Page last updated: 2024-12-05

2-nitroanisole

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

Description

2-Nitroanisole, also known as o-nitroanisole, is an organic compound with the formula CH3OC6H4NO2. It is a pale yellow solid that is used in the production of dyes and pharmaceuticals. 2-Nitroanisole is synthesized by the nitration of anisole, a reaction that typically involves the use of concentrated nitric acid and sulfuric acid. The compound can also be prepared by the oxidation of 2-aminoanisole. 2-Nitroanisole is a potential environmental contaminant and has been found in soil and water samples. It has been shown to be toxic to aquatic organisms and may also be harmful to human health. Research on 2-nitroanisole focuses on its environmental fate, toxicology, and potential applications in organic synthesis.'

2-nitroanisole : A member of the class of 2-nitroanisoles that is anisole in which one of the hydrogens ortho to the methoxy group is replaced by a nitro group. [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 CID7048
CHEMBL ID166415
CHEBI ID48722
SCHEMBL ID186551
SCHEMBL ID17347343
MeSH IDM0046812

Synonyms (68)

Synonym
STL356493
nsc-5506
o-nitroanisole
1-methoxy-2-nitrobenzene
2-methoxynitrobenzene
anisole, o-nitro-
benzene, 1-methoxy-2-nitro-
o-nitrophenyl methyl ether
91-23-6
nsc5506
2-nitroanisole
2-methoxy-1-nitrobenzene
1-nitro-2-methoxybenzene
ccris 2319
ai3-00230
nsc 5506
ortho-nitrobenzene methyl ether
nci-c60388
einecs 202-052-1
hsdb 5186
inchi=1/c7h7no3/c1-11-7-5-3-2-4-6(7)8(9)10/h2-5h,1h
NCGC00091551-01
CHEBI:48722 ,
o-methoxynitrobenzene
2-nitroanisole, >=99%
NCGC00091551-02
smr001372018
MLS002454428
CHEMBL166415
N0125
AKOS000119961
1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-1-oxido-4-oxo-quinolin-1-ium-3-carboxylic acid
A843769
NCGC00091551-03
29191-53-5
benzene, methoxynitro-
a8ba06542k ,
unii-a8ba06542k
1-methoxy-2-nitro-benzene
C19270
HMS3039G04
tox21_302981
dtxsid3020962 ,
dtxcid70962
cas-91-23-6
NCGC00256425-01
NCGC00259533-01
tox21_201984
zre7hlz17k ,
unii-zre7hlz17k
FT-0613174
SCHEMBL186551
2-nitroanisole [iarc]
2-nitroanisole [hsdb]
nitroanisole, o-
o-nitrobenzene methyl ether
o-nitroanisole [mi]
SCHEMBL17347343
un 2730
o-nitro(methoxy)benzene
W-100313
mfcd00007096
Z31131392
EN300-15565
o-nitroanisol
2-nitro-anisole
Q27121353
AS-30080

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Since the highest dose altered the urinary excretion rate of ONA, a dose of 25 mg/kg was used for subsequent pharmacokinetic studies."( Pharmacokinetics of o-nitroanisole in Fischer 344 rats.
Carter, DE; Miller, MJ; Perry, DF; Sipes, IG,
)
0.13

Dosage Studied

ExcerptRelevanceReference
" Statistics for dose-response trend tests are calculated within body weight strata and pooled to obtain an overall dose-response trend test."( Dose-response trend tests for tumorigenesis, adjusted for body weight.
Gaylor, DW; Kodell, RL, 1999
)
0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
carcinogenic agentA role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
[role 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]

Drug Classes (1)

ClassDescription
2-nitroanisolesAny member of the class of mononitroanisoles in which the nitro group is situated ortho to the methoxy group.
[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 (11)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency0.07080.003245.467312,589.2998AID2517
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency89.12510.004023.8416100.0000AID485290
interleukin 8Homo sapiens (human)Potency74.97800.047349.480674.9780AID651758
GLI family zinc finger 3Homo sapiens (human)Potency68.51990.000714.592883.7951AID1259369
thioredoxin glutathione reductaseSchistosoma mansoniPotency50.11870.100022.9075100.0000AID485364
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency25.11890.011212.4002100.0000AID1030
glucocorticoid receptor [Homo sapiens]Homo sapiens (human)Potency0.77610.000214.376460.0339AID720692
retinoid X nuclear receptor alphaHomo sapiens (human)Potency44.66840.000817.505159.3239AID588544
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency68.51990.001530.607315,848.9004AID1224841
chromobox protein homolog 1Homo sapiens (human)Potency79.43280.006026.168889.1251AID540317
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency5.01190.050127.073689.1251AID588590
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID1745845Primary qHTS for Inhibitors of ATXN expression
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.
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.
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.
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.
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.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID318681Anticarcinogenic activity in rat assessed as induction of tumors per day2008Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6
QSAR modeling of the rodent carcinogenicity of nitrocompounds.
AID200690Mutagenic activity in an Ames test on Salmonella Typhimurium TA98; Activity is log of revertants/nmol1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
Structure-activity relationship of mutagenic aromatic and heteroaromatic nitro compounds. Correlation with molecular orbital energies and hydrophobicity.
AID23442Partition coefficient (logP)1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
Structure-activity relationship of mutagenic aromatic and heteroaromatic nitro compounds. Correlation with molecular orbital energies and hydrophobicity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (30)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's8 (26.67)18.2507
2000's10 (33.33)29.6817
2010's10 (33.33)24.3611
2020's2 (6.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 35.71

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

MetricThis Compound (vs All)
Research Demand Index35.71 (24.57)
Research Supply Index3.50 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index45.04 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (35.71)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (9.38%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other29 (90.63%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]