Page last updated: 2024-12-05

2,4-dinitroanisole

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

Description

2,4-dinitroanisole : A member of the class of dinitroanisoles that is 2-nitroanisole in which the hydrogen para to the methoxy group is replaced by a second 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 CID8385
CHEMBL ID167820
CHEBI ID84559
SCHEMBL ID397931
SCHEMBL ID10548431
MeSH IDM0534056

Synonyms (50)

Synonym
ccris 1803
caswell no. 388a
ai3-00184
brn 1881474
epa pesticide chemical code 037503
einecs 204-310-9
nsc 8733
2,4-dinitrophenyl methyl ether
.alpha.-dinitroanisole
1-methoxy-2,4-dinitrobenzene
nsc8733
2,4-dinitroanisol
dinitroanisole
wln: wnr bo1 enw
nsc-8733
2,4-dinitrophenylmethyl ether
2,4-dinitroanisole
119-27-7
anisole, 2,4-dinitro-
benzene, 1-methoxy-2,4-dinitro-
inchi=1/c7h6n2o5/c1-14-7-3-2-5(8(10)11)4-6(7)9(12)13/h2-4h,1h
STK389285
CHEMBL167820
chebi:84559 ,
AKOS000121216
A804240
1-methoxy-2,4-dinitro-benzene
BBL002781
cas-119-27-7
dtxsid9041366 ,
tox21_302199
dtxcid7021366
NCGC00255537-01
D0816
unii-1l0od70295
4-06-00-01372 (beilstein handbook reference)
1l0od70295 ,
FT-0610199
2,4-dinitro-1-methoxy-benzene
2,4-nitroanisole
alpha-dinitroanisole
SCHEMBL397931
3,4-dinitromethoxybenzene
SCHEMBL10548431
W-108522
C21159
mfcd00035745
VS-01209
Q209211
EN300-15564

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" 2,4-DNP and DNOC showed the highest tryptophan fluorescence quenching constant values, these being also the most toxic compounds."( Quenching of tryptophan fluorescence in the presence of 2,4-DNP, 2,6-DNP, 2,4-DNA and DNOC and their mechanism of toxicity.
Huţanu, CA; Pintilie, O; Zaharia, M, 2013
)
0.39
" Methanogens were severely inhibited by 3-nitro-4-methoxyaniline (MENA), with a 50%-inhibiting concentration (IC50) of 25 μM, which is more toxic than DNAN with the same assay, but posed a lower toxicity to Allivibrio fischeri (IC50 = 219 μM)."( Microbial toxicity and characterization of DNAN (bio)transformation product mixtures.
Abrell, L; Alvarez-Nieto, C; Chorover, J; Field, JA; Olivares, CI; Sierra-Alvarez, R, 2016
)
0.43
" Without photodegradation, DNAN was more toxic (median lethal concentration [LC50] = 43 mg/L) than the other 2 constituents and it contributed predominantly to the toxicity of IMX-101 (LC50 = 206 mg/L) based on toxic units."( Aquatic toxicity of photo-degraded insensitive munition 101 (IMX-101) constituents.
Bednar, AJ; Gust, KA; Jordan, SM; Kennedy, AJ; Melby, NL; Moores, LC; Poda, AR, 2017
)
0.46

Bioavailability

ExcerptReferenceRelevance
" In soil, successive replacement of -NO2 by -NH2 in DNAN enhanced irreversible sorption and reduced bioavailability under oxic conditions."( Environmental fate of 2,4-dinitroanisole (DNAN) and its reduced products.
Ampleman, G; Deschamps, S; Halasz, A; Hawari, J; Monteil-Rivera, F; Paquet, L; Perreault, NN; Radovic-Hrapovic, Z; Thiboutot, S, 2015
)
0.73
" The bioavailability and bioaccumulative potential of the insensitive munitions compound 2,4-dinitroanisole (DNAN) to Eisenia fetida was assessed in soils with different geochemical characteristics."( Accumulation of 2,4-dinitroanisole in the earthworm Eisenia fetida from chemically spiked and aged natural soils.
Bednar, AJ; Brasfield, SM; Chappell, MA; Coleman, JG; Harmon, AR; Lotufo, GR; Russell, AL; Smith, JC, 2016
)
1
" However, DNAN is more soluble than TNT, which can influence transport and fate behavior and thus bioavailability and human exposure potential."( Batch soil adsorption and column transport studies of 2,4-dinitroanisole (DNAN) in soils.
Arthur, JD; Brusseau, ML; Dontsova, KM; Mark, NW; Šimunek, J; Taylor, S, 2017
)
0.7
" Multiple components/phases that vary among different soil types and affect the bioavailability of the MC, however, hinder the ability to separate the effects of soil characteristics from the MC chemical properties on the resulting plant bioconcentration."( Bioconcentration factors and plant-water partition coefficients of munitions compounds in barley.
Allen, HE; Di Toro, DM; Kuo, DTF; Torralba-Sanchez, TL, 2017
)
0.46

Dosage Studied

ExcerptRelevanceReference
" Male Sprague-Dawley rats were dosed by gavage (5, 20, or 80 mg DNAN/kg), and blood and tissue samples were analyzed to determine the levels of DNAN and its metabolite 2,4-dinitrophenol (DNP)."( Toxicokinetic Model Development for the Insensitive Munitions Component 2,4-Dinitroanisole.
Bannon, DI; Goodwin, MR; Gut, CP; Hulgan, AD; Sweeney, LM,
)
0.36
" To identify the target site of testicular toxicity of NTO and DNAN, Sprague Dawley rats were orally dosed with NTO (500 mg/kg/d) or DNAN (50 or 100 mg/kg/d) in corn oil for 1, 3, 7, or 14 days."( Characterization of the Testicular Toxicity of 3-Nitro-1,2,4-Triazol-5-One and 2,4-Dinitroanisole in Rats ( Rattus norvegicus).
Despain, KE; Honnold, CL; Lent, EM; May, AD; Mullins, AB,
)
0.36
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
explosiveA substance capable of undergoing rapid and highly exothermic decomposition.
[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
dinitroanisolesAny member of the class of nitroanisoles in which the anisole ring is substituted by two nitro groups.
[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 (1)

PathwayProteinsCompounds
2,4-dinitroanisole degradation25

Protein Targets (6)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
acetylcholinesteraseHomo sapiens (human)Potency37.74460.002541.796015,848.9004AID1347395; AID1347398
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency21.68990.001022.650876.6163AID1224838
pregnane X nuclear receptorHomo sapiens (human)Potency30.63790.005428.02631,258.9301AID1346982
estrogen nuclear receptor alphaHomo sapiens (human)Potency61.64480.000229.305416,493.5996AID743075
aryl hydrocarbon receptorHomo sapiens (human)Potency27.30600.000723.06741,258.9301AID743085
thyroid hormone receptor beta isoform 2Rattus norvegicus (Norway rat)Potency30.63790.000323.4451159.6830AID743065; AID743067
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID1512639Toxicity in ip dosed Sprague-Dawley rat2018Journal of medicinal chemistry, 06-14, Volume: 61, Issue:11
Small Molecule Mitochondrial Uncouplers and Their Therapeutic Potential.
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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (72)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (1.39)18.2507
2000's1 (1.39)29.6817
2010's58 (80.56)24.3611
2020's12 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 28.13

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

MetricThis Compound (vs All)
Research Demand Index28.13 (24.57)
Research Supply Index4.32 (2.92)
Research Growth Index6.66 (4.65)
Search Engine Demand Index31.58 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (28.13)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (2.70%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other72 (97.30%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]