Page last updated: 2024-11-05

5-methyltryptamine

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

Description

5-Methyltryptamine, also known as 5-HT, is a naturally occurring tryptamine derivative found in various plants and animals. It is structurally similar to serotonin and exerts effects on the serotonergic system. 5-HT is a potent agonist at the 5-HT2A receptor, leading to hallucinogenic effects. It is also a partial agonist at the 5-HT1A receptor, contributing to its anxiolytic and antidepressant properties. 5-HT is synthesized through the decarboxylation of 5-hydroxytryptophan, a precursor to serotonin. Research on 5-HT focuses on understanding its role in neurotransmission, its potential therapeutic applications, and its effects on mood, cognition, and behavior. It is studied due to its psychoactive properties and its potential as a therapeutic agent for conditions such as anxiety, depression, and migraine. 5-HT is also an important neurotransmitter in the gastrointestinal tract, regulating peristalsis and digestion.'

5-methyltryptamine: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID15760
CHEMBL ID331241
CHEBI ID125675
SCHEMBL ID1129793
MeSH IDM0089463

Synonyms (47)

Synonym
nsc90805
1821-47-2
nsc-90805
CBDIVE_014095
PDSP2_001102
bdbm50073691
5-methyl-tryptamine, 10
2-(5-methyl-1h-indol-3-yl)-ethylamine
SDCCGMLS-0065817.P001
5-methyl-3-(aminoethyl)indole
nsc 90805
indole, 3-(aminoethyl)-5-methyl-
IDI1_011476
1h-indole-3-ethanamine, 5-methyl
5-methyltryptamine
PDSP1_000762
OPREA1_689228
PDSP2_000750
2-(5-methyl-1h-indol-3-yl)ethanamine
STK352130
MAYBRIDGE3_000089
PDSP1_001118
CHEBI:125675
HMS1431E01
L001229
CHEMBL331241 ,
AKOS000546310
5-methyl-1h-indole-3-ethanamine
BBL022747
BRD-K93859331-001-01-0
AB01326088-02
5-metyltryptamine
SCHEMBL1129793
tryptamine, 5-methyl
2-(5-methyl-1h-indol-3-yl)ethylamine #
Q27216286
DTXSID10171250
1h-indole-3-ethanamine,5-methyl-
1h-indole-3-ethanamine, 5-methyl-
2-(5-methyl-1h-indol-3-yl)ethan-1-amine
cvw ,
2-(5-methyl-1~{h}-indol-3-yl)ethanamine
NCGC00332134-01
FT-0753519
D87934
EN300-223449
PD093943
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
tryptaminesTryptamine and its substitution derivatives.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
5-hydroxytryptamine receptor 1DHomo sapiens (human)Ki0.00640.00010.808710.0000AID4627
[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 2AHomo sapiens (human)EC50 (µMol)0.00600.00000.22763.4750AID1162842
TransporterRattus norvegicus (Norway rat)EC50 (µMol)0.00600.00050.04780.3300AID1162842
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (48)

