Page last updated: 2024-12-05

hemicholinium 3

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

Description

Hemicholinium 3: A potent inhibitor of the high affinity uptake system for CHOLINE. It has less effect on the low affinity uptake system. Since choline is one of the components of ACETYLCHOLINE, treatment with hemicholinium can deplete acetylcholine from cholinergic terminals. Hemicholinium 3 is commonly used as a research tool in animal and in vitro experiments. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID9399
CHEMBL ID197027
SCHEMBL ID564623
MeSH IDM0010073
PubMed CID3585
CHEMBL ID268697
CHEBI ID94343
SCHEMBL ID12638596
MeSH IDM0010073

Synonyms (100)

Synonym
morpholinium, 2,2'-[1,1'-biphenyl]-4,4'-diylbis[2-hydroxy-4,4-dimethyl-, dibromide
hemicholinium-3
EU-0100578
hemicholinium-3, solid, >=95% (hplc)
2,2'-(1,1'-biphenyl)-4,4'-diylbis(2-hydroxy-4,4-dimethyl-morpholinium) dibromide
nsc 527583
2,2'-(4,4'-biphenylene)bis(2-hydroxy-4,4-dimethylmorpholinium) dibromide
hc-3
einecs 206-227-3
morpholinium, 2,2'-(4,4'-biphenylylene)bis(2-hydroxy-4,4-dimethyl-, dibromide
morpholinium, 2,2'-(1,1'-biphenyl)-4,4'-diylbis(2-hydroxy-4,4-dimethyl-, dibromide
hemicholinium-3 dibromide
PRESTWICK_566
hemicholine
hemicholinium bromide
hemicholinium-3 bromide
hemicholinium 3
nsc-527583
hemicholinium dibromide
hemicholinium 3 dibromide
312-45-8
NCGC00093959-01
morpholinium, 2,2'-(1,1'-biphenyl)-4,4'-diylbis(2-hydroxy-4,4-dimethyl)-, dibromide
H-108
CHEMBL197027
HMS1569O07
HMS3261D18
HMS2096O07
unii-65ny3i7zd0
65ny3i7zd0 ,
morpholinium, 2,2'-(1,1'-biphenyl)-4,4'-diylbis(2-hydroxy-4,4-dimethyl-, bromide (1:2)
LP00578
[3h]hemicholinium-3
gtpl4493
[3h]-hc-3
[3h]-hemicholinium-3
[3h]hc-3
2-hydroxy-2-{4-[4-(2-hydroxy-4,4-dimethylmorpholin-4-ium-2-yl)phenyl]phenyl}-4,4-dimethylmorpholin-4-ium dibromide
SCHEMBL564623
CCG-220393
CCG-221882
tox21_500578
NCGC00261263-01
hemicholinium dibromide [mi]
2,2'-(4,4'-biphenylene)bis(2-hydroxy-4,4-dimethylmorpholinium bromide)
AKOS026750387
J-018290
SR-01000075620-5
sr-01000075620
SR-01000075620-1
HMS3713O07
2,2'-(biphenyl-4,4'-diyl)bis(2-hydroxy-4,4-dimethylmorpholin-4-ium) bromide
FT-0741707
DTXSID80883358
Q15409437
HMS3885F21
2-[4-[4-(2-hydroxy-4,4-dimethylmorpholin-4-ium-2-yl)phenyl]phenyl]-4,4-dimethylmorpholin-4-ium-2-ol;dibromide
hemicholinium 3 dibromide; hemicholinium bromide; hemicholinium dibromide; hemicholinium-3 bromide
2,2'-([1,1'-biphenyl]-4,4'-diyl)bis(2-hydroxy-4,4-dimethylmorpholin-4-ium) bromide
hemicholiniumdibromide
MS-30344
CS-0020304
HY-B2152
morpholinium, 2,2'-(4,4'-biphenylene)bis(2-hydroxy-4,4-dimethyl-
hemicholinium
2,2'-(4,4'-biphenylene)bis(2-hydroxy-4,4-dimethylmorpholinium)
morpholinium, 2,2'-(1,1'-biphenyl)-4,4'-diylbis(2-hydroxy-4,4-dimethyl-
2,2'-(biphenyl)-4,4'-diylbis(2-hydroxy-4,4-dimethylmorpholinium)
BPBIO1_000667
BSPBIO_000605
PRESTWICK2_000393
PRESTWICK3_000393
NCGC00163238-01
PRESTWICK0_000393
SPBIO_002526
PRESTWICK1_000393
LOPAC0_000578
NCGC00162192-01
NCGC00015485-03
L000813
CHEMBL268697
16478-59-4
inchi=1/c24h34n2o4/c1-25(2)13-15-29-23(27,17-25)21-9-5-19(6-10-21)20-7-11-22(12-8-20)24(28)18-26(3,4)14-16-30-24/h5-12,27-28h,13-18h2,1-4h3/q+2
2-[4-[4-(2-hydroxy-4,4-dimethylmorpholin-4-ium-2-yl)phenyl]phenyl]-4,4-dimethylm
jiwuesggkylppg-uhfffaoysa-
2-[4-[4-(2-hydroxy-4,4-dimethylmorpholin-4-ium-2-yl)phenyl]phenyl]-4,4-dimethylmorpholin-4-ium-2-ol
CCG-204667
unii-zk7jx4771p
zk7jx4771p ,
bdbm85206
cas_312-45-8
nsc_9399
NCGC00015485-02
gtpl4494
SCHEMBL12638596
hemicholinium [mi]
CHEBI:94343
DTXSID40936990
2,2'-([1,1'-biphenyl]-4,4'-diyl)bis(2-hydroxy-4,4-dimethylmorpholin-4-ium)
NCGC00015485-07

