Compounds > 4-methylquinoline
Page last updated: 2024-11-05

4-methylquinoline

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

Description

4-Methylquinoline is a heterocyclic aromatic compound with a quinoline core structure and a methyl substituent at the 4-position. It is a colorless liquid with a characteristic odor. It is synthesized via various methods, including the Skraup synthesis, the Doebner-Miller reaction, and the Friedländer synthesis. 4-Methylquinoline exhibits biological activity, including antibacterial, antifungal, and anti-inflammatory properties. It has been investigated for its potential use in pharmaceuticals and as a precursor for the synthesis of other important compounds. The compound's fluorescence properties have also made it a subject of study in materials science.'

4-methylquinoline: structure given in first source; RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

4-methylquinoline : A methylquinoline carrying a methyl substituent at position 4. [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 CID10285
CHEMBL ID9734
CHEBI ID48983
SCHEMBL ID31559
MeSH IDM0161077

Synonyms (62)

Synonym
4-lepidine
nsc3412
cincholepidine
p-methylquinoline
quinoline, 4-methyl-
lepidin
.gamma.-methylquinoline
491-35-0
4-methylquinoline
nsc-3412
lepidine
gamma-methylquinoline
hsdb 7153
einecs 207-734-2
brn 0110926
CHEBI:48983 ,
inchi=1/c10h9n/c1-8-6-7-11-10-5-3-2-4-9(8)10/h2-7h,1h
4-methylquinoline, >=99%
lepidine, 99%
ccris 2894
ai3-24277
nsc 3412
CHEMBL9734
4-methyl-quinoline
FT-0659357
L0024
AKOS000119150
A22510
methyl-4 isoquinoleine
NCGC00184238-03
NCGC00184238-01
NCGC00184238-10
NCGC00184238-06
NCGC00184238-05
NCGC00184238-04
NCGC00184238-02
NCGC00184238-08
NCGC00184238-09
NCGC00184238-07
dtxsid7047067 ,
cas-491-35-0
NCGC00256086-01
tox21_301829
dtxcid5027067
116169t3o8 ,
unii-116169t3o8
5-20-07-00389 (beilstein handbook reference)
FT-0627792
lepidine [mi]
4-methyl quinoline
SCHEMBL31559
PS-3771
STR06140
mfcd00006784
J-515822
F0001-1281
BCP27150
Q6527408
AMY13842
H10212
EN300-19081
Z104472668

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" The mechanisms of the toxic action remain unknown."( Metabolic activation and cytotoxicity of 4-methylquinoline mediated by CYP3A4 and sulfotransferases in rats.
Gao, X; Jia, Y; Li, K; Li, W; Peng, Y; Wang, Y; Yang, L; Zhang, X; Zhao, G; Zheng, J, 2023)		1.18
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
mutagenAn agent that increases the frequency of mutations above the normal background level, usually by interacting directly with DNA and causing it damage, including base substitution.
[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
methylquinolineAny member of the class of quinolines carrying at least one methyl substituent.
[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 (3)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
GLI family zinc finger 3Homo sapiens (human)Potency42.35590.000714.592883.7951AID1259369; AID1259392
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency68.83410.003041.611522,387.1992AID1159552; AID1159553
67.9K proteinVaccinia virusPotency11.22020.00018.4406100.0000AID720579
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID1491378Displacement of [3H]prazosin from alpha1 adrenoceptor in C57BL/6 mouse hippocampal homogenates assessed as remaining receptor bound [3H]prazosin levels at 10 uM after 40 mins by liquid scintillation counting method relative to control2017European journal of medicinal chemistry, Sep-08, Volume: 137Evaluation of the antidepressant therapeutic potential of isocyanine and pseudoisocyanine analogues of the organic cation decynium-22.
AID1491380Displacement of [3H]prazosin from alpha1 adrenoceptor in C57BL/6 mouse hippocampal homogenates assessed as remaining receptor bound [3H]prazosin levels at 100 uM after 40 mins by liquid scintillation counting method relative to control2017European journal of medicinal chemistry, Sep-08, Volume: 137Evaluation of the antidepressant therapeutic potential of isocyanine and pseudoisocyanine analogues of the organic cation decynium-22.
AID144732In vitro anti-mycobacterial activity against Mycobacterium tuberculosis H37Rv2003Bioorganic & medicinal chemistry letters, Mar-24, Volume: 13, Issue:6
Substituted 4-methylquinolines as a new class of anti-tuberculosis agents.
AID1491372Displacement of [3H]prazosin from alpha1 adrenoceptor in C57BL/6 mouse hippocampal homogenates assessed as remaining receptor bound [3H]prazosin levels at 0.01 uM after 40 mins by liquid scintillation counting method relative to control2017European journal of medicinal chemistry, Sep-08, Volume: 137Evaluation of the antidepressant therapeutic potential of isocyanine and pseudoisocyanine analogues of the organic cation decynium-22.
AID1491374Displacement of [3H]prazosin from alpha1 adrenoceptor in C57BL/6 mouse hippocampal homogenates assessed as remaining receptor bound [3H]prazosin levels at 0.1 uM after 40 mins by liquid scintillation counting method relative to control2017European journal of medicinal chemistry, Sep-08, Volume: 137Evaluation of the antidepressant therapeutic potential of isocyanine and pseudoisocyanine analogues of the organic cation decynium-22.
AID1491370Displacement of [3H]prazosin from alpha1 adrenoceptor in C57BL/6 mouse hippocampal homogenates assessed as remaining receptor bound [3H]prazosin levels at 0.001 uM after 40 mins by liquid scintillation counting method relative to control2017European journal of medicinal chemistry, Sep-08, Volume: 137Evaluation of the antidepressant therapeutic potential of isocyanine and pseudoisocyanine analogues of the organic cation decynium-22.
AID145291Minimum inhibitory concentration required to inhibit 90% of the inoculum of tuberculosis H37Rv2003Bioorganic & medicinal chemistry letters, Mar-24, Volume: 13, Issue:6
Substituted 4-methylquinolines as a new class of anti-tuberculosis agents.
AID1145387Partition coefficient, log P of the compound by HPLC analysis1976Journal of medicinal chemistry, May, Volume: 19, Issue:5
Direct measurement of octanol-water partition coefficients by high-pressure liquid chromatography.
AID1491376Displacement of [3H]prazosin from alpha1 adrenoceptor in C57BL/6 mouse hippocampal homogenates assessed as remaining receptor bound [3H]prazosin levels at 1 uM after 40 mins by liquid scintillation counting method relative to control2017European journal of medicinal chemistry, Sep-08, Volume: 137Evaluation of the antidepressant therapeutic potential of isocyanine and pseudoisocyanine analogues of the organic cation decynium-22.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (17)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (17.65)18.7374
1990's4 (23.53)18.2507
2000's3 (17.65)29.6817
2010's5 (29.41)24.3611
2020's2 (11.76)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 32.32

