Compounds > 5-methoxyluzindole
Page last updated: 2024-09-25

5-methoxyluzindole

Cross-References

ID SourceID
PubMed CID129776
CHEMBL ID339105
SCHEMBL ID9304037
MeSH IDM0189052

Synonyms (18)

Synonym
5-methoxy-luzindole
gtpl1364
n-[2-[5-methoxy-2-(phenylmethyl)-1h-indol-3-yl]ethyl]acetamide
5-methoxyluzindole
L000079
CHEMBL339105
n-[2-(2-benzyl-5-methoxy-1h-indol-3-yl)ethyl]acetamide
bdbm85066
luzindole,5-methoxy
122853-28-5
2-benzyl-5-methoxy-n-acetyltryptamine
n-0745 ,
n 0745
SCHEMBL9304037
DTXSID00153727
2-benzylmelatonin
Q27073990
PD046511

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Melatonin receptor type 1AHomo sapiens (human)Ki0.03270.00000.27359.1000AID1138127; AID1527850
Melatonin receptor type 1BHomo sapiens (human)Ki0.00030.00000.16289.1000AID1138128; AID1527851
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (18)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerMelatonin receptor type 1AHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwayMelatonin receptor type 1AHomo sapiens (human)
mating behaviorMelatonin receptor type 1AHomo sapiens (human)
circadian rhythmMelatonin receptor type 1AHomo sapiens (human)
G protein-coupled receptor signaling pathwayMelatonin receptor type 1AHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerMelatonin receptor type 1BHomo sapiens (human)
chemical synaptic transmissionMelatonin receptor type 1BHomo sapiens (human)
negative regulation of cGMP-mediated signalingMelatonin receptor type 1BHomo sapiens (human)
glucose homeostasisMelatonin receptor type 1BHomo sapiens (human)
camera-type eye developmentMelatonin receptor type 1BHomo sapiens (human)
negative regulation of neuron apoptotic processMelatonin receptor type 1BHomo sapiens (human)
negative regulation of vasoconstrictionMelatonin receptor type 1BHomo sapiens (human)
positive regulation of circadian sleep/wake cycle, non-REM sleepMelatonin receptor type 1BHomo sapiens (human)
negative regulation of insulin secretionMelatonin receptor type 1BHomo sapiens (human)
regulation of insulin secretionMelatonin receptor type 1BHomo sapiens (human)
negative regulation of cytosolic calcium ion concentrationMelatonin receptor type 1BHomo sapiens (human)
negative regulation of transmission of nerve impulseMelatonin receptor type 1BHomo sapiens (human)
positive regulation of transmission of nerve impulseMelatonin receptor type 1BHomo sapiens (human)
regulation of neuronal action potentialMelatonin receptor type 1BHomo sapiens (human)
G protein-coupled receptor signaling pathwayMelatonin receptor type 1BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
protein bindingMelatonin receptor type 1AHomo sapiens (human)
melatonin receptor activityMelatonin receptor type 1AHomo sapiens (human)
hormone bindingMelatonin receptor type 1AHomo sapiens (human)
organic cyclic compound bindingMelatonin receptor type 1AHomo sapiens (human)
G protein-coupled receptor activityMelatonin receptor type 1AHomo sapiens (human)
protein bindingMelatonin receptor type 1BHomo sapiens (human)
melatonin receptor activityMelatonin receptor type 1BHomo sapiens (human)
G protein-coupled receptor activityMelatonin receptor type 1BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
plasma membraneMelatonin receptor type 1AHomo sapiens (human)
receptor complexMelatonin receptor type 1AHomo sapiens (human)
plasma membraneMelatonin receptor type 1AHomo sapiens (human)
plasma membraneMelatonin receptor type 1BHomo sapiens (human)
synapseMelatonin receptor type 1BHomo sapiens (human)
plasma membraneMelatonin receptor type 1BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID1527850Displacement of 2-[1251]-iodomelatonin from human MT1 receptor expressed in COS7 cells incubated for 1.5 hrs by gamma counting method2020European journal of medicinal chemistry, Jan-01, Volume: 185Indole-based melatonin analogues: Synthetic approaches and biological activity.
AID1138128Displacement of [125I]2-iodomelatonin from human recombinant MT2 receptor expressed in African green monkey COS7 cells2014Journal of medicinal chemistry, Apr-24, Volume: 57, Issue:8
MT1 and MT2 melatonin receptors: ligands, models, oligomers, and therapeutic potential.
AID1527852Selectivity ratio of Ki for Displacement of 2-[1251]-iodomelatonin from human MT1 receptor expressed in COS7 cells to Displacement of 2-[1251]-iodomelatonin from human MT2 receptor expressed in COS7 cells2020European journal of medicinal chemistry, Jan-01, Volume: 185Indole-based melatonin analogues: Synthetic approaches and biological activity.
