Crystal violet

Not to be confused with Cresyl violet.
Crystal violet
Kekulé, skeletal formula of a crystal violet minor tautomer
Ball-and-stick model of crystal violet as a chloride salt
Names
Preferred IUPAC name
4-{Bis[4-(dimethylamino)phenyl]methylidene}-N,N-dimethylcyclohexa-2,5-dien-1-iminium 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
3D model (JSmol)
3580948
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.008.140 Edit this at Wikidata
EC Number
  • 208-953-6
KEGG
MeSH Gentian+violet
RTECS number
  • BO9000000
UNII
UN number 3077
  • 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 checkY
    Key: ZXJXZNDDNMQXFV-UHFFFAOYSA-M checkY
  • 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
  • [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
C25H30ClN3
Molar mass 407.99 g·mol−1
Melting point 205 °C (401 °F; 478 K)
4 g/L at 25 °C[1]
Pharmacology
D01AE02 (WHO) G01AX09 (WHO)
Hazards
GHS labelling:
GHS05: Corrosive GHS07: Exclamation mark GHS08: Health hazard GHS09: Environmental hazard
Danger
H302, H318, H351, H410
P273, P280, P305+P351+P338, P501
Lethal dose or concentration (LD, LC):
1.2 g/kg (oral, mice)

1.0 g/kg (oral, rats)[2]

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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 The medical use of the dye has been largely superseded by more modern drugs, although it is still listed by the World Health Organization.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.

  1. ^ Green, Floyd J. (1990). The Sigma-Aldrich Handbook of Stains, Dyes, and Indicators. Milwaukee, Wisconsin: Sigma-Aldrich Corp. pp. 239–240. ISBN 978-0-941633-22-2. OCLC 911335305.
  2. ^ Hodge, H. C.; Indra, J.; Drobeck, H. P.; Duprey, L. P.; Tainter, M. L. (1972). "Acute oral toxicity of methylrosaniline chloride". Toxicology and Applied Pharmacology. 22 (1): 1–5. Bibcode:1972ToxAP..22....1H. doi:10.1016/0041-008X(72)90219-0. PMID 5034986.