Compounds > 1,2-dihydro-2,2,4-trimethylquinoline
Page last updated: 2024-11-05

1,2-dihydro-2,2,4-trimethylquinoline

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

Description

1,2-dihydro-2,2,4-trimethylquinoline: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID8981
CHEMBL ID294154
SCHEMBL ID44875
MeSH IDM0150404

Synonyms (95)

Synonym
MLS002174246
smr001261421
147-47-7
acetone anil
flectol h
nsc-4175
nsc4175
acetonanil
acetone anil (quinoline derivative)
wln: t66 bm chj c1 c1 e1
2,4-trimethyl-1,2-dihydroquinoline
2,4-trimethyl-1,2-dihydroquinone
quinoline, 1,2-dihydro-2,2,4-trimethyl-
2,2,4-trimethyl-1,2-dihydroquinoline
NCGC00073733-02
NCGC00073733-03
26780-96-1
1,2-dihydro-2,2,4-trimethylquinoline (monomer)
vulkanox hs/powder
ccris 4914
permanax 45
flectol pastilles
antioxidant hsl
permanax tq
polnoks r
nonflex rd
nci-c60902
vulkanox hs/lg
nsc 4175
acetone anil (quinoline deriv.)
trimethyl-1,2-dihydroquinoline
agerite ma
polnox r
flectol a
ccris 4795
einecs 205-688-8
trimethyl dihydroquinoline
2,2,4-trimethyl-1,2-dihydrochinolin [czech]
nocrac 224
antigene rdf
ai3-17714
agerite resin d
hsdb 1103
antioxidant hs
2,2,4-trimethyl-1,2-dihydroquinone
1,2-dihydro-2,2,4-trimethylquinoline
AKOS000274374
CHEMBL294154
2,2,4-trimethyl-1h-quinoline
F1974-0002
FT-0654592
znrlmgfxspuznr-uhfffaoysa-
inchi=1/c12h15n/c1-9-8-12(2,3)13-11-7-5-4-6-10(9)11/h4-8,13h,1-3h3
HMS1655H02
A808648
NCGC00073733-04
HMS3039L13
dsstox_gsid_25071
dtxcid605070
tox21_202467
cas-26780-96-1
NCGC00258630-01
dsstox_rid_77651
cas-147-47-7
NCGC00260016-01
dtxsid0025070 ,
tox21_201077
dsstox_cid_5070
ec 500-051-3
0553m374q3 ,
2,2,4-trimethyl-1,2-dihydrochinolin
unii-0553m374q3
FT-0621798
1,2-dihydro-2,2,4-trimethylquinoline [hsdb]
antioxidant fr-sb
SCHEMBL44875
tmdq
mfcd00044248
SY029873
acetonanil (salt/mix)
acetonanyl (salt/mix)
W-109515
CS-0046816
AS-44332
methyl4-hydroxy-1-(4-methoxyphenyl)-6-oxo-1,6-dihydro-3-pyridazinecarboxylate
1,2-dihydro-2,2,4-trimethylquinoline (85per cent)
AMY41313
D70537
Q27236080
SB67449
1,2-dihydro-2,2,4-trimethylquinoline;
31014-67-2
hydroquin
good-rite 3140
EN300-57908

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" This chemical also produced birth defects-absent or short tail, cleft palate, and internal hydrocephalus-but only at doses toxic to the mother."( Evaluation of oral exposure to Polnoks R for female rats in developmental toxicity studies.
Barański, B; Berlińska, B; Sitarek, K, 1996)		0.29
" This chemical given per os to female rats induces also teratogenic effect but only at doses toxic to the mother."( Maternal-fetal distribution and prenatal toxicity of 2,2,4-trimethyl-1,2-dihydroquinoline in the rat.
Sapota, A; Sitarek, K, 2003)		0.32

