Page last updated: 2024-11-08

4,9-dihydro-7-methoxy-3h-pyrido(3,4b)indole

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Description

4,9-dihydro-7-methoxy-3H-pyrido(3,4b)indole: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID169339
CHEMBL ID6409
SCHEMBL ID2930783
MeSH IDM0173495

Synonyms (10)

Synonym
7-methoxy-4,9-dihydro-3h-beta-carboline
bdbm50079903
cgs 19281a
CHEMBL6409 ,
cgs-19281a
3h-pyrido(3,4-b)indole, 4,9-dihydro-7-methoxy-
31652-37-6
4,9-dihydro-7-methoxy-3h-pyrido(3,4b)indole
SCHEMBL2930783
DTXSID90185537
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (9)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cytochrome P450 3A4Homo sapiens (human)Ki10.00000.00011.41629.9000AID5539
5-hydroxytryptamine receptor 2CRattus norvegicus (Norway rat)Ki10.00000.00020.667710.0000AID5727
Phenylethanolamine N-methyltransferaseBos taurus (cattle)Ki2.70000.00312.329310.0000AID155137; AID155146; AID156051
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)Ki10.00000.00010.601710.0000AID5539; AID5541
Alpha-2B adrenergic receptorRattus norvegicus (Norway rat)Ki11.75000.00000.929610.0000AID35193; AID37089; AID37094; AID37366
Alpha-2C adrenergic receptorRattus norvegicus (Norway rat)Ki11.75000.00000.970810.0000AID35193; AID37089; AID37094; AID37366
Alpha-2A adrenergic receptorRattus norvegicus (Norway rat)Ki11.75000.00000.937510.0000AID35193; AID37089; AID37094; AID37366
5-hydroxytryptamine receptor 5AHomo sapiens (human)Ki10.00000.00080.94335.1600AID6500
Purine nucleoside phosphorylase Bos taurus (cattle)Ki2.70000.00000.53072.7000AID156051
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (29)

Processvia Protein(s)Taxonomy
lipid hydroxylationCytochrome P450 3A4Homo sapiens (human)
lipid metabolic processCytochrome P450 3A4Homo sapiens (human)
steroid catabolic processCytochrome P450 3A4Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 3A4Homo sapiens (human)
steroid metabolic processCytochrome P450 3A4Homo sapiens (human)
cholesterol metabolic processCytochrome P450 3A4Homo sapiens (human)
androgen metabolic processCytochrome P450 3A4Homo sapiens (human)
estrogen metabolic processCytochrome P450 3A4Homo sapiens (human)
alkaloid catabolic processCytochrome P450 3A4Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 3A4Homo sapiens (human)
calcitriol biosynthetic process from calciolCytochrome P450 3A4Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 3A4Homo sapiens (human)
vitamin D metabolic processCytochrome P450 3A4Homo sapiens (human)
vitamin D catabolic processCytochrome P450 3A4Homo sapiens (human)
retinol metabolic processCytochrome P450 3A4Homo sapiens (human)
retinoic acid metabolic processCytochrome P450 3A4Homo sapiens (human)
long-chain fatty acid biosynthetic processCytochrome P450 3A4Homo sapiens (human)
aflatoxin metabolic processCytochrome P450 3A4Homo sapiens (human)
oxidative demethylationCytochrome P450 3A4Homo sapiens (human)
methylationPhenylethanolamine N-methyltransferaseBos taurus (cattle)
epinephrine biosynthetic processPhenylethanolamine N-methyltransferaseBos taurus (cattle)
G protein-coupled receptor signaling pathway5-hydroxytryptamine receptor 5AHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathway5-hydroxytryptamine receptor 5AHomo sapiens (human)
hippocampus development5-hydroxytryptamine receptor 5AHomo sapiens (human)
response to estradiol5-hydroxytryptamine receptor 5AHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger5-hydroxytryptamine receptor 5AHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 5AHomo sapiens (human)
adenylate cyclase-inhibiting serotonin receptor signaling pathway5-hydroxytryptamine receptor 5AHomo sapiens (human)
purine ribonucleoside salvagePurine nucleoside phosphorylase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (29)

