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

Details

Stereochemistry ACHIRAL
Molecular Formula C23H25N2.Cl
Molecular Weight 364.911
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MALACHITE GREEN

SMILES

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

InChI

InChIKey=FDZZZRQASAIRJF-UHFFFAOYSA-M
InChI=1S/C23H25N2.ClH/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;1H/q+1;/p-1

HIDE SMILES / InChI
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
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 Jul 27
Inhibition of human plasma cholinesterase by malachite green and related triarylmethane dyes: mechanistic implications.
2005 Aug 15
Treatment of ichthyophthiriasis after malachite green. II. Earth ponds at salmonid farms.
2005 Aug 9
Decreased phosphoactive ERKs and JNKs in Malachite-green-transformed Syrian hamster embryo fibroblasts are associated with increased phosphoactive p38 kinase: possible therapeutic importance.
2006
Inhibition of electric eel acetylcholinesterase by triarylmethane dyes.
2008 Sep 25
Identification of quaternary ammonium compounds as potent inhibitors of hERG potassium channels.
2011 May 1
Patents
Name Type Language
MALACHITE GREEN
HSDB   MART.   MI  
Common Name English
BASIC GREEN 4
INCI  
INCI  
Official Name English
BASIC GREEN 4 [INCI]
Common Name English
MALACHITE GREEN [HSDB]
Common Name English
CI 42000
Code English
LOWACRYL GREEN 4
Brand Name English
NSC-47726
Code English
MALACHITE GREEN CHLORIDE
Common Name English
MALACHITE GREEN [MI]
Common Name English
MALACHITE GREEN [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C461
Created by admin on Fri Dec 15 15:39:20 GMT 2023 , Edited by admin on Fri Dec 15 15:39:20 GMT 2023
EPA PESTICIDE CODE 39504
Created by admin on Fri Dec 15 15:39:20 GMT 2023 , Edited by admin on Fri Dec 15 15:39:20 GMT 2023
WHO-VATC QP53AX16
Created by admin on Fri Dec 15 15:39:20 GMT 2023 , Edited by admin on Fri Dec 15 15:39:20 GMT 2023
Code System Code Type Description
NSC
47726
Created by admin on Fri Dec 15 15:39:20 GMT 2023 , Edited by admin on Fri Dec 15 15:39:20 GMT 2023
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EPA CompTox
DTXSID1025512
Created by admin on Fri Dec 15 15:39:20 GMT 2023 , Edited by admin on Fri Dec 15 15:39:20 GMT 2023
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WIKIPEDIA
MALACHITE GREEN
Created by admin on Fri Dec 15 15:39:20 GMT 2023 , Edited by admin on Fri Dec 15 15:39:20 GMT 2023
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CHEBI
44107
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MERCK INDEX
m7033
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PRIMARY Merck Index
CAS
569-64-2
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RXCUI
896038
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PRIMARY RxNorm
DAILYMED
12058M7ORO
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HSDB
1406
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DRUG BANK
DB03895
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ECHA (EC/EINECS)
209-322-8
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SMS_ID
100000135091
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PUBCHEM
11294
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MESH
C005095
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NCI_THESAURUS
C75426
Created by admin on Fri Dec 15 15:39:20 GMT 2023 , Edited by admin on Fri Dec 15 15:39:20 GMT 2023
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EVMPD
SUB69454
Created by admin on Fri Dec 15 15:39:20 GMT 2023 , Edited by admin on Fri Dec 15 15:39:20 GMT 2023
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CHEBI
72449
Created by admin on Fri Dec 15 15:39:20 GMT 2023 , Edited by admin on Fri Dec 15 15:39:20 GMT 2023
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FDA UNII
12058M7ORO
Created by admin on Fri Dec 15 15:39:20 GMT 2023 , Edited by admin on Fri Dec 15 15:39:20 GMT 2023
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