Page last updated: 2024-11-13

2,5-dimethoxy-4-bromoamphetamine, (s)-isomer

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 CID23983765
CHEMBL ID468880
SCHEMBL ID20553681
MeSH IDM0308458

Synonyms (19)

Synonym
PDSP1_001366
(s)-1-(4-bromo-2,5-dimethoxyphenyl)propan-2-amine
bdbm50274042
CHEMBL468880 ,
NCGC00247715-01
NXQ58PZ30E ,
brolamfetamine, (s)-
dob, (s)-
benzeneethanamine, 4-bromo-2,5-dimethoxy-.alpha.-methyl-, (s)-
43061-16-1
benzeneethanamine, 4-bromo-2,5-dimethoxy-.alpha.-methyl-, (.alpha.s)-
benzeneethanamine, 4-bromo-2,5-dimethoxy-alpha-methyl-, (alphas)-
unii-nxq58pz30e
benzeneethanamine, 4-bromo-2,5-dimethoxy-alpha-methyl-, (s)-
DTXSID30109994
s-(+)-2,5-dimethoxy-4-bromoamphetamine
SCHEMBL20553681
Q27285094
(s)-brolamfetamine
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (17)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
5-hydroxytryptamine receptor 2CRattus norvegicus (Norway rat)Ki0.10430.00020.667710.0000AID4762; AID5220; AID5221; AID5263; AID5270
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)Ki0.10930.00010.601710.0000AID5220; AID5221; AID5263; AID5270
5-hydroxytryptamine receptor 1ARattus norvegicus (Norway rat)Ki5.00000.00010.739610.0000AID3695
5-hydroxytryptamine receptor 2AHomo sapiens (human)Ki0.00190.00000.385510.0000AID389734
5-hydroxytryptamine receptor 1BRattus norvegicus (Norway rat)Ki5.00000.00031.29679.2440AID3695
5-hydroxytryptamine receptor 1DRattus norvegicus (Norway rat)Ki5.00000.00101.67479.2000AID3695
5-hydroxytryptamine receptor 1FRattus norvegicus (Norway rat)Ki5.00000.00101.67479.2000AID3695
5-hydroxytryptamine receptor 2BRattus norvegicus (Norway rat)Ki0.10930.00020.590910.0000AID5220; AID5221; AID5263; 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)Kd0.11750.00042.58328.5114AID6405
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)Kd0.11750.00012.62198.5114AID6405
5-hydroxytryptamine receptor 1ARattus norvegicus (Norway rat)Kd0.11750.00012.29338.5114AID6405
5-hydroxytryptamine receptor 1BRattus norvegicus (Norway rat)Kd0.11750.02342.74218.5114AID6405
5-hydroxytryptamine receptor 1DRattus norvegicus (Norway rat)Kd0.11750.02342.74218.5114AID6405
5-hydroxytryptamine receptor 1FRattus norvegicus (Norway rat)Kd0.11750.02342.74218.5114AID6405
5-hydroxytryptamine receptor 2BRattus norvegicus (Norway rat)Kd0.11750.00042.47358.5114AID6405
5-hydroxytryptamine receptor 6Rattus norvegicus (Norway rat)Kd0.11750.02342.74218.5114AID6405
5-hydroxytryptamine receptor 7 Rattus norvegicus (Norway rat)Kd0.11750.00012.70068.5114AID6405
5-hydroxytryptamine receptor 5ARattus norvegicus (Norway rat)Kd0.11750.02342.74218.5114AID6405
5-hydroxytryptamine receptor 5BRattus norvegicus (Norway rat)Kd0.11750.02342.74218.5114AID6405
5-hydroxytryptamine receptor 3ARattus norvegicus (Norway rat)Kd0.11750.00082.62148.5114AID6405
5-hydroxytryptamine receptor 4 Rattus norvegicus (Norway rat)Kd0.11750.02342.74218.5114AID6405
Trace amine-associated receptor 1Macaca mulatta (Rhesus monkey)EC50 (µMol)2.14001.01002.57755.3000AID635287
Trace amine-associated receptor 1Homo sapiens (human)EC50 (µMol)15.34000.01501.41437.1900AID635286
5-hydroxytryptamine receptor 3BRattus norvegicus (Norway rat)Kd0.11750.00082.62148.5114AID6405
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (41)

