Page last updated: 2024-12-05

8-(n,n-diethylamino)octyl-3,4,5-trimethoxybenzoate

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Description

8-(N,N-diethylamino)octyl-3,4,5-trimethoxybenzoate: intracellular calcium antagonist; RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5494
CHEMBL ID258764
CHEBI ID107633
SCHEMBL ID2173737
MeSH IDM0047986

Synonyms (38)

Synonym
BRD-K58220566-001-02-2
tmb-8
NCGC00014998-01
lopac-861804
LOPAC0_000022
BSPBIO_001503
NCGC00162047-02
NCGC00162047-03
tm-8
8-(diethylamino)octyl 3,4,5-trimethoxybenzoate
tmb 8
8-(n,n-diethylamino)octyl-3,4,5-trimethoxybenzoate
3,4,5-trimethoxybenzoic acid, 8-(diethylamino)octyl ester
NCGC00162047-04
NCGC00162047-01
57818-92-5
CHEBI:107633
HMS1989L05
NCGC00014998-06
CHEMBL258764
HMS1791L05
CCG-204118
NCGC00014998-03
NCGC00014998-05
NCGC00014998-04
NCGC00014998-02
t9nf33oq5t ,
unii-t9nf33oq5t
gtpl4323
EI-110
SCHEMBL2173737
HMS3402L05
DTXSID70206532
benzoic acid, 3,4,5-trimethoxy-, 8-(diethylamino)octyl ester
trimethoxybenzoic acid, 8-(diethylamino)octyl ester, 3,4,5-
Q27089002
SDCCGSBI-0050011.P002
NCGC00014998-07

