Page last updated: 2024-11-12

(2-(2',6'-dimethoxy)phenoxyethylamino)methylbenzodioxan hydrochloride

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Description

N-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-2-(2,6-dimethoxyphenoxy)ethanamine hydrochloride : A hydrochloride salt that is obtained by reaction of N-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-2-(2,6-dimethoxyphenoxy)ethanamine with one equivalent of hydrogen chloride. An alpha1A-adrenergic selective antagonist. [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 CID11957505
CHEMBL ID556001
CHEBI ID64094
SCHEMBL ID989002
MeSH IDM0056301

Synonyms (58)

Synonym
EU-0100335 ,
smr000326775
wb-4101 hydrochloride
MLS000859914 ,
NCGC00093775-02
SPECTRUM1503647
NCGC00093775-03
NCGC00093775-01
n-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-2-(2,6-dimethoxyphenoxy)ethanamine hydrochloride
2170-58-3
wb4101 hydrochloride
D 0411
2-(2,6-dimethoxyphenoxyethyl)aminomethyl-1,4-benzodioxane hydrochloride
chebi:64094 ,
CHEMBL556001
2- (2,6-dimethoxyphenoxyethyl)aminomethyl-1,4-benzodioxane hydrochloride (wb 4101)
1,4-benzodioxin-2-methanamine, n-(2-(2,6-dimethoxyphenoxy)ethyl)-2,3-dihydro-, hcl
DE86700000
1,4-benzodiaxan-2-methylamine, n-(2-(2,6-dimethoxyphenoxy)ethyl)-, hydrochloride
niosh/de8670000
2-(((2-(2,6-dimethoxyphenoxy)ethyl)amino)methyl)-1,4-benzodioxan hydrochloride
wb 4101 hydrochloride
n-(2-(2,6-dimethoxyphenoxy)ethyl)-1,4-benzodiaxan-2-methylamine hydrochloride
CCG-39353
einecs 218-520-3
(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)(2-(2,6-dimethoxyphenoxy)ethyl)ammonium chloride
n-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-2-(2,6-dimethoxyphenoxy)ethanaminium chloride
LP00335
tox21_500335
n-((2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl)-2-(2,6-dimethoxyphenoxy)ethanamine hydrochloride
NCGC00261020-01
DTXSID2042565
SCHEMBL989002
n-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)-2-(2,6-dimethoxyphenoxy)ethanamine;hydrochloride
AKOS024458707
wb-4101 hydrochloride, analytical standard
J-014246
SR-01000075254-3
SR-01000075254-1
sr-01000075254
Q27133026
E76693
2-[(2,6-dimethoxyphenoxyethyl)aminomethyl]-1,4-benzodioxane hydrochloride
(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)[2-(2,6-dimethoxyphenoxy)ethyl]ammonium chloride
2((2,6-dimethoxyphenoxy-ethyl)*aminomethyl)-1,4-benz
2,3-dihydro-1,4-benzodioxin-3-ylmethyl-[2-(2,6-dimethoxyphenoxy)ethyl]azanium;chloride
wb 4101 hydrochloride; wb-4101 hydrochloride ;wb 4101 (antagonist) hydrochloride
(+/-)-wb 4101 (hydrochloride)
BS-51626
()-wb 4101 (hydrochloride)
CAA17058
n-((2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl)-2-(2,6-dimethoxyphenoxy)ethanaminehydrochloride
( inverted exclamation marka)-wb 4101 (hydrochloride)
CS-0021157
HY-12718A
1,4-benzodioxin-2-methanamine, n-[2-(2,6-dimethoxyphenoxy)ethyl]-2,3-dihydro-, hydrochloride (1:1)
44UX7VL6F7
1,4-benzodioxin-2-methanamine, n-[2-(2,6-dimethoxyphenoxy)ethyl]-2,3-dihydro-, hydrochloride
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
alpha-adrenergic antagonistAn agent that binds to but does not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous alpha-adrenergic agonists. alpha-Adrenergic antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma.
[role 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]

Drug Classes (1)

