Page last updated: 2024-12-05

n,n,n',n'-tetramethyl-4,4'-methylenedianiline

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Description

N,N,N',N'-tetramethyl-4,4'-methylenedianiline: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID7567
CHEMBL ID1613260
CHEBI ID34370
SCHEMBL ID76217
MeSH IDM0108687

Synonyms (140)

Synonym
BIDD:ER0254
n,n',n'-tetramethyl-p,p'-diaminodiphenylmethane
tetramethyldiaminodiphenylmethane
4,4'-tetramethyldiaminodiphenylmethane
tetra-base
nsc4892
(p,p'-tetramethyl)diaminodiphenylmethane
bis[4-(n,n-dimethylamino)phenyl]methane
p,n-dimethylaminophenyl)methane
n,n',n'-tetramethyl-4,4'-diaminodiphenylmethane
bis[p-(n,n-dimethylamino)phenyl]methane
benzenamine,4'-methylenebis[n,n-dimethyl-
michler's base
101-61-1
methane base
p,p-tetramethyldiaminodiphenylmethane
nsc-4892
michler's methane
nci-c01990
tetrabase
diphenylmethane, tetramethyldiamino-
p,p-dimethylaminodiphenylmethane
bis[(4-dimethylamino)phenyl]methane
4,4'-(dimethylamino)diphenylmethane
p,p'-bis(dimethylamino)diphenylmethane
methanediamine,n'-diphenyl-
bis[(p-dimethylamino)phenyl]methane
n,n'-tetramethyldiaminodiphenylmethane
methane, bis[p-(dimethylamino)phenyl]-
aniline,4'-methylenebis[n,n-dimethyl-
michler's hydride
4,4'-bis(dimethylamino)diphenylmethane
(4,4'-tetramethyl)diaminodiphenylmethane
bis(p-dimethylaminophenyl)methane
methylene base
wln: 1n1 & r d1r dn1 & 1
nsc36782
nsc-36782
4,4'-methylenebis(n,n-dimethylaniline)
nsc-9029
nsc9029
benzenamine, 4,4'-methylenebis[n,n-dimethyl-
aniline, 4,4'-methylenebis[n,n-dimethyl-
4-[(4-dimethylaminophenyl)methyl]-n,n-dimethyl-aniline
IDI1_031125
NCGC00091580-01
4,4'-methylenebis(n,n-dimethyl)benzenamine
methanediamine, tetramethyl-n,n'-diphenyl-
methane, bis(p-(dimethylamino)phenyl)-
hsdb 2856
benzenamine, 4,4'-methylenebis(n,n-dimethyl-
reduced michler's ketone
bis(p-(n,n-dimethylamino)phenyl)methane
einecs 202-959-2
aniline, 4,4'-methylenebis(n,n-dimethyl-
bis(p-dimethylamino)diphenylmethane
4,4'-methylenebis(n,n-dimethylbenzenamine)
p,p'-tetramethyldiamindiphenylmethane
n,n,n'n'-tetramethyl-4,4'-diaminodiphenylmethane
baze michlerova [czech]
bis(p-(dimethylamino)phenyl)methane
nsc 36782
bis(4-(n,n-dimethylamino)phenyl)methane
p,p'-bis(n,n-dimethylaminophenyl)methane
michler's ketone, reduced
bis(4-(dimethylamino)phenyl)methane
bis[p-(dimethylamino)phenyl]methane
n,n,n',n'-tetramethyl-p,p'-diaminodiphenylmethane
ccris 390
n,n,n'n'-tetramethyl-p,p'-diaminodiphenylmethane
ai3-09165
n,n,n',n'-tetramethyl-4,4'-methylenedianiline
4,4'-methylenebis(n,n-dimethylaniline), 98%
NCGC00091580-02
MAYBRIDGE4_000543
4,4'-methylenebis(n,n'-dimethylaniline)
4,4'-methylene bis(n,n'-dimethyl)aniline
NCGC00091580-03
HMS1522I15
B0483
bis[4-(dimethylamino)phenyl]methane
tetra base
AKOS001574005
BRD-K62923262-001-01-4
smr001253703
MLS002454376
4,4'-bis-(dimethylamino)diphenylmethane
AC-907/25014337
4-[4-(dimethylamino)benzyl]-n,n-dimethylaniline
NCGC00091580-05
NCGC00091580-04
[4-[(4-dimethylaminophenyl)-methyl]-phenyl]-dimethyl-amine
HMS3055O04
NCGC00258940-01
dtxsid5020869 ,
dtxcid70869
tox21_300130
tox21_201389
cas-101-61-1
NCGC00253976-01
unii-l6spp9k4wq
l6spp9k4wq ,
baze michlerova
FT-0617017
n,n,n',n'-tetramethyl-4,4'-diaminodiphenylmethane
arnold's base
michler's base [mi]
4,4'-bis(dimethylaminophenyl)methane
n,n,n',n-tetramethyl-4,4'-methylenedianiline
4,4'-methylenebis[n,n-dimethylbenzenamine]
SCHEMBL76217
4,4'-methylenebis[n,n-dimethylaniline]
CHEBI:34370 ,
30135-64-9
CHEMBL1613260
p,p'-tetramethyldiaminodiphenylmethane
4,4'-methylenebis n,n-dimethylaniline
4,4'-methylene bis(n,n'-dimethylaniline)
aniline, 4,4'-methylenebis-(n,n-dimethyl)-
methane, bis(4,4'-dimethylaminophenyl)-
JNRLEMMIVRBKJE-UHFFFAOYSA-N
n-(4-[4-(dimethylamino)benzyl]phenyl)-n,n-dimethylamine #
benzenamine, 4-4'-methylenebis(n,n-dimethyl)-
W-108910
4-[[4-(dimethylamino)phenyl]methyl]-n,n-dimethyl-aniline
mfcd00008317
STL453594
4,4'-methanediylbis(n,n-dimethylaniline)
sr-01000394054
SR-01000394054-1
