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Details

Stereochemistry ACHIRAL
Molecular Formula C25H30N3.Cl
Molecular Weight 407.979
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GENTIAN VIOLET

SMILES

[Cl-].CN(C)C1=CC=C(C=C1)C(C2=CC=C(C=C2)N(C)C)=C3C=CC(C=C3)=[N+](C)C

InChI

InChIKey=ZXJXZNDDNMQXFV-UHFFFAOYSA-M
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

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C25H30N3
Molecular Weight 372.5258
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.drugbank.ca/drugs/DB00406

Gentian violet ((GV) hexamethyl pararosaniline, also known as crystal violet, methyl violet) is a triphenylmethane dye with anti-bacterial, anti-fungal, anti-helminithic, anti-trypanosomal, anti-angiogenic and anti-tumor properties. GV has a lengthy history and has been used successfully as monotherapy and an adjunct to treatment in a variety of diseases. Gentian violet interacts with negatively charged components of bacterial cells including the lipopolysaccharide (on the cell wall), the peptidoglycan and DNA. A similar cell penetration and DNA binding process is thought to take place for fungal cells as well. Because Gentian violet is a mutagen and mitotic poison, cell growth is consequently inhibited. A photodynamic action of gentian violet, apparently mediated by a free-radical mechanism, has recently been described in bacteria and in the protozoan T. cruzi. Evidence also suggests that gentian violet dissipates the bacterial (and mitochondrial) membrane potential by inducing permeability. This is followed by respiratory inhibition. This anti-mitochondrial activity might explain gentian violet's efficacy towards both bacteria and yeast with relatively mild effects on mammalian cells.

Originator

Curator's Comment: Synthesis of Gentian violet was attributed French chemist Charles Lauth in 1861 under the name of ‘Violet de Paris

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
GENTIAN VIOLET

Approved Use

Topical gentian violet is used to treat some types of fungus infections inside the mouth (thrush) and of the skin.
Preventing
GENTIAN VIOLET

Approved Use

Gentian violet has weak antibacterial effects and may be used on minor cuts and scrapes to prevent infection.
Doses

Doses

DosePopulationAdverse events​
1 % single, ophthalmic
Dose: 1 %
Route: ophthalmic
Route: single
Dose: 1 %
Sources:
unhealthy, 55 years
n = 1
Health Status: unhealthy
Age Group: 55 years
Sex: F
Population Size: 1
Sources:
Other AEs: Keratoconjunctivitis...
Other AEs:
Keratoconjunctivitis
Sources:
2 % 10 times / day multiple, oral
Dose: 2 %, 10 times / day
Route: oral
Route: multiple
Dose: 2 %, 10 times / day
Sources:
unhealthy, infant
n = 1
Health Status: unhealthy
Age Group: infant
Population Size: 1
Sources:
Disc. AE: Swollen tongue, Oral mucosa pain...
AEs leading to
discontinuation/dose reduction:
Swollen tongue
Oral mucosa pain
Sources:
AEs

AEs

AESignificanceDosePopulation
Keratoconjunctivitis
1 % single, ophthalmic
Dose: 1 %
Route: ophthalmic
Route: single
Dose: 1 %
Sources:
unhealthy, 55 years
n = 1
Health Status: unhealthy
Age Group: 55 years
Sex: F
Population Size: 1
Sources:
Oral mucosa pain Disc. AE
2 % 10 times / day multiple, oral
Dose: 2 %, 10 times / day
Route: oral
Route: multiple
Dose: 2 %, 10 times / day
Sources:
unhealthy, infant
n = 1
Health Status: unhealthy
Age Group: infant
Population Size: 1
Sources:
Swollen tongue Disc. AE
2 % 10 times / day multiple, oral
Dose: 2 %, 10 times / day
Route: oral
Route: multiple
Dose: 2 %, 10 times / day
Sources:
unhealthy, infant
n = 1
Health Status: unhealthy
Age Group: infant
Population Size: 1
Sources:
Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.
2013 Sep 5
Patents

