leucomalachite green

Synonyms: "Leuco malachite green", "Malachite green leuco", "Malachite green leuco base", "4,4'-Bis(dimethylamino)triphenylmethane", "Tetramethyldiaminotriphenylmethane", "bis(p-dimethylaminophenyl)phenylmethane", "p,p'-benzylidenebis(N,N-dimethylaniline)", "N,N,N',N'-tetramethyl-4,4'-benzylidenedianiline", "4,4'-benzylidenebis(N,N-dimethylaniline)".

Source: Leucomalachite green is the primary metabolite of malachite green, which is an organic compound that is used as a dyestuff and as antimicrobial.

Identifiers:

IUPAC Name: 4-[[4-(dimethylamino)phenyl]-phenylmethyl]-N,N-dimethylaniline
CAS Number: 129-73-7
PubChem ID: 67215
InChiKey: WZKXBGJNNCGHIC-UHFFFAOYSA-N
Canonical SMILES: CN(C)C1=CC=C(C=C1)C(C2=CC=CC=C2)C3=CC=C(C=C3)N(C)C

Structural Properties:

Molecular Formula: C23H26N2
Molecular Weight: 330.475

Pharmacophore Features:

Number of bond donors: 0
Number of bond acceptors: 2
Number of atoms different from hydrogen: 25

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Evidence Supporting This Chemical as an Endocrine Disruptor
TEDX List of Potential Endocrine Disruptors
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Culp, S.J., Blankenship, L.R., Kusewitt, D.F., Doerge, D.R., Mulligan, L.T. and Beland, F.A., 1999. Toxicity and metabolism of malachite green and leucomalachite green during short-term feeding to Fischer 344 rats and B6C3F1 mice. Chemico-biological interactions, 122(3), pp.153-170. DOI: https://doi.org/10.1016/S0009-2797(99)00119-2. URL: https://www.sciencedirect.com/science/article/pii/S0009279799001192.
Doerge, D.R., Chang, H.C., Divi, R.L. and Churchwell, M.I., 1998. Mechanism for inhibition of thyroid peroxidase by leucomalachite green. Chemical research in toxicology, 11(9), pp.1098-1104. DOI: 10.1021/tx970226o. URL: https://pubs.acs.org/doi/abs/10.1021/tx970226o.

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