Compounds > 2-bromomelatonin
Page last updated: 2024-12-07

2-bromomelatonin

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

Description

2-bromomelatonin: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID126731
CHEMBL ID33415
SCHEMBL ID1311849
MeSH IDM0204354

Synonyms (24)

Synonym
n-(2-(2-bromo-5-methoxy-1h-indol-3-yl)ethyl)acetamide
n-[2-(2-bromo-5-methoxy-1h-indol-3-yl)ethyl]acetamide
n-[2-(2-bromo-5-methoxy-1h-indol-3-yl)-ethyl]-acetamide(2-bromomelatonin)
n-[2-(2-bromo-5-methoxy-1h-indol-3-yl)-ethyl]-acetamide
melatonin,2-bromo
bdbm50043287
nsc674637
nsc-674637
PDSP2_001776
PDSP1_001793
2-bromomelatonin
CHEMBL33415 ,
FT-0663756
SCHEMBL1311849
2-bromo-melatonin
142959-59-9
acetamide, n-(2-(2-bromo-5-methoxy-1h-indol-3-yl)ethyl)-
AKOS015898573
DTXSID60162239
mfcd01076464
2-bromo melatonin
FNHLXIXCQDGUCQ-UHFFFAOYSA-N
acetamide,n-[2-(2-bromo-5-methoxy-1h-indol-3-yl)ethyl]-
n-[2-(2-bromo-5-methoxy-1h-indol-3-yl)ethyl]-acetamide
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Melatonin receptor type 1AHomo sapiens (human)IC50 (µMol)0.00010.00000.06401.0200AID107558; AID107559
Melatonin receptor type 1AHomo sapiens (human)Ki0.00000.00000.27359.1000AID107564; AID107565; AID107567
Melatonin receptor type 1BHomo sapiens (human)IC50 (µMol)0.00010.00000.34894.0000AID107558; AID107559
Melatonin receptor type 1BHomo sapiens (human)Ki0.00000.00000.16289.1000AID107564; AID107565; AID107567
[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 (24)

Assay IDTitleYearJournalArticle
AID227389GTPgammaS index is the ratio of the IC50 of compound with GTP and without GTP to the IC50 of melatonin with GTP and without GTP1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
1-(2-Alkanamidoethyl)-6-methoxyindole derivatives: a new class of potent indole melatonin analogues.
AID227179Activity considered from GTP-gamma-S index and cAMP index; A = agonist1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
1-(2-Alkanamidoethyl)-6-methoxyindole derivatives: a new class of potent indole melatonin analogues.
AID107565Binding affinity against melatonin receptor in the quail optica tecta using 2-[125] iodomelatonin as labelled ligand1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
Conformationally restrained melatonin analogues: synthesis, binding affinity for the melatonin receptor, evaluation of the biological activity, and molecular modeling study.
AID230718Relative binding to melatonin receptor compared to melatonin, ratio of IC501997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
Conformationally restrained melatonin analogues: synthesis, binding affinity for the melatonin receptor, evaluation of the biological activity, and molecular modeling study.
AID107876Relative Intrinsic activity evaluated on [35S]GTP-gamma-S, binding in NIH3T3 cells stably transfected with human Melatonin receptor type 1A2003Journal of medicinal chemistry, Apr-10, Volume: 46, Issue:8
Three-dimensional quantitative structure-activity relationship studies on selected MT1 and MT2 melatonin receptor ligands: requirements for subtype selectivity and intrinsic activity modulation.
AID227173Activity considered from GTP-gamma-S and cAMP index values; A = Agonist1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
Conformationally restrained melatonin analogues: synthesis, binding affinity for the melatonin receptor, evaluation of the biological activity, and molecular modeling study.
AID107559Inhibitory activity against melatonin receptor in the quail optica tecta using 2-[125] iodomelatonin as radiolabeled ligand1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
Conformationally restrained melatonin analogues: synthesis, binding affinity for the melatonin receptor, evaluation of the biological activity, and molecular modeling study.
AID107568Compound was tested in vivo for its activity against melatonin receptor in rabbit parietal cortex model; Agonist1993Journal of medicinal chemistry, Dec-10, Volume: 36, Issue:25
2-Substituted 5-methoxy-N-acyltryptamines: synthesis, binding affinity for the melatonin receptor, and evaluation of the biological activity.
AID1527842Displacement of 2-[1251]-iodomelatonin from rabbit parietal cortex melatonin receptor2020European journal of medicinal chemistry, Jan-01, Volume: 185Indole-based melatonin analogues: Synthetic approaches and biological activity.
AID230719Ratio of the IC50 of compound to the IC50 of melatonin1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
1-(2-Alkanamidoethyl)-6-methoxyindole derivatives: a new class of potent indole melatonin analogues.
AID227388GTPgammaS index is the ratio of the IC50 of compound with GTP and without GTP to the IC50 of melatonin with GTP and without GTP1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
Conformationally restrained melatonin analogues: synthesis, binding affinity for the melatonin receptor, evaluation of the biological activity, and molecular modeling study.
AID108040Relative Intrinsic activity evaluated on [35S]GTP-gamma-S, binding in NIH3T3 cells stably transfected with human Melatonin receptor type 1B2003Journal of medicinal chemistry, Apr-10, Volume: 46, Issue:8
Three-dimensional quantitative structure-activity relationship studies on selected MT1 and MT2 melatonin receptor ligands: requirements for subtype selectivity and intrinsic activity modulation.
AID227390Inhibition of forskolin stimulated cAMP accumulation and represented as cAMP index which is the ratio of percent inhibition to percent inhibition of melatonin1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
Conformationally restrained melatonin analogues: synthesis, binding affinity for the melatonin receptor, evaluation of the biological activity, and molecular modeling study.
AID1527841Potency index, ratio of melatonin Ki to compound Ki for Displacement of 2-[1251]-iodomelatonin from rabbit parietal cortex melatonin receptor2020European journal of medicinal chemistry, Jan-01, Volume: 185Indole-based melatonin analogues: Synthetic approaches and biological activity.
AID107564Binding affinity against melatonin receptor in the quail optica tecta using 2-[125] iodomelatonin (100 pM) as labelled ligand1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
1-(2-Alkanamidoethyl)-6-methoxyindole derivatives: a new class of potent indole melatonin analogues.
AID108056Relative Binding Affinity (pRA1) to cloned human Melatonin receptor type 1B, stably expressed in NIH3T3 rat fibroblast cells, determined using 2-[125I]iodomelatonin2003Journal of medicinal chemistry, Apr-10, Volume: 46, Issue:8
Three-dimensional quantitative structure-activity relationship studies on selected MT1 and MT2 melatonin receptor ligands: requirements for subtype selectivity and intrinsic activity modulation.
AID107563Inhibition of 2-[125I]iodomelatonin binding to melatonin receptor in quail brain1993Journal of medicinal chemistry, Dec-10, Volume: 36, Issue:25
2-Substituted 5-methoxy-N-acyltryptamines: synthesis, binding affinity for the melatonin receptor, and evaluation of the biological activity.
AID108023Relative Binding Affinity (pRA1) to cloned human Melatonin receptor type 1A, stably expressed in NIH3T3 rat fibroblast cells, determined using 2-[125I]iodomelatonin2003Journal of medicinal chemistry, Apr-10, Volume: 46, Issue:8
Three-dimensional quantitative structure-activity relationship studies on selected MT1 and MT2 melatonin receptor ligands: requirements for subtype selectivity and intrinsic activity modulation.
AID227391Inhibition of forskolin stimulated cAMP accumulation and represented as cAMP index which is the ratio of percent inhibition to percent inhibition of melatonin1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
1-(2-Alkanamidoethyl)-6-methoxyindole derivatives: a new class of potent indole melatonin analogues.
AID107548Compound was tested in vivo for its activity against melatonin receptor in Syrian hamster gonadal regression model; Agonist1993Journal of medicinal chemistry, Dec-10, Volume: 36, Issue:25
2-Substituted 5-methoxy-N-acyltryptamines: synthesis, binding affinity for the melatonin receptor, and evaluation of the biological activity.
AID107558Inhibitory activity against melatonin receptor in the quail optica tecta using 2-[125] iodomelatonin as labelled ligand1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
1-(2-Alkanamidoethyl)-6-methoxyindole derivatives: a new class of potent indole melatonin analogues.
AID166149Inhibition of spontaneous firing activity of single cortical neurons in the rabbit parietal cortex model at 1 x 10 e-6 M (agonist)1993Journal of medicinal chemistry, Dec-10, Volume: 36, Issue:25
2-Substituted 5-methoxy-N-acyltryptamines: synthesis, binding affinity for the melatonin receptor, and evaluation of the biological activity.
AID107567Inhibition of 2-[125I]iodomelatonin binding to melatonin receptor in quail brain as 1/Ka1993Journal of medicinal chemistry, Dec-10, Volume: 36, Issue:25
2-Substituted 5-methoxy-N-acyltryptamines: synthesis, binding affinity for the melatonin receptor, and evaluation of the biological activity.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's5 (55.56)18.2507
2000's3 (33.33)29.6817
2010's0 (0.00)24.3611
2020's1 (11.11)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.93

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 Index11.93 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.24 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.93)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (11.11%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (88.89%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
gamma-aminobutyric acid
gamma-Aminobutyric Acid: The most common inhibitory neurotransmitter in the central nervous system.. gamma-aminobutyric acid : A gamma-amino acid that is butanoic acid with the amino substituent located at C-4.		1.9810amino acid zwitterion;
gamma-amino acid;
monocarboxylic acid		human metabolite;
neurotransmitter;
Saccharomyces cerevisiae metabolite;
signalling molecule
melatonin
[no description available]		4.7190acetamides;
tryptamines		anticonvulsant;
central nervous system depressant;
geroprotector;
hormone;
human metabolite;
immunological adjuvant;
mouse metabolite;
radical scavenger
n-acetylserotonin
N-acetylserotonin : An N-acylserotonin resulting from the formal condensation of the primary amino group of serotonin with the carboxy group of acetic acid.		2.4120acetamides;
N-acylserotonin;
phenols		antioxidant;
human metabolite;
mouse metabolite;
tropomyosin-related kinase B receptor agonist
6-chloromelatonin
[no description available]		4.3660acetamides
6-hydroxymelatonin
6-hydroxymelatonin : A member of the class of tryptamines that is melatonin with a hydroxy group substituent at position 6.		3.5520acetamides;
tryptamines		metabolite;
mouse metabolite
propofol
Propofol: An intravenous anesthetic agent which has the advantage of a very rapid onset after infusion or bolus injection plus a very short recovery period of a couple of minutes. (From Smith and Reynard, Textbook of Pharmacology, 1992, 1st ed, p206). Propofol has been used as ANTICONVULSANTS and ANTIEMETICS.. propofol : A phenol resulting from the formal substitution of the hydrogen at the 2 position of 1,3-diisopropylbenzene by a hydroxy group.		2.0110phenolsanticonvulsant;
antiemetic;
intravenous anaesthetic;
radical scavenger;
sedative
6-fluoromelatonin
[no description available]		1.9910
bromosuccinimide
Bromosuccinimide: A brominating agent that replaces hydrogen atoms in benzylic or allylic positions. It is used in the oxidation of secondary alcohols to ketones and in controlled low-energy brominations. (From Miall's Dictionary of Chemistry, 5th ed; Hawley's Condensed Chemical Dictionary, 12th ed,).		1.9810dicarboximide;
organobromine compound;
pyrrolidinone		reagent
n-acetyltryptamine
N-acetyltryptamine: antagonizes the melatonin-induced inhibition of dopamine release from retina; RN given refers to parent cpd. N-acetyltryptamine : A tryptamine compound having an acetyl substituent attached to the side-chain amino function.		2.4120acetamides;
indoles
N-Acetylhomoveratrylamine
[no description available]		1.9910acetamides
s20098
[no description available]		1.9910acetamides
6-methoxy-2,3,4,9-tetrahydropyrido[3,4-b]indol-1-one
[no description available]		1.9910beta-carbolines
2-iodomelatonin
[no description available]		4.0340acetamides
luzindole
luzindole: melatonin receptor antagonist; structure given in first source. luzindole : A member of the class of indoles that is tryptamine in which one of the amino hydrogens is replaced by an acetyl group while the hydrogen at position 2 is replaced by a benzyl group.		2.0110acetamides;
indoles		melatonin receptor antagonist
5-methoxyluzindole
[no description available]		3.5520
ah 001
AH 001: structure given in first source; a melatonin agonist		1.9910
4-phenyl-2-propionamidotetraline
4-phenyl-2-propionamidotetraline: melatonin receptor antagonist; structure in first source		2.0110tetralins
2-phenylmelatonin
[no description available]		4.3660phenylindole
iik7
IIK7: structure in first source		2.0110
8-methoxy-2-propionamidotetralin
8-methoxy-2-propionamidotetralin: enhances sperm hyperactivation via the MT1 receptor		1.9910tetralins
n-acetyl-4-aminomethyl-6-methoxy-9-methyl-1,2,3,4-tetrahydrocarbazole
N-acetyl-4-aminomethyl-6-methoxy-9-methyl-1,2,3,4-tetrahydrocarbazole: a melatonin receptor agonist; (-)-isomer is more active than the (+)-isomer; structure in first source		2.420
n-butanoyl-5-methoxytryptamine
N-butanoyl-5-methoxytryptamine: mimics melatonin's antigonadal activity and inhibits 2-iodomelatonin binding		2.0110
ucm 454
[no description available]		2.0110
5-hydroxyethoxy-n-acetyltryptamine
5-hydroxyethoxy-N-acetyltryptamine: structure in first source		3.5520
ConditionIndicatedRelationship StrengthStudiesTrials