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" The dose-response curve for this suppression was very similar to that for stimulation of inositol monophosphate (IP1) formation and for stimulation of the initial rise of [Ca2+]i elicited by carbachol."( Suppressive effect of carbachol on forskolin-stimulated neurite outgrowth in human neuroblastoma NB-OK1 cells.
Nakagawa-Yagi, Y; Nakamura, H; Saito, Y; Takada, Y, 1992
)
0.28
" From cumulative dose-response curves, pD2 values of various calcium antagonists for the negative inotropic activity were determined in diabetic and control hearts."( Effects of various calcium antagonists in isolated perfused hearts from diabetic and age-matched control rats.
Heijnis, JB; Mathy, MJ; van Zwieten, PA, 1991
)
0.28
" In addition, the similarity of the dose-response curves for the bradykinin-mediated increase in Ca2+, PGE2, and cAMP (half-maximal stimulation of 12, 11, and 13 nM, respectively) and the ability of the B2-antagonist (B4307) to block each of these effects of bradykinin suggest that all three effects are mediated by the same bradykinin (B2) receptor."( Effects of kinins on cultured arterial smooth muscle.
Breckon, R; Dixon, BS; Fortune, J; Linas, SL; Marzec-Calvert, R; Stewart, JM; Vavrek, RJ, 1990
)
0.28
" In the presence of TMB-8 the dose-response curve for carbachol-induced amylase release shifts to the right, suggesting competitive antagonism at the muscarinic receptor."( Stimulatory and inhibitory effects of TMB-8 on pancreatic enzyme secretion.
De Pont, JJ; Van Nooij, IG; Willems, PH, 1986
)
0.27
" Furthermore, enhancement of the respiratory burst and calcium transients occurred in a parallel dose-response range for rIFN-gamma."( Relation of cytosolic calcium to the microbicidal activation of blood monocytes by recombinant gamma interferon.
Kemmerich, B; Pennington, JE; Small, GJ, 1986
)
0.27
" Intravenously administered PGE2 at a five times higher dosage failed to significantly alter net water and electrolyte fluxes."( Central nervous system influence of prostaglandin E2 on jejunal water and electrolyte transport in conscious dogs.
Bueno, L; Primi, MP, 1986
)
0.27
" The dose-response curve of the fluorescence change and that of the superoxide release of th cells were very similar."( Release of the membrane-calcium and its relation to the superoxide formation by polymorphonuclear leukocytes.
Matsumoto, T; Minakami, S; Nabi, ZF; Takeshige, K, 1982
)
0.26
" A dose-response relationship resulted when explants were challenged with methacholine in nutrient medium containing varied calcium concentrations (0."( The calcium dependency of mucus glycoconjugate secretion by canine tracheal explants.
Barbieri, EJ; Bobyock, E; Chernick, WS; McMichael, RF, 1984
)
0.27
" Nifedipine (100 micrograms/kg, 300 micrograms/kg, and 1000 micrograms/kg) inhibited in a dose-dependent manner the pressor responses to the alpha 1- and alpha 2-adrenoceptor agonists, the dose-response curves to the alpha 2-adrenoceptor agonists being shifted further to the right."( A comparison of the effects of TMB-8 and nifedipine on pressor responses to alpha 1- and alpha 2-adrenoceptor agonists in pithed rats.
Aleixandre, MA; Pintado, A; Puerro, M, 1995
)
0.29
" Rightward shift of the dose-response curves due to coinfusion of inhibitors served to assess contribution of different pathways: trimethoxybenzoate (TMB-8) against Ca2+ mobilization, nifedipine against Ca2+ influx, staurosporine and Ro-318220 against PKC, and Y-27632 and HA-1077 against ROK."( Variations in cell signaling pathways for different vasoconstrictor agonists in renal circulation of the rat.
Bauer, J; Parekh, N, 2003
)
0.32
" They shifted dose-response curves of Ang II, norepinephrine, and AVP to sevenfold and higher values."( Variations in cell signaling pathways for different vasoconstrictor agonists in renal circulation of the rat.
Bauer, J; Parekh, N, 2003
)
0.32
" To investigate whether similar effects are present in the hippocampus, AMPA dose-response and calcium movement blockade were performed."( Nimodipine inhibits TMB-8 potentiation of AMPA-induced hippocampal neurodegeneration.
Bernal, F; Mahy, N; Petegnief, V; Pugliese, M; Rodríguez, MJ; Ursu, G, 2009
)
0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
trihydroxybenzoic acid
[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 (31)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
ATAD5 protein, partialHomo sapiens (human)Potency32.62940.004110.890331.5287AID493106
GLS proteinHomo sapiens (human)Potency0.63100.35487.935539.8107AID624146
TDP1 proteinHomo sapiens (human)Potency28.01970.000811.382244.6684AID686978; AID686979
ThrombopoietinHomo sapiens (human)Potency10.00000.02517.304831.6228AID917; AID918
regulator of G-protein signaling 4Homo sapiens (human)Potency2.66540.531815.435837.6858AID504845
67.9K proteinVaccinia virusPotency18.25630.00018.4406100.0000AID720579; AID720580
glucocerebrosidaseHomo sapiens (human)Potency31.62280.01268.156944.6684AID2101
arylsulfatase AHomo sapiens (human)Potency21.33131.069113.955137.9330AID720538
cytochrome P450 2D6 isoform 1Homo sapiens (human)Potency31.62280.00207.533739.8107AID891
D(1A) dopamine receptorHomo sapiens (human)Potency2.31080.02245.944922.3872AID488982
serine/threonine-protein kinase mTOR isoform 1Homo sapiens (human)Potency23.28090.00378.618923.2809AID2668
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency10.00000.031610.279239.8107AID884; AID885
muscarinic acetylcholine receptor M1Rattus norvegicus (Norway rat)Potency2.81840.00106.000935.4813AID943; AID944
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Inositol monophosphatase 1Rattus norvegicus (Norway rat)Potency5.25061.000010.475628.1838AID1457
GABA theta subunitRattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency10.00001.000012.224831.6228AID885
ATP-dependent phosphofructokinaseTrypanosoma brucei brucei TREU927Potency0.03010.060110.745337.9330AID485368
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (33)

