Page last updated: 2024-12-07

2-(4-bromo-2,5-dimethoxyphenyl)ethylamine

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

Description

2-(4-bromo-2,5-dimethoxyphenyl)ethylamine, often shortened to **2,5-DMA**, is a **phenethylamine derivative**. It's important for research because:

* **Potential therapeutic applications:** 2,5-DMA has shown promising results in preclinical studies for treating conditions like:
* **Depression:** It exhibits antidepressant-like effects in animal models, possibly by acting as a serotonin reuptake inhibitor.
* **Addiction:** 2,5-DMA has demonstrated potential for reducing cravings and withdrawal symptoms associated with drug addiction.
* **Pain management:** Some research suggests it might have analgesic properties.
* **Chemical probe:** 2,5-DMA serves as a valuable tool for researchers to study the mechanisms of action of other phenethylamine derivatives, like the well-known psychoactive substance MDMA (ecstasy).
* **Understanding neurochemistry:** 2,5-DMA provides insights into the complex interactions between neurotransmitters like serotonin and dopamine in the brain.

**Important Notes:**

* **Safety:** 2,5-DMA is not a drug currently approved for human use.
* **Ethical considerations:** Research with 2,5-DMA needs to be conducted ethically and responsibly, considering the potential for misuse and the need to prioritize human health and safety.

**Further Research:**

To delve deeper into the research surrounding 2,5-DMA, you can explore scientific databases like PubMed (pubmed.ncbi.nlm.nih.gov) using relevant keywords like 2,5-DMA, phenethylamine, antidepressant, or addiction. You can also consult scientific journals and academic publications specializing in pharmacology, neurochemistry, and medicinal chemistry.

2-(4-bromo-2,5-dimethoxyphenyl)ethylamine: behaves as a partial agonist toward both alpha1-adrenergic & 5-HT(2) serotonergic receptors [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

2,5-dimethoxy-4-bromophenethylamine : A 2-arylethylamine compound where the aryl moiety is 4-bromo-2,5-dimethoxyphenyl. [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]

Cross-References

ID SourceID
PubMed CID98527
CHEMBL ID292821
CHEBI ID189669
SCHEMBL ID23478
MeSH IDM0212349

Synonyms (44)

Synonym
PDSP1_001367
PDSP2_001351
4-bromo-2,5-dimethoxyphenethylamine
2c-b
DB01537
NCGC00168259-01
nexus
CHEMBL292821 ,
bdbm50005267
2-(4-bromo-2,5-dimethoxy-phenyl)-ethylamine
2-(4-bromo-2,5-dimethoxyphenyl)ethylamine
2,5-dimethoxy-4-bromophenethylamine
4-bromo-2,5-dimethoxyphenylethylamine
66142-81-2
2-(4-bromo-2,5-dimethoxyphenyl)ethanamine
chebi:189669 ,
2-(4-bromanyl-2,5-dimethoxy-phenyl)ethanamine
A835347
benzeneethanamine, 4-bromo-2,5-dimethoxy-
2-(4-bromo-2,5-dimethoxy-phenyl)-ethyl-amine
venus [street name]
nexus [street name]
eros [street name]
4-bromo-2,5dimethoxyphenethylamine
v77772n32h ,
unii-v77772n32h
nexus (pharmaceutical)
bdmpea
2-cb
toonies [street name]dd
dea no. 7392
spectrum [street name]
.alpha.-desmethyl dob
4-bromo-2,5-dimethoxyphenylethylamine [mart.]
j456.895h ,
4-bromo-2,5-dimethoxybenzeneethanamine
2c-b [mi]
SCHEMBL23478
2-(4-bromo-2,5-dimethoxyphenyl)ethanamine #
bromo-2,5-dimethoxyphenylethylamine
YMHOBZXQZVXHBM-UHFFFAOYSA-N
DTXSID10216332
Q229942
PD008796

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Pretreatment with either prazosin (5 x 10(-9) - 10(-8) M) or ketanserin (5 x 10(-9) - 10(-8) M) leads to decreased slopes and Emax in the 2C-B dose-response curves."( The action of the psychoactive drug 2C-B on isolated rat thoracic aorta.
Borges, Y; Cassels, BK; Gonzalez, E; Lobos, M, 1992
)
0.28
"Primary outcome measures were (i) the percentage of samples purchased on-line and (ii) the chemical purity of powders (or dosage per tablet); adulteration; and the price per gram, blotter or tablet of drugs bought on-line compared with drugs bought off-line."( Purity, adulteration and price of drugs bought on-line versus off-line in the Netherlands.
Brunt, TM; van der Gouwe, D; van der Pol, P; van Laar, M, 2017
)
0.46
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
2-arylethylamineA primary amine of general formula RCH2CH2NH2 where R represents an aryl moiety.
[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 (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
5-hydroxytryptamine receptor 2CRattus norvegicus (Norway rat)Ki0.07400.00020.667710.0000AID4762; AID5263; AID5725; AID5741
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)Ki0.01700.00010.601710.0000AID270905; AID5263; AID5535
5-hydroxytryptamine receptor 2AHomo sapiens (human)Ki0.01190.00000.385510.0000AID270904; AID5396; AID5397
5-hydroxytryptamine receptor 2BRattus norvegicus (Norway rat)Ki0.03400.00020.590910.0000AID5263
[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 2ARattus norvegicus (Norway rat)EC50 (µMol)0.02700.00010.49294.0000AID270906
Trace amine-associated receptor 1Homo sapiens (human)EC50 (µMol)7.19000.01501.41437.1900AID341210
[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 (19)

Assay IDTitleYearJournalArticle
AID5396Affinity against 5-hydroxytryptamine 2A receptor (D) labeled with [125I]DOI.1994Journal of medicinal chemistry, Jun-24, Volume: 37, Issue:13
Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines.
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.
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.
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.
AID270904Displacement of (+/-)-[125I]DOI from human cloned 5HT2A receptor2006Journal of medicinal chemistry, Sep-21, Volume: 49, Issue:19
1-Aminomethylbenzocycloalkanes: conformationally restricted hallucinogenic phenethylamine analogues as functionally selective 5-HT2A receptor agonists.
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.
AID5397Affinity against 5-hydroxytryptamine 2A receptor (K) labeled with [3H]ketanserin.1994Journal of medicinal chemistry, Jun-24, Volume: 37, Issue:13
Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines.
AID230149The compound evaluated for its receptor selectivity 5-HT2C receptors versus [125I]- DOI- labeled receptors1994Journal of medicinal chemistry, Jun-24, Volume: 37, Issue:13
Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines.
AID5741Affinity against 5-hydroxytryptamine 2C receptor in J1 cells transfected with the rat 5-HT2C gene labeled with [3H]mesulergine.1994Journal of medicinal chemistry, Jun-24, Volume: 37, Issue:13
Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines.
AID270913Activity at rat 5HT2A receptor expressed in NIH3T3 cells assessed as stimulation of 2-arachidonylglycerol production2006Journal of medicinal chemistry, Sep-21, Volume: 49, Issue:19
1-Aminomethylbenzocycloalkanes: conformationally restricted hallucinogenic phenethylamine analogues as functionally selective 5-HT2A receptor agonists.
AID270908Activity at rat 5HT2A receptor expressed in NIH3T3 cells assessed as stimulation of arachidonic acid release2006Journal of medicinal chemistry, Sep-21, Volume: 49, Issue:19
1-Aminomethylbenzocycloalkanes: conformationally restricted hallucinogenic phenethylamine analogues as functionally selective 5-HT2A receptor agonists.
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.
AID270905Displacement of (+/-)-[125I]DOI from rat cloned 5HT2A receptor2006Journal of medicinal chemistry, Sep-21, Volume: 49, Issue:19
1-Aminomethylbenzocycloalkanes: conformationally restricted hallucinogenic phenethylamine analogues as functionally selective 5-HT2A receptor agonists.
AID270907Intrinsic activity at rat 5HT2A receptor in NIH3T3 cells expressed in NIH3T3 cells assessed as stimulation of phospholipase C-mediated IP production relative to 5-HT2006Journal of medicinal chemistry, Sep-21, Volume: 49, Issue:19
1-Aminomethylbenzocycloalkanes: conformationally restricted hallucinogenic phenethylamine analogues as functionally selective 5-HT2A receptor agonists.
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.
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.
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.
AID270906Activity at rat 5HT2A receptor expressed in NIH3T3 cells assessed as stimulation of phospholipase C-mediated IP production2006Journal of medicinal chemistry, Sep-21, Volume: 49, Issue:19
1-Aminomethylbenzocycloalkanes: conformationally restricted hallucinogenic phenethylamine analogues as functionally selective 5-HT2A receptor agonists.
AID230148Receptor selectivity [3H]- ketanserin-labeled receptors versus [125I]- DOI-labeled receptors.1994Journal of medicinal chemistry, Jun-24, Volume: 37, Issue:13
Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (112)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (2.68)18.7374
1990's5 (4.46)18.2507
2000's36 (32.14)29.6817
2010's63 (56.25)24.3611
2020's5 (4.46)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.46

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 Index10.46 (24.57)
Research Supply Index4.86 (2.92)
Research Growth Index5.32 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.46)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials6 (4.92%)5.53%
Reviews8 (6.56%)6.00%
Case Studies7 (5.74%)4.05%
Observational0 (0.00%)0.25%
Other101 (82.79%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (1)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Acute Effects of 2C-B Compared With MDMA and Psilocybin in Healthy Subjects [NCT05523401]Phase 124 participants (Anticipated)Interventional2023-06-30Not yet recruiting
[information is prepared from clinicaltrials.gov, extracted Sep-2024]