Page last updated: 2024-11-08

deformylflustrabromine

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

Description

deformylflustrabromine: has antineoplastic activity; isolated from Flustra folicea; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID637026
CHEMBL ID231592
CHEBI ID188610
SCHEMBL ID20741471
MeSH IDM0448118

Synonyms (18)

Synonym
n-(2-[6-bromo-2(1,1-dimethyl-2-propenyl)-1h-indol-3-yl]ethyl)-n-methylamine
1h-indole-3-ethanamine, 6-bromo-2-(1,1-dimethyl-2-propenyl)-n-methyl-
{2-[6-bromo-2-(1,1-dimethyl-allyl)-1h-indol-3-yl]-ethyl}-methyl-amine
inchi=1/c16h21brn2/c1-5-16(2,3)15-13(8-9-18-4)12-7-6-11(17)10-14(12)19-15/h5-7,10,18-19h,1,8-9h2,2-4h
2-[6-bromo-2-(1,1-dimethylprop-2-en-1-yl)-1h-indol-3-yl]-n-methylethanamine
deformylflustrabromine
CHEMBL231592 ,
bdbm50217055
CHEBI:188610
2-[6-bromo-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]-n-methylethanamine
desformylflustrabromine
474657-72-2
Q5264123
SCHEMBL20741471
6-bromo-2-(1,1-dimethyl-2-propen-1-yl)-n-methyl-1h-indole-3-ethanamine
24c2sy7kuv ,
1h-indole-3-ethanamine, 6-bromo-2-(1,1-dimethyl-2-propen-1-yl)-n-methyl-
DTXSID601046502

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Coapplication of dFBr with acetylcholine (ACh) produces a bell-shaped dose-response curve with a peak potentiation of more than 265% (Bioorg Med Chem Lett 17:4855-4860, 2007) at dFBr concentrations <10 microM and inhibition of responses at concentrations >10 microM."( Pharmacological characterization of the allosteric modulator desformylflustrabromine and its interaction with alpha4beta2 neuronal nicotinic acetylcholine receptor orthosteric ligands.
Schulte, MK; Weltzin, MM, 2010
)
0.36
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
tryptaminesTryptamine and its substitution derivatives.
[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 (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Neuronal acetylcholine receptor subunit beta-2Homo sapiens (human)IC50 (µMol)150.00000.00110.539010.0000AID292427
Neuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)IC50 (µMol)44.00000.00204.15279.9000AID292428
Neuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)IC50 (µMol)150.00000.00110.491110.0000AID292427
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (71)

Processvia Protein(s)Taxonomy
response to hypoxiaNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
monoatomic ion transportNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
calcium ion transportNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
smooth muscle contractionNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
signal transductionNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
synaptic transmission, cholinergicNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
visual perceptionNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
sensory perception of soundNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
learningNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
memoryNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
locomotory behaviorNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
associative learningNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
visual learningNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
regulation of dopamine secretionNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
sensory perception of painNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
vestibulocochlear nerve developmentNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
optic nerve morphogenesisNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
lateral geniculate nucleus developmentNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
central nervous system projection neuron axonogenesisNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
positive regulation of B cell proliferationNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
regulation of synaptic transmission, dopaminergicNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
positive regulation of dopamine secretionNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
monoatomic ion transmembrane transportNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
response to nicotineNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
behavioral response to nicotineNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
social behaviorNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
regulation of dopamine metabolic processNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
B cell activationNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
response to cocaineNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
regulation of circadian sleep/wake cycle, REM sleepNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
response to ethanolNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
negative regulation of action potentialNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
regulation of dendrite morphogenesisNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
nervous system processNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
cognitionNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
membrane depolarizationNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
regulation of synapse assemblyNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
excitatory postsynaptic potentialNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
synaptic transmission involved in micturitionNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
acetylcholine receptor signaling pathwayNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
response to acetylcholineNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
chemical synaptic transmissionNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
negative regulation of tumor necrosis factor productionNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
response to hypoxiaNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of protein phosphorylationNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
monoatomic ion transportNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
calcium ion transportNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
intracellular calcium ion homeostasisNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
signal transductionNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
synaptic transmission, cholinergicNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
learning or memoryNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
memoryNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
short-term memoryNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of cell population proliferationNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
negative regulation of tumor necrosis factor productionNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
monoatomic ion transmembrane transportNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
response to nicotineNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of MAPK cascadeNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of angiogenesisNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
synapse organizationNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
cognitionNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
sensory processingNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of protein metabolic processNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
excitatory postsynaptic potentialNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
calcium ion transmembrane transportNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
acetylcholine receptor signaling pathwayNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
dendritic spine organizationNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
modulation of excitatory postsynaptic potentialNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
dendrite arborizationNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of long-term synaptic potentiationNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of amyloid-beta formationNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
negative regulation of amyloid-beta formationNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
regulation of amyloid precursor protein catabolic processNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
response to amyloid-betaNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
response to acetylcholineNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
regulation of amyloid fibril formationNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of CoA-transferase activityNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of excitatory postsynaptic potentialNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
regulation of membrane potentialNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
chemical synaptic transmissionNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
action potentialNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
response to hypoxiaNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
DNA repairNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
monoatomic ion transportNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
calcium ion transportNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
response to oxidative stressNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
signal transductionNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
chemical synaptic transmissionNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
synaptic transmission, cholinergicNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
regulation of dopamine secretionNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
sensory perception of painNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
monoatomic ion transmembrane transportNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
response to nicotineNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
behavioral response to nicotineNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
B cell activationNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
regulation of membrane potentialNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
nervous system processNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
cognitionNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
membrane depolarizationNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
excitatory postsynaptic potentialNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
inhibitory postsynaptic potentialNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
acetylcholine receptor signaling pathwayNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (14)