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 Index32.32 (24.57)
Research Supply Index3.00 (2.92)
Research Growth Index4.79 (4.65)
Search Engine Demand Index36.59 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (32.32)

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%
Other19 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
benzene
[no description available]		2.4110aromatic annulene;
benzenes;
volatile organic compound		carcinogenic agent;
environmental contaminant;
non-polar solvent
acetanilide
acetanilide: a phenylacetamide; use ACETANILIDES for the plural group meaning of the singular term. N-phenylacetamide : A member of the class of acetamides that is acetamide in which one of the hydrogens attached to the nitrogen is substituted by a phenyl group.		1.9510acetamides;
anilide		analgesic
niacin
Niacin: A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has PELLAGRA-curative, vasodilating, and antilipemic properties.. vitamin B3 : Any member of a group of vitamers that belong to the chemical structural class called pyridines that exhibit biological activity against vitamin B3 deficiency. Vitamin B3 deficiency causes a condition known as pellagra whose symptoms include depression, dermatitis and diarrhea. The vitamers include nicotinic acid and nicotinamide (and their ionized and salt forms).. nicotinic acid : A pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group.		2.0410pyridine alkaloid;
pyridinemonocarboxylic acid;
vitamin B3		antidote;
antilipemic drug;
EC 3.5.1.19 (nicotinamidase) inhibitor;
Escherichia coli metabolite;
human urinary metabolite;
metabolite;
mouse metabolite;
plant metabolite;
vasodilator agent
phenol
[no description available]		1.9510phenolsantiseptic drug;
disinfectant;
human xenobiotic metabolite;
mouse metabolite
pyridine
azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.		1.9510azaarene;
mancude organic heteromonocyclic parent;
monocyclic heteroarene;
pyridines		environmental contaminant;
NMR chemical shift reference compound
4-aminopyridine
[no description available]		1.9510aminopyridine;
aromatic amine		avicide;
orphan drug;
potassium channel blocker
caffeine
[no description available]		1.9510purine alkaloid;
trimethylxanthine		adenosine A2A receptor antagonist;
adenosine receptor antagonist;
adjuvant;
central nervous system stimulant;
diuretic;
EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor;
EC 3.1.4.* (phosphoric diester hydrolase) inhibitor;
environmental contaminant;
food additive;
fungal metabolite;
geroprotector;
human blood serum metabolite;
mouse metabolite;
mutagen;
plant metabolite;
psychotropic drug;
ryanodine receptor agonist;
xenobiotic
4-chlorophenol
4-chlorophenol: used as a root canal irrigant. 4-chlorophenol : A monochlorophenol substituted at the pare position by a chlorine atom.		1.9510monochlorophenol
phenazine
[no description available]		1.9510azaarene;
heteranthrene;
mancude organic heterotricyclic parent;
phenazines;
polycyclic heteroarene
practolol
Practolol: A beta-1 adrenergic antagonist that has been used in the emergency treatment of CARDIAC ARRYTHMIAS.. practolol : N-(4-Hydroxyphenyl)acetamide in which the hydrogen of the phenolic hydroxy group is substituted by a 3-(isopropylaminoamino)-2-hydroxypropyl group. A selective beta blocker, it has been used in the emergency treatment of cardiac arrhythmias.		1.9510acetamides;
ethanolamines;
propanolamine;
secondary alcohol;
secondary amino compound		anti-arrhythmia drug;
beta-adrenergic antagonist
4-nitroquinoline-1-oxide
4-nitroquinoline N-oxide : A quinoline N-oxide carrying a nitro substituent at position 4.		2.1110C-nitro compound;
quinoline N-oxide		carcinogenic agent
aniline
[no description available]		1.9510anilines;
primary arylamine
benzo(f)quinoline
[no description available]		1.9710
quinoxalines
quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.		2.1710mancude organic heterobicyclic parent;
naphthyridine;
ortho-fused heteroarene
quinoline
[no description available]		2.3620azaarene;
mancude organic heterobicyclic parent;
ortho-fused heteroarene;
quinolines
anisole
anisole : A monomethoxybenzene that is benzene substituted by a methoxy group.		1.9510monomethoxybenzeneplant metabolite
4-methylpyridine
4-methylpyridine: structure in first source. 4-methylpyridine : A methylpyridine in which the methyl substituent is at position 4.		2.0410methylpyridine
chlorobenzene
[no description available]		1.9510monochlorobenzenessolvent
3-methylpyridine
3-methylpyridine : A methylpyridine that is pyridine substituted by a methyl group at position 3.		1.9510methylpyridine
isoquinoline
[no description available]		1.9510azaarene;
isoquinolines;
mancude organic heterobicyclic parent;
ortho-fused heteroarene
acridines
Acridines: Compounds that include the structure of acridine.. acridine : A polycyclic heteroarene that is anthracene in which one of the central CH groups is replaced by a nitrogen atom.		1.9510acridines;
mancude organic heterotricyclic parent;
polycyclic heteroarene		genotoxin
propadiene
[no description available]		7.1110allenes
8-methylquinoline
[no description available]		1.9710methylquinoline
1-phenyl-3,3-dimethyltriazene
[no description available]		2.1710
deuterium
Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.		1.9910dihydrogen
ozone
Ozone: The unstable triatomic form of oxygen, O3. It is a powerful oxidant that is produced for various chemical and industrial uses. Its production is also catalyzed in the ATMOSPHERE by ULTRAVIOLET RAY irradiation of oxygen or other ozone precursors such as VOLATILE ORGANIC COMPOUNDS and NITROGEN OXIDES. About 90% of the ozone in the atmosphere exists in the stratosphere (STRATOSPHERIC OZONE).. ozone : An elemental molecule with formula O3. An explosive, pale blue gas (b.p. -112degreeC) that has a characteristic, pungent odour, it is continuously produced in the upper atmosphere by the action of solar ultraviolet radiation on atmospheric oxygen. It is an antimicrobial agent used in the production of bottled water, as well as in the treatment of meat, poultry and other foodstuffs.		2.4110elemental molecule;
gas molecular entity;
reactive oxygen species;
triatomic oxygen		antiseptic drug;
disinfectant;
electrophilic reagent;
greenhouse gas;
mutagen;
oxidising agent;
tracer
1,7-phenanthroline
[no description available]		2.1710phenanthroline
cobalt
Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.		2.1710cobalt group element atom;
metal allergen		micronutrient
tamsulosin
[no description available]		2.15105-(2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl)-2-methoxybenzenesulfonamidealpha-adrenergic antagonist;
antineoplastic agent
hydroxyl radical
Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.		2.4110oxygen hydride;
oxygen radical;
reactive oxygen species
singlet oxygen
Singlet Oxygen: An excited state of molecular oxygen generated photochemically or chemically. Singlet oxygen reacts with a variety of biological molecules such as NUCLEIC ACIDS; PROTEINS; and LIPIDS; causing oxidative damages.		2.4110chalcogen;
monoatomic oxygen;
nonmetal atom		macronutrient
aluminum
Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.		2.4110boron group element atom;
elemental aluminium;
metal atom
sulfur
Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.		2.1110chalcogen;
nonmetal atom		macronutrient
ConditionIndicatedRelationship StrengthStudiesTrials
Food Poisoning
[description not available]		02.110
Cancer of Liver
[description not available]		01.9710
Cancer of Lung
[description not available]		01.9710
Experimental Neoplasms
[description not available]		01.9710
Liver Neoplasms
Tumors or cancer of the LIVER.		01.9710
Lung Neoplasms
Tumors or cancer of the LUNG.		01.9710