Page last updated: 2024-11-12

2-(4-iodo-2,5-dimethoxyphenyl)-n-(2-methoxybenzyl)ethanamine

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

Description

2-(4-iodo-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethanamine: a PET radioligand and 5-HT(2A) receptor agonist; also used as a designer drug; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID10251906
CHEMBL ID482496
CHEMBL ID1908863
SCHEMBL ID17287299
MeSH IDM0552582

Synonyms (30)

Synonym
bdbm50271706
n-(2-[3h-och3]benzyl)-2-(2-[3h-och3]-5-methoxy-4-iodophenyl)ethylamine
CHEMBL482496 ,
919797-19-6
nbome-2c-i
2-(4-iodo-2,5-dimethoxyphenyl)-n-(2-(11c-och3)methoxybenzyl)ethanamine
547kgl06ip ,
2c-i-nbome
2-(4-iodo-2,5-dimethoxyphenyl)-n-((2-methoxyphenyl)methyl)ethanamine
4-iodo-2,5-dimethoxy-n-((2-methoxyphenyl)methyl)-benzeneethanamine
n-bomb compound
dea no. 7538
cimbi-5
unii-547kgl06ip
11c-cimbi-5
25i-nbome
AKOS015904372
2-(4-iodo-2,5-dimethoxyphenyl)-n-(2-methoxybenzyl)ethanamine
benzeneethanamine, 4-iodo-2,5-dimethoxy-n-((2-methoxyphenyl)methyl)-
2,5-dimethoxy-4-iodo-n-(2-methoxybenzyl)phenethylamine
CHEMBL1908863
ZFUOLNAKPBFDIJ-UHFFFAOYSA-N
SCHEMBL17287299
4-iodo-2,5-dimethoxy-n-[(2-methoxyphenyl)methyl]benzeneethanamine
DTXSID20238808
2-(4-iodo-2,5-dimethoxyphenyl)-n-[(2-methoxyphenyl)methyl]ethanamine
25-i-nbome
Q4632141
n-(2-methoxybenzyl)-2-(4-iodo-2,5-dimethoxyphenyl)ethanamine
PD047504

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" This report describes a series of 10 patients who suffered adverse effects from 25B-NBOMe."( Case series: toxicity from 25B-NBOMe--a cluster of N-bomb cases.
Barrington, S; Gee, P; Jensen, BP; Moore, G; Schep, LJ, 2016
)
0.43

Dosage Studied

ExcerptRelevanceReference
" The active dosage is very low, supposed to be less than 100 µg."( Retrospective Demonstration of 25I-NBOMe Acute Poisoning Using Hair Analysis.
Ameline, A; Farrugia, A; Kintz, P; Raul, JS, 2017
)
0.46
" In particular, little is known about the incorporation into the keratin matrix after intake and the correlation between dosage frequency of use, and hair concentrations."( Retrospective Demonstration of 25I-NBOMe Acute Poisoning Using Hair Analysis.
Ameline, A; Farrugia, A; Kintz, P; Raul, JS, 2017
)
0.46
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)Ki0.00220.00010.601710.0000AID1855114
5-hydroxytryptamine receptor 2CHomo sapiens (human)Ki0.00700.00010.954910.0000AID1855116
5-hydroxytryptamine receptor 2BHomo sapiens (human)Ki0.00230.00030.769310.0000AID1855115
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (46)