Processvia Protein(s)Taxonomy
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)
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 (12)

Processvia Protein(s)Taxonomy
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)
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 (13)

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

Bioassays (32)

Assay IDTitleYearJournalArticle
AID5221Affinity towards [3H]- ketanserin-labeled 5-hydroxytryptamine 2 receptor sites in rat cortical homogenates1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
N-methyl derivatives of the 5-HT2 agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane.
AID193021The number of animals responding per number of animals receiving the drug(3/3) in the stimulus-generation studies was calculated at dose 0.7 mg / kg1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
N-methyl derivatives of the 5-HT2 agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane.
AID188587Number of rats responding out of 5 treated rats at a dose of 1.5 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.
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.
AID175418Dose required to produce 50% hallucinogenic potency in rat was determined at a dose of 0.75 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.
AID180516The compound was tested for effective dose ( ED 50) against stimulus generation with rats trained to discriminate (R) (-)-DOB from saline.1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
N-methyl derivatives of the 5-HT2 agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane.
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.
AID193020The number of animals responding per number of animals receiving the drug(3/3) in the stimulus-generation studies was calculated at dose 0.2 mg / kg1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
N-methyl derivatives of the 5-HT2 agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane.
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.
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.
AID175420Dose required to produce 50% hallucinogenic potency in rat was determined at a dose of 1.5 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.
AID195995The mean responses per minute during the 2.5 min extinction session in the stimulus-generation studies was calculated at dose 0.2 mg / kg1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
N-methyl derivatives of the 5-HT2 agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane.
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.
AID190545The number of responses made on the (R)(-)-DOB appropriate level, generation studies was calculated at dose 0.2 mg / kg1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
N-methyl derivatives of the 5-HT2 agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane.
AID193023The number of animals responding per number of animals receiving the drug(3/4) in the stimulus-generation studies was calculated at dose 0.4 mg / kg1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
N-methyl derivatives of the 5-HT2 agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane.
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.
AID195998The mean responses per minute during the 2.5 min extinction session in the stimulus-generation studies was calculated at dose 0.4 mg / kg1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
N-methyl derivatives of the 5-HT2 agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane.
AID190548The number of responses made on the (R)(-)-DOB appropriate level, generation studies was calculated at dose 0.7 mg / kg1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
N-methyl derivatives of the 5-HT2 agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane.
AID196002The mean responses per minute during the 2.5 min extinction session in the stimulus-generation studies was calculated at dose 1.1 mg / kg1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
N-methyl derivatives of the 5-HT2 agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane.
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.
AID5220Affinity towards [3H]- DOB -labeled 5-hydroxytryptamine 2 receptor sites in rat cortical homogenates1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
N-methyl derivatives of the 5-HT2 agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane.
AID190549The number of responses made on the (R)(-)-DOB appropriate level, generation studies was calculated at dose 1.1 mg / kg1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
N-methyl derivatives of the 5-HT2 agonist 1-(4-bromo-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.
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.
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.
AID190547The number of responses made on the (R)(-)-DOB appropriate level, generation studies was calculated at dose 0.4 mg / kg1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
N-methyl derivatives of the 5-HT2 agonist 1-(4-bromo-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.
AID196000The mean responses per minute during the 2.5 min extinction session in the stimulus-generation studies was calculated at dose 0.7 mg / kg1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
N-methyl derivatives of the 5-HT2 agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane.
AID195764The number of animals responding per number of animals receiving the drug(4/4) in the stimulus-generation studies was calculated at dose 1.1 mg / kg1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
N-methyl derivatives of the 5-HT2 agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane.
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.
AID188585Number of rats responding out of 5 treated rats at a dose of 0.75 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.
AID389734Displacement of [3H]ketanserin from 5HT2A receptor expressed in NIH3T3 cells2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Potential modes of interaction of 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives with the 5-HT2A receptor: a ligand structure-affinity relationship, receptor mutagenesis and receptor modeling investigation.
[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-19903 (50.00)18.7374
1990's1 (16.67)18.2507
2000's1 (16.67)29.6817
2010's1 (16.67)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: 12.44

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 Index12.44 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.39 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.44)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (16.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (83.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]