Page last updated: 2024-11-07

3-(1-methyl-1,2,3,6-tetrahydropyrid-4-yl)indole

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Description

3-(1-methyl-1,2,3,6-tetrahydropyrid-4-yl)indole: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID152215
CHEMBL ID26655
SCHEMBL ID4674658
MeSH IDM0172959

Synonyms (32)

Synonym
CCG-200094
CHEMDIV2_002846
MLS000120058 ,
smr000096975
CHEMBL26655 ,
HMS1377B08
3-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)-1h-indole
A811599
17403-03-1
3-mtpi
1h-indole, 3-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)-
3-(1-methyl-1,2,3,6-tetrahydropyrid-4-yl)indole
AKOS005747101
HMS2244L18
STL146810
3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1h-indole
BBL032028
REGID_FOR_CID_152215
SCHEMBL4674658
IUENQRYBZHHPBN-UHFFFAOYSA-N
3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)indole
3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1h-indole
cid_152215
bdbm31034
DTXSID30169750
mfcd11840338
Z821687384
SR-01000143891-1
sr-01000143891
VS-10929
CS-0214688
EN300-186664

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Compound 6a was found to give a dose-response similar to the SSRI fluoxetine in microdialysis studies in rats."( Conformationally restricted homotryptamines 3. Indole tetrahydropyridines and cyclohexenylamines as selective serotonin reuptake inhibitors.
Beno, BR; Cipollina, JA; Deskus, JA; Dextraze, P; Epperson, JR; Gao, Q; Krause, RG; Lodge, NJ; Ma, B; Mattson, GK; Mattson, RJ; Molski, TF; Qian-Cutrone, J; Sloan, CP; Taber, MT, 2007
)
0.34
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (35)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Beta-lactamaseEscherichia coli K-12Potency0.63100.044717.8581100.0000AID485294
Chain A, HADH2 proteinHomo sapiens (human)Potency31.62280.025120.237639.8107AID893
Chain B, HADH2 proteinHomo sapiens (human)Potency31.62280.025120.237639.8107AID893
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency31.62280.177814.390939.8107AID2147
15-lipoxygenase, partialHomo sapiens (human)Potency0.63100.012610.691788.5700AID887
Smad3Homo sapiens (human)Potency14.12540.00527.809829.0929AID588855
nonstructural protein 1Influenza A virus (A/WSN/1933(H1N1))Potency2.23870.28189.721235.4813AID2326
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency9.09780.00419.984825.9290AID504444; AID720524
DNA polymerase betaHomo sapiens (human)Potency1.77830.022421.010289.1251AID485314
lethal(3)malignant brain tumor-like protein 1 isoform IHomo sapiens (human)Potency31.62280.075215.225339.8107AID485360
lamin isoform A-delta10Homo sapiens (human)Potency12.58930.891312.067628.1838AID1487
[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)
5-hydroxytryptamine receptor 3ACavia porcellus (domestic guinea pig)IC50 (µMol)0.69000.69004.19007.6900AID295434
5-hydroxytryptamine receptor 2CRattus norvegicus (Norway rat)Ki0.06700.00020.667710.0000AID5086
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)Ki0.06700.00010.601710.0000AID5086
5-hydroxytryptamine receptor 1ARattus norvegicus (Norway rat)Ki0.14540.00010.739610.0000AID4411; AID4412
5-hydroxytryptamine receptor 2BRattus norvegicus (Norway rat)Ki0.06700.00020.590910.0000AID5086
Sodium-dependent serotonin transporterHomo sapiens (human)IC50 (µMol)0.69000.00010.86458.7096AID295434
5-hydroxytryptamine receptor 6Homo sapiens (human)Ki0.09800.00020.522910.0000AID239088
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
5-hydroxytryptamine receptor 1AHomo sapiens (human)EC50 (µMol)12.00000.07001.46505.1000AID718
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)EC50 (µMol)12.00000.01901.70547.0000AID718
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)EC50 (µMol)12.00000.01901.70547.0000AID718
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)EC50 (µMol)12.00000.01901.70547.0000AID718
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)EC50 (µMol)12.00000.01901.73677.0000AID718
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)EC50 (µMol)12.00000.01901.70547.0000AID718
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)EC50 (µMol)12.00000.01901.70547.0000AID718
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)EC50 (µMol)12.00000.01901.70547.0000AID718
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)EC50 (µMol)12.00000.00011.46937.0000AID718
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)EC50 (µMol)12.00000.01901.70547.0000AID718
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)EC50 (µMol)12.00000.01901.70547.0000AID718
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)EC50 (µMol)12.00000.01901.70547.0000AID718
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)EC50 (µMol)12.00000.01902.149910.0000AID718
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)EC50 (µMol)12.00000.01901.70547.0000AID718
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)EC50 (µMol)12.00000.01901.73677.0000AID718
GABA theta subunitRattus norvegicus (Norway rat)EC50 (µMol)12.00000.01901.70547.0000AID718
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)EC50 (µMol)12.00000.01901.70547.0000AID718
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (37)

