Page last updated: 2024-12-05

dimethisoquin

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

Dimethisoquin is a topical anesthetic that is used to relieve pain, itching, and irritation. It is typically used to treat skin conditions such as eczema, psoriasis, and poison ivy. Dimethisoquin works by blocking the transmission of pain signals to the brain. It is available over-the-counter in various formulations, including creams, lotions, and sprays. The synthesis of dimethisoquin involves a series of chemical reactions starting with the aromatic compound 2-chloro-4-nitrophenol. This compound undergoes a nucleophilic substitution reaction with dimethylamine to yield 2-dimethylamino-4-nitrophenol. The nitro group is then reduced to an amino group using a suitable reducing agent, such as iron powder and hydrochloric acid. The resulting compound is then reacted with a suitable alkylating agent, such as methyl iodide, to introduce the methyl group at the nitrogen atom. Dimethisoquin is a relatively safe and effective topical anesthetic. However, some individuals may experience side effects, such as skin irritation, dryness, and redness. In rare cases, dimethisoquin can cause allergic reactions. Dimethisoquin is not recommended for use on open wounds or mucous membranes. It is also not recommended for use in children under the age of two years without the supervision of a doctor. Dimethisoquin is a valuable medication for the treatment of a variety of skin conditions. It is a safe and effective topical anesthetic that can provide relief from pain, itching, and irritation. The compound is widely studied for its anesthetic properties and potential applications in the treatment of various skin conditions. Research focuses on exploring its mechanism of action, efficacy, safety, and potential for new formulations and delivery systems.'

Cross-References

ID SourceID
PubMed CID6857
CHEMBL ID127643
CHEBI ID93295
SCHEMBL ID8191
MeSH IDM0053603

Synonyms (73)

Synonym
BRD-K73391359-003-03-7
ethanamine, 2-[(3-butyl-1-isoquinolinyl)oxy]-n,n-dimethyl-
isoquinoline, 3-butyl-1-(2-(dimethylamino)ethoxy)-
AO-080/43342670
n-{2-[(3-butyl-1-isoquinolinyl)oxy]ethyl}-n,n-dimethylamine
chinisocain
1-(.beta.-dimethylaminoethoxy)-3-n-butylisoquinoline
86-80-6
dimethisoquin
prulantex
nsc39695
quinisocaine
pruralgin
pruralgan
isochinol
2-(dimethylamino)ethoxy-3-butyl-isoquinoline
3-butyl-1-[2-(dimethylamino)ethoxy]isoquinoline
quinisocain
wln: t66 cnj bo2n1&1 d4
histaderme
3-butyl-1-[2-(dimethylamino)ethyl]isoquinoline
isoquinoline, 3-butyl-1-[2-(dimethylamino)ethyl]-
nsc-39695
quinoleine
isoquinoline, 3-butyl-1-[2-(dimethylamino)ethoxy]-
kinisokain
chinisocainum
quinisocaine [inn:ban]
quinisocainum [inn-latin]
einecs 201-700-0
3-butyl-1-(2-dimethylaminoethoxy)isoquinoline
brn 0018179
quinisocaina [inn-spanish]
1-(2-dimethylaminoethoxy)-3-butylisochinolin
ethanamine, 2-((3-butyl-1-isoquinolinyl)oxy)-n,n-dimethyl-
PRESTWICK3_000630
cas-2773-92-4
NCGC00016618-01
PRESTWICK2_000630
BPBIO1_000660
AB00514685
BSPBIO_000600
SPBIO_002819
PRESTWICK1_000630
PRESTWICK0_000630
NCGC00016618-02
2-(3-butylisoquinolin-1-yl)oxy-n,n-dimethylethanamine
CHEMBL127643
quinisocaine (inn)
D08462
[2-(3-butylisoquinolyloxy)ethyl]dimethylamine
5-21-03-00414 (beilstein handbook reference)
quinisocaina
nsc 39695
quinisocainum
772en3bh6i ,
unii-772en3bh6i
quinisocaine [inn]
quinisocaine [who-dd]
3-butyl-1-(2-(dimethylamino)ethoxy)isoquinoline
dimethisoquin [mi]
AKOS022143560
SCHEMBL8191
2-[(3-butyl-1-isoquinolinyl)oxy]-n,n-dimethylethanamine
DTXSID8048525
quinolein
2-[(3-butyl-1-isoquinolinyl)oxy]-n,n-dimethylethanamine #
CHEBI:93295
DB13683
bdbm50225699
Q1478199
2-((3-butylisoquinolin-1-yl)oxy)-n,n-dimethylethanamine
EX-A7590
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
isoquinolinesA class of organic heteropolycyclic compound consisting of isoquinoline 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 (8)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency0.01120.004023.8416100.0000AID485290
cytochrome P450 2D6 isoform 1Homo sapiens (human)Potency1.99530.00207.533739.8107AID891
histone acetyltransferase KAT2A isoform 1Homo sapiens (human)Potency12.58930.251215.843239.8107AID504327
lethal factor (plasmid)Bacillus anthracis str. A2012Potency3.98110.020010.786931.6228AID912
lamin isoform A-delta10Homo sapiens (human)Potency0.07940.891312.067628.1838AID1487
Polyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)Potency12.58930.316212.765731.6228AID881
Histamine H2 receptorCavia porcellus (domestic guinea pig)Potency12.58930.00638.235039.8107AID881
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Bile salt export pumpHomo sapiens (human)IC50 (µMol)68.68000.11007.190310.0000AID1449628
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (43)

