6060. Methylene Blue

Nomenclature

CAS number: 61-73-4
3,7-Bis(dimethylamino)phenothiazin-5-ium chloride; C.I. Basic Blue 9; methylthioninium chloride; tetramethylthionine chloride; 3,7-bis(dimethylamino)phenazathionium chloride; Swiss blue; C.I. 52015; C.I. Solvent Blue 8; Urolene Blue (Star).
C16H18ClN3S; mol wt 319.85.
C 60.08%, H 5.67%, Cl 11.08%, N 13.14%, S 10.03%.

Description and references

First prepd by Caro in 1876. Provided technically as the zinc double chloride; used medically in a zinc free form. Prepn: H. E. Fierz-David, L. Blangey, Fundamental Processes of Dye Chemistry (Interscience, New York, 1949) p 311. See also Colour Index vol. 4 (3rd ed., 1971) p 4470. TLC determn: G. Balansard et al., Ann. Pharm. Fr. 46, 129 (1988). Use as marker for reticulocytes: B. Rudensky, Scand. J. Clin. Lab. Invest. 57, 291 (1997); in melanoma targeted radiotherapy: E. M. Link et al., Pigment Cell Res. 7, 358 (1994); P. J. Blower et al., Nucl. Med. Biol. 24, 305 (1997). Review of use as vital dye: P. Barbosa, T. M. Peters, Histochem. J. 3, 71-93 (1971). History and properties: R. D. Lillie, P. T. Donaldson, Stain Technol. 54, 33-39 (1979). Review of photochemistry: E. M. Tuite, J. M. Kelly, J. Photochem. Photobiol. B 21, 103-124 (1993). Review of use as cationic dye in ceramic quality control: J. E, Funk, D. R. Dinger in Science of Whitewares, V. E. Henkes et al., Eds. (American Ceramic Society, OH, 1996) pp 21-31. Review of use in methemoglobinaemia: J. W. Harvey, A. S. Keitt, Br. J. Haematol. 54, 29-41 (1983).

Chemical structure

Derivative

Trihydrate.

Nomenclature

CAS number: 7220-79-3

Properties

Dark green crystals or crystalline powder with bronze luster. Odorless; stable in air. Absorption max: 668, 609 nm. Sol in water and chloroform; sparingly sol in alcohol. Deep blue soln in water or alcohol. Forms double salts.

Use

Stain in bacteriology; reagent for several chemicals; as mixed indicator; as redox colorimetric agent. Targeting agent for melanoma.

Therapeutic Category

Antimethemoglobinemic; antidote (cyanide).

Therapeutic Category (Veterinary)

Antiseptic; disinfectant; antidote (cyanide and nitrate).

Keywords

Antidote (Cyanide); Antimethemoglobinemic