass 259.74 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Acriflavine is a topical antiseptic. It has the form of an orange or brown powder. It may be harmful in the eyes or if inhaled. It is a dye and it stains the skin and may irritate. Commercial preparations are often mixtures with proflavine. It is known by a variety of commercial names.

Acriflavine was developed in 1912 by Paul Ehrlich, a German medical researcher and was used during the First World War against sleeping sickness. It is derived from acridine. The hydrochloride form is more irritating than the neutral form.

Acriflavine is also used as treatment for external fungal infections of aquarium fish. In recent years Acriflavine has been shown to have anti-cancer activity.

References

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