Page last updated: 2024-12-07

2-(2,5-dimethoxyphenyl)ethanamine

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

Cross-References

ID SourceID
PubMed CID76632
CHEMBL ID287047
CHEBI ID125507
SCHEMBL ID479514

Synonyms (33)

Synonym
AC-6627
2c-h
nsc 168525
9a8xf4ga0x ,
unii-9a8xf4ga0x
dea no. 7517
3600-86-0
nsc-168525
nsc168525
2-(2,5-dimethoxyphenyl)ethanamine
2,5-dimethoxyphenethylamine
2,5-dimethoxyphenethylamine, 97%
CHEBI:125507
2-(2,5-dimethoxyphenyl)ethylamine
CHEMBL287047 ,
AKOS000162038
FT-0667267
2-(2,5-dimethoxy-phenyl)-ethylamine
bdbm50026778
A6257
2,5-dimethoxyphenethyl amine
benzeneethanamine, 2,5-dimethoxy-
2-(2,5-dimethoxy-phenyl)-ethylamine hcl
BRD-K20985754-001-01-9
(2,5-dimethoxyphenyl)ethylamine
phenethylamine, 2,5-dimethoxy-
2-(2-aminoethyl)-1,4-dimethoxybenzene
SCHEMBL479514
2-(2,5-dimethoxyphenyl)ethanamine #
DTXSID80189564
Q4633049
BCP10409
PD046579
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
dimethoxybenzeneAny methoxybenzene that consists of a benzene skeleton substituted with two methoxy groups and its 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 (16)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
5-hydroxytryptamine receptor 2CRattus norvegicus (Norway rat)Ki5.96000.00020.667710.0000AID5720; AID5725
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)Ki2.88000.00010.601710.0000AID1442363; AID5518; AID5535
Sigma non-opioid intracellular receptor 1Cavia porcellus (domestic guinea pig)Ki2.82000.00000.338510.0000AID1442363
[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 2CRattus norvegicus (Norway rat)Kd0.14120.00042.58328.5114AID6406
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)Kd0.14120.00012.62198.5114AID6406
5-hydroxytryptamine receptor 1ARattus norvegicus (Norway rat)Kd0.14120.00012.29338.5114AID6406
5-hydroxytryptamine receptor 1BRattus norvegicus (Norway rat)Kd0.14120.02342.74218.5114AID6406
5-hydroxytryptamine receptor 1DRattus norvegicus (Norway rat)Kd0.14120.02342.74218.5114AID6406
5-hydroxytryptamine receptor 1FRattus norvegicus (Norway rat)Kd0.14120.02342.74218.5114AID6406
5-hydroxytryptamine receptor 2BRattus norvegicus (Norway rat)Kd0.14120.00042.47358.5114AID6406
5-hydroxytryptamine receptor 6Rattus norvegicus (Norway rat)Kd0.14120.02342.74218.5114AID6406
5-hydroxytryptamine receptor 7 Rattus norvegicus (Norway rat)Kd0.14120.00012.70068.5114AID6406
5-hydroxytryptamine receptor 5ARattus norvegicus (Norway rat)Kd0.14120.02342.74218.5114AID6406
5-hydroxytryptamine receptor 5BRattus norvegicus (Norway rat)Kd0.14120.02342.74218.5114AID6406
5-hydroxytryptamine receptor 3ARattus norvegicus (Norway rat)Kd0.14120.00082.62148.5114AID6406
5-hydroxytryptamine receptor 4 Rattus norvegicus (Norway rat)Kd0.14120.02342.74218.5114AID6406
Trace amine-associated receptor 1Homo sapiens (human)EC50 (µMol)2.01000.01501.41437.1900AID341210
5-hydroxytryptamine receptor 3BRattus norvegicus (Norway rat)Kd0.14120.00082.62148.5114AID6406
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (1)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathwayTrace amine-associated receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (2)

Processvia Protein(s)Taxonomy
G protein-coupled receptor activityTrace amine-associated receptor 1Homo sapiens (human)
trace-amine receptor activityTrace amine-associated receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
plasma membraneTrace amine-associated receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (12)

