Crystal violet or gentian violet, also known as methyl violet 10B or hexamethyl pararosaniline chloride, is a triarylmethane dye used as a histological stain and in Gram's method of classifying bacteria. Crystal violet has antibacterial, antifungal, and anthelmintic (vermicide) properties and was formerly important as a topical antiseptic. The medical use of the dye has been largely superseded by more modern drugs, although it is still listed by the World Health Organization. The name gentian violet was originally used for a mixture of methyl pararosaniline dyes (methyl violet), but is now often considered a synonym for crystal violet. The name refers to its colour, being like that of the petals of certain gentian flowers; it is not made from gentians or violets. Production A number of possible routes can be used to prepare crystal violet. The original procedure developed by the German chemists Kern and Caro involved the reaction of dimethylaniline with phosgene to give 4,4′-bis(dimethylamino)benzophenone (Michler's ketone) as an intermediate. This was then reacted with additional dimethylaniline in the presence of phosphorus oxychloride and hydrochloric acid. The dye can also be prepared by the condensation of formaldehyde and dimethylaniline to give a leuco dye: CH2O + 3 C6H5N(CH3)2 → CH(C6H4N(CH3)2)3 + H2O Second, this colourless compound is oxidized to the coloured cationic form (hereafter with oxygen, but a typical oxidizing agent is manganese dioxide, MnO2): CH(C6H4N(CH3)2)3 + HCl + O2 → [C(C6H4N(CH3)2)3]Cl + H2O Dye colour When dissolved in water, the dye has a blue-violet colour with an absorbance maximum at 590 nm and an extinction coefficient of 87,000 M−1 cm−1. The colour of the dye depends on the acidity of the solution. At a pH of +1.0, the dye is green with absorption maxima at 420 nm and 620 nm, while in a strongly acidic solution (pH −1.0), the dye is yellow with an absorption maximum at 420 nm. The different colours are a result of the different charged states of the dye molecule. In the yellow form, all three nitrogen atoms carry a positive charge, of which two are protonated, while the green colour corresponds to a form of the dye with two of the nitrogen atoms positively charged. At neutral pH, both extra protons are lost to the solution, leaving only one of the nitrogen atoms positive charged. The pKa for the loss of the two protons are approximately 1.15 and 1.8. In alkaline solutions, nucleophilic