Gentian violet

Crystal violet
Names


IUPAC name Tris(4-(dimethylamino)phenyl)methylium chloride
Other names Aniline violet Basic violet 3 Baszol Violet 57L Brilliant Violet 58 Hexamethyl-p-rosaniline chloride Methylrosanilide chloride Methyl Violet 10B Methyl Violet 10BNS Pyoktanin
Identifiers
CAS Number	548-62-9^Y 1733-13-7 (base)^N
3D model (Jmol)	Interactive image Interactive image
Beilstein Reference	3580948
ChEBI	CHEBI:41688^N
ChEMBL	ChEMBL64894^Y
ChemSpider	10588^Y
DrugBank	DB00406^N
ECHA InfoCard	100.034.892
EC Number	208-953-6
KEGG	D01046^Y
MeSH	Gentian+violet
PubChem	11057 CID 68050 from PubChem (base)
RTECS number	BO9000000
UNII	J4Z741D6O5^Y B4JIJ2C6AT (base)^N
UN number	3077
InChI InChI=1S/C25H30N3.ClH/c1-26(2)22-13-7-19(8-14-22)25(20-9-15-23(16-10-20)27(3)4)21-11-17-24(18-12-21)28(5)6;/h7-18H,1-6H3;1H/q+1;/p-1^Y Key: ZXJXZNDDNMQXFV-UHFFFAOYSA-M^Y InChI=1/C25H30N3.ClH/c1-26(2)22-13-7-19(8-14-22)25(20-9-15-23(16-10-20)27(3)4)21-11-17-24(18-12-21)28(5)6;/h7-18H,1-6H3;1H/q+1;/p-1 Key: ZXJXZNDDNMQXFV-REWHXWOFAV
SMILES [Cl-].CN(C)c1ccc(cc1)[C+](c1ccc(cc1)N(C)C)c1ccc(cc1)N(C)C [Cl-].CN(C)C1=CC=C(C=C1)[C+](C1=CC=C(C=C1)N(C)C)C1=CC=C(C=C1)N(C)C
Properties
Chemical formula	C₂₅H₃₀ClN₃
Molar mass	407.99 g·mol⁻¹
Melting point	205 °C (401 °F; 478 K)
Pharmacology
ATC code	D01AE02 (WHO) G01AX09 (WHO)
Hazards
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H302, H318, H351, H410
GHS precautionary statements	P273, P280, P305+351+338, P501
EU classification (DSD)	Xn N
R-phrases	R22, R40, R41, R50/53
S-phrases	(S2), S26, S36/37/39, S46, S60, S61
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	1.2 g/kg (oral, mice) 1.0 g/kg (oral, rats)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is ^YN ?)
Infobox references

1.0 g/kg (oral, rats)

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 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 The medical use of the dye has been largely superseded by more modern drugs, although it is still listed by the World Health Organization.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 a gentian flower; it is not made from gentians or from violets.

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:

Second, this colourless compound is oxidized to the coloured cationic form: (A typical oxidizing agent is manganese dioxide).

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