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
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
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL614058 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16061355 |
15.0 µM [IC50] | ||
Target ID: CHEMBL614735 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16061355 |
2.0 µM [IC50] | ||
Target ID: CHEMBL1075358 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25085484 |
PubMed
Title | Date | PubMed |
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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 |
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Inhibition of human plasma cholinesterase by malachite green and related triarylmethane dyes: mechanistic implications. | 2005 Aug 15 |
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Treatment of ichthyophthiriasis after malachite green. II. Earth ponds at salmonid farms. | 2005 Aug 9 |
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Decreased phosphoactive ERKs and JNKs in Malachite-green-transformed Syrian hamster embryo fibroblasts are associated with increased phosphoactive p38 kinase: possible therapeutic importance. | 2006 |
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Inhibition of electric eel acetylcholinesterase by triarylmethane dyes. | 2008 Sep 25 |
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Identification of quaternary ammonium compounds as potent inhibitors of hERG potassium channels. | 2011 May 1 |
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NCI_THESAURUS |
C461
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EPA PESTICIDE CODE |
39504
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WHO-VATC |
QP53AX16
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47726
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DTXSID1025512
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MALACHITE GREEN
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44107
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m7033
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569-64-2
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896038
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12058M7ORO
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209-322-8
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C005095
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C75426
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SUB69454
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72449
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12058M7ORO
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ACTIVE MOIETY
SUBSTANCE RECORD