Processvia Protein(s)Taxonomy
monoamine transportSodium-dependent serotonin transporterHomo sapiens (human)
response to hypoxiaSodium-dependent serotonin transporterHomo sapiens (human)
neurotransmitter transportSodium-dependent serotonin transporterHomo sapiens (human)
response to nutrientSodium-dependent serotonin transporterHomo sapiens (human)
memorySodium-dependent serotonin transporterHomo sapiens (human)
circadian rhythmSodium-dependent serotonin transporterHomo sapiens (human)
response to xenobiotic stimulusSodium-dependent serotonin transporterHomo sapiens (human)
response to toxic substanceSodium-dependent serotonin transporterHomo sapiens (human)
positive regulation of gene expressionSodium-dependent serotonin transporterHomo sapiens (human)
positive regulation of serotonin secretionSodium-dependent serotonin transporterHomo sapiens (human)
negative regulation of cerebellar granule cell precursor proliferationSodium-dependent serotonin transporterHomo sapiens (human)
negative regulation of synaptic transmission, dopaminergicSodium-dependent serotonin transporterHomo sapiens (human)
response to estradiolSodium-dependent serotonin transporterHomo sapiens (human)
social behaviorSodium-dependent serotonin transporterHomo sapiens (human)
vasoconstrictionSodium-dependent serotonin transporterHomo sapiens (human)
sperm ejaculationSodium-dependent serotonin transporterHomo sapiens (human)
negative regulation of neuron differentiationSodium-dependent serotonin transporterHomo sapiens (human)
positive regulation of cell cycleSodium-dependent serotonin transporterHomo sapiens (human)
negative regulation of organ growthSodium-dependent serotonin transporterHomo sapiens (human)
behavioral response to cocaineSodium-dependent serotonin transporterHomo sapiens (human)
enteric nervous system developmentSodium-dependent serotonin transporterHomo sapiens (human)
brain morphogenesisSodium-dependent serotonin transporterHomo sapiens (human)
serotonin uptakeSodium-dependent serotonin transporterHomo sapiens (human)
membrane depolarizationSodium-dependent serotonin transporterHomo sapiens (human)
platelet aggregationSodium-dependent serotonin transporterHomo sapiens (human)
cellular response to retinoic acidSodium-dependent serotonin transporterHomo sapiens (human)
cellular response to cGMPSodium-dependent serotonin transporterHomo sapiens (human)
regulation of thalamus sizeSodium-dependent serotonin transporterHomo sapiens (human)
conditioned place preferenceSodium-dependent serotonin transporterHomo sapiens (human)
sodium ion transmembrane transportSodium-dependent serotonin transporterHomo sapiens (human)
amino acid transportSodium-dependent serotonin transporterHomo sapiens (human)
cerebral cortex cell migration5-hydroxytryptamine receptor 6Homo sapiens (human)
positive regulation of TOR signaling5-hydroxytryptamine receptor 6Homo sapiens (human)
G protein-coupled serotonin receptor signaling pathway5-hydroxytryptamine receptor 6Homo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 6Homo sapiens (human)
adenylate cyclase-modulating G protein-coupled receptor signaling pathway5-hydroxytryptamine receptor 6Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger5-hydroxytryptamine receptor 6Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (17)

