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

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

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

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
Effect of metanil yellow and malachite green on DNA synthesis in N-nitrosodiethylamine induced preneoplastic rat livers.
2001 Sep
Decreased phosphoactive ERKs and JNKs in Malachite-green-transformed Syrian hamster embryo fibroblasts are associated with increased phosphoactive p38 kinase: possible therapeutic importance.
2006
Establishment of a transgenic yeast screening system for estrogenicity and identification of the anti-estrogenic activity of malachite green.
2008 Dec 15
Identification of quaternary ammonium compounds as potent inhibitors of hERG potassium channels.
2011 May 1
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:39:20 UTC 2023
Edited
by admin
on Fri Dec 15 15:39:20 UTC 2023
Record UNII
12058M7ORO
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Fri Dec 15 15:39:20 UTC 2023
EPA PESTICIDE CODE 39504
Created by admin on Fri Dec 15 15:39:20 UTC 2023 , Edited by admin on Fri Dec 15 15:39:20 UTC 2023
WHO-VATC QP53AX16
Created by admin on Fri Dec 15 15:39:20 UTC 2023 , Edited by admin on Fri Dec 15 15:39:20 UTC 2023
Code System Code Type Description
NSC
47726
Created by admin on Fri Dec 15 15:39:20 UTC 2023 , Edited by admin on Fri Dec 15 15:39:20 UTC 2023
PRIMARY
EPA CompTox
DTXSID1025512
Created by admin on Fri Dec 15 15:39:20 UTC 2023 , Edited by admin on Fri Dec 15 15:39:20 UTC 2023
PRIMARY
WIKIPEDIA
MALACHITE GREEN
Created by admin on Fri Dec 15 15:39:20 UTC 2023 , Edited by admin on Fri Dec 15 15:39:20 UTC 2023
PRIMARY
CHEBI
44107
Created by admin on Fri Dec 15 15:39:20 UTC 2023 , Edited by admin on Fri Dec 15 15:39:20 UTC 2023
PRIMARY
MERCK INDEX
m7033
Created by admin on Fri Dec 15 15:39:20 UTC 2023 , Edited by admin on Fri Dec 15 15:39:20 UTC 2023
PRIMARY Merck Index
CAS
569-64-2
Created by admin on Fri Dec 15 15:39:20 UTC 2023 , Edited by admin on Fri Dec 15 15:39:20 UTC 2023
PRIMARY
RXCUI
896038
Created by admin on Fri Dec 15 15:39:20 UTC 2023 , Edited by admin on Fri Dec 15 15:39:20 UTC 2023
PRIMARY RxNorm
DAILYMED
12058M7ORO
Created by admin on Fri Dec 15 15:39:20 UTC 2023 , Edited by admin on Fri Dec 15 15:39:20 UTC 2023
PRIMARY
HSDB
1406
Created by admin on Fri Dec 15 15:39:20 UTC 2023 , Edited by admin on Fri Dec 15 15:39:20 UTC 2023
PRIMARY
DRUG BANK
DB03895
Created by admin on Fri Dec 15 15:39:20 UTC 2023 , Edited by admin on Fri Dec 15 15:39:20 UTC 2023
PRIMARY
ECHA (EC/EINECS)
209-322-8
Created by admin on Fri Dec 15 15:39:20 UTC 2023 , Edited by admin on Fri Dec 15 15:39:20 UTC 2023
PRIMARY
SMS_ID
100000135091
Created by admin on Fri Dec 15 15:39:20 UTC 2023 , Edited by admin on Fri Dec 15 15:39:20 UTC 2023
PRIMARY
PUBCHEM
11294
Created by admin on Fri Dec 15 15:39:20 UTC 2023 , Edited by admin on Fri Dec 15 15:39:20 UTC 2023
PRIMARY
MESH
C005095
Created by admin on Fri Dec 15 15:39:20 UTC 2023 , Edited by admin on Fri Dec 15 15:39:20 UTC 2023
PRIMARY
NCI_THESAURUS
C75426
Created by admin on Fri Dec 15 15:39:20 UTC 2023 , Edited by admin on Fri Dec 15 15:39:20 UTC 2023
PRIMARY
EVMPD
SUB69454
Created by admin on Fri Dec 15 15:39:20 UTC 2023 , Edited by admin on Fri Dec 15 15:39:20 UTC 2023
PRIMARY
CHEBI
72449
Created by admin on Fri Dec 15 15:39:20 UTC 2023 , Edited by admin on Fri Dec 15 15:39:20 UTC 2023
PRIMARY
FDA UNII
12058M7ORO
Created by admin on Fri Dec 15 15:39:20 UTC 2023 , Edited by admin on Fri Dec 15 15:39:20 UTC 2023
PRIMARY
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY