Page last updated: 2024-12-06

2,5-dimethoxy-4-bromoamphetamine

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-bromoamphetamine: RN given refers to (alpha)-isomer; a serotonin agonist that interferes with Meth A tumor growth in mice by selective vasoconstrictive action [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID62065
CHEMBL ID6607
SCHEMBL ID714339
MeSH IDM0045079

Synonyms (61)

Synonym
[3h](+)dob
gtpl155
gtpl163
4-bromo-2,5-dimethoxyamphetamine
brolamfetamine
(+-)2,5-dimethoxy-4-bromoamphetamine
benzeneethanamine,4-bromo-2,5-dimethoxy-.alpha.-methyl-(.+/-.)-
PDSP2_001339
DOB ,
DB01484
PDSP1_001355
2,5-dimethoxy-4-bromoamphetamine
4-bromo-dma
4-bromo-2,5-dimethoxyphenylisopropylamine
dea no. 7391
benzeneethanamine, 4-bromo-2,5-dimethoxy-alpha-methyl-
NCGC00168267-01
L000010
j275.083j ,
bromo-dma
CHEMBL6607 ,
2-(4-bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine((r)-(-)-dob)
(+/-)2-(4-bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine
2-(4-bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine[r(-)dob]
(-)2-(4-bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine
2-(4-bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine((s)-(+)-dob)
bdbm50005257
1-(4-bromo-2,5-dimethoxyphenyl)propan-2-amine
(-)-2-(4-bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine
2-(4-bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine((-)-dob)
2-(4-bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine
2-(4-bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine(dob)
(+)2-(4-bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine
racemic dob
(+)-2-(4-bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine
NCGC00168267-02
32156-26-6
(+-)-4-bromo-2,5-dimethoxy-alpha-methylphenethylamine
brolanfetamina [spanish]
benzeneethanamine, 4-bromo-2,5-dimethoxy-alpha-methyl-, (+-)-
brolamfetaminum
(+-)-1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane
64638-07-9
brolamfetaminum [latin]
dl-2,5-dimethoxy-4-bromoamphetamine
unii-67wjc4y2qy
brolanfetamina
(+-)-2,5-dimethoxy-4-bromoamphetamine
67wjc4y2qy ,
brolamfetamine [inn]
4-bromo-2,5-dimethoxy-amphetamine
brolamfetamine [mart.]
benzeneethanamine, 4-bromo-2,5-dimethoxy-.alpha.-methyl-
(+/-)-4-bromo-2,5-dimethoxy-.alpha.-methylphenethylamine
brolamfetamine [incb green list]
SCHEMBL714339
DTXSID5050428
2,5-dimethoxy-4-bromamphetamin
FXMWUTGUCAKGQL-UHFFFAOYSA-N
(rs)-brolamfetamine
Q209241

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" A description of dosage forms has been included and variations in drug concentration is discussed."( 4-bromo-2,5-dimethoxyamphetamine: psychoactivity, toxic effects and analytical methods.
Delliou, D,
)
0.13
" The dose-response relationship indicated that percent drug lever responding was dose-dependent."( Discriminative stimulus properties of 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane [(+/-)DOI] in C57BL/6J mice.
Barrett, RJ; Sanders-Bush, E; Smith, RL, 2003
)
0.32
"5, 1, 2, 4, 8, 16, and 32 h after dosing (three animals per time point)."( Distribution profile of 2,5-dimethoxy-4-bromoamphetamine (DOB) in rats after oral and subcutaneous doses.
Balíková, M; Beránková, K; Szkutová, M, 2007
)
0.65
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (16)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
5-hydroxytryptamine receptor 2CRattus norvegicus (Norway rat)Ki0.03700.00020.667710.0000AID4762; AID5220; AID5221; AID5263; AID5270; AID5721; AID5725; AID5738; AID5740
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)Ki0.02250.00010.601710.0000AID1442357; AID1442358; AID1442359; AID1442363; AID238590; AID385347; AID408069; AID5220; AID5221; AID5263; AID5270; AID5518; AID5520; AID5531; AID5533; AID5535; AID5577
5-hydroxytryptamine receptor 1ARattus norvegicus (Norway rat)Ki3.34000.00010.739610.0000AID3695
5-hydroxytryptamine receptor 2AHomo sapiens (human)Ki0.02750.00000.385510.0000AID1442359; AID389734; AID5395
5-hydroxytryptamine receptor 1BRattus norvegicus (Norway rat)Ki3.34000.00031.29679.2440AID3695
5-hydroxytryptamine receptor 1DRattus norvegicus (Norway rat)Ki3.34000.00101.67479.2000AID3695
5-hydroxytryptamine receptor 1FRattus norvegicus (Norway rat)Ki3.34000.00101.67479.2000AID3695
5-hydroxytryptamine receptor 2BRattus norvegicus (Norway rat)Ki0.03090.00020.590910.0000AID5220; AID5221; AID5263; AID5270
Sigma non-opioid intracellular receptor 1Cavia porcellus (domestic guinea pig)Ki0.03200.00000.338510.0000AID1442363
[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)Kd0.04470.00042.58328.5114AID6405; AID6406
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)EC50 (µMol)0.05650.00010.49294.0000AID246226; AID408070; AID5459; AID5466
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)Kd0.04470.00012.62198.5114AID6405; AID6406
5-hydroxytryptamine receptor 1ARattus norvegicus (Norway rat)Kd0.04470.00012.29338.5114AID6405; AID6406
5-hydroxytryptamine receptor 1BRattus norvegicus (Norway rat)Kd0.04470.02342.74218.5114AID6405; AID6406
5-hydroxytryptamine receptor 1DRattus norvegicus (Norway rat)Kd0.04470.02342.74218.5114AID6405; AID6406
5-hydroxytryptamine receptor 1FRattus norvegicus (Norway rat)Kd0.04470.02342.74218.5114AID6405; AID6406
5-hydroxytryptamine receptor 2BRattus norvegicus (Norway rat)Kd0.04470.00042.47358.5114AID6405; AID6406
5-hydroxytryptamine receptor 6Rattus norvegicus (Norway rat)Kd0.04470.02342.74218.5114AID6405; AID6406
5-hydroxytryptamine receptor 7 Rattus norvegicus (Norway rat)Kd0.04470.00012.70068.5114AID6405; AID6406
5-hydroxytryptamine receptor 5ARattus norvegicus (Norway rat)Kd0.04470.02342.74218.5114AID6405; AID6406
5-hydroxytryptamine receptor 5BRattus norvegicus (Norway rat)Kd0.04470.02342.74218.5114AID6405; AID6406
5-hydroxytryptamine receptor 3ARattus norvegicus (Norway rat)Kd0.04470.00082.62148.5114AID6405; AID6406
5-hydroxytryptamine receptor 4 Rattus norvegicus (Norway rat)Kd0.04470.02342.74218.5114AID6405; AID6406
5-hydroxytryptamine receptor 3BRattus norvegicus (Norway rat)Kd0.04470.00082.62148.5114AID6405; AID6406
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (40)

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)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

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)
[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)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (98)

Assay IDTitleYearJournalArticle
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.
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.
AID1442358Displacement of [3H]DOB from 5HT2A in Sprague-Dawley rat cortex membranes measured after 15 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.
AID90250Human hallucinogenic activity relative to mescaline1981Journal of medicinal chemistry, Dec, Volume: 24, Issue:12
Photoelectron spectra of psychotropic drugs. 6. Relationships between the physical properties and pharmacological actions of amphetamine analogues.
AID178034Effective dose for behavioral activity or hallucinogenic potential in drug discrimination studies in LSD(d-lysergic acid N,N-diethylamide) trained rats1996Journal of medicinal chemistry, Jul-19, Volume: 39, Issue:15
Dihydrobenzofuran analogues of hallucinogens. 3. Models of 4-substituted (2,5-dimethoxyphenyl)alkylamine derivatives with rigidified methoxy groups.
AID408073Hallucinogenic activity in D-lysergic acid N,N-diethylamide-trained Sprague-Dawley rat assessed as disrupted behavior at 0.50 mg/kg, ip after 30 mins by two-lever drug discrimination assay2008Bioorganic & medicinal chemistry, Jun-01, Volume: 16, Issue:11
'Hybrid' benzofuran-benzopyran congeners as rigid analogs of hallucinogenic phenethylamines.
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.
AID1131956Hallucinogenic activity in human1977Journal of medicinal chemistry, Dec, Volume: 20, Issue:12
Structure-activity studies on hallucinogenic amphetamines using molecular connectivity.
AID408078Hallucinogenic activity in D-lysergic acid N,N-diethylamide-trained Sprague-Dawley rat assessed as selection of drug-appropriate lever at 0.25 mg/kg, ip after 30 mins by two-lever drug discrimination assay2008Bioorganic & medicinal chemistry, Jun-01, Volume: 16, Issue:11
'Hybrid' benzofuran-benzopyran congeners as rigid analogs of hallucinogenic phenethylamines.
AID3863Tested in vitro for its ability to bind to 5-hydroxytryptamine 1A receptor using [3H]8-OH-DPAT as radioligand2003Journal of medicinal chemistry, Jul-31, Volume: 46, Issue:16
Synthesis and pharmacological characterization of a series of geometrically constrained 5-HT(2A/2C) receptor ligands.
AID408085Hallucinogenic potency in ip dosed D-lysergic acid N,N-diethylamide-trained Sprague-Dawley rat after 30 mins2008Bioorganic & medicinal chemistry, Jun-01, Volume: 16, Issue:11
'Hybrid' benzofuran-benzopyran congeners as rigid analogs of hallucinogenic phenethylamines.
AID5721Binding affinity at cloned rat 5-hydroxytryptamine 2C receptor using [3H]DOI as radioligand2001Journal of medicinal chemistry, Mar-15, Volume: 44, Issue:6
Enantiospecific synthesis and pharmacological evaluation of a series of super-potent, conformationally restricted 5-HT(2A/2C) receptor agonists.
AID5740The compound evaluated for its affinity against 5-hydroxytryptamine 2C receptor1994Journal of medicinal chemistry, Jun-24, Volume: 37, Issue:13
Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines.
AID19561Hill coefficient as determined.1991Journal of medicinal chemistry, Jan, Volume: 34, Issue:1
2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines.
AID4021Binding affinity towards rat hippocampal 5-hydroxytryptamine 1A receptor using [3H]8-OH-DPAT as radioligand1996Journal of medicinal chemistry, Jul-19, Volume: 39, Issue:15
Dihydrobenzofuran analogues of hallucinogens. 3. Models of 4-substituted (2,5-dimethoxyphenyl)alkylamine derivatives with rigidified methoxy groups.
AID241440Inhibitory concentration against monoamine oxidase A in rat brain mitochondrial suspension2005Journal of medicinal chemistry, Apr-07, Volume: 48, Issue:7
Sulfur-substituted alpha-alkyl phenethylamines as selective and reversible MAO-A inhibitors: biological activities, CoMFA analysis, and active site modeling.
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.
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.
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.
AID408080Hallucinogenic activity in D-lysergic acid N,N-diethylamide-trained Sprague-Dawley rat assessed as selection of drug-appropriate lever at 0.50 mg/kg, ip after 30 mins by two-lever drug discrimination assay2008Bioorganic & medicinal chemistry, Jun-01, Volume: 16, Issue:11
'Hybrid' benzofuran-benzopyran congeners as rigid analogs of hallucinogenic phenethylamines.
AID188582Number of rats responding out of 5 treated rats at a dose of 0.20 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.
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.
AID190259The percentage of rats selecting the drug lever at each dose1994Journal of medicinal chemistry, Dec-09, Volume: 37, Issue:25
1-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)-2-aminopropane: a potent serotonin 5-HT2A/2C agonist.
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.
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.
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.
AID246226Serotonin 5-HT2A receptor-mediated intracellular calcium [Ca2+] mobilization in rat A7r5 cells2004Journal of medicinal chemistry, Nov-18, Volume: 47, Issue:24
Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane.
AID408069Displacement of [3H]ketanserin from rat 5HT2A receptor expressed in mouse NIH3T3 cells2008Bioorganic & medicinal chemistry, Jun-01, Volume: 16, Issue:11
'Hybrid' benzofuran-benzopyran congeners as rigid analogs of hallucinogenic phenethylamines.
AID5395The compound evaluated for its affinity against 5-hydroxytryptamine 2A receptor1994Journal of medicinal chemistry, Jun-24, Volume: 37, Issue:13
Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines.
AID251173Efficacy as 5-HT2A receptor-mediated intracellular calcium [Ca2+] mobilization in rat A7r5 cells2004Journal of medicinal chemistry, Nov-18, Volume: 47, Issue:24
Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-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.
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.
AID6406Affinity against 5-hydroxytryptamine receptors in rat fundus model1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Serotonin receptor affinities of psychoactive phenalkylamine analogues.
AID408068Hallucinogenic activity in D-lysergic acid N,N-diethylamide-trained Sprague-Dawley rat assessed as disrupted behavior at 0.25 mg/kg, ip after 30 mins by two-lever drug discrimination assay2008Bioorganic & medicinal chemistry, Jun-01, Volume: 16, Issue:11
'Hybrid' benzofuran-benzopyran congeners as rigid analogs of hallucinogenic phenethylamines.
AID23503Partition coefficient (logP)1981Journal of medicinal chemistry, Dec, Volume: 24, Issue:12
Photoelectron spectra of psychotropic drugs. 6. Relationships between the physical properties and pharmacological actions of amphetamine analogues.
AID178730Effective dose in rat1994Journal of medicinal chemistry, Dec-09, Volume: 37, Issue:25
1-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)-2-aminopropane: a potent serotonin 5-HT2A/2C agonist.
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.
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.
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.
AID408071Intrinsic activity at rat 5HT2A receptor expressed in mouse NIH3T3 cells assessed as stimulation of inositol phosphate accumulation relative to serotonin2008Bioorganic & medicinal chemistry, Jun-01, Volume: 16, Issue:11
'Hybrid' benzofuran-benzopyran congeners as rigid analogs of hallucinogenic phenethylamines.
AID5738In vitro binding to 5-hydroxytryptamine 2C receptor using [125 I]-DOI2003Journal of medicinal chemistry, Jul-31, Volume: 46, Issue:16
Synthesis and pharmacological characterization of a series of geometrically constrained 5-HT(2A/2C) receptor ligands.
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.
AID5577In vitro binding to 5-hydroxytryptamine 2A receptor using [125 I]-DOI2003Journal of medicinal chemistry, Jul-31, Volume: 46, Issue:16
Synthesis and pharmacological characterization of a series of geometrically constrained 5-HT(2A/2C) receptor ligands.
AID5531Binding affinity towards 5-hydroxytryptamine 2A receptor sites by using [3H]ketanserin as radioligand2003Bioorganic & medicinal chemistry letters, Aug-04, Volume: 13, Issue:15
Ring substituted analogues of 5-aminomethyl-10,11-dihydro-dibenzo[a,d]cycloheptene (AMDH): potential modes of binding to the 5-HT(2A) receptor.
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.
AID238590Binding affinity for 5-HT2A serotonin receptor2004Journal of medicinal chemistry, Nov-18, Volume: 47, Issue:24
Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane.
AID1442357Displacement of [3H]ketanserin from 5HT2A in Sprague-Dawley rat cortex membranes measured after 15 mins2017Journal 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.