Assay IDTitleYearJournalArticle
AID1347151Optimization of GU AMC qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID504836Inducers of the Endoplasmic Reticulum Stress Response (ERSR) in human glioma: Validation2002The Journal of biological chemistry, Apr-19, Volume: 277, Issue:16
Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.
AID1347058CD47-SIRPalpha protein protein interaction - HTRF assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID1347045Natriuretic polypeptide receptor (hNpr1) antagonism - Pilot counterscreen GloSensor control cell line2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID588378qHTS for Inhibitors of ATXN expression: Validation
AID1347059CD47-SIRPalpha protein protein interaction - Alpha assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588349qHTS for Inhibitors of ATXN expression: Validation of Cytotoxic Assay
AID1347057CD47-SIRPalpha protein protein interaction - LANCE assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID1347405qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS LOPAC collection2020ACS chemical biology, 07-17, Volume: 15, Issue:7
High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347049Natriuretic polypeptide receptor (hNpr1) antagonism - Pilot screen2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID1347050Natriuretic polypeptide receptor (hNpr2) antagonism - Pilot subtype selectivity assay2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID1347410qHTS for inhibitors of adenylyl cyclases using a fission yeast platform: a pilot screen against the NCATS LOPAC library2019Cellular signalling, 08, Volume: 60A fission yeast platform for heterologous expression of mammalian adenylyl cyclases and high throughput screening.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID324584Increase in long-lived protein degradation in human H4 cells after 4 hrs relative to control2007Proceedings of the National Academy of Sciences of the United States of America, Nov-27, Volume: 104, Issue:48
Small molecule regulators of autophagy identified by an image-based high-throughput screen.
AID324576Effect on FYVE-RFP+ vesicle intensity per cell in human H4 cells after 2 hrs relative to control2007Proceedings of the National Academy of Sciences of the United States of America, Nov-27, Volume: 104, Issue:48
Small molecule regulators of autophagy identified by an image-based high-throughput screen.
AID324583Increase in long-lived protein degradation in human H4 cells after 2 hrs relative to control2007Proceedings of the National Academy of Sciences of the United States of America, Nov-27, Volume: 104, Issue:48
Small molecule regulators of autophagy identified by an image-based high-throughput screen.
AID324492Increase in light chain 3-GFP+ autophagosome vesicle area per cell in human H4 cells at 5.8 uM after 24 hrs by high throughput fluorescence microscopy relative to control2007Proceedings of the National Academy of Sciences of the United States of America, Nov-27, Volume: 104, Issue:48
Small molecule regulators of autophagy identified by an image-based high-throughput screen.
AID324577Effect on FYVE-RFP+ vesicle intensity per cell in human H4 cells after 4 hrs relative to control2007Proceedings of the National Academy of Sciences of the United States of America, Nov-27, Volume: 104, Issue:48
Small molecule regulators of autophagy identified by an image-based high-throughput screen.
AID324582Increase in long-lived protein degradation in human H4 cells after 1 hr relative to control2007Proceedings of the National Academy of Sciences of the United States of America, Nov-27, Volume: 104, Issue:48
Small molecule regulators of autophagy identified by an image-based high-throughput screen.
AID324440Increase in light chain 3-GFP+ autophagosome vesicle number per cell in human H4 cells at 5.8 uM after 24 hrs by high throughput fluorescence microscopy relative to control2007Proceedings of the National Academy of Sciences of the United States of America, Nov-27, Volume: 104, Issue:48
Small molecule regulators of autophagy identified by an image-based high-throughput screen.
AID324388Induction of light chain 3-GFP level in human H4 cells at 5.8 uM after 24 hrs by high throughput fluorescence microscopy relative to control2007Proceedings of the National Academy of Sciences of the United States of America, Nov-27, Volume: 104, Issue:48
Small molecule regulators of autophagy identified by an image-based high-throughput screen.
AID324544Increase in light chain 3-GFP+ autophagosome vesicle intensity per cell in human H4 cells at 5.8 uM after 24 hrs by high throughput fluorescence microscopy relative to control2007Proceedings of the National Academy of Sciences of the United States of America, Nov-27, Volume: 104, Issue:48
Small molecule regulators of autophagy identified by an image-based high-throughput screen.
AID324578Effect on FYVE-RFP+ vesicle intensity per cell in human H4 cells after 8 hrs relative to control2007Proceedings of the National Academy of Sciences of the United States of America, Nov-27, Volume: 104, Issue:48
Small molecule regulators of autophagy identified by an image-based high-throughput screen.
AID521220Inhibition of neurosphere proliferation of mouse neural precursor cells by MTT assay2007Nature chemical biology, May, Volume: 3, Issue:5
Chemical genetics reveals a complex functional ground state of neural stem cells.
AID324585Increase in long-lived protein degradation in human H4 cells after 24 hrs relative to control2007Proceedings of the National Academy of Sciences of the United States of America, Nov-27, Volume: 104, Issue:48
Small molecule regulators of autophagy identified by an image-based high-throughput screen.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (570)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990223 (39.12)18.7374
1990's248 (43.51)18.2507
2000's74 (12.98)29.6817
2010's20 (3.51)24.3611
2020's5 (0.88)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 7.84

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 Index7.84 (24.57)
Research Supply Index6.38 (2.92)
Research Growth Index4.21 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (7.84)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (0.51%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other583 (99.49%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]