Processvia Protein(s)Taxonomy
regulation of DNA-templated transcriptionTrp operon repressorEscherichia coli K-12
regulation of DNA-templated transcriptionTrp operon repressorEscherichia coli K-12
negative regulation of DNA-templated transcriptionTrp operon repressorEscherichia coli K-12
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathway5-hydroxytryptamine receptor 1DHomo sapiens (human)
intestine smooth muscle contraction5-hydroxytryptamine receptor 1DHomo sapiens (human)
regulation of locomotion5-hydroxytryptamine receptor 1DHomo sapiens (human)
vasoconstriction5-hydroxytryptamine receptor 1DHomo sapiens (human)
regulation of behavior5-hydroxytryptamine receptor 1DHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 1DHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger5-hydroxytryptamine receptor 1DHomo sapiens (human)
adenylate cyclase-inhibiting serotonin receptor signaling pathway5-hydroxytryptamine receptor 1DHomo sapiens (human)
temperature homeostasis5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of cytokine production involved in immune response5-hydroxytryptamine receptor 2AHomo sapiens (human)
glycolytic process5-hydroxytryptamine receptor 2AHomo sapiens (human)
intracellular calcium ion homeostasis5-hydroxytryptamine receptor 2AHomo sapiens (human)
activation of phospholipase C activity5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of cytosolic calcium ion concentration5-hydroxytryptamine receptor 2AHomo sapiens (human)
memory5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of cell population proliferation5-hydroxytryptamine receptor 2AHomo sapiens (human)
response to xenobiotic stimulus5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of phosphatidylinositol biosynthetic process5-hydroxytryptamine receptor 2AHomo sapiens (human)
regulation of dopamine secretion5-hydroxytryptamine receptor 2AHomo sapiens (human)
artery smooth muscle contraction5-hydroxytryptamine receptor 2AHomo sapiens (human)
urinary bladder smooth muscle contraction5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of heat generation5-hydroxytryptamine receptor 2AHomo sapiens (human)
negative regulation of potassium ion transport5-hydroxytryptamine receptor 2AHomo sapiens (human)
phosphatidylinositol 3-kinase/protein kinase B signal transduction5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of neuron apoptotic process5-hydroxytryptamine receptor 2AHomo sapiens (human)
protein localization to cytoskeleton5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of fat cell differentiation5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of glycolytic process5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of vasoconstriction5-hydroxytryptamine receptor 2AHomo sapiens (human)
symbiont entry into host cell5-hydroxytryptamine receptor 2AHomo sapiens (human)
sensitization5-hydroxytryptamine receptor 2AHomo sapiens (human)
behavioral response to cocaine5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of inflammatory response5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of peptidyl-tyrosine phosphorylation5-hydroxytryptamine receptor 2AHomo sapiens (human)
detection of temperature stimulus involved in sensory perception of pain5-hydroxytryptamine receptor 2AHomo sapiens (human)
detection of mechanical stimulus involved in sensory perception of pain5-hydroxytryptamine receptor 2AHomo sapiens (human)
release of sequestered calcium ion into cytosol5-hydroxytryptamine receptor 2AHomo sapiens (human)
negative regulation of synaptic transmission, glutamatergic5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of ERK1 and ERK2 cascade5-hydroxytryptamine receptor 2AHomo sapiens (human)
G protein-coupled serotonin receptor signaling pathway5-hydroxytryptamine receptor 2AHomo sapiens (human)
presynaptic modulation of chemical synaptic transmission5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of execution phase of apoptosis5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of platelet aggregation5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of DNA biosynthetic process5-hydroxytryptamine receptor 2AHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger5-hydroxytryptamine receptor 2AHomo sapiens (human)
phospholipase C-activating serotonin receptor signaling pathway5-hydroxytryptamine receptor 2AHomo sapiens (human)
serotonin receptor signaling pathway5-hydroxytryptamine receptor 2AHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 2AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (13)

Processvia Protein(s)Taxonomy
DNA bindingTrp operon repressorEscherichia coli K-12
DNA-binding transcription factor activityTrp operon repressorEscherichia coli K-12
sequence-specific DNA bindingTrp operon repressorEscherichia coli K-12
G protein-coupled serotonin receptor activity5-hydroxytryptamine receptor 1DHomo sapiens (human)
neurotransmitter receptor activity5-hydroxytryptamine receptor 1DHomo sapiens (human)
Gq/11-coupled serotonin receptor activity5-hydroxytryptamine receptor 2AHomo sapiens (human)
virus receptor activity5-hydroxytryptamine receptor 2AHomo sapiens (human)
G protein-coupled serotonin receptor activity5-hydroxytryptamine receptor 2AHomo sapiens (human)
protein binding5-hydroxytryptamine receptor 2AHomo sapiens (human)
protein tyrosine kinase activator activity5-hydroxytryptamine receptor 2AHomo sapiens (human)
identical protein binding5-hydroxytryptamine receptor 2AHomo sapiens (human)
protein-containing complex binding5-hydroxytryptamine receptor 2AHomo sapiens (human)
serotonin binding5-hydroxytryptamine receptor 2AHomo sapiens (human)
1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine binding5-hydroxytryptamine receptor 2AHomo sapiens (human)
neurotransmitter receptor activity5-hydroxytryptamine receptor 2AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (15)

