U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C23H25N2.HO
Molecular Weight 346.4653
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIMETHYL(4-((4-(DIMETHYLAMINO)PHENYL)BENZYLIDENE)-2,5-CYCLOHEXADIEN-1-YLIDENE)AMMONIUM HYDROXIDE

SMILES

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

InChI

InChIKey=WETHTEMZJSDITG-UHFFFAOYSA-M
InChI=1S/C23H25N2.H2O/c1-24(2)21-14-10-19(11-15-21)23(18-8-6-5-7-9-18)20-12-16-22(17-13-20)25(3)4;/h5-17H,1-4H3;1H2/q+1;/p-1

HIDE SMILES / InChI

Molecular Formula HO
Molecular Weight 17.0073
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C23H25N2
Molecular Weight 329.458
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Malachite green, an N-methylated diaminotriphenylmethane dye, is used primarily as a therapeutic agent in aquaculture. It controls fungal attacks, protozoan infections and some other diseases caused by helminths on a wide variety of fish and other aquatic organisms. In solution, the dye exists as a mixture of the cation (chromatic malachite green) and its carbinol base, with the ratio depending on the pH of the solution; the dye also can undergo chemical and metabolic reduction to a leuco derivative. Malachite green intercalates with DNA, with a preference for A:T-rich regions, and the leuco derivative bears a structural resemblance to carcinogenic aromatic amines that can form covalent DNA adducts. In mammalian cells, it shows marked cytotoxicity and the ability to induce cell transformation and lipid peroxidation. The toxicity of this dye increases with exposure time, temperature and concentration. It has been reported to cause carcinogenesis, mutagenesis, chromosomal fractures, teratogenecity and respiratory toxicity.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL614058
15.0 µM [IC50]
Target ID: CHEMBL614735
2.0 µM [IC50]
PubMed

PubMed

TitleDatePubMed
Population-based in vitro hazard and concentration-response assessment of chemicals: the 1000 genomes high-throughput screening study.
2015-05
Identification of quaternary ammonium compounds as potent inhibitors of hERG potassium channels.
2011-05-01
Disrupting actions of bisphenol A and malachite green on growth hormone receptor gene expression and signal transduction in seabream.
2010-06
Establishment of a transgenic yeast screening system for estrogenicity and identification of the anti-estrogenic activity of malachite green.
2008-12-15
Inhibition of electric eel acetylcholinesterase by triarylmethane dyes.
2008-09-25
Methemoglobinemia due to malachite green ingestion in a child.
2008-04
Elevated phosphorylation of Chk1 and decreased phosphorylation of Chk2 are associated with abrogation of G2/M checkpoint control during transformation of Syrian hamster embryo (SHE) cells by Malachite green.
2006-06-18
Decreased phosphoactive ERKs and JNKs in Malachite-green-transformed Syrian hamster embryo fibroblasts are associated with increased phosphoactive p38 kinase: possible therapeutic importance.
2006
DNA damage and G2/M arrest in Syrian hamster embryo cells during Malachite green exposure are associated with elevated phosphorylation of ERK1 and JNK1.
2005-12-18
Inhibition of human plasma cholinesterase by malachite green and related triarylmethane dyes: mechanistic implications.
2005-08-15
Treatment of ichthyophthiriasis after malachite green. II. Earth ponds at salmonid farms.
2005-08-09
Treatment of ichthyophthiriasis after malachite green. I. Concrete tanks at salmonid farms.
2005-04-06
Hyperphosphorylation of extracellular regulated kinase 2 (ERK2) and inhibition of JNK2 phosphorylation are associated with increased S-phase during transformation of Syrian hamster embryo cells by Malachite Green.
2004
Tumor promotion by metanil yellow and malachite green during rat hepatocarcinogenesis is associated with dysregulated expression of cell cycle regulatory proteins.
2003
Effect of metanil yellow and malachite green on DNA synthesis in N-nitrosodiethylamine induced preneoplastic rat livers.
2001-09
Overexpression of G1/S cyclins and PCNA and their relationship to tyrosine phosphorylation and dephosphorylation during tumor promotion by metanil yellow and malachite green.
2000-07-27
Malachite green induced malignant transformation of Syrian hamster embryo (SHE) cells in primary culture: transformation is associated with enhanced expression of altered p53, bcl-2 and decreased sensitivity to apoptosis.
2000-03
Patents
Substance Class Chemical
Created
by admin
on Wed Apr 02 11:43:48 GMT 2025
Edited
by admin
on Wed Apr 02 11:43:48 GMT 2025
Record UNII
ZB3Z3WF9UT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIMETHYL(4-((4-(DIMETHYLAMINO)PHENYL)BENZYLIDENE)-2,5-CYCLOHEXADIEN-1-YLIDENE)AMMONIUM HYDROXIDE
Systematic Name English
METHANAMINIUM, N-(4-((4-(DIMETHYLAMINO)PHENYL)PHENYLMETHYLENE)-2,5-CYCLOHEXADIEN-1-YLIDENE)-N-METHYL-, HYDROXIDE (1:1)
Preferred Name English
Code System Code Type Description
CAS
93966-68-8
Created by admin on Wed Apr 02 11:43:48 GMT 2025 , Edited by admin on Wed Apr 02 11:43:48 GMT 2025
PRIMARY
ECHA (EC/EINECS)
301-021-0
Created by admin on Wed Apr 02 11:43:48 GMT 2025 , Edited by admin on Wed Apr 02 11:43:48 GMT 2025
PRIMARY
EPA CompTox
DTXSID80240048
Created by admin on Wed Apr 02 11:43:48 GMT 2025 , Edited by admin on Wed Apr 02 11:43:48 GMT 2025
PRIMARY
PUBCHEM
3023128
Created by admin on Wed Apr 02 11:43:48 GMT 2025 , Edited by admin on Wed Apr 02 11:43:48 GMT 2025
PRIMARY
FDA UNII
ZB3Z3WF9UT
Created by admin on Wed Apr 02 11:43:48 GMT 2025 , Edited by admin on Wed Apr 02 11:43:48 GMT 2025
PRIMARY