Page last updated: 2024-11-05

2,5-dimethoxy-4-ethylamphetamine

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

Description

2,5-dimethoxy-4-ethylamphetamine: psychedelic agent; ethyl homolog of dimethoxymethylamphetamine; RN given refers to parent cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID27402
CHEMBL ID8224
CHEBI ID191249
SCHEMBL ID1740704
MeSH IDM0041050

Synonyms (32)

Synonym
PDSP2_000785
PDSP1_000797
PDSP1_001371
2,5-dimethoxy-4-ethylamphetamine
DB01467
PDSP2_001355
L001150
CHEMBL8224 ,
CHEBI:191249
22004-32-6
1-(4-ethyl-2,5-dimethoxyphenyl)propan-2-amine
cas_62066
bdbm81965
doet,(-)
nsc_62066
unii-9sk6k682ul
phenethylamine, 4-ethyl-2,5-dimethoxy-alpha-methyl-
benzeneethanamine, 4-ethyl-2,5-dimethoxy-alpha-methyl-
9sk6k682ul ,
4-ethyl-2,5-dimethoxyamphetamine
SCHEMBL1740704
2,5-dimethoxy-4-ethylamphetamine (''doet'')
HXJKWPGVENNMCC-UHFFFAOYSA-N
1-(4-ethyl-2,5-dimethoxyphenyl)-2-propanamine #
(+/-)-1-(2,5-dimethoxy-4-ethylphenyl)-2-aminopropane
(+/-)-4-ethyl-2,5-dimethoxy-.alpha.-methylphenethylamine
phenethylamine, 4-ethyl-2,5-dimethoxy-.alpha.-methyl-
benzeneethanamine, 4-ethyl-2,5-dimethoxy-.alpha.-methyl-
hecate
J71.136E ,
Q947249
DTXSID00860585

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" The dithio analogue of DOM was synthesized and found to be without central activity at a dosage of approximately 50 times the mean effective dose of DOM."( Sulfur analogues of psychotomimetic agents. 2. Analogues of (2,5-dimethoxy-4-methylphenyl)-and (2,5-dimethoxy-4-ethylphenyl)isopropylamine.
Jacob, P; Shulgin, AT, 1983
)
0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
amphetaminesAmines that constitute a class of central nervous system stimulants based on the structure of the parent amphetamine 1-phenylpropan-2-amine.
[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)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
5-hydroxytryptamine receptor 2CRattus norvegicus (Norway rat)Ki0.10030.00020.667710.0000AID4762; AID5263; AID5270
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)Ki0.10000.00010.601710.0000AID385347; AID5263; AID5270
5-hydroxytryptamine receptor 1ARattus norvegicus (Norway rat)Ki4.57000.00010.739610.0000AID3695
5-hydroxytryptamine receptor 1BRattus norvegicus (Norway rat)Ki4.57000.00031.29679.2440AID3695
5-hydroxytryptamine receptor 1DRattus norvegicus (Norway rat)Ki4.57000.00101.67479.2000AID3695
5-hydroxytryptamine receptor 1FRattus norvegicus (Norway rat)Ki4.57000.00101.67479.2000AID3695
5-hydroxytryptamine receptor 2BRattus norvegicus (Norway rat)Ki0.10000.00020.590910.0000AID5263; AID5270
[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)Kd0.06610.00042.58328.5114AID6405; AID6406
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)Kd0.06610.00012.62198.5114AID6405; AID6406
5-hydroxytryptamine receptor 1ARattus norvegicus (Norway rat)Kd0.06610.00012.29338.5114AID6405; AID6406
5-hydroxytryptamine receptor 1BRattus norvegicus (Norway rat)Kd0.06610.02342.74218.5114AID6405; AID6406
5-hydroxytryptamine receptor 1DRattus norvegicus (Norway rat)Kd0.06610.02342.74218.5114AID6405; AID6406
5-hydroxytryptamine receptor 1FRattus norvegicus (Norway rat)Kd0.06610.02342.74218.5114AID6405; AID6406
5-hydroxytryptamine receptor 2BRattus norvegicus (Norway rat)Kd0.06610.00042.47358.5114AID6405; AID6406
5-hydroxytryptamine receptor 6Rattus norvegicus (Norway rat)Kd0.06610.02342.74218.5114AID6405; AID6406
5-hydroxytryptamine receptor 7 Rattus norvegicus (Norway rat)Kd0.06610.00012.70068.5114AID6405; AID6406
5-hydroxytryptamine receptor 5ARattus norvegicus (Norway rat)Kd0.06610.02342.74218.5114AID6405; AID6406
5-hydroxytryptamine receptor 5BRattus norvegicus (Norway rat)Kd0.06610.02342.74218.5114AID6405; AID6406
5-hydroxytryptamine receptor 3ARattus norvegicus (Norway rat)Kd0.06610.00082.62148.5114AID6405; AID6406
5-hydroxytryptamine receptor 4 Rattus norvegicus (Norway rat)Kd0.06610.02342.74218.5114AID6405; AID6406
5-hydroxytryptamine receptor 3BRattus norvegicus (Norway rat)Kd0.06610.00082.62148.5114AID6405; AID6406
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (24)

