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Details

Stereochemistry ACHIRAL
Molecular Formula C25H31N3O
Molecular Weight 389.5331
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Methylrosaniline

SMILES

CN(C)C1=CC=C(C=C1)C(O)(C2=CC=C(C=C2)N(C)C)C3=CC=C(C=C3)N(C)C

InChI

InChIKey=QFVDKARCPMTZCS-UHFFFAOYSA-N
InChI=1S/C25H31N3O/c1-26(2)22-13-7-19(8-14-22)25(29,20-9-15-23(16-10-20)27(3)4)21-11-17-24(18-12-21)28(5)6/h7-18,29H,1-6H3

HIDE SMILES / InChI

Description

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

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
22.13 nM [EC50]
30.6 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
GENTIAN VIOLET
Preventing
GENTIAN VIOLET

Doses

AEs

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Tox targets

Sourcing

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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).