Page last updated: 2024-12-07

5-benzyloxytryptamine

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

5-Benzyloxytryptamine, also known as 5-Bz-T, is a serotonin analog with structural similarities to the psychedelic drug psilocin. It is synthesized by attaching a benzyl group to the 5-position of tryptamine. Research suggests 5-Bz-T exhibits various pharmacological effects, including agonistic activity at serotonin receptors, particularly the 5-HT1A receptor. This activity has implications for its potential therapeutic use in conditions such as depression, anxiety, and Parkinson's disease. Additionally, 5-Bz-T has been shown to modulate dopamine release in the brain, indicating potential therapeutic applications in treating addiction and attention-deficit/hyperactivity disorder (ADHD). Its unique chemical structure and pharmacological profile make it an interesting subject of study for understanding the role of serotonin in various neurological and psychiatric disorders.'

Cross-References

ID SourceID
PubMed CID89576
CHEMBL ID1288652
SCHEMBL ID2537373
MeSH IDM0191241

Synonyms (63)

Synonym
nsc 73394
einecs 257-626-4
5-(phenylmethoxy)-1h-indole-3-ethylamine monohydrochloride
BB 0242425
5-benzyloxytryptamine
gtpl265
2-[5-(phenylmethoxy)-1h-indol-3-yl]ethanamine
5-bt
CBDIVE_004615
PDSP1_000769
PDSP2_000757
OPREA1_485666
EU-0045275
2-(5-benzyloxy-1h-indol-3-yl)-ethylamine
smr000437938
MLS000762453
B-2100
20776-45-8
5-benzyloxytryptamine, free base
2-[5-(benzyloxy)-1h-indol-3-yl]ethanamine
STK500562
L000876
2-(5-phenylmethoxy-1h-indol-3-yl)ethanamine
AKOS001676606
NCGC00246513-01
BBL001424
CHEMBL1288652 ,
2-[5-(benzyloxy)-1h-indol-3-yl]ethylamine
CCG-20533
5-bzt
bdbm82302
cas_20776-45-8
unii-a83p5gde4q
einecs 244-024-1
5-benzyloxy-3-(2-ethylamino)indole hydrochloride
a83p5gde4q ,
HMS2808A18
niosh/nl4050000
indole, 3-aminoethyl-5-benzyloxy-
NL40500000
FT-0620055
5-benzyloxy-tryptamine
5-benzyloxy tryptamine
SCHEMBL2537373
5-benzyloxytriptamine
2-[5-(benzyloxy)-1h-indol-3-yl]ethylamine #
1h-indole-3-ethanamine, 5-(phenylmethoxy)-
3-(2-aminoethyl)-5-benzyloxyindole
2-(5-benzyloxy-1h-indol-3-yl)ethylamine
mfcd00037972
2-(5-(benzyloxy)-1h-indol-3-yl)ethanamine
Q4639574
F15650
AS-47706
DTXSID60942992
2-[5-(benzyloxy)-1h-indol-3-yl]ethan-1-amine
EN300-370576
PD047944
5-benzyloxy n-methyl serotonin
ba-2810
o-benzylserotonin
5-(phenylmethoxy)-1h-indole-3-ethanamine
5-(benzyloxy)tryptamine
[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)
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency39.81070.177814.390939.8107AID2147
bromodomain adjacent to zinc finger domain 2BHomo sapiens (human)Potency35.48130.707936.904389.1251AID504333
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency50.11870.035520.977089.1251AID504332
gemininHomo sapiens (human)Potency16.43690.004611.374133.4983AID624296; AID624297
Glycoprotein hormones alpha chainHomo sapiens (human)Potency28.18384.46688.344810.0000AID624291
[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)
Transient receptor potential cation channel subfamily M member 8Homo sapiens (human)IC50 (µMol)0.50000.02001.27553.9000AID538746; AID538747
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (20)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of cell population proliferationGlycoprotein hormones alpha chainHomo sapiens (human)
hormone-mediated signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
regulation of signaling receptor activityGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of steroid biosynthetic processGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of cell migrationGlycoprotein hormones alpha chainHomo sapiens (human)
thyroid gland developmentGlycoprotein hormones alpha chainHomo sapiens (human)
luteinizing hormone secretionGlycoprotein hormones alpha chainHomo sapiens (human)
organ growthGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIGlycoprotein hormones alpha chainHomo sapiens (human)
negative regulation of organ growthGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone secretionGlycoprotein hormones alpha chainHomo sapiens (human)
thyroid hormone generationGlycoprotein hormones alpha chainHomo sapiens (human)
intracellular calcium ion homeostasisTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
response to coldTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
calcium-mediated signalingTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
thermoceptionTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
calcium ion transmembrane transportTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
positive regulation of cold-induced thermogenesisTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
hormone activityGlycoprotein hormones alpha chainHomo sapiens (human)
protein bindingGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone activityGlycoprotein hormones alpha chainHomo sapiens (human)
calcium channel activityTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
protein bindingTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
identical protein bindingTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
ligand-gated calcium channel activityTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
extracellular regionGlycoprotein hormones alpha chainHomo sapiens (human)
extracellular spaceGlycoprotein hormones alpha chainHomo sapiens (human)
Golgi lumenGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone complexGlycoprotein hormones alpha chainHomo sapiens (human)
pituitary gonadotropin complexGlycoprotein hormones alpha chainHomo sapiens (human)
extracellular spaceGlycoprotein hormones alpha chainHomo sapiens (human)
endoplasmic reticulum membraneTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
plasma membraneTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
external side of plasma membraneTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
membrane raftTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
plasma membraneTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (24)

Assay IDTitleYearJournalArticle
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.
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.
AID1745845Primary qHTS for Inhibitors of ATXN expression
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.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
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.
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.
AID1345154Rat 5-HT6 receptor (5-Hydroxytryptamine receptors)
AID1345154Rat 5-HT6 receptor (5-Hydroxytryptamine receptors)1993Molecular pharmacology, Mar, Volume: 43, Issue:3
Cloning and expression of a novel serotonin receptor with high affinity for tricyclic psychotropic drugs.
AID1345154Rat 5-HT6 receptor (5-Hydroxytryptamine receptors)1998Journal of neurochemistry, Nov, Volume: 71, Issue:5
Identification of residues in transmembrane regions III and VI that contribute to the ligand binding site of the serotonin 5-HT6 receptor.
AID538749Inhibition of TRPV4 receptor up to 10 uM2010Bioorganic & medicinal chemistry letters, Dec-01, Volume: 20, Issue:23
5-benzyloxytryptamine as an antagonist of TRPM8.
AID538751Antagonist activity at human TRPM8 receptor expressed in HEK cells assessed as inhibition of WS-12-stimulated current at 1 uM pretreated for 2 mins by patch clamp assay2010Bioorganic & medicinal chemistry letters, Dec-01, Volume: 20, Issue:23
5-benzyloxytryptamine as an antagonist of TRPM8.
AID538746Antagonist activity at human TRPM8 receptor expressed in human T-REx-293 cells assessed as inhibition of menthol-induced 45calcium influx treated 5 mins before menthol challenge measured after 5 mins2010Bioorganic & medicinal chemistry letters, Dec-01, Volume: 20, Issue:23
5-benzyloxytryptamine as an antagonist of TRPM8.
AID538748Inhibition of TRPV1 receptor up to 10 uM2010Bioorganic & medicinal chemistry letters, Dec-01, Volume: 20, Issue:23
5-benzyloxytryptamine as an antagonist of TRPM8.
AID538750Inhibition of TRPA1 receptor up to 10 uM2010Bioorganic & medicinal chemistry letters, Dec-01, Volume: 20, Issue:23
5-benzyloxytryptamine as an antagonist of TRPM8.
AID538747Antagonist activity at human TRPM8 receptor expressed in human T-REx-293 cells assessed as inhibition of icilin-induced 45calcium influx treated 5 mins before icilin challenge measured after 5 mins2010Bioorganic & medicinal chemistry letters, Dec-01, Volume: 20, Issue:23
5-benzyloxytryptamine as an antagonist of TRPM8.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's6 (37.50)18.2507
2000's1 (6.25)29.6817
2010's6 (37.50)24.3611
2020's3 (18.75)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.48

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 Index11.48 (24.57)
Research Supply Index2.89 (2.92)
Research Growth Index4.37 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.48)

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%
Other17 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]