ClassDescription
hydrochlorideA salt formally resulting from the reaction of hydrochloric acid with an organic base.
[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 (30)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency0.02240.003245.467312,589.2998AID2517
thioredoxin reductaseRattus norvegicus (Norway rat)Potency0.15000.100020.879379.4328AID588453
TDP1 proteinHomo sapiens (human)Potency17.42380.000811.382244.6684AID686978; AID686979
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency18.95860.001530.607315,848.9004AID1224819; AID1224820
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency0.05010.035520.977089.1251AID504332
peripheral myelin protein 22 isoform 1Homo sapiens (human)Potency95.283423.934123.934123.9341AID1967
parathyroid hormone/parathyroid hormone-related peptide receptor precursorHomo sapiens (human)Potency112.20203.548119.542744.6684AID743266
potassium voltage-gated channel subfamily H member 2 isoform dHomo sapiens (human)Potency11.22020.01789.637444.6684AID588834
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency56.23410.050127.073689.1251AID588590
gemininHomo sapiens (human)Potency0.23110.004611.374133.4983AID624297
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency3.16230.031610.279239.8107AID884; AID885
lamin isoform A-delta10Homo sapiens (human)Potency5.62340.891312.067628.1838AID1487
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency3.16231.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency3.16231.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency3.16231.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency3.16231.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency3.16231.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency3.16231.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency3.16231.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency3.16231.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency3.16231.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency3.16231.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency3.16231.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency3.16231.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency3.16231.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency3.16231.000012.224831.6228AID885
GABA theta subunitRattus norvegicus (Norway rat)Potency3.16231.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency3.16231.000012.224831.6228AID885
[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)
Hsf1 proteinMus musculus (house mouse)EC50 (µMol)260.00000.160024.4900236.5000AID435004
glycogen synthase kinase-3 beta isoform 1Homo sapiens (human)EC50 (µMol)300.00000.212522.156283.9400AID434954
[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 (28)

Assay IDTitleYearJournalArticle
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID977599Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID977602Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID524796Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR green assay2009Nature chemical biology, Oct, Volume: 5, Issue:10
Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.
AID35722Alpha-1 adrenergic receptor antagonist activity against agonist (norepinephrine) in isolated rat vas deferens1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
2-[[[2-(2,6-Dimethoxyphenoxy)ethyl]amino]-methyl] -1,4-benzoxathian: a new antagonist with high potency and selectivity toward alpha 1-adrenoreceptors.
AID524790Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR green assay2009Nature chemical biology, Oct, Volume: 5, Issue:10
Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.
AID197109Alpha-2-adrenoceptor blocking activity was determined by antagonism of clonidine induced depression of the twitch responses of the field stimulated prostatic portion of the vas deferens and the potency was expressed as pA2.1985Journal of medicinal chemistry, Sep, Volume: 28, Issue:9
Structure-activity relationships for prazosin and WB 4101 analogues as alpha 1-adrenoreceptor antagonists.
AID524793Antiplasmodial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR green assay2009Nature chemical biology, Oct, Volume: 5, Issue:10
Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.
AID524795Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR green assay2009Nature chemical biology, Oct, Volume: 5, Issue:10
Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.
AID35343Alpha-2 adrenergic receptor antagonist activity against agonist (clonidine) in isolated rat vas deferens1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
2-[[[2-(2,6-Dimethoxyphenoxy)ethyl]amino]-methyl] -1,4-benzoxathian: a new antagonist with high potency and selectivity toward alpha 1-adrenoreceptors.
AID196662Alpha-1-Adrenoceptor blocking activity as antagonism of (-)-norepinephrine induced contractions of epididymal vas deferens1985Journal of medicinal chemistry, Sep, Volume: 28, Issue:9
Structure-activity relationships for prazosin and WB 4101 analogues as alpha 1-adrenoreceptor antagonists.
AID524794Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR green assay2009Nature chemical biology, Oct, Volume: 5, Issue:10
Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.
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.
AID524791Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR green assay2009Nature chemical biology, Oct, Volume: 5, Issue:10
Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.
AID235726Selectivity as the ratio of pA2 value against alpha 1 receptor to that of alpha-2 receptor.1985Journal of medicinal chemistry, Sep, Volume: 28, Issue:9
Structure-activity relationships for prazosin and WB 4101 analogues as alpha 1-adrenoreceptor antagonists.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
AID1159550Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening2015Nature cell biology, Nov, Volume: 17, Issue:11
6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (16.67)18.7374
1990's0 (0.00)18.2507
2000's3 (25.00)29.6817
2010's5 (41.67)24.3611
2020's2 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.63

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 Index11.63 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index4.19 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.63)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (8.33%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (91.67%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]