Compounds > 1-methylisoquinoline
Page last updated: 2024-12-05

1-methylisoquinoline

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

Description

1-Methylisoquinoline is a heterocyclic aromatic compound that has been studied for its potential pharmacological properties. It is a derivative of isoquinoline, a naturally occurring compound found in plants. The synthesis of 1-methylisoquinoline typically involves the reaction of an appropriate starting material with a methylating agent. Research on 1-methylisoquinoline has focused on its potential as a therapeutic agent. It has been shown to exhibit anti-inflammatory and analgesic activities in animal models. Its importance stems from its potential to be developed into a new drug for the treatment of various diseases. The study of 1-methylisoquinoline is driven by its unique chemical structure and its potential to interact with biological targets in a way that could provide therapeutic benefits.'

1-methylisoquinoline : An isoquinoline substituted by a methyl group at position 1. [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 CID15592
CHEMBL ID364698
CHEBI ID125469
SCHEMBL ID70488
MeSH IDM0270500

Synonyms (39)

Synonym
unii-z96hox9rt9
einecs 217-017-6
z96hox9rt9 ,
nsc 101175
AKOS015842462
inchi=1/c10h9n/c1-8-10-5-3-2-4-9(10)6-7-11-8/h2-7h,1h
isoquinoline, 1-methyl-
1721-93-3
nsc-101175
1-methylisoquinoline
isoquinaldine
nsc101175
1-methylisoquinoline, 97%
CHEBI:125469
bdbm50159268
CHEMBL364698 ,
1-methyl-isoquinoline
M0298
A811385
58853-80-8
BP-12703
FT-0633794
BRD-K02603382-001-01-0
SCHEMBL70488
1-methyl isoquinoline
TS-01867
methylisoquinoline; 97%
mfcd00006902
Q27216088
isoquinoline, methyl-
J-505001
DTXSID20870904
AMY13709
isoquinoline, methyl-;1-methyl isoquinoline
BCP30416
Y10177
EN300-120889
Z1255415440
1-methylisoquinoline; isoquinaldine; nsc 101175

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" Potent and specific inhibitors of the CYP2A6 enzyme can be used in the future to increase nicotine bioavailability and thus make oral nicotine administration feasible in smoking cessation therapy."( Quantitative structure-activity relationship analysis of inhibitors of the nicotine metabolizing CYP2A6 enzyme.
Juvonen, RO; Poso, A; Rahnasto, M; Raunio, H; Wittekindt, C, 2005)		0.33
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
isoquinolinesA class of organic heteropolycyclic compound consisting of isoquinoline and its substitution derivatives.
[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 (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cytochrome P450 2A6Homo sapiens (human)IC50 (µMol)59.98950.00443.889510.0000AID241172; AID420671
Cytochrome P450 2A5Mus musculus (house mouse)IC50 (µMol)169.91201.00004.20259.7051AID241174; AID420670
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (6)