AID408072Hallucinogenic activity in D-lysergic acid N,N-diethylamide-trained Sprague-Dawley rat assessed as disrupted behavior at 0.38 mg/kg, ip after 30 mins by two-lever drug discrimination assay2008Bioorganic & medicinal chemistry, Jun-01, Volume: 16, Issue:11
'Hybrid' benzofuran-benzopyran congeners as rigid analogs of hallucinogenic phenethylamines.
AID178352Compound was tested for effective dose in DOI trained rats2003Journal of medicinal chemistry, Jul-31, Volume: 46, Issue:16
Synthesis and pharmacological characterization of a series of geometrically constrained 5-HT(2A/2C) receptor ligands.
AID5797Affinity against 5-hydroxytryptamine 2B receptor in the isolated rat stomach fundus1981Journal of medicinal chemistry, Dec, Volume: 24, Issue:12
Photoelectron spectra of psychotropic drugs. 6. Relationships between the physical properties and pharmacological actions of amphetamine analogues.
AID185557Maximum 5-HT stimulation was determined in cloned rats2003Journal of medicinal chemistry, Jul-31, Volume: 46, Issue:16
Synthesis and pharmacological characterization of a series of geometrically constrained 5-HT(2A/2C) receptor ligands.
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.
AID167866Hyperthermic potency in rabbit relative to DOM1981Journal of medicinal chemistry, Dec, Volume: 24, Issue:12
Photoelectron spectra of psychotropic drugs. 6. Relationships between the physical properties and pharmacological actions of amphetamine 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.
AID5257Compound was evaluated for its ability to displace 0.25 nM [125I](R)-DOI from binding sites in rat frontal cortex.1991Journal of medicinal chemistry, Jan, Volume: 34, Issue:1
2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines.
AID5459Ability to stimulate phosphoinositide hydrolysis in NIH3T3 cells expressing the 5-hydroxytryptamine 2A receptor2001Journal of medicinal chemistry, Mar-15, Volume: 44, Issue:6
Enantiospecific synthesis and pharmacological evaluation of a series of super-potent, conformationally restricted 5-HT(2A/2C) receptor agonists.
AID3696Binding affinity for 5-hydroxytryptamine 1 receptor of rat prefrontal cortex1986Journal of medicinal chemistry, Feb, Volume: 29, Issue:2
5-HT1 and 5-HT2 binding characteristics of 1-(2,5-dimethoxy-4-bromophenyl)-2-aminopropane analogues.
AID175414Dose required to produce 50% hallucinogenic potency in rat was determined at a dose of 0.2 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.
AID408070Agonist activity at rat 5HT2A receptor expressed in mouse NIH3T3 cells assessed as stimulation of inositol phosphate accumulation2008Bioorganic & medicinal chemistry, Jun-01, Volume: 16, Issue:11
'Hybrid' benzofuran-benzopyran congeners as rigid analogs of hallucinogenic phenethylamines.
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.
AID5299Displacement of [3H]ketanserin from rat prefrontal cortex 5-hydroxytryptamine 2 receptor1986Journal of medicinal chemistry, Feb, Volume: 29, Issue:2
5-HT1 and 5-HT2 binding characteristics of 1-(2,5-dimethoxy-4-bromophenyl)-2-aminopropane analogues.
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.
AID5533Binding affinity towards rat cortical 5-hydroxytryptamine 2A receptor using [3H]ketanserin as radioligand1996Journal of medicinal chemistry, Jul-19, Volume: 39, Issue:15
Dihydrobenzofuran analogues of hallucinogens. 3. Models of 4-substituted (2,5-dimethoxyphenyl)alkylamine derivatives with rigidified methoxy groups.
AID178353Compound was tested for effective dose in LSD trained rats2003Journal of medicinal chemistry, Jul-31, Volume: 46, Issue:16
Synthesis and pharmacological characterization of a series of geometrically constrained 5-HT(2A/2C) receptor ligands.
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.
AID5599Percent maximal 5-HT stimulation at cloned rat 5-hydroxytryptamine 2A receptor (phosphoinositide hydrolysis study) at a conc of 100 uM2001Journal of medicinal chemistry, Mar-15, Volume: 44, Issue:6
Enantiospecific synthesis and pharmacological evaluation of a series of super-potent, conformationally restricted 5-HT(2A/2C) receptor agonists.
