Page last updated: 2024-11-12

2,5-dimethoxy-4-methylamphetamine, (r)-isomer

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

Cross-References

ID SourceID
PubMed CID11735949
CHEMBL ID317634
SCHEMBL ID1742173
MeSH IDM0330397

Synonyms (18)

Synonym
PDSP2_000453
CHEMBL317634 ,
bdbm50367392
SCHEMBL1742173
43061-13-8
benzeneethanamine, 2,5-dimethoxy-alpha,4-dimethyl-, (alphar)-
lx3mc6ob9x ,
(r)-2,5-dimethoxy-4-methylamphetamine
(r)-(-)-2,5-dimethoxy-4-methylamphetamine
2,5-dimethoxy-4-methylamphetamine, (r)-
unii-lx3mc6ob9x
(-)-dom
DTXSID50110007
(-)-1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane
benzeneethanamine, 2,5-dimethoxy-.alpha.,4-dimethyl-, (.alpha.r)-
dom, (r)-
r-2,5-dimethoxy-4-methylamphetamine
Q209257
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (8)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
5-hydroxytryptamine receptor 2CRattus norvegicus (Norway rat)Ki0.07170.00020.667710.0000AID4762; AID5263; AID5270
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)Ki0.06250.00010.601710.0000AID5263; AID5270
5-hydroxytryptamine receptor 1ARattus norvegicus (Norway rat)Ki3.55000.00010.739610.0000AID3695
5-hydroxytryptamine receptor 1BRattus norvegicus (Norway rat)Ki3.55000.00031.29679.2440AID3695
5-hydroxytryptamine receptor 1DRattus norvegicus (Norway rat)Ki3.55000.00101.67479.2000AID3695
5-hydroxytryptamine receptor 1FRattus norvegicus (Norway rat)Ki3.55000.00101.67479.2000AID3695
5-hydroxytryptamine receptor 2BRattus norvegicus (Norway rat)Ki0.06250.00020.590910.0000AID5263; AID5270
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (7)

Processvia Protein(s)Taxonomy
long-chain fatty acid metabolic processCytochrome P450 2C19Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 2C19Homo sapiens (human)
steroid metabolic processCytochrome P450 2C19Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 2C19Homo sapiens (human)
epoxygenase P450 pathwayCytochrome P450 2C19Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 2C19Homo sapiens (human)
omega-hydroxylase P450 pathwayCytochrome P450 2C19Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (14)

Processvia Protein(s)Taxonomy
monooxygenase activityCytochrome P450 2C19Homo sapiens (human)
iron ion bindingCytochrome P450 2C19Homo sapiens (human)
steroid hydroxylase activityCytochrome P450 2C19Homo sapiens (human)
oxidoreductase activityCytochrome P450 2C19Homo sapiens (human)
(S)-limonene 6-monooxygenase activityCytochrome P450 2C19Homo sapiens (human)
(S)-limonene 7-monooxygenase activityCytochrome P450 2C19Homo sapiens (human)
oxygen bindingCytochrome P450 2C19Homo sapiens (human)
enzyme bindingCytochrome P450 2C19Homo sapiens (human)
heme bindingCytochrome P450 2C19Homo sapiens (human)
(R)-limonene 6-monooxygenase activityCytochrome P450 2C19Homo sapiens (human)
aromatase activityCytochrome P450 2C19Homo sapiens (human)
long-chain fatty acid omega-1 hydroxylase activityCytochrome P450 2C19Homo sapiens (human)
arachidonic acid epoxygenase activityCytochrome P450 2C19Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygenCytochrome P450 2C19Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
endoplasmic reticulum membraneCytochrome P450 2C19Homo sapiens (human)
plasma membraneCytochrome P450 2C19Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 2C19Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 2C19Homo sapiens (human)
cytoplasmCytochrome P450 2C19Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (31)

