Compounds > 3-methyl-1,2,3,4-tetrahydroisoquinoline
Page last updated: 2024-12-09

3-methyl-1,2,3,4-tetrahydroisoquinoline

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

Description

3-methyl-1,2,3,4-tetrahydroisoquinoline: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID568974
CHEMBL ID60434
SCHEMBL ID1011182
SCHEMBL ID15334650
MeSH IDM0528753

Synonyms (25)

Synonym
HMS1698C16
1,2,3,4-tetrahydro-3-methylisoquinoline
3-methyl-1,2,3,4-tetrahydro-isoquinoline
CHEMBL60434 ,
AKOS000650337
29726-60-1
3-methyl-1,2,3,4-tetrahydroisoquinoline
bdbm50023304
EN300-86328
NCGC00184271-01
SCHEMBL1011182
AB39365
AB30586
AKOS016843414
isoquinoline, 1,2,3,4-tetrahydro-3-methyl-
SCHEMBL15334650
BS-13528
DTXSID10874097
FT-0729461
mfcd07187817
C74526
SB47999
PD178296
SY344004
Z979717380
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (6)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Smad3Homo sapiens (human)Potency3.98110.00527.809829.0929AID588855
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency89.12510.050127.073689.1251AID588590
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Phenylethanolamine N-methyltransferaseBos taurus (cattle)Ki2.32560.00312.329310.0000AID155135; AID155137; AID155141; AID155142; AID155145; AID155146; AID155167; AID155172; AID313558
Alpha-2B adrenergic receptorRattus norvegicus (Norway rat)Ki0.76890.00000.929610.0000AID35193; AID35195; AID37364; AID37366; AID37379
Alpha-2C adrenergic receptorRattus norvegicus (Norway rat)Ki0.76890.00000.970810.0000AID35193; AID35195; AID37364; AID37366; AID37379
Alpha-2A adrenergic receptorRattus norvegicus (Norway rat)Ki0.76890.00000.937510.0000AID35193; AID35195; AID37364; AID37366; AID37379
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (2)

Processvia Protein(s)Taxonomy
methylationPhenylethanolamine N-methyltransferaseBos taurus (cattle)
epinephrine biosynthetic processPhenylethanolamine N-methyltransferaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (1)

Processvia Protein(s)Taxonomy
phenylethanolamine N-methyltransferase activityPhenylethanolamine N-methyltransferaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (23)