Processvia Protein(s)Taxonomy
protein bindingNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
ligand-gated monoatomic ion channel activityNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
acetylcholine receptor activityNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
acetylcholine-gated monoatomic cation-selective channel activityNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
acetylcholine bindingNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
protein-containing complex bindingNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
quaternary ammonium group bindingNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
heterocyclic compound bindingNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
amyloid-beta bindingNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
monoatomic ion channel activityNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
calcium channel activityNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
protein bindingNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
acetylcholine receptor activityNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
toxic substance bindingNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
chloride channel regulator activityNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
acetylcholine-gated monoatomic cation-selective channel activityNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
acetylcholine bindingNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
protein homodimerization activityNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
protein bindingNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
ligand-gated monoatomic ion channel activityNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
acetylcholine receptor activityNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
acetylcholine-gated monoatomic cation-selective channel activityNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
acetylcholine bindingNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
plasma membraneNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
external side of plasma membraneNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
membraneNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
presynaptic membraneNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
plasma membrane raftNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
cholinergic synapseNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
postsynaptic specialization membraneNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
acetylcholine-gated channel complexNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
plasma membraneNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
neuron projectionNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
synapseNeuronal acetylcholine receptor subunit beta-2Homo sapiens (human)
plasma membraneNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
membraneNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
plasma membrane raftNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
postsynaptic membraneNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
postsynapseNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
acetylcholine-gated channel complexNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
plasma membraneNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
neuron projectionNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
synapseNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
plasma membraneNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
external side of plasma membraneNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
membraneNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
dendriteNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
neuronal cell bodyNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
postsynaptic membraneNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
acetylcholine-gated channel complexNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
synapseNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
neuron projectionNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
plasma membraneNeuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID1858701Antibiofilm activity against Staphylococcus aureus ATCC 29213 assessed as inhibition of biofilm formation incubated for 24 hrs by crystal violet method2021European journal of medicinal chemistry, Jan-01, Volume: 209Tryptophan derived natural marine alkaloids and synthetic derivatives as promising antimicrobial agents.
AID397818Blockade of voltage-activated rat Kv1.1 potassium channel expressed in Xenopus laevis oocytes assessed as effect on evoked current upto 10 uM by two-electrode voltage clamp method2002Journal of natural products, Nov, Volume: 65, Issue:11
Four new bromotryptamine derivatives from the marine bryozoan Flustra foliacea.
AID292427Activity at human alpha-4-beta-2 nACh receptor expressed in Xenopus oocytes assessed as inhibition of acetyl chlone-induced currents by two-electrode voltage clamp method2007Bioorganic & medicinal chemistry letters, Sep-01, Volume: 17, Issue:17
Synthesis of desformylflustrabromine and its evaluation as an alpha4beta2 and alpha7 nACh receptor modulator.
AID1858700Antibiofilm activity against Escherichia coli K12 ER2718 assessed as inhibition of biofilm formation incubated for 24 hrs by crystal violet method2021European journal of medicinal chemistry, Jan-01, Volume: 209Tryptophan derived natural marine alkaloids and synthetic derivatives as promising antimicrobial agents.
AID397820Blockade of voltage-activated rat brain Nav1.2 sodium channel type 2 channel expressed in Xenopus laevis oocytes assessed as effect on evoked current by two-electrode voltage clamp method2002Journal of natural products, Nov, Volume: 65, Issue:11
Four new bromotryptamine derivatives from the marine bryozoan Flustra foliacea.
AID292429Activity at human alpha-4-beta-2 nACh receptor expressed in Xenopus oocytes assessed as potentiation of acetyl chlone-induced currents by two-electrode voltage clamp method relative to control2007Bioorganic & medicinal chemistry letters, Sep-01, Volume: 17, Issue:17
Synthesis of desformylflustrabromine and its evaluation as an alpha4beta2 and alpha7 nACh receptor modulator.
AID292428Activity at human alpha7 nACh receptor expressed in Xenopus oocytes assessed as inhibition of acetyl chlone-induced currents by two-electrode voltage clamp method2007Bioorganic & medicinal chemistry letters, Sep-01, Volume: 17, Issue:17
Synthesis of desformylflustrabromine and its evaluation as an alpha4beta2 and alpha7 nACh receptor modulator.
AID397819Blockade of voltage-activated rat Kv1.4 potassium channel expressed in Xenopus laevis oocytes assessed as effect on evoked current upto 10 uM by two-electrode voltage clamp method2002Journal of natural products, Nov, Volume: 65, Issue:11
Four new bromotryptamine derivatives from the marine bryozoan Flustra foliacea.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (25)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's4 (16.00)29.6817
2010's17 (68.00)24.3611
2020's4 (16.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.73

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 Index11.73 (24.57)
Research Supply Index3.30 (2.92)
Research Growth Index5.02 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.73)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (7.69%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other24 (92.31%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]