Sample Use Guides

Clean the affected area and apply a small amount of this product on the area 1 to 3 times daily. May be covered with a sterile bandage.
Route of Administration: Topical
Gentian violet showed the most potent activity against all Candida isolates tested (MIC range, MIC for 50% of the organisms (MIC(50)) and MIC for 90% of the organisms (MIC(90)) of 0.03-0.25 ug/mL, 0.06 ug/mL and 0.1 2 ug/mL, respectively).
Substance Class Chemical
Created
by admin
on Sat Dec 16 15:54:31 UTC 2023
Edited
by admin
on Sat Dec 16 15:54:31 UTC 2023
Record UNII
J4Z741D6O5
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GENTIAN VIOLET
HSDB   MI   ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
METHYLROSANILINIUM CHLORIDE [MART.]
Common Name English
METHANAMINIUM, N-(4-(BIS(4-(DIMETHYLAMINO)PHENYL)METHYLENE)-2,5-CYCLOHEXADIEN-1-YLIDENE)-N-METHYL-, CHLORIDE
Systematic Name English
GENTIAN VIOLET [VANDF]
Common Name English
C.I. Basic violet 3
Common Name English
GENTIAN VIOLET [USP MONOGRAPH]
Common Name English
BASIC VIOLET 3 [INCI]
Common Name English
METHYLROSANILINIUM CHLORIDE [JAN]
Common Name English
(4-(BIS(P-(DIMETHYLAMINO)PHENYL)METHYLENE)-2,5-CYCLOHEXADIEN-1-YLIDENE)DIMETHYLAMMONIUM CHLORIDE
Common Name English
METHYLROSANILINE CHLORIDE
Common Name English
GENTIAN VIOLET [MI]
Common Name English
METHYLROSANILINII CHLORIDUM [WHO-IP LATIN]
Common Name English
GVS
Brand Name English
METHANAMINIUM, N-(4-(BIS(4-(DIMETHYLAMINO)PHENYL)METHYLENE)-2,5-CYCLOHEXADIEN-1-YLIDENE)-N-METHYL-, CHLORIDE (1:1)
Systematic Name English
GENTIAN VIOLET [HSDB]
Common Name English
GENAPAX
Brand Name English
METHYLROSANILINIUM CHLORIDE
EP   INN   MART.   WHO-DD   WHO-IP  
INN  
Official Name English
METHYLROSANILINIUM CHLORIDE [WHO-IP]
Common Name English
GENTIAN VIOLET [USP-RS]
Common Name English
Methylrosanilinium chloride [WHO-DD]
Common Name English
METHYL VIOLET 10B
Common Name English
HEXAMETHYL PARAROSANILINE CHLORIDE
Common Name English
CRYSTAL VIOLET
Common Name English
GENTIAN VIOLET [USP IMPURITY]
Common Name English
METHYLROSANILINIUM CHLORIDE [EP MONOGRAPH]
Common Name English
NSC-3090
Code English
GENTIAN VIOLET [ORANGE BOOK]
Common Name English
methylrosanilinium chloride [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C461
Created by admin on Sat Dec 16 15:54:31 UTC 2023 , Edited by admin on Sat Dec 16 15:54:31 UTC 2023
EPA PESTICIDE CODE 39502
Created by admin on Sat Dec 16 15:54:31 UTC 2023 , Edited by admin on Sat Dec 16 15:54:31 UTC 2023
CFR 21 CFR 589.1000
Created by admin on Sat Dec 16 15:54:31 UTC 2023 , Edited by admin on Sat Dec 16 15:54:31 UTC 2023
Code System Code Type Description
MESH
D005840
Created by admin on Sat Dec 16 15:54:31 UTC 2023 , Edited by admin on Sat Dec 16 15:54:31 UTC 2023
PRIMARY
PUBCHEM
11057
Created by admin on Sat Dec 16 15:54:31 UTC 2023 , Edited by admin on Sat Dec 16 15:54:31 UTC 2023
PRIMARY
SMS_ID
100000080908
Created by admin on Sat Dec 16 15:54:31 UTC 2023 , Edited by admin on Sat Dec 16 15:54:31 UTC 2023
PRIMARY
HSDB
4366
Created by admin on Sat Dec 16 15:54:31 UTC 2023 , Edited by admin on Sat Dec 16 15:54:31 UTC 2023
PRIMARY
ECHA (EC/EINECS)
208-953-6