Assay IDTitleYearJournalArticle
AID176716Dose at which the rats perform 50% appropriate drug -lever responding was determined1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane.
AID385349Lipophilicity of compound by immobilized artificial membrane column containing phosphatidylcholine head groups HPLC2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands.
AID188584Number of rats responding out of 5 treated rats at a dose of 0.5 mg/Kg1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane.
AID6405Binding affinity at rat 5-hydroxytryptamine receptor.1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane.
AID5226Binding affinity against 5-hydroxytryptamine 2 receptor of rat frontal cortex using [3H]ketanserin radioligand1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors.
AID89084Hallucinogenic potency was determined in humans1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane.
AID188580Number of rats responding out of 5 treated rats at a dose of 0.125 mg/Kg1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane.
AID385347Displacement of [3H]ketanserin from 5HT2A receptor in Sprague-Dawley rat brain by liquid scintillation spectroscopy2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands.
AID1131956Hallucinogenic activity in human1977Journal of medicinal chemistry, Dec, Volume: 20, Issue:12
Structure-activity studies on hallucinogenic amphetamines using molecular connectivity.
AID6406Affinity against 5-hydroxytryptamine receptors in rat fundus model1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Serotonin receptor affinities of psychoactive phenalkylamine analogues.
AID175415Dose required to produce 50% hallucinogenic potency in rat was determined at a dose of 0.25 mg/kg1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane.
AID4762Binding affinity towards 5-hydroxytryptamine 1C receptor from frontal cortical regions of male Sprague-Dawley rat homogenates, using [3H]mesulergine as radioligand1992Journal of medicinal chemistry, Feb-21, Volume: 35, Issue:4
Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity.
AID3695Evaluated for binding affinity towards rat cortical membranes at 5-hydroxytryptamine 1 receptor binding site by using [3H]-5-HT as a radioligand.1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Central serotonin receptors as targets for drug research.
AID175416Dose required to produce 50% hallucinogenic potency in rat was determined at a dose of 0.5 mg/kg1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane.
AID88883Hallucinogenic activity i.e; ratio of effective dose of mescaline to the effective dose in human1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Structure-activity correlations for psychotomimetics. 1. Phenylalkylamines: electronic, volume, and hydrophobicity parameters.
AID175412Dose required to produce 50% hallucinogenic potency in rat was determined at a dose of 0.125 mg/kg1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane.
AID5270Binding affinity to rat cortical membranes at 5-hydroxytryptamine 2 (5-HT2) receptor using [3H]KET as a radioligand1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Central serotonin receptors as targets for drug research.
AID91217Compound tested for hallucinogenic activity in humans was reported; Value reported in (A)= Mescaline units1998Journal of medicinal chemistry, Sep-24, Volume: 41, Issue:20
The frontier orbital phase angles: novel QSAR descriptors for benzene derivatives, applied to phenylalkylamine hallucinogens.
AID188583Number of rats responding out of 5 treated rats at a dose of 0.25 mg/Kg1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane.
AID385350Agonist activity at Sprague-Dawley rat 5HT2A receptor by drug discrimination assay2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands.
AID19263Log value of hallucinogenic activity was determined1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Structure-activity correlations for psychotomimetics. 1. Phenylalkylamines: electronic, volume, and hydrophobicity parameters.
AID5263Binding affinity towards 5-hydroxytryptamine 2 receptor from frontal cortical regions of male Sprague-Dawley rat homogenates, using [3H]ketanserin as radioligand1992Journal of medicinal chemistry, Feb-21, Volume: 35, Issue:4
Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity.
AID2330285-HT1C selectivity was defined as the ratio between Ki(5-HT2)/Ki(5-HT1C)1992Journal of medicinal chemistry, Feb-21, Volume: 35, Issue:4
Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity.
AID178403Effective dose in rats trained on 1 mg/kg DOM.1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Structure-activity correlations for psychotomimetics. 1. Phenylalkylamines: electronic, volume, and hydrophobicity parameters.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19908 (61.54)18.7374
1990's4 (30.77)18.2507
2000's1 (7.69)29.6817
2010's0 (0.00)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: 21.88

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 Index21.88 (24.57)
Research Supply Index2.77 (2.92)
Research Growth Index4.07 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.88)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (15.38%)5.53%
Reviews1 (7.69%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other10 (76.92%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]