Assay IDTitleYearJournalArticle
AID35216Ratio for binding affinity towards alpha-2 adrenoceptor to PNMT1999Journal of medicinal chemistry, Sep-09, Volume: 42, Issue:18
Synthesis and biochemical evaluation of 3-fluoromethyl-1,2,3, 4-tetrahydroisoquinolines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor.
AID313560Selectivity of Ki for bovine PNMT over Ki for rat alpha-2 adrenoceptor2008Bioorganic & medicinal chemistry, Jan-01, Volume: 16, Issue:1
Synthesis of 4,5,6,7-tetrahydrothieno[3,2-c]pyridines and comparison with their isosteric 1,2,3,4-tetrahydroisoquinolines as inhibitors of phenylethanolamine N-methyltransferase.
AID35335Selectivity determined by Ki of alpha 2 receptor / Ki of PNMT1999Journal of medicinal chemistry, Aug-26, Volume: 42, Issue:17
Synthesis and evaluation of 3-trifluoromethyl-7-substituted-1,2,3, 4-tetrahydroisoquinolines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor.
AID313559Displacement of [3H]clonidine from adrenergic alpha-1 receptor in Sprague-Dawley rat cortex2008Bioorganic & medicinal chemistry, Jan-01, Volume: 16, Issue:1
Synthesis of 4,5,6,7-tetrahydrothieno[3,2-c]pyridines and comparison with their isosteric 1,2,3,4-tetrahydroisoquinolines as inhibitors of phenylethanolamine N-methyltransferase.
AID37366Compound was tested in vitro for its affinity towards rat Alpha-2 adrenergic receptor1999Journal of medicinal chemistry, Sep-09, Volume: 42, Issue:18
Synthesis and biochemical evaluation of 3-fluoromethyl-1,2,3, 4-tetrahydroisoquinolines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor.
AID235162Selectivity ratio between PNMT and alpha-2 receptors1999Journal of medicinal chemistry, Jun-03, Volume: 42, Issue:11
3,7-Disubstituted-1,2,3,4-tetrahydroisoquinolines display remarkable potency and selectivity as inhibitors of phenylethanolamine N-methyltransferase versus the alpha2-adrenoceptor.
AID37364In vitro for binding affinity against Alpha-2 adrenergic receptor by radioligand [3H]clonidine in rat1996Journal of medicinal chemistry, Aug-30, Volume: 39, Issue:18
Effect of ring size or an additional heteroatom on the potency and selectivity of bicyclic benzylamine-type inhibitors of phenylethanolamine N-methyltransferase.
AID155146Inhibition of PNMT (Phenylethanolamine N-Methyltransferase) in vitro 1999Journal of medicinal chemistry, Aug-26, Volume: 42, Issue:17
Synthesis and evaluation of 3-trifluoromethyl-7-substituted-1,2,3, 4-tetrahydroisoquinolines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor.
AID229906Selectivity ratio between Ki of alpha-2 adrenoceptor and Ki of PNMT1996Journal of medicinal chemistry, Aug-30, Volume: 39, Issue:18
Effect of ring size or an additional heteroatom on the potency and selectivity of bicyclic benzylamine-type inhibitors of phenylethanolamine N-methyltransferase.
AID155135In vitro for inhibition of Phenylethanolamine N-Methyltransferase (PNMT)1996Journal of medicinal chemistry, Aug-30, Volume: 39, Issue:18
Effect of ring size or an additional heteroatom on the potency and selectivity of bicyclic benzylamine-type inhibitors of phenylethanolamine N-methyltransferase.
AID155142In vitro inhibitory activity against bovine adrenal phenylethanolamine N-methyl transferase (for +- stereoisomer)1999Journal of medicinal chemistry, Jun-03, Volume: 42, Issue:11
3,7-Disubstituted-1,2,3,4-tetrahydroisoquinolines display remarkable potency and selectivity as inhibitors of phenylethanolamine N-methyltransferase versus the alpha2-adrenoceptor.
AID35195In vitro inhibition of [3H]clonidine binding at the alpha-2 adrenergic receptor.1999Journal of medicinal chemistry, Oct-21, Volume: 42, Issue:21
Enantiospecific synthesis of 3-fluoromethyl-, 3-hydroxymethyl-, and 3-chloromethyl-1,2,3,4-tetrahydroisoquinolines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor.
AID313558Inhibition of bovine PNMT by radiochemical assay2008Bioorganic & medicinal chemistry, Jan-01, Volume: 16, Issue:1
Synthesis of 4,5,6,7-tetrahydrothieno[3,2-c]pyridines and comparison with their isosteric 1,2,3,4-tetrahydroisoquinolines as inhibitors of phenylethanolamine N-methyltransferase.
AID155145In vitro inhibition of PNMT (Phenylethanolamine N-Methyltransferase).1999Journal of medicinal chemistry, Oct-21, Volume: 42, Issue:21
Enantiospecific synthesis of 3-fluoromethyl-, 3-hydroxymethyl-, and 3-chloromethyl-1,2,3,4-tetrahydroisoquinolines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor.
AID35193The compound was tested in vitro for binding affinity against Alpha-2 adrenergic receptor using [3H]clonidine1999Journal of medicinal chemistry, Aug-26, Volume: 42, Issue:17
Synthesis and evaluation of 3-trifluoromethyl-7-substituted-1,2,3, 4-tetrahydroisoquinolines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor.
AID37379In vitro binding affinity towards cortical membranes of male Sprague-Dawley rats alpha-2 adrenergic receptor by replacing [3H]clonidine1999Journal of medicinal chemistry, Jun-03, Volume: 42, Issue:11
3,7-Disubstituted-1,2,3,4-tetrahydroisoquinolines display remarkable potency and selectivity as inhibitors of phenylethanolamine N-methyltransferase versus the alpha2-adrenoceptor.
AID233623Ratio of binding affinity of PNMT to alpha-2 receptors.1999Journal of medicinal chemistry, Oct-21, Volume: 42, Issue:21
Enantiospecific synthesis of 3-fluoromethyl-, 3-hydroxymethyl-, and 3-chloromethyl-1,2,3,4-tetrahydroisoquinolines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor.
AID155141In vitro inhibitory activity against bovine adrenal phenylethanolamine N-methyl transferase1999Journal of medicinal chemistry, Jun-03, Volume: 42, Issue:11
3,7-Disubstituted-1,2,3,4-tetrahydroisoquinolines display remarkable potency and selectivity as inhibitors of phenylethanolamine N-methyltransferase versus the alpha2-adrenoceptor.
AID155172Inhibition of phenylethanolamine N-methyl-transferase (PNMT)1988Journal of medicinal chemistry, Feb, Volume: 31, Issue:2
Conformational and steric aspects of the inhibition of phenylethanolamine N-methyltransferase by benzylamines.
AID155137Affinity for bovine Phenylethanolamine N-Methyltransferase (PNMT)1999Journal of medicinal chemistry, Sep-09, Volume: 42, Issue:18
Synthesis and biochemical evaluation of 3-fluoromethyl-1,2,3, 4-tetrahydroisoquinolines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor.
AID155167In vitro inhibitory activity measured against bovine adrenal phenylethanolamine N-methyltransferase(PNMT)1988Journal of medicinal chemistry, Apr, Volume: 31, Issue:4
Synthesis and evaluation of 3-substituted analogues of 1,2,3,4-tetrahydroisoquinoline as inhibitors of phenylethanolamine N-methyltransferase.
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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (16.67)18.7374
1990's5 (41.67)18.2507
2000's2 (16.67)29.6817
2010's3 (25.00)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: 12.04