Processvia Protein(s)Taxonomy
xenobiotic metabolic processCytochrome P450 2A6Homo sapiens (human)
steroid metabolic processCytochrome P450 2A6Homo sapiens (human)
coumarin metabolic processCytochrome P450 2A6Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 2A6Homo sapiens (human)
coumarin catabolic processCytochrome P450 2A6Homo sapiens (human)
epoxygenase P450 pathwayCytochrome P450 2A6Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
iron ion bindingCytochrome P450 2A6Homo sapiens (human)
coumarin 7-hydroxylase activityCytochrome P450 2A6Homo sapiens (human)
enzyme bindingCytochrome P450 2A6Homo sapiens (human)
heme bindingCytochrome P450 2A6Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygenCytochrome P450 2A6Homo sapiens (human)
arachidonic acid epoxygenase activityCytochrome P450 2A6Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
endoplasmic reticulum membraneCytochrome P450 2A6Homo sapiens (human)
cytoplasmic microtubuleCytochrome P450 2A6Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 2A6Homo sapiens (human)
cytoplasmCytochrome P450 2A6Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID242975Ratio of IC50 for human CYP2A6 to that of mouse CYP2A5 was determined2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Quantitative structure-activity relationship analysis of inhibitors of the nicotine metabolizing CYP2A6 enzyme.
AID420670Inhibition of mouse CYP2A52009European journal of medicinal chemistry, May, Volume: 44, Issue:5
Exploring QSAR and QAAR for inhibitors of cytochrome P450 2A6 and 2A5 enzymes using GFA and G/PLS techniques.
AID1156431Selectivity index, ratio of CC50 for human HepG2 cells to IC50 for chloroquine-, pyrimethamine- and proguanil-resistant Plasmodium falciparum K1 infected in human erythrocytes2014European journal of medicinal chemistry, Aug-18, Volume: 83Synthesis and in vitro evaluation of 4-trichloromethylpyrrolo[1,2-a]quinoxalines as new antiplasmodial agents.
AID241174Inhibitory concentration against mouse cytochrome P450 2A52005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Quantitative structure-activity relationship analysis of inhibitors of the nicotine metabolizing CYP2A6 enzyme.
AID1156429Antiplasmodial activity against chloroquine-, pyrimethamine- and proguanil-resistant Plasmodium falciparum K1 infected in human erythrocytes after 72 hrs by SYBR Green I fluorescence-based method2014European journal of medicinal chemistry, Aug-18, Volume: 83Synthesis and in vitro evaluation of 4-trichloromethylpyrrolo[1,2-a]quinoxalines as new antiplasmodial agents.
AID1156430Cytotoxicity against human HepG2 cells after 72 hrs by MTT assay2014European journal of medicinal chemistry, Aug-18, Volume: 83Synthesis and in vitro evaluation of 4-trichloromethylpyrrolo[1,2-a]quinoxalines as new antiplasmodial agents.
AID241172Inhibitory concentration against human cytochrome P450 2A62005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Quantitative structure-activity relationship analysis of inhibitors of the nicotine metabolizing CYP2A6 enzyme.
AID420671Inhibition of human CYP2A62009European journal of medicinal chemistry, May, Volume: 44, Issue:5
Exploring QSAR and QAAR for inhibitors of cytochrome P450 2A6 and 2A5 enzymes using GFA and G/PLS techniques.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (16.67)18.2507
2000's2 (33.33)29.6817
2010's3 (50.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.12

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 Index22.12 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.77 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.12)