Processvia Protein(s)Taxonomy
monooxygenase activityCytochrome P450 3A4Homo sapiens (human)
steroid bindingCytochrome P450 3A4Homo sapiens (human)
iron ion bindingCytochrome P450 3A4Homo sapiens (human)
protein bindingCytochrome P450 3A4Homo sapiens (human)
steroid hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
retinoic acid 4-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
oxidoreductase activityCytochrome P450 3A4Homo sapiens (human)
oxygen bindingCytochrome P450 3A4Homo sapiens (human)
enzyme bindingCytochrome P450 3A4Homo sapiens (human)
heme bindingCytochrome P450 3A4Homo sapiens (human)
vitamin D3 25-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
caffeine oxidase activityCytochrome P450 3A4Homo sapiens (human)
quinine 3-monooxygenase activityCytochrome P450 3A4Homo sapiens (human)
testosterone 6-beta-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
1-alpha,25-dihydroxyvitamin D3 23-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
anandamide 8,9 epoxidase activityCytochrome P450 3A4Homo sapiens (human)
anandamide 11,12 epoxidase activityCytochrome P450 3A4Homo sapiens (human)
anandamide 14,15 epoxidase activityCytochrome P450 3A4Homo sapiens (human)
aromatase activityCytochrome P450 3A4Homo sapiens (human)
vitamin D 24-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
estrogen 16-alpha-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
estrogen 2-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
1,8-cineole 2-exo-monooxygenase activityCytochrome P450 3A4Homo sapiens (human)
phenylethanolamine N-methyltransferase activityPhenylethanolamine N-methyltransferaseBos taurus (cattle)
G protein-coupled serotonin receptor activity5-hydroxytryptamine receptor 5AHomo sapiens (human)
neurotransmitter receptor activity5-hydroxytryptamine receptor 5AHomo sapiens (human)
serotonin binding5-hydroxytryptamine receptor 5AHomo sapiens (human)
purine-nucleoside phosphorylase activityPurine nucleoside phosphorylase Bos taurus (cattle)
guanosine phosphorylase activityPurine nucleoside phosphorylase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
cytoplasmCytochrome P450 3A4Homo sapiens (human)
endoplasmic reticulum membraneCytochrome P450 3A4Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 3A4Homo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 5AHomo sapiens (human)
perikaryon5-hydroxytryptamine receptor 5AHomo sapiens (human)
postsynaptic specialization membrane5-hydroxytryptamine receptor 5AHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 5AHomo sapiens (human)
dendrite5-hydroxytryptamine receptor 5AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID5727Binding affinity towards cloned rat 5-hydroxytryptamine 2C receptor from fundus tissue by [3H]mesulergine displacement.2003Bioorganic & medicinal chemistry letters, Dec-15, Volume: 13, Issue:24
Binding of beta-carbolines at 5-HT(2) serotonin receptors.
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.
AID37094Binding affinity to alpha-2 adrenergic receptor by displacement of [3H]clonidine2001Journal of medicinal chemistry, Aug-16, Volume: 44, Issue:17
Synthesis and evaluation of 4-fluoro-8-substituted-2,3,4,5-tetrahydro-1H-2-benzazapines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor.
AID6500Binding affinity towards 5-hydroxytryptamine 5A receptor using lysergic acid diethylamide (LSD) as radioligand2003Journal of medicinal chemistry, Aug-28, Volume: 46, Issue:18
Binding of tetrahydrocarboline derivatives at human 5-HT5A receptors.
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.
AID223253Binding affinity at rat imidazoline receptor I-22004Bioorganic & medicinal chemistry letters, Feb-23, Volume: 14, Issue:4
Binding of beta-carbolines at imidazoline I2 receptors: a structure-affinity investigation.
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.
AID5541Binding affinity towards cloned rat 5-hydroxytryptamine 2A receptor by [3H]ketanserin displacement.2003Bioorganic & medicinal chemistry letters, Dec-15, Volume: 13, Issue:24
Binding of beta-carbolines at 5-HT(2) serotonin receptors.
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.
AID156051Ability to inhibit phenylethanolamine N-methyl-transferase (PNMT)2001Journal of medicinal chemistry, Aug-16, Volume: 44, Issue:17
Synthesis and evaluation of 4-fluoro-8-substituted-2,3,4,5-tetrahydro-1H-2-benzazapines 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.
AID5539Binding affinity for rat 5-hydroxytryptamine 2A receptor using [3H]DOB2003Bioorganic & medicinal chemistry letters, Dec-15, Volume: 13, Issue:24
Binding of beta-carbolines at 5-HT(2) serotonin receptors.
AID37089Binding affinity at alpha-2 adrenergic receptors of rat.2004Bioorganic & medicinal chemistry letters, Feb-23, Volume: 14, Issue:4
Binding of beta-carbolines at imidazoline I2 receptors: a structure-affinity investigation.
AID234631Selectivity ratio (alpha2/PNMT)2001Journal of medicinal chemistry, Aug-16, Volume: 44, Issue:17
Synthesis and evaluation of 4-fluoro-8-substituted-2,3,4,5-tetrahydro-1H-2-benzazapines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor.
AID223254Displacement of [3H]2-BFI from imidazoline receptor I-22004Bioorganic & medicinal chemistry letters, Feb-23, Volume: 14, Issue:4
Pyrazino[1,2-a]indoles as novel high-affinity and selective imidazoline I(2) receptor ligands.
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.
[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-19900 (0.00)18.7374
1990's5 (50.00)18.2507
2000's5 (50.00)29.6817
2010's0 (0.00)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: 11.96

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 Index11.96 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.36 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.96)

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]