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Mouse toxicity studies (LD50) indicate that while 12 is approximately as toxic as HC-3 (1) and AcHC-3 (3), 11 is 226 times less toxic."( Effect of sulfur substitution for the noncarbonyl oxygen in hemicholinium-3 and acetyl-seco-hemicholinium-3. Synthesis, biological activity, and structure-toxicity relationships.
Charles, HC; Chihal, DM; Domer, FR; Rege, AB, 1977
)
0.26
" Mouse toxicity studies (LD50) indicate that 2 is approximately as toxic as HC-3 (1), whereas 3, 4, and 5 are 14."( Synthesis and structure-toxicity relationships of three new stable analogues of acetyl-seco-hemicholinium-3.
Charles, HC; Chihal, DM; Domer, FR; Haarstad, VB; Rege, AB, 1976
)
0.26
"Soman inhibits the enzyme acetylcholinesterase, essentially irreversibly, producing an accumulation of acetylcholine (ACh) which is responsible for many of its toxic effects."( In vivo protection against soman toxicity by known inhibitors of acetylcholine synthesis in vitro.
Doukas, PH; O'Neill, JJ; Sheldon, RJ; Sterling, GH, 1988
)
0.27
" HC-3 increased the LD50 values for both physostigmine and neostigmine but did not alter the effect on brain ACh levels produced by these agents."( Antagonism of acute physostigmine and neostigmine toxicity in mice by hemicholinium-3.
Freeman, JJ; Kosh, JW; Lin, J, 1987
)
0.27
" The toxic effect of AF64A correlated well with the affinity of the choline transport system detected in each cell type."( Direct cytotoxicity of ethylcholine mustard aziridinium in cerebral microvascular endothelial cells.
Estrada, C; Galea, E; Gómez, C; Martín, C, 1993
)
0.29
" Pretreatment, cotreatment, or delayed treatment with acetylcholine or choline prevented the adverse effects of DMAE."( The sea urchin embryo as a model for mammalian developmental neurotoxicity: ontogenesis of the high-affinity choline transporter and its role in cholinergic trophic activity.
Buznikov, GA; Lauder, JM; Nikitina, LA; Qiao, D; Seidler, FJ; Slotkin, TA, 2003
)
0.32
" We evaluated indices for acetylcholine (ACh) synaptic function throughout adolescence, young adulthood and later adulthood, in brain regions possessing the majority of ACh projections and cell bodies; we measured nicotinic ACh receptor binding, hemicholinium-3 binding to the presynaptic choline transporter and choline acetyltransferase activity, all known targets for the adverse developmental effects of dexamethasone and chlorpyrifos given individually."( Prenatal dexamethasone augments the sex-selective developmental neurotoxicity of chlorpyrifos: implications for vulnerability after pharmacotherapy for preterm labor.
Card, J; Infante, A; Seidler, FJ; Slotkin, TA,
)
0.13
" We evaluated indices for acetylcholine (ACh) synaptic function throughout adolescence, young adulthood and later adulthood, in brain regions possessing the majority of ACh projections and cell bodies; we measured nicotinic ACh receptor binding, hemicholinium-3 binding to the presynaptic choline transporter and choline acetyltransferase activity, all known targets for the adverse developmental effects of nicotine and chlorpyrifos given individually."( Prenatal nicotine alters the developmental neurotoxicity of postnatal chlorpyrifos directed toward cholinergic systems: better, worse, or just "different?".
Seidler, FJ; Slotkin, TA, 2015
)
0.42
" Mouse toxicity studies (LD50) indicate that 2 is approximately as toxic as HC-3 (1), whereas 3, 4, and 5 are 14."( Synthesis and structure-toxicity relationships of three new stable analogues of acetyl-seco-hemicholinium-3.
Charles, HC; Chihal, DM; Domer, FR; Haarstad, VB; Rege, AB, 1976
)
0.26