Assay IDTitleYearJournalArticle
AID1442363Displacement of [3H]ketanserin from rat 5HT2A expressed in mouse NIH/3T3 cell membranes after 30 mins by scintillation counting method2017Journal of medicinal chemistry, 04-13, Volume: 60, Issue:7
The 2014 Philip S. Portoghese Medicinal Chemistry Lectureship: The "Phenylalkylaminome" with a Focus on Selected Drugs of Abuse.
AID231553Ratio of binding affinity towards rat 5-HT2C and 5-HT2A receptors2001Journal of medicinal chemistry, Sep-27, Volume: 44, Issue:20
1-[2-methoxy-5-(3-phenylpropyl)]-2-aminopropane unexpectedly shows 5-HT(2A) serotonin receptor affinity and antagonist character.
AID5535Displacement of [3H]ketanserin from NIH3T3 cells stably expressing rat 5-hydroxytryptamine 2A receptor2000Journal of medicinal chemistry, Aug-10, Volume: 43, Issue:16
1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT(2A) partial agonists.
AID36419Alpha-1 adrenergic receptor agonist activity in rabbit ear artery1981Journal of medicinal chemistry, Dec, Volume: 24, Issue:12
Alpha-adrenergic agents. 1. Direct-acting alpha 1 agonists related to methoxamine.
AID166802Phentolamine dissociation constant was evaluated in rabbit ear artery1981Journal of medicinal chemistry, Dec, Volume: 24, Issue:12
Alpha-adrenergic agents. 1. Direct-acting alpha 1 agonists related to methoxamine.
AID5725Displacement of [3H]mesulergine from A9 cells stably expressing rat 5-hydroxytryptamine 2C receptor2000Journal of medicinal chemistry, Aug-10, Volume: 43, Issue:16
1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT(2A) partial agonists.
AID5720Binding affinity against rat 5-hydroxytryptamine 2C receptor using [3H]mesulergine as radioligand2001Journal of medicinal chemistry, Sep-27, Volume: 44, Issue:20
1-[2-methoxy-5-(3-phenylpropyl)]-2-aminopropane unexpectedly shows 5-HT(2A) serotonin receptor affinity and antagonist character.
AID341211Agonist activity at human trace amine associated receptor 1 expressed in RD-HGA16 CHO-K1 cells coexpressed with Galpha16 protein assessed as internal calcium mobilization by calcium 3 assay relative to 2-phenylethanamine2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Structure-activity correlations for beta-phenethylamines at human trace amine receptor 1.
AID341210Agonist activity at human trace amine associated receptor 1 expressed in RD-HGA16 CHO-K1 cells coexpressed with Galpha16 protein assessed as internal calcium mobilization by calcium 3 assay2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Structure-activity correlations for beta-phenethylamines at human trace amine receptor 1.
AID5518Binding affinity against rat 5-hydroxytryptamine 2A receptor using [3H]ketanserin as radioligand2001Journal of medicinal chemistry, Sep-27, Volume: 44, Issue:20
1-[2-methoxy-5-(3-phenylpropyl)]-2-aminopropane unexpectedly shows 5-HT(2A) serotonin receptor affinity and antagonist character.
AID1146450Competitive antagonist activity at 5-HT serotonin receptor in Sprague-Dawley rat stomach fundus model assessed as inhibition of 5-HT-induced contractile response1978Journal of medicinal chemistry, Aug, Volume: 21, Issue:8
Serotonin receptor binding affinities of several hallucinogenic phenylalkylamine and N,N-dimethyltryptamine analogues.
AID6406Affinity against 5-hydroxytryptamine receptors in rat fundus model1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Serotonin receptor affinities of psychoactive phenalkylamine analogues.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (42.86)18.7374
1990's0 (0.00)18.2507
2000's3 (42.86)29.6817
2010's1 (14.29)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.36

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 Index12.36 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.43 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.36)

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%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]