Processvia Protein(s)Taxonomy
behavioral fear response5-hydroxytryptamine receptor 2CHomo sapiens (human)
intracellular calcium ion homeostasis5-hydroxytryptamine receptor 2CHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathway5-hydroxytryptamine receptor 2CHomo sapiens (human)
phospholipase C-activating serotonin receptor signaling pathway5-hydroxytryptamine receptor 2CHomo sapiens (human)
locomotory behavior5-hydroxytryptamine receptor 2CHomo sapiens (human)
feeding behavior5-hydroxytryptamine receptor 2CHomo sapiens (human)
positive regulation of phosphatidylinositol biosynthetic process5-hydroxytryptamine receptor 2CHomo sapiens (human)
cGMP-mediated signaling5-hydroxytryptamine receptor 2CHomo sapiens (human)
regulation of nervous system process5-hydroxytryptamine receptor 2CHomo sapiens (human)
regulation of appetite5-hydroxytryptamine receptor 2CHomo sapiens (human)
regulation of corticotropin-releasing hormone secretion5-hydroxytryptamine receptor 2CHomo sapiens (human)
positive regulation of fat cell differentiation5-hydroxytryptamine receptor 2CHomo sapiens (human)
positive regulation of calcium-mediated signaling5-hydroxytryptamine receptor 2CHomo sapiens (human)
release of sequestered calcium ion into cytosol5-hydroxytryptamine receptor 2CHomo sapiens (human)
positive regulation of ERK1 and ERK2 cascade5-hydroxytryptamine receptor 2CHomo sapiens (human)
G protein-coupled serotonin receptor signaling pathway5-hydroxytryptamine receptor 2CHomo sapiens (human)
serotonin receptor signaling pathway5-hydroxytryptamine receptor 2CHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger5-hydroxytryptamine receptor 2CHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 2CHomo sapiens (human)
neural crest cell migration5-hydroxytryptamine receptor 2BHomo sapiens (human)
positive regulation of cytokine production5-hydroxytryptamine receptor 2BHomo sapiens (human)
positive regulation of endothelial cell proliferation5-hydroxytryptamine receptor 2BHomo sapiens (human)
G protein-coupled receptor internalization5-hydroxytryptamine receptor 2BHomo sapiens (human)
heart morphogenesis5-hydroxytryptamine receptor 2BHomo sapiens (human)
cardiac muscle hypertrophy5-hydroxytryptamine receptor 2BHomo sapiens (human)
intracellular calcium ion homeostasis5-hydroxytryptamine receptor 2BHomo sapiens (human)
G protein-coupled receptor signaling pathway5-hydroxytryptamine receptor 2BHomo sapiens (human)
activation of phospholipase C activity5-hydroxytryptamine receptor 2BHomo sapiens (human)
protein kinase C-activating G protein-coupled receptor signaling pathway5-hydroxytryptamine receptor 2BHomo sapiens (human)
phospholipase C-activating serotonin receptor signaling pathway5-hydroxytryptamine receptor 2BHomo sapiens (human)
positive regulation of cell population proliferation5-hydroxytryptamine receptor 2BHomo sapiens (human)
response to xenobiotic stimulus5-hydroxytryptamine receptor 2BHomo sapiens (human)
positive regulation of phosphatidylinositol biosynthetic process5-hydroxytryptamine receptor 2BHomo sapiens (human)
neural crest cell differentiation5-hydroxytryptamine receptor 2BHomo sapiens (human)
intestine smooth muscle contraction5-hydroxytryptamine receptor 2BHomo sapiens (human)
phosphorylation5-hydroxytryptamine receptor 2BHomo sapiens (human)
calcium-mediated signaling5-hydroxytryptamine receptor 2BHomo sapiens (human)
cGMP-mediated signaling5-hydroxytryptamine receptor 2BHomo sapiens (human)
vasoconstriction5-hydroxytryptamine receptor 2BHomo sapiens (human)
negative regulation of apoptotic process5-hydroxytryptamine receptor 2BHomo sapiens (human)
positive regulation of canonical NF-kappaB signal transduction5-hydroxytryptamine receptor 2BHomo sapiens (human)
positive regulation of MAP kinase activity5-hydroxytryptamine receptor 2BHomo sapiens (human)
phosphatidylinositol 3-kinase/protein kinase B signal transduction5-hydroxytryptamine receptor 2BHomo sapiens (human)
embryonic morphogenesis5-hydroxytryptamine receptor 2BHomo sapiens (human)
regulation of behavior5-hydroxytryptamine receptor 2BHomo sapiens (human)
