Page last updated: 2024-12-09

2-(2,3-dihydroindol-1-yl)-N,N-dimethylethanamine

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

2-(2,3-dihydroindol-1-yl)-N,N-dimethylethanamine, often abbreviated as **2-DHI**, is a research chemical known for its **agonist activity at the 5-HT2A receptor**. This means that it can bind to and activate this specific type of serotonin receptor in the brain.

Here's why it's important for research:

* **Understanding 5-HT2A receptor function:** The 5-HT2A receptor is involved in a wide range of brain functions, including:
* **Perception:** It plays a role in sensory processing, including visual perception.
* **Cognition:** It's involved in learning, memory, and attention.
* **Mood and emotion:** It's implicated in anxiety, depression, and psychosis.
* **Sleep and appetite:** It influences sleep-wake cycles and food intake.

* **Developing new treatments:** Because of its role in these important brain functions, 5-HT2A receptor agonists and antagonists are being investigated for their potential therapeutic applications in conditions like:
* **Depression:** Some antidepressants are thought to work by modulating the 5-HT2A receptor.
* **Anxiety:** 5-HT2A antagonists are being explored as potential treatments for anxiety disorders.
* **Schizophrenia:** Certain atypical antipsychotics act as 5-HT2A antagonists.
* **Migraines:** 5-HT2A agonists are used as abortive treatments for migraines.

* **Investigating psychedelic effects:** 2-DHI, like other 5-HT2A receptor agonists, has been observed to possess **psychedelic effects**, which are often associated with altered perception and consciousness. This has sparked interest in its use as a research tool to study the mechanisms underlying psychedelic experiences and their potential therapeutic applications in conditions like addiction and end-of-life anxiety.

**Important Considerations:**

* 2-DHI is a research chemical and **not a drug approved for medical use**. Its safety and efficacy in humans are not fully established.
* Research involving 2-DHI should be conducted **ethically and responsibly** with appropriate safeguards in place.

**In summary, 2-DHI is a valuable research tool that helps scientists understand the complex role of the 5-HT2A receptor in the brain and its potential for therapeutic applications.** Its psychedelic properties further enhance its importance for investigating the mechanisms behind altered states of consciousness.

Cross-References

ID SourceID
PubMed CID744368
CHEMBL ID422471
CHEBI ID114471
SCHEMBL ID7680979

Synonyms (20)

Synonym
EU-0011905
CBDIVE_015848
smr000122729
MLS000523656
cid_744368
bdbm50150979
[2-(2,3-dihydro-indol-1-yl)-ethyl]-dimethyl-amine
CHEMDIV2_000952
2-(2,3-dihydro-1h-indol-1-yl)-n,n-dimethylethanamine
STK386817
CHEBI:114471
CHEMBL422471 ,
HMS1371L06
2-(2,3-dihydroindol-1-yl)-n,n-dimethylethanamine
AKOS001675959
SCHEMBL7680979
HMS2370M08
AB00073802-01
Q27195874
[2-(2,3-dihydro-indol-1-yl)-ethyl]-dimethyl-amine, aldrichcpr
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
indolesAny compound containing an indole skeleton.
[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 (14)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency44.66840.003245.467312,589.2998AID2517
Chain A, Putative fructose-1,6-bisphosphate aldolaseGiardia intestinalisPotency25.11890.140911.194039.8107AID2451
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency39.81070.177814.390939.8107AID2147
Microtubule-associated protein tauHomo sapiens (human)Potency25.11890.180013.557439.8107AID1460
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency19.95260.011212.4002100.0000AID1030
bromodomain adjacent to zinc finger domain 2BHomo sapiens (human)Potency44.66840.707936.904389.1251AID504333
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency22.38720.035520.977089.1251AID504332
lamin isoform A-delta10Homo sapiens (human)Potency15.84890.891312.067628.1838AID1487
Polyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)Potency25.11890.316212.765731.6228AID881
Histamine H2 receptorCavia porcellus (domestic guinea pig)Potency25.11890.00638.235039.8107AID881
[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)
PTK2B protein tyrosine kinase 2 betaHomo sapiens (human)IC50 (µMol)6.46201.53704.08056.9220AID1641
estrogen receptor beta isoform 1Homo sapiens (human)IC50 (µMol)0.05791.91098.316518.7976AID1060
5-hydroxytryptamine receptor 6Homo sapiens (human)Ki5.00000.00020.522910.0000AID238424
[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 2BRattus norvegicus (Norway rat)Kd0.26910.00042.47358.5114AID168920
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (27)

Processvia Protein(s)Taxonomy
lipid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
phospholipid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
apoptotic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of cell population proliferationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of macrophage derived foam cell differentiationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
arachidonic acid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of cell migrationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
prostate gland developmentPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
regulation of epithelial cell differentiationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of chemokine productionPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of peroxisome proliferator activated receptor signaling pathwayPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of keratinocyte differentiationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of cell cyclePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of growthPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
hepoxilin biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
endocannabinoid signaling pathwayPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cannabinoid biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipoxin A4 biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
linoleic acid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipid oxidationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipoxygenase pathwayPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cerebral cortex cell migration5-hydroxytryptamine receptor 6Homo sapiens (human)
positive regulation of TOR signaling5-hydroxytryptamine receptor 6Homo sapiens (human)
G protein-coupled serotonin receptor signaling pathway5-hydroxytryptamine receptor 6Homo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 6Homo sapiens (human)
adenylate cyclase-modulating G protein-coupled receptor signaling pathway5-hydroxytryptamine receptor 6Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger5-hydroxytryptamine receptor 6Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (11)

Processvia Protein(s)Taxonomy
iron ion bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
calcium ion bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
protein bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipid bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
linoleate 13S-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
arachidonate 8(S)-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
arachidonate 15-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
linoleate 9S-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
histamine receptor activity5-hydroxytryptamine receptor 6Homo sapiens (human)
protein binding5-hydroxytryptamine receptor 6Homo sapiens (human)
neurotransmitter receptor activity5-hydroxytryptamine receptor 6Homo sapiens (human)
G protein-coupled serotonin receptor activity5-hydroxytryptamine receptor 6Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
nucleusPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cytosolPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cytoskeletonPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
plasma membranePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
adherens junctionPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
focal adhesionPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
membranePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
extracellular exosomePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 6Homo sapiens (human)
cilium5-hydroxytryptamine receptor 6Homo sapiens (human)
synapse5-hydroxytryptamine receptor 6Homo sapiens (human)
dendrite5-hydroxytryptamine receptor 6Homo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 6Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

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.
AID1745845Primary qHTS for Inhibitors of ATXN expression
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.
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
AID238424Binding affinity against 5-hydroxytryptamine 6 receptor2004Bioorganic & medicinal chemistry letters, Sep-06, Volume: 14, Issue:17
Possible differences in modes of agonist and antagonist binding at human 5-HT6 receptors.
AID168920Displacement of [3H]5-HT binding to serotonin receptor of rat fundus membranes1984Journal of medicinal chemistry, Jan, Volume: 27, Issue:1
Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (16.67)18.7374
1990's0 (0.00)18.2507
2000's2 (33.33)29.6817
2010's2 (33.33)24.3611
2020's1 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.19

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 Index12.19 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.14 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.19)

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%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]