Dosage Studied

ExcerptRelevanceReference
" Multiple exposure of rats to high TMQ doses (1150 mumol/kg) resulted in some bioaccumulation of TMQ-derived radioactivity in all tissues examined, but these residues did not persist when dosing was discontinued."( Absorption, distribution, metabolism, and excretion of 1,2-dihydro-2,2,4-trimethylquinoline in the male F344 rat.
Burka, LT; Ioannou, YM; Matthews, HB; Moorman, MP; Sanders, JM, )		0.38
" The highest concentration of 14C in maternal tissues 24 hr after oral dosing was found in adipose tissue, sciatic nerve, muscles, kidneys, and liver."( Maternal-fetal distribution and prenatal toxicity of 2,2,4-trimethyl-1,2-dihydroquinoline in the rat.
Sapota, A; Sitarek, K, 2003)		0.32
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (44)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency28.18380.004023.8416100.0000AID485290
Chain A, HADH2 proteinHomo sapiens (human)Potency29.45480.025120.237639.8107AID886; AID893
Chain B, HADH2 proteinHomo sapiens (human)Potency29.45480.025120.237639.8107AID886; AID893
Chain A, CruzipainTrypanosoma cruziPotency15.84890.002014.677939.8107AID1476
acid sphingomyelinaseHomo sapiens (human)Potency25.118914.125424.061339.8107AID504937
interleukin 8Homo sapiens (human)Potency66.82420.047349.480674.9780AID651758
thioredoxin reductaseRattus norvegicus (Norway rat)Potency79.43280.100020.879379.4328AID588456
pregnane X receptorRattus norvegicus (Norway rat)Potency44.66840.025127.9203501.1870AID651751
RAR-related orphan receptor gammaMus musculus (house mouse)Potency60.95030.006038.004119,952.5996AID1159521; AID1159523
GLS proteinHomo sapiens (human)Potency35.48130.35487.935539.8107AID624170
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency39.81070.011212.4002100.0000AID1030
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency33.46930.001022.650876.6163AID1224839
progesterone receptorHomo sapiens (human)Potency26.58560.000417.946075.1148AID1346795
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency54.70600.003041.611522,387.1992AID1159552; AID1159553; AID1159555
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency64.07770.001530.607315,848.9004AID1224841; AID1224848; AID1224849; AID1259401; AID1259403
farnesoid X nuclear receptorHomo sapiens (human)Potency35.81150.375827.485161.6524AID743217; AID743220
pregnane X nuclear receptorHomo sapiens (human)Potency11.91440.005428.02631,258.9301AID1346982; AID720659
estrogen nuclear receptor alphaHomo sapiens (human)Potency58.03560.000229.305416,493.5996AID743080
vitamin D (1,25- dihydroxyvitamin D3) receptorHomo sapiens (human)Potency58.52070.023723.228263.5986AID743223
aryl hydrocarbon receptorHomo sapiens (human)Potency63.80500.000723.06741,258.9301AID743085; AID743122
cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_aHomo sapiens (human)Potency49.70790.001723.839378.1014AID743083
thyroid stimulating hormone receptorHomo sapiens (human)Potency50.67610.001628.015177.1139AID1224843; AID1224895; AID1259385
thyroid hormone receptor beta isoform aHomo sapiens (human)Potency44.66840.010039.53711,122.0200AID588545
thyroid hormone receptor beta isoform 2Rattus norvegicus (Norway rat)Potency33.71990.000323.4451159.6830AID743065; AID743067
heat shock protein beta-1Homo sapiens (human)Potency60.06440.042027.378961.6448AID743210
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency74.97800.000627.21521,122.0200AID651741
gemininHomo sapiens (human)Potency0.02220.004611.374133.4983AID624296; AID624297
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency10.00000.031610.279239.8107AID884; AID885
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
GABA theta subunitRattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
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 (17)

Assay IDTitleYearJournalArticle
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.
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.
AID1745845Primary qHTS for Inhibitors of ATXN expression
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.
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
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.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID29157Dissociation constant of compound at 20 degree C1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
2,4-Diamino-5-benzylpyrimidines and analogues as antibacterial agents. 12. 1,2-Dihydroquinolylmethyl analogues with high activity and specificity for bacterial dihydrofolate reductase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (18)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (5.56)18.7374
1990's1 (5.56)18.2507
2000's3 (16.67)29.6817
2010's9 (50.00)24.3611
2020's4 (22.22)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 23.87

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 Index23.87 (24.57)
Research Supply Index3.04 (2.92)
Research Growth Index5.27 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (23.87)