Processvia Protein(s)Taxonomy
integrin bindingSodium-dependent serotonin transporterHomo sapiens (human)
monoatomic cation channel activitySodium-dependent serotonin transporterHomo sapiens (human)
neurotransmitter transmembrane transporter activitySodium-dependent serotonin transporterHomo sapiens (human)
serotonin:sodium:chloride symporter activitySodium-dependent serotonin transporterHomo sapiens (human)
protein bindingSodium-dependent serotonin transporterHomo sapiens (human)
monoamine transmembrane transporter activitySodium-dependent serotonin transporterHomo sapiens (human)
antiporter activitySodium-dependent serotonin transporterHomo sapiens (human)
syntaxin-1 bindingSodium-dependent serotonin transporterHomo sapiens (human)
cocaine bindingSodium-dependent serotonin transporterHomo sapiens (human)
sodium ion bindingSodium-dependent serotonin transporterHomo sapiens (human)
identical protein bindingSodium-dependent serotonin transporterHomo sapiens (human)
nitric-oxide synthase bindingSodium-dependent serotonin transporterHomo sapiens (human)
actin filament bindingSodium-dependent serotonin transporterHomo sapiens (human)
serotonin bindingSodium-dependent serotonin transporterHomo sapiens (human)
histamine receptor activity5-hydroxytryptamine receptor 6Homo sapiens (human)
protein binding5-hydroxytryptamine receptor 6Homo sapiens (human)
neurotransmitter receptor activity5-hydroxytryptamine receptor 6Homo sapiens (human)
G protein-coupled serotonin receptor activity5-hydroxytryptamine receptor 6Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
plasma membraneSodium-dependent serotonin transporterHomo sapiens (human)
focal adhesionSodium-dependent serotonin transporterHomo sapiens (human)
endosome membraneSodium-dependent serotonin transporterHomo sapiens (human)
endomembrane systemSodium-dependent serotonin transporterHomo sapiens (human)
presynaptic membraneSodium-dependent serotonin transporterHomo sapiens (human)
membrane raftSodium-dependent serotonin transporterHomo sapiens (human)
synapseSodium-dependent serotonin transporterHomo sapiens (human)
postsynaptic membraneSodium-dependent serotonin transporterHomo sapiens (human)
serotonergic synapseSodium-dependent serotonin transporterHomo sapiens (human)
synapseSodium-dependent serotonin transporterHomo sapiens (human)
plasma membraneSodium-dependent serotonin transporterHomo sapiens (human)
neuron projectionSodium-dependent serotonin transporterHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 6Homo sapiens (human)
cilium5-hydroxytryptamine receptor 6Homo sapiens (human)
synapse5-hydroxytryptamine receptor 6Homo sapiens (human)
dendrite5-hydroxytryptamine receptor 6Homo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 6Homo sapiens (human)
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 (18)

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.
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.
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
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
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.
AID4412Binding affinity towards 5-hydroxytryptamine 1A receptor using [3H]8-OH-DPAT as radioligand.1993Journal of medicinal chemistry, Dec-10, Volume: 36, Issue:25
Three-dimensional quantitative structure-activity relationships of 5-HT receptor binding data for tetrahydropyridinylindole derivatives: a comparison of the Hansch and CoMFA methods.
AID5086Binding affinity towards 5-hydroxytryptamine 2 receptor using [3H]-ketanserin as radioligand.1993Journal of medicinal chemistry, Dec-10, Volume: 36, Issue:25
Three-dimensional quantitative structure-activity relationships of 5-HT receptor binding data for tetrahydropyridinylindole derivatives: a comparison of the Hansch and CoMFA methods.
AID4411Binding affinity of a compound to rat brain 5-hydroxytryptamine 1A (serotonin) receptor assayed by radiolabeled [3H]-8-OH-DPAT ligand displacement1996Journal of medicinal chemistry, Jan-05, Volume: 39, Issue:1
Binding of arylpiperazines, (aryloxy)propanolamines, and tetrahydropyridylindoles to the 5-HT1A receptor: contribution of the molecular lipophilicity potential to three-dimensional quantitative structure-affinity relationship models.
AID295434Displacement of [3H]citalopram from human SERT expressed in HEK293 cells2007Bioorganic & medicinal chemistry letters, Jun-01, Volume: 17, Issue:11
Conformationally restricted homotryptamines 3. Indole tetrahydropyridines and cyclohexenylamines as selective serotonin reuptake inhibitors.
AID239088Binding affinity against cloned human 5-hydroxytryptamine 6 receptor expressed in HeLa cells using [3H]LSD2005Bioorganic & medicinal chemistry letters, Jan-17, Volume: 15, Issue:2
N1-arylsulfonyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole derivatives are potent and selective 5-HT6 receptor antagonists.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (10.00)18.7374
1990's2 (20.00)18.2507
2000's3 (30.00)29.6817
2010's3 (30.00)24.3611
2020's1 (10.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.42

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 Index12.42 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.82 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.42)

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%
Other10 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]