AID1442359Displacement of [125I]DOI from recombinant human 5HT2A expressed in Syrian hamster AV12 cell membranes2017Journal 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.
AID408079Hallucinogenic activity in D-lysergic acid N,N-diethylamide-trained Sprague-Dawley rat assessed as selection of drug-appropriate lever at 0.38 mg/kg, ip after 30 mins by two-lever drug discrimination assay2008Bioorganic & medicinal chemistry, Jun-01, Volume: 16, Issue:11
'Hybrid' benzofuran-benzopyran congeners as rigid analogs of hallucinogenic phenethylamines.
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.
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.
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.
AID5520Binding affinity at cloned rat 5-hydroxytryptamine 2A receptor using [3H]DOB as radioligand2001Journal of medicinal chemistry, Mar-15, Volume: 44, Issue:6
Enantiospecific synthesis and pharmacological evaluation of a series of super-potent, conformationally restricted 5-HT(2A/2C) receptor agonists.
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.
AID176367Concentration required to produce DOM like response when administered in rats1986Journal of medicinal chemistry, Feb, Volume: 29, Issue:2
5-HT1 and 5-HT2 binding characteristics of 1-(2,5-dimethoxy-4-bromophenyl)-2-aminopropane analogues.
AID5466Tested for its ability to activate phospholipase C by quantification of IP3 at cloned rat 5-hydroxytryptamine 2A receptor2003Journal of medicinal chemistry, Jul-31, Volume: 46, Issue:16
Synthesis and pharmacological characterization of a series of geometrically constrained 5-HT(2A/2C) receptor ligands.
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.
AID1346893Human 5-HT2C receptor (5-Hydroxytryptamine receptors)2000Synapse (New York, N.Y.), Feb, Volume: 35, Issue:2
Agonist high and low affinity state ratios predict drug intrinsic activity and a revised ternary complex mechanism at serotonin 5-HT(2A) and 5-HT(2C) receptors.
AID624219Agonists at Human 5-Hydroxytryptamine receptor 5-HT2B1999Naunyn-Schmiedeberg's archives of pharmacology, Jan, Volume: 359, Issue:1
Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, -HT(2B) and 5-HT2C receptors.
AID1259419Human 5-HT2A receptor (5-Hydroxytryptamine receptors)1999Naunyn-Schmiedeberg's archives of pharmacology, Jan, Volume: 359, Issue:1
Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, -HT(2B) and 5-HT2C receptors.
AID624234Agonists at Rat 5-Hydroxytryptamine receptor 5-HT2A1998The Journal of pharmacology and experimental therapeutics, Jul, Volume: 286, Issue:1
Creation of a constitutively activated state of the 5-hydroxytryptamine2A receptor by site-directed mutagenesis: inverse agonist activity of antipsychotic drugs.
AID624214Agonists at Rat 5-Hydroxytryptamine receptor 5-HT2C1997Journal of neurochemistry, Sep, Volume: 69, Issue:3
Activating mutations of the serotonin 5-HT2C receptor.
AID624219Agonists at Human 5-Hydroxytryptamine receptor 5-HT2B2004Naunyn-Schmiedeberg's archives of pharmacology, Aug, Volume: 370, Issue:2
Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors.
AID1346868Rat 5-HT2C receptor (5-Hydroxytryptamine receptors)1997Journal of neurochemistry, Sep, Volume: 69, Issue:3
Activating mutations of the serotonin 5-HT2C receptor.
AID1346867Human 5-HT2B receptor (5-Hydroxytryptamine receptors)1999Naunyn-Schmiedeberg's archives of pharmacology, Jan, Volume: 359, Issue:1
Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, -HT(2B) and 5-HT2C receptors.