Processvia Protein(s)Taxonomy
cytoplasmTrp operon repressorEscherichia coli K-12
plasma membrane5-hydroxytryptamine receptor 1DHomo sapiens (human)
synapse5-hydroxytryptamine receptor 1DHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 1DHomo sapiens (human)
dendrite5-hydroxytryptamine receptor 1DHomo sapiens (human)
neurofilament5-hydroxytryptamine receptor 2AHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 2AHomo sapiens (human)
caveola5-hydroxytryptamine receptor 2AHomo sapiens (human)
axon5-hydroxytryptamine receptor 2AHomo sapiens (human)
cytoplasmic vesicle5-hydroxytryptamine receptor 2AHomo sapiens (human)
presynaptic membrane5-hydroxytryptamine receptor 2AHomo sapiens (human)
neuronal cell body5-hydroxytryptamine receptor 2AHomo sapiens (human)
dendritic shaft5-hydroxytryptamine receptor 2AHomo sapiens (human)
postsynaptic membrane5-hydroxytryptamine receptor 2AHomo sapiens (human)
cell body fiber5-hydroxytryptamine receptor 2AHomo sapiens (human)
glutamatergic synapse5-hydroxytryptamine receptor 2AHomo sapiens (human)
G protein-coupled serotonin receptor complex5-hydroxytryptamine receptor 2AHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 2AHomo sapiens (human)
dendrite5-hydroxytryptamine receptor 2AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (10)

Assay IDTitleYearJournalArticle
AID1162841Induction of NET-mediated norepinephrine release in rat brain synaptosomes by [3H]NE release assay2014Bioorganic & medicinal chemistry letters, Oct-01, Volume: 24, Issue:19
Alpha-ethyltryptamines as dual dopamine-serotonin releasers.
AID1162843Agonist activity at 5HT2A receptor (unknown origin) by cell based calcium mobilization assay relative to control2014Bioorganic & medicinal chemistry letters, Oct-01, Volume: 24, Issue:19
Alpha-ethyltryptamines as dual dopamine-serotonin releasers.
AID1162839Induction of DAT-mediated dopamine release in rat brain synaptosomes by [3H]DA release assay2014Bioorganic & medicinal chemistry letters, Oct-01, Volume: 24, Issue:19
Alpha-ethyltryptamines as dual dopamine-serotonin releasers.
AID1162840Induction of 5-HTT-mediated 5-HT release in rat brain synaptosomes by [3H]5-HT release assay2014Bioorganic & medicinal chemistry letters, Oct-01, Volume: 24, Issue:19
Alpha-ethyltryptamines as dual dopamine-serotonin releasers.
AID4867The compound was tested for intrinsic activity against 5-HT1D receptor1995Journal of medicinal chemistry, Sep-01, Volume: 38, Issue:18
Computer-aided design and synthesis of 5-substituted tryptamines and their pharmacology at the 5-HT1D receptor: discovery of compounds with potential anti-migraine properties.
AID5452The compound was tested for binding affinity against 5-HT2A receptor1995Journal of medicinal chemistry, Sep-01, Volume: 38, Issue:18
Computer-aided design and synthesis of 5-substituted tryptamines and their pharmacology at the 5-HT1D receptor: discovery of compounds with potential anti-migraine properties.
AID1162842Agonist activity at 5HT2A receptor (unknown origin) by cell based calcium mobilization assay2014Bioorganic & medicinal chemistry letters, Oct-01, Volume: 24, Issue:19
Alpha-ethyltryptamines as dual dopamine-serotonin releasers.
AID4869The compound was tested for binding affinity against 5-HT1D receptor1995Journal of medicinal chemistry, Sep-01, Volume: 38, Issue:18
Computer-aided design and synthesis of 5-substituted tryptamines and their pharmacology at the 5-HT1D receptor: discovery of compounds with potential anti-migraine properties.
AID4627In vitro receptor binding affinity for cloned human 5-hydroxytryptamine 1D receptor1999Journal of medicinal chemistry, Feb-11, Volume: 42, Issue:3
N-Methyl-5-tert-butyltryptamine: A novel, highly potent 5-HT1D receptor agonist.
AID1799822Binding Assay from Article : \\The structural basis for the interaction between L-tryptophan and the Escherichia coli trp aporepressor.\\1987The Journal of biological chemistry, Apr-05, Volume: 262, Issue:10
The structural basis for the interaction between L-tryptophan and the Escherichia coli trp aporepressor.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (18)

TimeframeStudies, This Drug (%)All Drugs %
pre-19907 (38.89)18.7374
1990's7 (38.89)18.2507
2000's2 (11.11)29.6817
2010's1 (5.56)24.3611
2020's1 (5.56)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.24

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index22.24 (24.57)
Research Supply Index2.94 (2.92)
Research Growth Index4.59 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.24)

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%
Other18 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]