Crystal violet

Crystal violet
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
CAS Number	548-62-9 ; 1733-13-7 (base) ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	3580948
ChEBI	CHEBI:41688 ;
ChEMBL	ChEMBL64894 ;
ChemSpider	10588 ;
DrugBank	DB00406 ;
ECHA InfoCard	100.008.140
EC Number	208-953-6;
KEGG	D01046 ;
MeSH	Gentian+violet
PubChem CID	11057; CID 68050 from PubChem (base);
RTECS number	BO9000000;
UNII	J4Z741D6O5 ; B4JIJ2C6AT (base) ;
UN number	3077
CompTox Dashboard (EPA)	DTXSID5020653 ;
	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 Key: ZXJXZNDDNMQXFV-UHFFFAOYSA-M ; 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)
Solubility in water	4 g/L at 25 °C
Pharmacology
ATC code	D01AE02 (WHO) G01AX09 (WHO)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H318, H351, H410
Precautionary statements	P273, P280, P305+P351+P338, P501
	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). verify (what is ?) Infobox references

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 The medical use of the dye has been largely superseded by more modern drugs, although it is still listed by the World Health Organization.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

^ 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.
^ 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.

[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.

[1]

[2]

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
CAS Number	548-62-9^Y 1733-13-7 (base)^Y
3D model (JSmol)	Interactive image Interactive image
Beilstein Reference	3580948
ChEBI	CHEBI:41688^Y
ChEMBL	ChEMBL64894^Y
ChemSpider	10588^Y
DrugBank	DB00406^N
ECHA InfoCard	100.008.140
EC Number	208-953-6
KEGG	D01046^Y
MeSH	Gentian+violet
PubChem CID	11057 CID 68050 from PubChem (base)
RTECS number	BO9000000
UNII	J4Z741D6O5^Y B4JIJ2C6AT (base)^Y
UN number	3077
CompTox Dashboard (EPA)	DTXSID5020653
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)
Solubility in water	4 g/L at 25 °C^[1]
Pharmacology
ATC code	D01AE02 (WHO) G01AX09 (WHO)
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H318, H351, H410
Precautionary statements	P273, P280, P305+P351+P338, P501
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	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 ^YN ?) Infobox references