Page last updated: 2024-12-05

4-nitrotoluene

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

4-nitrotoluene: RN given refers to parent cpd; structure in Merck Index, 9th ed, #6470 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

mononitrotoluene : A nitrotoluene bearing a single nitro substituent at any position. A "closed class". [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]

4-nitrotoluene : A mononitrotoluene that consists of toluene bearing a nitro substituent at the 4-position. [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]

Cross-References

ID SourceID
PubMed CID7473
CHEMBL ID155320
CHEBI ID35227
SCHEMBL ID7147554
SCHEMBL ID73252
SCHEMBL ID14468668
MeSH IDM0068429

Synonyms (79)

Synonym
BIDD:ER0243
AC-14710
CHEBI:35227 ,
nci-c60537
ccris 2313
nitrotoluene, p-
nitrotoluenos [spanish]
nsc 9579
nitrotoluene, p-isomer
ai3-15394
para-nitrotoluol
hsdb 1158
nci 9579
einecs 202-808-0
1-methyl-4-nitrobenzene
99-99-0
wln: wnr d1
4-nitrotoluol
nsc9579
nsc-9579
toluene, p-nitro-
p-nitrotoluene
4-nitrotoluene
p-methylnitrobenzene
benzene, 1-methyl-4-nitro-
4-methylnitrobenzene
toluene,4-nitro mfc7 h7 n1 o2
inchi=1/c7h7no2/c1-6-2-4-7(5-3-6)8(9)10/h2-5h,1h
NCGC00090790-01
4-nitrotoluene, 99%
smr000677947
MLS001055386
4nt ,
CHEMBL155320 ,
N0276
bdbm50008545
AKOS000120058
NCGC00090790-03
NCGC00090790-02
HMS3039N17
mononitrotoluene
dtxsid5023792 ,
NCGC00254101-01
dtxcid203792
tox21_201464
NCGC00259015-01
cas-99-99-0
tox21_300017
SCHEMBL7147554
1-methyl-4-nitro-benzene
FT-0673017
nitrotoluenos
e88img14ex ,
unii-e88img14ex
ec 202-808-0
p-nitrotoluene, liquid or solid [un1664] [poison]
p-nitrotoluene, liquid or solid
FT-0619304
4-nitrophenylmethane
p-nitrotoluene [mi]
4-nitrotoluene [hsdb]
SCHEMBL73252
4-nitro toluene
para-nitrotoluene
SCHEMBL14468668
CS-M3393
J-515893
F0001-2342
4-nitrotoluene, purum, >=98.0% (gc)
mfcd00007366
4-nitrotoluene, analytical standard
4-nitrotoluene 10 microg/ml in acetonitrile
BCP26111
1-methyl-4-nitrobenzene;p-nitrotoluene
Q2048380
STL185581
BS-42204
EN300-20074
Z104476692

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Thus, the possibility that 4-NT exerted endocrine disrupting effects seems to be very low under the conditions of this study, and when the substance was administered to rats over two generations, doses less than 160 mg/kg/day did not induce any marked adverse effects on the reproductive capacity in the parental animals, with the no observed effect level (NOEL) and the no observed adverse effect (NOAEL) on growth and development in the offspring concluded to be 40 mg/kg/day."( A two-generation reproductive toxicity study of 4-nitrotoluene in rats.
Aso, S; Ehara, H; Hosyuyama, S; Minobe, Y; Miyata, K; Shiraishi, K; Umano, T, 2005
)
0.58

Compound-Compound Interactions

ExcerptReferenceRelevance
" The degradation of PNT in aqueous solution by ozonation (O(3)) combined with sonolysis (US) was investigated in laboratory-scale experiments in which pH, initial concentration of PNT, O(3) dose and temperature were varied."( Degradation of p-nitrotoluene in aqueous solution by ozonation combined with sonolysis.
Chen, J; He, Z; Lü, B; Song, S; Xia, M; Ying, H, 2007
)
0.34
"Supercritical fluid extraction (SFE) combined with dispersive liquid-liquid microextraction (DLLME) followed by gas chromatography with flame ionization detector (GC-FID) was developed for the extraction and determination of 4-nitrotoluene and 3-nitrotoluene in soil sample."( Optimization of supercritical fluid extraction combined with dispersive liquid-liquid microextraction as an efficient sample preparation method for determination of 4-nitrotoluene and 3-nitrotoluene in a complex matrix.
Jowkarderis, M; Raofie, F, 2012
)
0.76

Dosage Studied

ExcerptRelevanceReference
" Decreased body weights relative to controls occurred in dosed rats and mice in all studies at the higher dose levels and were most pronounced in rats receiving o-nitrotoluene."( Comparative toxicities of o-, m-, and p-nitrotoluene in 13-week feed studies in F344 rats and B6C3F1 mice.
Bucher, JR; Dunnick, JK; Elwell, MR, 1994
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
mononitrotolueneA nitrotoluene bearing a single nitro substituent at any position. A "closed class".
[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]

Pathways (2)

PathwayProteinsCompounds
4-nitrotoluene degradation I310
4-nitrotoluene degradation II021