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%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
benzaldehyde
[no description available]		2.0210benzaldehydesEC 3.1.1.3 (triacylglycerol lipase) inhibitor;
EC 3.5.5.1 (nitrilase) inhibitor;
flavouring agent;
fragrance;
odorant receptor agonist;
plant metabolite
coumarin
2H-chromen-2-one: coumarin derivative		2.0210coumarinsfluorescent dye;
human metabolite;
plant metabolite
naphthalene
[no description available]		2.4420naphthalenes;
ortho-fused bicyclic arene		apoptosis inhibitor;
carcinogenic agent;
environmental contaminant;
mouse metabolite;
plant metabolite;
volatile oil component
phenanthrene
phenanthrene : A polycyclic aromatic hydrocarbon composed of three fused benzene rings which takes its name from the two terms 'phenyl' and 'anthracene.'		2.4420ortho-fused polycyclic arene;
ortho-fused tricyclic hydrocarbon;
phenanthrenes		environmental contaminant;
mouse metabolite
phenethylamine
phenethylamine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7016. 2-phenylethylamine : A phenylethylamine having the phenyl substituent at the 2-position.		2.0210alkaloid;
aralkylamine;
phenylethylamine		Escherichia coli metabolite;
human metabolite;
mouse metabolite
pyridine
azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.		2.0810azaarene;
mancude organic heteromonocyclic parent;
monocyclic heteroarene;
pyridines		environmental contaminant;
NMR chemical shift reference compound
chloroquine
Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.		2.110aminoquinoline;
organochlorine compound;
secondary amino compound;
tertiary amino compound		anticoronaviral agent;
antimalarial;
antirheumatic drug;
autophagy inhibitor;
dermatologic drug
amphetamine
Amphetamine: A powerful central nervous system stimulant and sympathomimetic. Amphetamine has multiple mechanisms of action including blocking uptake of adrenergics and dopamine, stimulation of release of monamines, and inhibiting monoamine oxidase. Amphetamine is also a drug of abuse and a psychotomimetic. The l- and the d,l-forms are included here. The l-form has less central nervous system activity but stronger cardiovascular effects. The d-form is DEXTROAMPHETAMINE.. 1-phenylpropan-2-amine : A primary amine that is isopropylamine in which a hydrogen attached to one of the methyl groups has been replaced by a phenyl group.. amphetamine : A racemate comprising equimolar amounts of (R)-amphetamine (also known as levamphetamine or levoamphetamine) and (S)-amphetamine (also known as dexamfetamine or dextroamphetamine.		2.0210primary amine
4-dichlorobenzene
dichlorobenzene : Any member of the class of chlorobenzenes carrying two chloro groups at unspecified positions.. 1,4-dichlorobenzene : A dichlorobenzene carrying chloro groups at positions 1 and 4.		2.4420dichlorobenzeneinsecticide
1-methylnaphthalene
1-methylnaphthalene : A methylnaphthalene carrying a methyl substituent at position 1.		2.4420methylnaphthalenecarcinogenic agent;
plant metabolite
1-chloronaphthalene
1-chloronaphthalene: word preservative; in xylamon the active ingredient is 60% 1-chloronaphthalene; structure in Merck Index, 9th ed, #2126		2.4420
1-naphthol
1-naphthol: RN given refers to parent cpd. 1-naphthol : A naphthol carrying a hydroxy group at position 1.. hydroxynaphthalene : Any member of the class of naphthalenes that is naphthalene carrying one or more hydroxy groups.		2.4420naphtholgenotoxin;
human xenobiotic metabolite
quinoxalines
quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.		2.110mancude organic heterobicyclic parent;
naphthyridine;
ortho-fused heteroarene
2-methylnaphthalene
2-methylnaphthalene: RN given refers to parent cpd. 2-methylnaphthalene : A methylnaphthalene carrying a methyl substituent at position 2.		2.4420methylnaphthalene
2-chloronaphthalene
2-chloronaphthalene: structure in first source		2.4420
2-methylquinoline
2-methylquinoline: RN given refers to parent cpd. methylquinoline : Any member of the class of quinolines carrying at least one methyl substituent.. quinaldine : A quinoline compound in which the quinoline skeleton is substituted at C-2 with a methyl group.		2.7430quinolines
2-methoxynaphthalene
[no description available]		2.4420naphthalenes
4-methylbenzaldehyde
p-tolualdehyde : A tolualdehyde compound with the methyl substituent at the 4-position.		2.0210tolualdehydeplant metabolite
1,4-dibromobenzene
[no description available]		2.4420dibromobenzene
2-picoline
2-picoline: structure in first source. 2-methylpyridine : A methylpyridine carrying a methyl substituent at position 2.		2.0810methylpyridine
pyrroles
1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.		2.1310pyrrole;
secondary amine
isoquinoline
[no description available]		2.1310azaarene;
isoquinolines;
