4395. Gentian Violet

Nomenclature

CAS number: 548-62-9
N-[4-[Bis[4-(dimethylamino)phenyl]methylene]-2,5-cyclohexadien-1-ylidene]-N-methylmethanaminium chloride (1:1); C.I. Basic Violet 3; hexamethylpararosaniline chloride; hexamethyl-p-rosaniline chloride; aniline violet; crystal violet; methylrosanilinium chloride; C.I. 42555; Axuris (Fournier); Badil (Bayer); Gentiaverm (Berlin-Chemie); Pyoktanin (Merck KGaA).
C25H30ClN3; mol wt 407.98.
C 73.60%, H 7.41%, Cl 8.69%, N 10.30%.

Description and references

Prepn and properties: Colour Index vol. 4 (3rd ed., 1971) p 4391. Toxicity studies: H. C. Hodge et al., Toxicol. Appl. Pharmacol. 22, 1 (1972). Review of metabolism and mode of action: R. Docampo, S. N. Moreno, Drug Metab. Rev. 22, 161-178 (1990); of use as a biological stain: Conn's Biological Stains, R. W. Horobin, J. A. Kiernan, Eds. (BIOS Scientific Publishers Ltd, Oxford, UK, 10th ed., 2002) 193-195.

Chemical structure

Properties

Dark green powder or greenish, glistening pieces with metallic luster. Soly (%): water 0.2-1.7; ethanol 3-14; acetone 0.4; chloroform 5.1. Insol in xylene. Absorption max (water): 590 nm. Changes from yellow at pH 0.0 to blue-violet at pH 2.0. LD50 orally in mice, rats: 1.2, 1.0 g/kg (Hodge).

Note

Commercial product, which is usually admixed with pentamethylpararosaniline chloride and tetramethylpararosaniline chloride, contains not less than 96% gentian violet.

Use

As dye for wood, silk, paper; in inks. Biological stain for bacterial components, vascular plant tissues, amyloid, etc. Used in Gram stain. As addition to microbiological culture media. Indicator for copper salts. Used to quench autofluorescence.

Therapeutic Category

Anti-infective (topical). Has been used as anthelmintic (Nematodes). Blood additive to prevent transmission of Chagas' disease by blood transfusion.

Therapeutic Category (Veterinary)

Antimicrobial (topical); mycostatic agent in poultry feed.

Keywords

Anthelmintic (Nematodes); Antiseptic/Disinfectant; Dyes