Protein Targets (12)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, HADH2 proteinHomo sapiens (human)Potency39.81070.025120.237639.8107AID886
Chain B, HADH2 proteinHomo sapiens (human)Potency39.81070.025120.237639.8107AID886
glucocorticoid receptor [Homo sapiens]Homo sapiens (human)Potency0.19490.000214.376460.0339AID720691
retinoid X nuclear receptor alphaHomo sapiens (human)Potency21.93930.000817.505159.3239AID1159527
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency8.66130.001530.607315,848.9004AID1224841
estrogen nuclear receptor alphaHomo sapiens (human)Potency21.93930.000229.305416,493.5996AID743069
chromobox protein homolog 1Homo sapiens (human)Potency79.43280.006026.168889.1251AID540317
thyroid hormone receptor beta isoform 2Rattus norvegicus (Norway rat)Potency68.79890.000323.4451159.6830AID743065
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency74.97800.000627.21521,122.0200AID651741
gemininHomo sapiens (human)Potency6.51310.004611.374133.4983AID624296
Nuclear receptor ROR-gammaHomo sapiens (human)Potency0.26600.026622.448266.8242AID651802
[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)
AcetylcholinesteraseHomo sapiens (human)IC50 (µMol)2.50000.00000.933210.0000AID32248; AID32280
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (27)

Processvia Protein(s)Taxonomy
acetylcholine catabolic process in synaptic cleftAcetylcholinesteraseHomo sapiens (human)
regulation of receptor recyclingAcetylcholinesteraseHomo sapiens (human)
osteoblast developmentAcetylcholinesteraseHomo sapiens (human)
acetylcholine catabolic processAcetylcholinesteraseHomo sapiens (human)
cell adhesionAcetylcholinesteraseHomo sapiens (human)
nervous system developmentAcetylcholinesteraseHomo sapiens (human)
synapse assemblyAcetylcholinesteraseHomo sapiens (human)
receptor internalizationAcetylcholinesteraseHomo sapiens (human)
negative regulation of synaptic transmission, cholinergicAcetylcholinesteraseHomo sapiens (human)
amyloid precursor protein metabolic processAcetylcholinesteraseHomo sapiens (human)
positive regulation of protein secretionAcetylcholinesteraseHomo sapiens (human)
retina development in camera-type eyeAcetylcholinesteraseHomo sapiens (human)
acetylcholine receptor signaling pathwayAcetylcholinesteraseHomo sapiens (human)
positive regulation of cold-induced thermogenesisAcetylcholinesteraseHomo sapiens (human)
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 (19)

Processvia Protein(s)Taxonomy
amyloid-beta bindingAcetylcholinesteraseHomo sapiens (human)
acetylcholinesterase activityAcetylcholinesteraseHomo sapiens (human)
cholinesterase activityAcetylcholinesteraseHomo sapiens (human)
protein bindingAcetylcholinesteraseHomo sapiens (human)
collagen bindingAcetylcholinesteraseHomo sapiens (human)
hydrolase activityAcetylcholinesteraseHomo sapiens (human)
serine hydrolase activityAcetylcholinesteraseHomo sapiens (human)
acetylcholine bindingAcetylcholinesteraseHomo sapiens (human)
protein homodimerization activityAcetylcholinesteraseHomo sapiens (human)
laminin bindingAcetylcholinesteraseHomo sapiens (human)
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 (16)

Processvia Protein(s)Taxonomy
extracellular regionAcetylcholinesteraseHomo sapiens (human)
basement membraneAcetylcholinesteraseHomo sapiens (human)
extracellular spaceAcetylcholinesteraseHomo sapiens (human)
nucleusAcetylcholinesteraseHomo sapiens (human)
Golgi apparatusAcetylcholinesteraseHomo sapiens (human)
plasma membraneAcetylcholinesteraseHomo sapiens (human)
cell surfaceAcetylcholinesteraseHomo sapiens (human)
membraneAcetylcholinesteraseHomo sapiens (human)
neuromuscular junctionAcetylcholinesteraseHomo sapiens (human)
synaptic cleftAcetylcholinesteraseHomo sapiens (human)
synapseAcetylcholinesteraseHomo sapiens (human)
perinuclear region of cytoplasmAcetylcholinesteraseHomo sapiens (human)
side of membraneAcetylcholinesteraseHomo sapiens (human)
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)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID1555240Octanol/water partition co-efficient, log P of compound by UV-spectrophotometry-based shake-flask method
AID32248Inhibition of acetylcholinesterase.1992Journal of medicinal chemistry, Feb-07, Volume: 35, Issue:3
QSAR analyses of the substituted indanone and benzylpiperidine rings of a series of indanone-benzylpiperidine inhibitors of acetylcholinesterase.
AID32280IC50 against acetylcholinesterase; value ranges from 1-4900 nM.1992Journal of medicinal chemistry, Feb-07, Volume: 35, Issue:3
QSAR analyses of the substituted indanone and benzylpiperidine rings of a series of indanone-benzylpiperidine inhibitors of acetylcholinesterase.
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.
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.
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.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (70)

TimeframeStudies, This Drug (%)All Drugs %
pre-199013 (18.57)18.7374
1990's14 (20.00)18.2507
2000's18 (25.71)29.6817
2010's23 (32.86)24.3611
2020's2 (2.86)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 63.63

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 very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index63.63 (24.57)
Research Supply Index4.30 (2.92)
Research Growth Index4.54 (4.65)
Search Engine Demand Index104.49 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (63.63)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (1.37%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other72 (98.63%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]