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

MetricThis Compound (vs All)
Research Demand Index12.04 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index4.60 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.04)

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%
Other12 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
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.		2.0410alkaloid;
aralkylamine;
phenylethylamine		Escherichia coli metabolite;
human metabolite;
mouse metabolite
hydroxyindoleacetic acid
(5-hydroxyindol-3-yl)acetic acid : A member of the class of indole-3-acetic acids that is indole-3-acetic acid substituted by a hydroxy group at C-5.		2.0810indole-3-acetic acidsdrug metabolite;
human metabolite;
mouse metabolite
sk&f 29661
1,2,3,4-tetrahydroisoquinoline-7-sulfonamide: structure		3.150
1,2,3,4-tetrahydroisoquinoline
1,2,3,4-tetrahydroisoquinoline: RN given refers to cpd with locants as specified		3.3870isoquinolines
benzylamine
aminotoluene : Any member of the class of toluenes carrying one or more amino groups.		2.6830aralkylamine;
primary amine		allergen;
EC 3.5.5.1 (nitrilase) inhibitor;
plant metabolite
thiazoles
[no description available]		2.04101,3-thiazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
2-aminotetralin
2-aminotetralin: RN given refers to parent cpd without isomeric designation; structure		1.9710tetralins
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.		2.0410pyridinium ionapoptosis inducer;
herbicide;
human xenobiotic metabolite;
neurotoxin
thiazolyl blue
thiazolyl blue: RN & II refers to bromide. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide : The bromide salt of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium.		2.0410organic bromide saltcolorimetric reagent;
dye
4-methylbenzylamine
[no description available]		1.9710
4-fluorobenzylamine
[no description available]		1.9710
4-methoxybenzylamine
1-(4-methoxyphenyl)methanamine : An aralkylamino compound that is benzylamine substituted by a methoxy group at the para position.		1.9710aralkylamino compound;
aromatic ether;
primary amino compound
1-methyl-1,2,3,4-tetrahydroisoquinoline
1-methyl-1,2,3,4-tetrahydroisoquinoline: endogenous amine from rat brain		1.9710isoquinolines
1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid: used as a substitute for amino acids in synthetic peptides		2.3920
ly 134046
LY 134046: RN given refers to parent cpd; structure in first source		2.420
7,8-dichloro-1,2,3,4-tetrahydroisoquinoline
7,8-dichloro-1,2,3,4-tetrahydroisoquinoline: potent reversible inhibitor of phenylethanolamine N-methyltransferase; structure. 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline : A 1,2,3,4-tetrahydroisoquinoline hacing chloro substituents at the 7- and 8-positions.		3.0950isoquinolines;
organochlorine compound
4,9-dihydro-7-methoxy-3h-pyrido(3,4b)indole
4,9-dihydro-7-methoxy-3H-pyrido(3,4b)indole: structure given in first source		2.420
3-trifluoromethyl-7-bromo-1,2,3,4-tetrahydroisoquinoline
3-trifluoromethyl-7-bromo-1,2,3,4-tetrahydroisoquinoline: structure in first source		2.730
ConditionIndicatedRelationship StrengthStudiesTrials
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
Bradykinesia
[description not available]		02.0810
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.0810
MPTP Neurotoxicity Syndrome
[description not available]		02.0810