mancude organic heterobicyclic parent;
ortho-fused heteroarene
2-naphthol
2-naphthol: RN given refers to parent cpd. 2-naphthol : A naphthol carrying a hydroxy group at position 2.. naphthols : Any hydroxynaphthalene derivative that has a single hydroxy substituent.		2.4420naphtholantinematodal drug;
genotoxin;
human urinary metabolite;
human xenobiotic metabolite;
mouse metabolite;
radical scavenger
tetraphenylborate
Tetraphenylborate: An anionic compound that is used as a reagent for determination of potassium, ammonium, rubidium, and cesium ions. It also uncouples oxidative phosphorylation and forms complexes with biological materials, and is used in biological assays.		1.9910
1,2-dimethylnaphthalene
1,2-dimethylnaphthalene : A dimethylnaphthalene carrying methyl groups at positions 1 and 2.. dimethylnaphthalene : Any member of the class of naphthalenes carrying two methyl groups at unspecified positions.		2.4420dimethylnaphthalene
1,6-dimethylnaphthalene
1,6-dimethylnaphthalene: structure in first source		2.4420dimethylnaphthalene
2,6-dimethylnaphthalene
2,6-dimethylnaphthalene: RN given refers to parent cpd. 2,6-dimethylnaphthalene : A dimethylnaphthalene carrying methyl groups at positions 2 and 6.		2.4420dimethylnaphthaleneenvironmental contaminant
3-methylquinoline
[no description available]		2.4420methylquinolinexenobiotic
2,6-dimethylquinoline
2,6-dimethylquinoline: from roots of Peucedanum praeruptorum II		2.4420
4-chlorobiphenyl
4-chlorobiphenyl : A monochlorobiphenyl carrying a chloro substituent at position 4.		2.4420monochlorobiphenyl
2-methylquinoxaline
2-methylquinoxaline: structure given in first source. 2-methylquinoxaline : A quinoxaline derivative in which the quinoxaline (1,4-naphthyridine) skeleton is substituted at C-2 with a methyl group.		2.110quinoxaline derivative
4-anisaldehyde
4-anisaldehyde: RN given refers to cpd with specified locants for methoxy moieties; structure in Merck, 9th ed, #696. p-methoxybenzaldehyde : A member of the class of benzaldehydes consisting of benzaldehyde itself carrying a methoxy substituent at position 4.		2.0210benzaldehydesbacterial metabolite;
human urinary metabolite;
insect repellent;
plant metabolite
1-methyl-4-phenylpyridinium
1-Methyl-4-phenylpyridinium: An active neurotoxic metabolite of 1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE. The compound reduces dopamine levels, inhibits the biosynthesis of catecholamines, depletes cardiac norepinephrine and inactivates tyrosine hydroxylase. These and other toxic effects lead to cessation of oxidative phosphorylation, ATP depletion, and cell death. The compound, which is related to PARAQUAT, has also been used as an herbicide.. N-methyl-4-phenylpyridinium : A pyridinium ion that is N-methylpyridinium having a phenyl substituent at the 4-position.		1.9910pyridinium ionapoptosis inducer;
herbicide;
human xenobiotic metabolite;
neurotoxin
beta-tetralone
[no description available]		2.4420
nicotine
(S)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.		2.05103-(1-methylpyrrolidin-2-yl)pyridineanxiolytic drug;
biomarker;
immunomodulator;
mitogen;
neurotoxin;
nicotinic acetylcholine receptor agonist;
peripheral nervous system drug;
phytogenic insecticide;
plant metabolite;
psychotropic drug;
teratogenic agent;
xenobiotic
pseudonicotine
pseudonicotine: structure. (R)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has R-configuration.		2.02103-(1-methylpyrrolidin-2-yl)pyridine
2-chlorobiphenyl
2-chlorobiphenyl: RN from Toxlit. 2-chlorobiphenyl : A monochlorobiphenyl carrying a single chloro substituent at position 2.. monochlorobiphenyl : A chlorobiphenyl carrying a single chloro substituent at unspecified position.. chlorobiphenyl : A chloroarene that consists of a biphenyl skeleton substituted by one or more chloro groups.		2.4420monochlorobiphenyl
lamellarin h
lamellarin H: a benzo-isoquinoline-coumarin		2.1310
cotinine
Cotinine: The N-glucuronide conjugate of cotinine is a major urinary metabolite of NICOTINE. It thus serves as a biomarker of exposure to tobacco SMOKING. It has CNS stimulating properties.. (-)-cotinine : An N-alkylpyrrolidine that consists of N-methylpyrrolidinone bearing a pyridin-3-yl substituent at position C-5 (the 5S-enantiomer). It is an alkaloid commonly found in Nicotiana tabacum.		2.0210N-alkylpyrrolidine;
pyridines;
pyrrolidin-2-ones;
pyrrolidine alkaloid		antidepressant;
biomarker;
human xenobiotic metabolite;
plant metabolite
ytterbium(iii) triflate
[no description available]		2.1310
3-nitrocoumarin
[no description available]		2.1310
lamellarin d
lamellarin D: a benzo-isoquinoline-coumarin		2.1310
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.		2.1310benzenes;
hydroxycoumarin;
methyl ketone
ConditionIndicatedRelationship StrengthStudiesTrials