FT-0699810
4-{[4-(dimethylamino)phenyl]methyl}-n,n-dimethylaniline
EN300-199936
bis-(4-dimethylaminophenyl)methane
4-(4-(dimethylamino)benzyl)-n,n-dimethylbenzenamine
137198-51-7
E76078
4-[[4-(dimethylamino)phenyl]methyl]-n,n-dimethylaniline
Q27116024
CS-W012590
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
diarylmethaneAny compound containing two aryl groups connected by a single C atom.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (47)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency22.38720.004023.8416100.0000AID485290
Chain A, JmjC domain-containing histone demethylation protein 3AHomo sapiens (human)Potency25.11890.631035.7641100.0000AID504339
glp-1 receptor, partialHomo sapiens (human)Potency28.18380.01846.806014.1254AID624417
GLI family zinc finger 3Homo sapiens (human)Potency30.76250.000714.592883.7951AID1259369
AR proteinHomo sapiens (human)Potency57.47970.000221.22318,912.5098AID1259243; AID1259247; AID743042; AID743054
apical membrane antigen 1, AMA1Plasmodium falciparum 3D7Potency14.12540.707912.194339.8107AID720542
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency39.81070.011212.4002100.0000AID1030
thyroid stimulating hormone receptorHomo sapiens (human)Potency10.00000.001318.074339.8107AID926; AID938
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency15.67450.001022.650876.6163AID1224838; AID1224839; AID1224893
glucocorticoid receptor [Homo sapiens]Homo sapiens (human)Potency0.19580.000214.376460.0339AID720692
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency19.33610.003041.611522,387.1992AID1159552; AID1159555
retinoid X nuclear receptor alphaHomo sapiens (human)Potency30.30010.000817.505159.3239AID588544
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency24.61980.001530.607315,848.9004AID1224841; AID1224848; AID1224849; AID1259401; AID1259403
farnesoid X nuclear receptorHomo sapiens (human)Potency22.38720.375827.485161.6524AID588527
pregnane X nuclear receptorHomo sapiens (human)Potency46.81350.005428.02631,258.9301AID1346982; AID720659
estrogen nuclear receptor alphaHomo sapiens (human)Potency58.49670.000229.305416,493.5996AID1259248; AID743079; AID743080
aryl hydrocarbon receptorHomo sapiens (human)Potency24.89950.000723.06741,258.9301AID743085; AID743122
chromobox protein homolog 1Homo sapiens (human)Potency19.95260.006026.168889.1251AID540317
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency0.81990.00419.984825.9290AID504444
parathyroid hormone/parathyroid hormone-related peptide receptor precursorHomo sapiens (human)Potency89.12513.548119.542744.6684AID743266
potassium voltage-gated channel subfamily H member 2 isoform dHomo sapiens (human)Potency70.79460.01789.637444.6684AID588834
mitogen-activated protein kinase 1Homo sapiens (human)Potency12.58930.039816.784239.8107AID995
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency74.97800.000627.21521,122.0200AID651741
VprHuman immunodeficiency virus 1Potency12.58931.584919.626463.0957AID651644
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency12.58930.031610.279239.8107AID884; AID885
lethal factor (plasmid)Bacillus anthracis str. A2012Potency12.58930.020010.786931.6228AID912
DNA dC->dU-editing enzyme APOBEC-3F isoform aHomo sapiens (human)Potency3.16230.025911.239831.6228AID602313
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Nuclear receptor ROR-gammaHomo sapiens (human)Potency59.55720.026622.448266.8242AID651802
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
GABA theta subunitRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
nonstructural protein 1Influenza A virus (A/California/07/2009(H1N1))IC50 (µMol)36.62100.200024.4540100.0000AID504329
rac GTPase-activating protein 1 isoform aHomo sapiens (human)IC50 (µMol)73.15007.390057.8904301.2400AID624330
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
protein AF-9 isoform aHomo sapiens (human)AC5012.06000.08008.380217.9800AID720495
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (13)

