Safranin

Safranin (Safranin O or basic red 2) is a biological stain used in histology and cytology. Safranin is used as a counterstain in some staining protocols, colouring cell nuclei red. This is the classic counterstain in both Gram stains and endospore staining. It can also be used for the detection of cartilage, mucin and mast cell granules.

Safranin
Solid safranin
Safranin in aqueous solution
Names
Preferred IUPAC name
3,7-Diamino-2,8-dimethyl-5-phenylphenazin-5-ium chloride
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.836
UNII
  • InChI=1S/C20H18N4.ClH/c1-12-8-17-19(10-15(12)21)24(14-6-4-3-5-7-14)20-11-16(22)13(2)9-18(20)23-17;/h3-11H,1-2H3,(H3,21,22);1H Y
    Key: OARRHUQTFTUEOS-UHFFFAOYSA-N Y
  • InChI=1/C20H18N4.ClH/c1-12-8-17-19(10-15(12)21)24(14-6-4-3-5-7-14)20-11-16(22)13(2)9-18(20)23-17;/h3-11H,1-2H3,(H3,21,22);1H
    Key: OARRHUQTFTUEOS-UHFFFAOYAR
  • InChI=1/C20H18N4/c1-12-8-17-19(10-15(12)21)24(14-6-4-3-5-7-14)20-11-16(22)13(2)9-18(20)23-17/h3-11H,1-2H3,(H3,21,22)/p+1
  • [Cl-].n1c4c([n+](c2c1cc(c(N)c2)C)c3ccccc3)cc(c(c4)C)N
Properties
C20H19ClN4
Molar mass 350.85 g·mol−1
Soluble
Hazards
GHS labelling:
Danger
H315, H318
P264, P280, P302+P352, P305+P351+P338, P310, P332+P313, P362
NFPA 704 (fire diamond)
2
0
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Safranin typically has the chemical structure shown at right (sometimes described as dimethyl safranin). There is also trimethyl safranin, which has an added methyl group in the ortho- position (see Arene substitution pattern) of the lower ring. Both compounds behave essentially identically in biological staining applications, and most manufacturers of safranin do not distinguish between the two. Commercial safranin preparations often contain a blend of both types.

Safranin is also used as redox indicator in analytical chemistry.

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