AID624216Agonists at Human 5-Hydroxytryptamine receptor 5-HT2C2000Synapse (New York, N.Y.), Feb, Volume: 35, Issue:2
Agonist high and low affinity state ratios predict drug intrinsic activity and a revised ternary complex mechanism at serotonin 5-HT(2A) and 5-HT(2C) receptors.
AID624216Agonists at Human 5-Hydroxytryptamine receptor 5-HT2C1999Naunyn-Schmiedeberg's archives of pharmacology, Jan, Volume: 359, Issue:1
Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, -HT(2B) and 5-HT2C receptors.
AID624235Agonists at Human 5-Hydroxytryptamine receptor 5-HT2A1999Naunyn-Schmiedeberg's archives of pharmacology, Jan, Volume: 359, Issue:1
Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, -HT(2B) and 5-HT2C receptors.
AID1259419Human 5-HT2A receptor (5-Hydroxytryptamine receptors)2004Naunyn-Schmiedeberg's archives of pharmacology, Aug, Volume: 370, Issue:2
Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors.
AID1346867Human 5-HT2B receptor (5-Hydroxytryptamine receptors)2004Naunyn-Schmiedeberg's archives of pharmacology, Aug, Volume: 370, Issue:2
Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors.
AID624216Agonists at Human 5-Hydroxytryptamine receptor 5-HT2C2004Naunyn-Schmiedeberg's archives of pharmacology, Aug, Volume: 370, Issue:2
Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors.
AID1346893Human 5-HT2C receptor (5-Hydroxytryptamine receptors)2004Naunyn-Schmiedeberg's archives of pharmacology, Aug, Volume: 370, Issue:2
Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors.
AID1346893Human 5-HT2C receptor (5-Hydroxytryptamine receptors)1999Naunyn-Schmiedeberg's archives of pharmacology, Jan, Volume: 359, Issue:1
Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, -HT(2B) and 5-HT2C receptors.
AID624235Agonists at Human 5-Hydroxytryptamine receptor 5-HT2A2004Naunyn-Schmiedeberg's archives of pharmacology, Aug, Volume: 370, Issue:2
Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors.
AID1346919Rat 5-HT2A receptor (5-Hydroxytryptamine receptors)1998The Journal of pharmacology and experimental therapeutics, Jul, Volume: 286, Issue:1
Creation of a constitutively activated state of the 5-hydroxytryptamine2A receptor by site-directed mutagenesis: inverse agonist activity of antipsychotic drugs.
AID624235Agonists at Human 5-Hydroxytryptamine receptor 5-HT2A2001Molecular pharmacology, Oct, Volume: 60, Issue:4
Multiple conformations of native and recombinant human 5-hydroxytryptamine(2a) receptors are labeled by agonists and discriminated by antagonists.
AID1259419Human 5-HT2A receptor (5-Hydroxytryptamine receptors)1996Biochemical pharmacology, Jan-12, Volume: 51, Issue:1
Radiolabelling of the human 5-HT2A receptor with an agonist, a partial agonist and an antagonist: effects on apparent agonist affinities.
AID1259419Human 5-HT2A receptor (5-Hydroxytryptamine receptors)2001Molecular pharmacology, Oct, Volume: 60, Issue:4
Multiple conformations of native and recombinant human 5-hydroxytryptamine(2a) receptors are labeled by agonists and discriminated by antagonists.
AID624235Agonists at Human 5-Hydroxytryptamine receptor 5-HT2A1996Biochemical pharmacology, Jan-12, Volume: 51, Issue:1
Radiolabelling of the human 5-HT2A receptor with an agonist, a partial agonist and an antagonist: effects on apparent agonist affinities.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (98)

TimeframeStudies, This Drug (%)All Drugs %
pre-199035 (35.71)18.7374
1990's30 (30.61)18.2507
2000's28 (28.57)29.6817
2010's5 (5.10)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: 21.18

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 Index21.18 (24.57)
Research Supply Index4.67 (2.92)
Research Growth Index4.21 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.18)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (2.83%)6.00%
Case Studies5 (4.72%)4.05%
Observational0 (0.00%)0.25%
Other98 (92.45%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]