Processvia Protein(s)Taxonomy
negative regulation of transcription by RNA polymerase IINuclear receptor ROR-gammaHomo sapiens (human)
xenobiotic metabolic processNuclear receptor ROR-gammaHomo sapiens (human)
regulation of glucose metabolic processNuclear receptor ROR-gammaHomo sapiens (human)
regulation of steroid metabolic processNuclear receptor ROR-gammaHomo sapiens (human)
intracellular receptor signaling pathwayNuclear receptor ROR-gammaHomo sapiens (human)
circadian regulation of gene expressionNuclear receptor ROR-gammaHomo sapiens (human)
cellular response to sterolNuclear receptor ROR-gammaHomo sapiens (human)
positive regulation of circadian rhythmNuclear receptor ROR-gammaHomo sapiens (human)
regulation of fat cell differentiationNuclear receptor ROR-gammaHomo sapiens (human)
positive regulation of DNA-templated transcriptionNuclear receptor ROR-gammaHomo sapiens (human)
adipose tissue developmentNuclear receptor ROR-gammaHomo sapiens (human)
T-helper 17 cell differentiationNuclear receptor ROR-gammaHomo sapiens (human)
regulation of transcription by RNA polymerase IINuclear receptor ROR-gammaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
RNA polymerase II cis-regulatory region sequence-specific DNA bindingNuclear receptor ROR-gammaHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificNuclear receptor ROR-gammaHomo sapiens (human)
DNA-binding transcription repressor activity, RNA polymerase II-specificNuclear receptor ROR-gammaHomo sapiens (human)
DNA-binding transcription factor activityNuclear receptor ROR-gammaHomo sapiens (human)
protein bindingNuclear receptor ROR-gammaHomo sapiens (human)
oxysterol bindingNuclear receptor ROR-gammaHomo sapiens (human)
zinc ion bindingNuclear receptor ROR-gammaHomo sapiens (human)
ligand-activated transcription factor activityNuclear receptor ROR-gammaHomo sapiens (human)
sequence-specific double-stranded DNA bindingNuclear receptor ROR-gammaHomo sapiens (human)
nuclear receptor activityNuclear receptor ROR-gammaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
nucleusNuclear receptor ROR-gammaHomo sapiens (human)
nucleoplasmNuclear receptor ROR-gammaHomo sapiens (human)
nuclear bodyNuclear receptor ROR-gammaHomo sapiens (human)
chromatinNuclear receptor ROR-gammaHomo sapiens (human)
nucleusNuclear receptor ROR-gammaHomo sapiens (human)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504799Counterscreen for activators of the Protein Kinase A-R1A (PKA-R1A) complex: fluorescence polarization-based biochemical high throughput screening assay to identify fluorescence polarization assay artifacts2006Analytical chemistry, Dec-15, Volume: 78, Issue:24
Assay principle for modulators of protein-protein interactions and its application to non-ATP-competitive ligands targeting protein kinase A.
AID504800Fluorescence polarization-based biochemical high throughput confirmation assay for activators of the Protein Kinase A-R1A (PKA-R1A) complex2006Analytical chemistry, Dec-15, Volume: 78, Issue:24
Assay principle for modulators of protein-protein interactions and its application to non-ATP-competitive ligands targeting protein kinase A.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (24)

TimeframeStudies, This Drug (%)All Drugs %
pre-19909 (37.50)18.7374
1990's1 (4.17)18.2507
2000's5 (20.83)29.6817
2010's7 (29.17)24.3611
2020's2 (8.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.90

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.90 (24.57)
Research Supply Index3.26 (2.92)
Research Growth Index5.15 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.90)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other25 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]