Created by admin on Sat Dec 16 15:54:31 UTC 2023 , Edited by admin on Sat Dec 16 15:54:31 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
GENTIAN VIOLET
Created by admin on Sat Dec 16 15:54:31 UTC 2023 , Edited by admin on Sat Dec 16 15:54:31 UTC 2023
PRIMARY Other names: Crystal violet, gentian violet. Description: A dark green powder or greenish, glistening pieces having a metallic lustre; odourless or almost odourless. Solubility: Sparingly soluble in water; soluble in ethanol (~750 g/l) TS and glycerol R; practically insoluble in ether R. Category: Anti-infective drug. Storage: Methylrosanilinium chloride should be kept in a tightly closed container, protected from light. Requirements: Methylrosanilinium chloride contains not less than 96.0% and not more than the equivalent of 101.0% of C25H30ClN3, calculated with reference to the anhydrous substance.
EPA CompTox
DTXSID5020653
Created by admin on Sat Dec 16 15:54:31 UTC 2023 , Edited by admin on Sat Dec 16 15:54:31 UTC 2023
PRIMARY
DRUG CENTRAL
4138
Created by admin on Sat Dec 16 15:54:31 UTC 2023 , Edited by admin on Sat Dec 16 15:54:31 UTC 2023
PRIMARY
MERCK INDEX
m5700
Created by admin on Sat Dec 16 15:54:31 UTC 2023 , Edited by admin on Sat Dec 16 15:54:31 UTC 2023
PRIMARY Merck Index
INN
113
Created by admin on Sat Dec 16 15:54:31 UTC 2023 , Edited by admin on Sat Dec 16 15:54:31 UTC 2023
PRIMARY
ChEMBL
CHEMBL459265
Created by admin on Sat Dec 16 15:54:31 UTC 2023 , Edited by admin on Sat Dec 16 15:54:31 UTC 2023
PRIMARY
EVMPD
SUB08875MIG
Created by admin on Sat Dec 16 15:54:31 UTC 2023 , Edited by admin on Sat Dec 16 15:54:31 UTC 2023
PRIMARY
LACTMED
Gentian Violet
Created by admin on Sat Dec 16 15:54:31 UTC 2023 , Edited by admin on Sat Dec 16 15:54:31 UTC 2023
PRIMARY
CHEBI
41688
Created by admin on Sat Dec 16 15:54:31 UTC 2023 , Edited by admin on Sat Dec 16 15:54:31 UTC 2023
PRIMARY
MESH
C548657
Created by admin on Sat Dec 16 15:54:31 UTC 2023 , Edited by admin on Sat Dec 16 15:54:31 UTC 2023
PRIMARY
WIKIPEDIA
CRYSTAL VIOLET
Created by admin on Sat Dec 16 15:54:31 UTC 2023 , Edited by admin on Sat Dec 16 15:54:31 UTC 2023
PRIMARY
DRUG BANK
DBSALT000604
Created by admin on Sat Dec 16 15:54:31 UTC 2023 , Edited by admin on Sat Dec 16 15:54:31 UTC 2023
PRIMARY
RXCUI
4778
Created by admin on Sat Dec 16 15:54:31 UTC 2023 , Edited by admin on Sat Dec 16 15:54:31 UTC 2023
PRIMARY RxNorm
NCI_THESAURUS
C61776
Created by admin on Sat Dec 16 15:54:31 UTC 2023 , Edited by admin on Sat Dec 16 15:54:31 UTC 2023
PRIMARY
NSC
3090
Created by admin on Sat Dec 16 15:54:31 UTC 2023 , Edited by admin on Sat Dec 16 15:54:31 UTC 2023
PRIMARY
RS_ITEM_NUM
1290002
Created by admin on Sat Dec 16 15:54:31 UTC 2023 , Edited by admin on Sat Dec 16 15:54:31 UTC 2023
PRIMARY
FDA UNII
J4Z741D6O5
Created by admin on Sat Dec 16 15:54:31 UTC 2023 , Edited by admin on Sat Dec 16 15:54:31 UTC 2023
PRIMARY
DAILYMED
J4Z741D6O5
Created by admin on Sat Dec 16 15:54:31 UTC 2023 , Edited by admin on Sat Dec 16 15:54:31 UTC 2023
PRIMARY
CAS
548-62-9
Created by admin on Sat Dec 16 15:54:31 UTC 2023 , Edited by admin on Sat Dec 16 15:54:31 UTC 2023
PRIMARY
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