Assay IDTitleYearJournalArticle
AID123228Evaluated for ear-scratch response (hallucinogen like activity) in mice at a dose of 2.00 mg/Kg1982Journal of medicinal chemistry, May, Volume: 25, Issue:5
Isomeric cyclopropyl ring-methylated homologues of trans-2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine, an hallucinogen analogue.
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.
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.
AID55412Inhibitory effect in formation of metabolic intermediate complex between Cytochrome P450 and racemic compound 2 at extent, on pre-incubation with compound at 300 uM1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Studies on chiral interactions of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane and the corresponding N-hydroxy metabolites with cytochrome P-450.
AID635287Activation of rhesus monkey TAAR1 expressed in RD-HGA16 cells co-expressing Gq protein assessed as cAMP accumulation by fluorescence plate reader2011Bioorganic & medicinal chemistry, Dec-01, Volume: 19, Issue:23
Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class.
AID53090Inhibitory effect in formation of metabolic intermediate complex between Cytochrome P450 and racemic compound 2 initially, on pre-incubation with compound at 150 uM1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Studies on chiral interactions of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane and the corresponding N-hydroxy metabolites with cytochrome P-450.
AID55410Inhibitory effect in formation of metabolic intermediate complex between Cytochrome P450 and racemic compound 2 at extent, on pre-incubation with Racemic 2 (300 uM) at 300 uM1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Studies on chiral interactions of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane and the corresponding N-hydroxy metabolites with cytochrome P-450.
AID123357Evaluated for ear-scratch response (hallucinogen like activity) in mice at a dose of 4.00 mg/Kg1982Journal of medicinal chemistry, May, Volume: 25, Issue:5
Isomeric cyclopropyl ring-methylated homologues of trans-2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine, an hallucinogen analogue.
AID22913Initial rates of formation of metabolic intermediate Cytochrome P-450 at compound concentration of 3.75-120 uM1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Studies on chiral interactions of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane and the corresponding N-hydroxy metabolites with cytochrome P-450.
AID53089Inhibitory effect in formation of metabolic intermediate complex between Cytochrome P450 and racemic compound 2 initially, on preincubation with Racemic compound 2 (300 uM) at 150 uM1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Studies on chiral interactions of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane and the corresponding N-hydroxy metabolites with cytochrome P-450.
AID53093Inhibitory effect in formation of metabolic intermediate complex between Cytochrome P450 and racemic 2 initially, on pre-incubation with Racemic compound 2 (300 uM) at 300 uM1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Studies on chiral interactions of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane and the corresponding N-hydroxy metabolites with cytochrome P-450.
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.
AID635286Activation of C-terminal HA epitope tagged human TAAR1 expressed in RD-HGA16 cells co-expressing Gq protein, Galpha16 by cAMP accumulation assay2011Bioorganic & medicinal chemistry, Dec-01, Volume: 19, Issue:23
Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class.
AID22917Initial rates of formation of metabolic intermediate Cytochrome P-450 with compound concentration of 150 uM1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Studies on chiral interactions of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane and the corresponding N-hydroxy metabolites with cytochrome P-450.
AID53092Inhibitory effect in formation of metabolic intermediate complex between Cytochrome P450 and racemic compound 2 initially, on pre-incubation with compound at 30 uM1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Studies on chiral interactions of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane and the corresponding N-hydroxy metabolites with cytochrome P-450.
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.
AID22914Initial rates of formation of metabolic intermediate Cytochrome P-450 at compound concentration of 30 uM1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Studies on chiral interactions of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane and the corresponding N-hydroxy metabolites with cytochrome P-450.
AID55409Inhibitory effect in formation of metabolic intermediate complex between Cytochrome P450 and racemic compound 2 at extent, on pre-incubation with Racemic 2 (300 uM) at 150 uM1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Studies on chiral interactions of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane and the corresponding N-hydroxy metabolites with cytochrome P-450.
AID18770Lag time between the addition of compound (30 uM) and the first appearance of chromophore1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Studies on chiral interactions of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane and the corresponding N-hydroxy metabolites with cytochrome P-450.
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.
AID55543Inhibitory effect in formation of metabolic intermediate complex between Cytochrome P450 and racemic compound 2 at extent, on pre-incubation with compound at 30 uM1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Studies on chiral interactions of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane and the corresponding N-hydroxy metabolites with cytochrome P-450.
AID53086Apparent binding affinity constant of compound (10.8-60.0) for Cytochrome P4501981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Studies on chiral interactions of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane and the corresponding N-hydroxy metabolites with cytochrome P-450.
AID22919Initial rates of formation of metabolic intermediate Cytochrome P-450 with compound concentration of 300 uM1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Studies on chiral interactions of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane and the corresponding N-hydroxy metabolites with cytochrome P-450.
AID123224Evaluated for ear-scratch response (hallucinogen like activity) in mice at a dose of 1.00 mg/Kg1982Journal of medicinal chemistry, May, Volume: 25, Issue:5
Isomeric cyclopropyl ring-methylated homologues of trans-2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine, an hallucinogen analogue.
AID55403Inhibitory effect in formation of metabolic intermediate complex between Cytochrome P450 and racemic compound 2 initially, on pre-incubation with Racemic 2 (300 uM) at 30 uM1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Studies on chiral interactions of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane and the corresponding N-hydroxy metabolites with cytochrome P-450.
AID55544Inhibitory effect in formation of metabolic intermediate complex between Cytochrome P450 and racemic 2 at extent, on preincubation with Racemic compound 2 (300 uM) at 30 uM1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Studies on chiral interactions of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane and the corresponding N-hydroxy metabolites with cytochrome P-450.
AID17769Extent rates of formation of metabolic intermediate Cytochrome P-450 at compound concentration of 3.75-120 uM1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Studies on chiral interactions of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane and the corresponding N-hydroxy metabolites with cytochrome P-450.
AID22918Initial rates of formation of metabolic intermediate Cytochrome P-450 with compound concentration of 30 uM1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Studies on chiral interactions of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane and the corresponding N-hydroxy metabolites with cytochrome P-450.
AID17770Extent rates of formation of metabolic intermediate Cytochrome P-450 at compound concentration of 30 uM1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Studies on chiral interactions of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane and the corresponding N-hydroxy metabolites with cytochrome P-450.
AID55411Inhibitory effect in formation of metabolic intermediate complex between Cytochrome P450 and racemic compound 2 at extent, on preincubation with compound at 150 uM1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Studies on chiral interactions of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane and the corresponding N-hydroxy metabolites with cytochrome P-450.
AID53091Inhibitory effect in formation of metabolic intermediate complex between Cytochrome P450 and racemic compound 2 initially, on pre-incubation with compound at 300 uM1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Studies on chiral interactions of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane and the corresponding N-hydroxy metabolites with cytochrome P-450.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (60.00)18.7374
1990's1 (20.00)18.2507
2000's0 (0.00)29.6817
2010's1 (20.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (20.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other4 (80.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]