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%
Other20 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
trimethoprim
Trimethoprim: A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to PYRIMETHAMINE. It is potentiated by SULFONAMIDES and the TRIMETHOPRIM, SULFAMETHOXAZOLE DRUG COMBINATION is the form most often used. It is sometimes used alone as an antimalarial. TRIMETHOPRIM RESISTANCE has been reported.. trimethoprim : An aminopyrimidine antibiotic whose structure consists of pyrimidine 2,4-diamine and 1,2,3-trimethoxybenzene moieties linked by a methylene bridge.		1.9710aminopyrimidine;
methoxybenzenes		antibacterial drug;
diuretic;
drug allergen;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor;
environmental contaminant;
xenobiotic
isoprene
isoprene: used in manufacture of ''synthetic'' rubber, butyl rubber; copolymer in production of elastomers; structure. isoprene : A hemiterpene with the formula CH2=C(CH3)CH=CH2; the monomer of natural rubber and a common structure motif to the isoprenoids, a large class of other naturally occurring compounds.		2.0210alkadiene;
hemiterpene;
volatile organic compound		plant metabolite
azides
Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.		2.110pseudohalide anionmitochondrial respiratory-chain inhibitor
warfarin
Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.		2.0710benzenes;
hydroxycoumarin;
methyl ketone
ConditionIndicatedRelationship StrengthStudiesTrials
Innate Inflammatory Response
[description not available]		02.8630
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.8630
Encephalitis, Polio
[description not available]		02.0610
Poliomyelitis
An acute infectious disease of humans, particularly children, caused by any of three serotypes of human poliovirus (POLIOVIRUS). Usually the infection is limited to the gastrointestinal tract and nasopharynx, and is often asymptomatic. The central nervous system, primarily the spinal cord, may be affected, leading to rapidly progressive paralysis, coarse FASCICULATION and hyporeflexia. Motor neurons are primarily affected. Encephalitis may also occur. The virus replicates in the nervous system, and may cause significant neuronal loss, most notably in the spinal cord. A rare related condition, nonpoliovirus poliomyelitis, may result from infections with nonpoliovirus enteroviruses. (From Adams et al., Principles of Neurology, 6th ed, pp764-5)		02.0610
Anemia, Fanconi
[description not available]		02.1310
Fanconi Anemia
Congenital disorder affecting all bone marrow elements, resulting in ANEMIA; LEUKOPENIA; and THROMBOPENIA, and associated with cardiac, renal, and limb malformations as well as dermal pigmentary changes. Spontaneous CHROMOSOME BREAKAGE is a feature of this disease along with predisposition to LEUKEMIA. There are at least 7 complementation groups in Fanconi anemia: FANCA, FANCB, FANCC, FANCD1, FANCD2, FANCE, FANCF, FANCG, and FANCL. (from Online Mendelian Inheritance in Man, http://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=227650, August 20, 2004)		02.1310
Anterior Choroidal Artery Infarction
[description not available]		02.4110
Cerebral Infarction
The formation of an area of NECROSIS in the CEREBRUM caused by an insufficiency of arterial or venous blood flow. Infarcts of the cerebrum are generally classified by hemisphere (i.e., left vs. right), lobe (e.g., frontal lobe infarction), arterial distribution (e.g., INFARCTION, ANTERIOR CEREBRAL ARTERY), and etiology (e.g., embolic infarction).		02.4110
Acute Liver Injury, Drug-Induced
[description not available]		02.2110
Chemical and Drug Induced Liver Injury
A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.		02.2110
Brain Vascular Disorders
[description not available]		02.3110
Injury, Ischemia-Reperfusion
[description not available]		02.3110
Cerebrovascular Disorders
A spectrum of pathological conditions of impaired blood flow in the brain. They can involve vessels (ARTERIES or VEINS) in the CEREBRUM, the CEREBELLUM, and the BRAIN STEM. Major categories include INTRACRANIAL ARTERIOVENOUS MALFORMATIONS; BRAIN ISCHEMIA; CEREBRAL HEMORRHAGE; and others.		02.3110
Reperfusion Injury
Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.		02.3110
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		02.730
Abnormalities, Drug-Induced
Congenital abnormalities caused by medicinal substances or drugs of abuse given to or taken by the mother, or to which she is inadvertently exposed during the manufacture of such substances. The concept excludes abnormalities resulting from exposure to non-medicinal chemicals in the environment.		02.730
Delayed Effects, Prenatal Exposure
[description not available]		02.4220
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		02.730
Fetal Death
Death of the developing young in utero. BIRTH of a dead FETUS is STILLBIRTH.		02.0210