positive regulation of nitric-oxide synthase activity5-hydroxytryptamine receptor 2BHomo sapiens (human)
release of sequestered calcium ion into cytosol5-hydroxytryptamine receptor 2BHomo sapiens (human)
positive regulation of cell division5-hydroxytryptamine receptor 2BHomo sapiens (human)
ERK1 and ERK2 cascade5-hydroxytryptamine receptor 2BHomo sapiens (human)
positive regulation of ERK1 and ERK2 cascade5-hydroxytryptamine receptor 2BHomo sapiens (human)
protein kinase C signaling5-hydroxytryptamine receptor 2BHomo sapiens (human)
cellular response to temperature stimulus5-hydroxytryptamine receptor 2BHomo sapiens (human)
G protein-coupled serotonin receptor signaling pathway5-hydroxytryptamine receptor 2BHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger5-hydroxytryptamine receptor 2BHomo sapiens (human)
serotonin receptor signaling pathway5-hydroxytryptamine receptor 2BHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 2BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
Gq/11-coupled serotonin receptor activity5-hydroxytryptamine receptor 2CHomo sapiens (human)
G protein-coupled serotonin receptor activity5-hydroxytryptamine receptor 2CHomo sapiens (human)
protein binding5-hydroxytryptamine receptor 2CHomo sapiens (human)
identical protein binding5-hydroxytryptamine receptor 2CHomo sapiens (human)
serotonin binding5-hydroxytryptamine receptor 2CHomo sapiens (human)
1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine binding5-hydroxytryptamine receptor 2CHomo sapiens (human)
neurotransmitter receptor activity5-hydroxytryptamine receptor 2CHomo sapiens (human)
Gq/11-coupled serotonin receptor activity5-hydroxytryptamine receptor 2BHomo sapiens (human)
G-protein alpha-subunit binding5-hydroxytryptamine receptor 2BHomo sapiens (human)
G protein-coupled serotonin receptor activity5-hydroxytryptamine receptor 2BHomo sapiens (human)
GTPase activator activity5-hydroxytryptamine receptor 2BHomo sapiens (human)
protein binding5-hydroxytryptamine receptor 2BHomo sapiens (human)
serotonin binding5-hydroxytryptamine receptor 2BHomo sapiens (human)
neurotransmitter receptor activity5-hydroxytryptamine receptor 2BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
plasma membrane5-hydroxytryptamine receptor 2CHomo sapiens (human)
synapse5-hydroxytryptamine receptor 2CHomo sapiens (human)
G protein-coupled serotonin receptor complex5-hydroxytryptamine receptor 2CHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 2CHomo sapiens (human)
dendrite5-hydroxytryptamine receptor 2CHomo sapiens (human)
nucleoplasm5-hydroxytryptamine receptor 2BHomo sapiens (human)
cytoplasm5-hydroxytryptamine receptor 2BHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 2BHomo sapiens (human)
synapse5-hydroxytryptamine receptor 2BHomo sapiens (human)
G protein-coupled serotonin receptor complex5-hydroxytryptamine receptor 2BHomo sapiens (human)
dendrite5-hydroxytryptamine receptor 2BHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 2BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID1855115Binding affinity to 5-HT2B (unknown origin) assessed as inhibition constant by liquid scintillation counter analysis2022Journal of medicinal chemistry, 08-25, Volume: 65, Issue:16
Positron Emission Tomography (PET) Imaging Tracers for Serotonin Receptors.
AID1855114Binding affinity to rat 5-HT2A assessed as inhibition constant by liquid scintillation counter analysis2022Journal of medicinal chemistry, 08-25, Volume: 65, Issue:16
Positron Emission Tomography (PET) Imaging Tracers for Serotonin Receptors.
AID1855116Binding affinity to 5-HT2C (unknown origin) assessed as inhibition constant by liquid scintillation counter analysis2022Journal of medicinal chemistry, 08-25, Volume: 65, Issue:16
Positron Emission Tomography (PET) Imaging Tracers for Serotonin Receptors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (41)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's32 (78.05)24.3611
2020's9 (21.95)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%
Reviews4 (9.09%)6.00%
Case Studies17 (38.64%)4.05%
Observational1 (2.27%)0.25%
Other22 (50.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]