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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
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
Inhibition of human plasma cholinesterase by malachite green and related triarylmethane dyes: mechanistic implications.
2005 Aug 15
Patents
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)
Common Name English
Code System Code Type Description
CAS
93966-68-8
Created by admin on Sat Dec 16 18:37:10 GMT 2023 , Edited by admin on Sat Dec 16 18:37:10 GMT 2023
PRIMARY
ECHA (EC/EINECS)
301-021-0
Created by admin on Sat Dec 16 18:37:10 GMT 2023 , Edited by admin on Sat Dec 16 18:37:10 GMT 2023
PRIMARY
EPA CompTox
DTXSID80240048
Created by admin on Sat Dec 16 18:37:10 GMT 2023 , Edited by admin on Sat Dec 16 18:37:10 GMT 2023
PRIMARY
PUBCHEM
3023128
Created by admin on Sat Dec 16 18:37:10 GMT 2023 , Edited by admin on Sat Dec 16 18:37:10 GMT 2023
PRIMARY
FDA UNII
ZB3Z3WF9UT
Created by admin on Sat Dec 16 18:37:10 GMT 2023 , Edited by admin on Sat Dec 16 18:37:10 GMT 2023
PRIMARY