AID1527851Displacement of 2-[1251]-iodomelatonin from human MT2 receptor expressed in COS7 cells incubated for 1.5 hrs by gamma counting method2020European journal of medicinal chemistry, Jan-01, Volume: 185Indole-based melatonin analogues: Synthetic approaches and biological activity.
AID1138140Selectivity ratio of Ki for human recombinant MT1 receptor to Ki for human recombinant MT2 receptor2014Journal of medicinal chemistry, Apr-24, Volume: 57, Issue:8
MT1 and MT2 melatonin receptors: ligands, models, oligomers, and therapeutic potential.
AID1138127Displacement of [125I]2-iodomelatonin from human recombinant MT1 receptor expressed in African green monkey COS7 cells2014Journal of medicinal chemistry, Apr-24, Volume: 57, Issue:8
MT1 and MT2 melatonin receptors: ligands, models, oligomers, and therapeutic potential.
AID107400Negative logarithm of relative affinity (pRA) towards melatonin receptor (relative to N-acetyl-5-methoxytryptamine (aMT))1998Journal of medicinal chemistry, Sep-24, Volume: 41, Issue:20
Melatonin receptor ligands: synthesis of new melatonin derivatives and comprehensive comparative molecular field analysis (CoMFA) study.
AID1346274Human MT2 receptor (Melatonin receptors)1997Naunyn-Schmiedeberg's archives of pharmacology, Mar, Volume: 355, Issue:3
Melatonin receptor antagonists that differentiate between the human Mel1a and Mel1b recombinant subtypes are used to assess the pharmacological profile of the rabbit retina ML1 presynaptic heteroreceptor.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's3 (60.00)18.2507
2000's0 (0.00)29.6817
2010's1 (20.00)24.3611
2020's1 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (20.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other4 (80.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceDescriptionRelationhip StrengthStudiesTrialsClassesRoles
melatonin[no description available]medium50acetamides;
tryptamines		anticonvulsant;
central nervous system depressant;
geroprotector;
hormone;
human metabolite;
immunological adjuvant;
mouse metabolite;
radical scavenger
6-chloromelatonin[no description available]medium40acetamides
6-hydroxymelatonin[no description available]medium30acetamides;
tryptamines		metabolite;
mouse metabolite
2-iodomelatonin[no description available]medium40acetamides
luzindole[no description available]medium30acetamides;
indoles		melatonin receptor antagonist
4-phenyl-2-propionamidotetraline[no description available]medium20tetralins
n-acetylserotonin[no description available]medium10acetamides;
N-acylserotonin;
phenols		antioxidant;
human metabolite;
mouse metabolite;
tropomyosin-related kinase B receptor agonist
6-fluoromelatonin[no description available]medium10
n-acetyltryptamine[no description available]medium10acetamides;
indoles
N-Acetylhomoveratrylamine[no description available]medium10acetamides
s20098[no description available]medium10acetamides
2-bromomelatonin[no description available]medium20
ah 001[no description available]medium10
2-phenylmelatonin[no description available]medium20phenylindole
8-methoxy-2-propionamidotetralin[no description available]medium10tetralins
n-acetyl-4-aminomethyl-6-methoxy-9-methyl-1,2,3,4-tetrahydrocarbazole[no description available]medium10
5-hydroxyethoxy-n-acetyltryptamine[no description available]medium20
ramelteon[no description available]medium10indanes
iik7[no description available]medium10
k 185[no description available]medium10
ucm 454[no description available]medium10
methysergide[no description available]medium10ergoline alkaloid
ConditionIndicatedRelationship StrengthStudiesTrials
Body Weight0low10
Chronic Insomnia0low10
Depression, Endogenous0low10
Depression, Neurotic0low10
Depression, Unipolar0low10
Depressive Disorder0low10
Depressive Syndrome0low10
DIMS (Disorders of Initiating and Maintaining Sleep)0low10
Disorders of Initiating and Maintaining Sleep0low10
Early Awakening0low10
Insomnia0low10
Insomnia Disorder0low10
Melancholia0low10
Neurosis, Depressive0low10
Nonorganic Insomnia0low10
Primary Insomnia0low10
Psychophysiological Insomnia0low10
Rebound Insomnia0low10
Secondary Insomnia0low10
Sleep Initiation and Maintenance Disorders0low10
Sleep Initiation Dysfunction0low10
Sleeplessness0low10
Transient Insomnia0low10
Unipolar Depression0low10