Processvia Protein(s)Taxonomy
lipid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
phospholipid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
apoptotic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of cell population proliferationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of macrophage derived foam cell differentiationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
arachidonic acid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of cell migrationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
prostate gland developmentPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
regulation of epithelial cell differentiationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of chemokine productionPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of peroxisome proliferator activated receptor signaling pathwayPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of keratinocyte differentiationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of cell cyclePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of growthPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
hepoxilin biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
endocannabinoid signaling pathwayPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cannabinoid biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipoxin A4 biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
linoleic acid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipid oxidationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipoxygenase pathwayPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
fatty acid metabolic processBile salt export pumpHomo sapiens (human)
bile acid biosynthetic processBile salt export pumpHomo sapiens (human)
xenobiotic metabolic processBile salt export pumpHomo sapiens (human)
xenobiotic transmembrane transportBile salt export pumpHomo sapiens (human)
response to oxidative stressBile salt export pumpHomo sapiens (human)
bile acid metabolic processBile salt export pumpHomo sapiens (human)
response to organic cyclic compoundBile salt export pumpHomo sapiens (human)
bile acid and bile salt transportBile salt export pumpHomo sapiens (human)
canalicular bile acid transportBile salt export pumpHomo sapiens (human)
protein ubiquitinationBile salt export pumpHomo sapiens (human)
regulation of fatty acid beta-oxidationBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transportBile salt export pumpHomo sapiens (human)
bile acid signaling pathwayBile salt export pumpHomo sapiens (human)
cholesterol homeostasisBile salt export pumpHomo sapiens (human)
response to estrogenBile salt export pumpHomo sapiens (human)
response to ethanolBile salt export pumpHomo sapiens (human)
xenobiotic export from cellBile salt export pumpHomo sapiens (human)
lipid homeostasisBile salt export pumpHomo sapiens (human)
phospholipid homeostasisBile salt export pumpHomo sapiens (human)
positive regulation of bile acid secretionBile salt export pumpHomo sapiens (human)
regulation of bile acid metabolic processBile salt export pumpHomo sapiens (human)
transmembrane transportBile salt export pumpHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (15)

Processvia Protein(s)Taxonomy
iron ion bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
calcium ion bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
protein bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipid bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
linoleate 13S-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
arachidonate 8(S)-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
arachidonate 15-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
linoleate 9S-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
protein bindingBile salt export pumpHomo sapiens (human)
ATP bindingBile salt export pumpHomo sapiens (human)
ABC-type xenobiotic transporter activityBile salt export pumpHomo sapiens (human)
bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
canalicular bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transporter activityBile salt export pumpHomo sapiens (human)
ABC-type bile acid transporter activityBile salt export pumpHomo sapiens (human)
ATP hydrolysis activityBile salt export pumpHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (17)

Processvia Protein(s)Taxonomy
nucleusPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cytosolPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cytoskeletonPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
plasma membranePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
adherens junctionPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
focal adhesionPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
membranePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
extracellular exosomePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
basolateral plasma membraneBile salt export pumpHomo sapiens (human)
Golgi membraneBile salt export pumpHomo sapiens (human)
endosomeBile salt export pumpHomo sapiens (human)
plasma membraneBile salt export pumpHomo sapiens (human)
cell surfaceBile salt export pumpHomo sapiens (human)
apical plasma membraneBile salt export pumpHomo sapiens (human)
intercellular canaliculusBile salt export pumpHomo sapiens (human)
intracellular canaliculusBile salt export pumpHomo sapiens (human)
recycling endosomeBile salt export pumpHomo sapiens (human)
recycling endosome membraneBile salt export pumpHomo sapiens (human)
extracellular exosomeBile salt export pumpHomo sapiens (human)
membraneBile salt export pumpHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
AID1449628Inhibition of human BSEP expressed in baculovirus transfected fall armyworm Sf21 cell membranes vesicles assessed as reduction in ATP-dependent [3H]-taurocholate transport into vesicles incubated for 5 mins by Topcount based rapid filtration method2012Drug metabolism and disposition: the biological fate of chemicals, Dec, Volume: 40, Issue:12
Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.
AID1061889Displacement of [3H]BTX-B from neuronal voltage-gated sodium channel in rat cerebral cortex synaptoneurosomes after 60 mins by scintillation counting2014Bioorganic & medicinal chemistry, Jan-01, Volume: 22, Issue:1
A highly predictive 3D-QSAR model for binding to the voltage-gated sodium channel: design of potent new ligands.
AID205267Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on voltage dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex1985Journal of medicinal chemistry, Mar, Volume: 28, Issue:3
[3H]Batrachotoxinin A 20 alpha-benzoate binding to voltage-sensitive sodium channels: a rapid and quantitative assay for local anesthetic activity in a variety of drugs.
AID205268Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on voltage dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex at 10 uM1985Journal of medicinal chemistry, Mar, Volume: 28, Issue:3
[3H]Batrachotoxinin A 20 alpha-benzoate binding to voltage-sensitive sodium channels: a rapid and quantitative assay for local anesthetic activity in a variety of drugs.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19905 (50.00)18.7374
1990's0 (0.00)18.2507
2000's1 (10.00)29.6817
2010's4 (40.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.87

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index21.87 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.97 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.87)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other10 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]