Dosage Studied

ExcerptRelevanceReference
" Bell-shaped log dose-response curves were obtained for McN."( A comparative study of the effects induced by MCN-A-343 and acetylcholine on the isolated toad rectus abdominis.
Corrado, AP; Jurkiewicz, A; Simioni, LR, 1976
)
0.26
" Anticholinesterase treatment shifted the dose-response curve for carbachol markedly to the left as far as the contracture attained after 4-6 min incubation was concerned."( An analysis of the mode of action of carbachol on the chick biventer cervicis nerve--muscle preparation.
Chang, CC; Su, MJ; Tang, SS, 1976
)
0.26
" Interestingly, the VIP receptor antagonist [d-parachloro-Phe6,Leu17[VIP shifted the dose-response curve for carbachol significantly to the right, indicating inhibition of phosphoinositide hydrolysis."( Neuropeptide modulation of muscarinic receptors and function in cerebral cortex of young and senescent rats.
Pedigo, NW; Rice, MA, 1992
)
0.28
"001) of the mean dose-response relationship."( Cholinergic mechanisms involved with histamine hyperreactivity in immune rabbit airways challenged with ragweed antigen.
Ando, RE; Irvin, CG; Larsen, GL; Tanaka, DT, 1991
)
0.28
" The results indicated that: 1) The effect of electroacupuncture analgesia can be enhanced by subcutaneous injection of neostigmine which related to the dosage used."( [Acetylcholine and the primary input of acupuncture sensation--influence of peripheral acetylcholine on the role of electroacupuncture analgesia].
Guan, X; Liang, X; Liu, X, 1990
)
0.28
" comparison of routes of administration, dose-response relationships, and time to effect."( In vivo protection against soman toxicity by known inhibitors of acetylcholine synthesis in vitro.
Doukas, PH; O'Neill, JJ; Sheldon, RJ; Sterling, GH, 1988
)
0.27
" Log dose-response curves to oxotremorine and acetylcholine were similar and both drugs were competitively antagonized by atropine."( Investigation of the mechanism of action of oxotremorine on the guinea-pig isolated ileum preparation.
Cox, B; Hecker, SE, 1971
)
0.25
" Young males showed greater responsiveness to both drugs than young females, this being reflected in higher maxima of the dose-response curves obtained for the males."( The responsiveness of human eccrine sweat glands to choline and carbachol. Application to the study of peripheral cholinergic functioning in Alzheimer-type dementia.
Bradshaw, CM; Lamb, K; Szabadi, E, 1983
)
0.27
" In each instance, hemicholinium-3 causes a significant inhibition of control activity at a concentration of 30 microM, a dosage that causes complete photoreceptor outer segment degeneration in mammalian retinas."( Alteration of retinal choline metabolism in an experimental model for photoreceptor cell degeneration.
Anderson, RE; Pu, GA, 1983
)
0.27
" 4 The dose-response curve following intraventricular administration demonstrated that hemicholinium-3 was not as lethal after central administration as it was after peripheral administration."( Peripheral toxicity of hemicholinium-3 in mice.
Freeman, JJ; Kosh, JW; Parrish, JS, 1982
)
0.26
" 3 Hemicholinium-3 (HC-3) caused a rightward shift of the dose-response curve to DL-muscarine on the ileal longitudinal muscle of the guinea-pig ileum."( Mechanism of action of muscarine on the longitudinal muscle of the guinea-pig isolated ileum.
Ochillo, RF; Tsai, CS; Tsai, MH, 1981
)
0.26
" In Ca2+ -free buffer the BaCl2 dose-response curve was shifted to the right."( BaCl2-induced contractions in the guinea pig ileum longitudinal muscle: role of presynaptic release of neurotransmitters and Ca2+ translocation in the postsynaptic membrane.
Clement, JG, 1981
)
0.26
" Similar studies were conducted with rats treated at the highest lead dosage which did not result in weight loss (100 microgram lead as lead acetate/g body weight/day via intubation)."( Developmental studies of the uptake of choline, GABA and dopamine by crude synaptosomal preparations after in vivo or in vitro lead treatment.
Krigman, MR; Morell, P; Ramsay, PB, 1980
)
0.26
" Dose-response curves for the effect of NPPB on swelling-activated choline transport and the swelling-activated transport of taurine, a sulfonic amino acid, were superimposable."( Two pathways for choline transport in eel erythrocytes: a saturable carrier and a volume-activated channel.
Joyner, SE; Kirk, K, 1994
)
0.29
"kg-1) shifted the dose-response curve of xylazine induced sedation to the right, hemicholinum-3 (3 micrograms icv), which inhibits the synthesis of acetylcholine, shifted the dose-response curve to the left."( [Antagonistic effects of cholinergic drugs on xylazine induced sedation].
Ding, RG; Huang, SJ; Yang, JS, 1993
)
0.29
" A muscarinic agonist, carbachol, produced a dose-related rightward shift of the dose-response curve to IMI."( Suppression of the rat micturition reflex by imipramine.
Kim, CY; Sohn, UD, 1997
)
0.3
" Depletion of endogenous ACh in the presence of HC-3 was achieved by construction of an ACh dose-response curve, using exogenous ACh, prior to re-testing the effects of emodin in the presence of HC-3."( The stimulant cathartic, emodin, contracts the rat isolated ileum by triggering release of endogenous acetylcholine.
Ali, S; Osborne, RH; Watson, MS, 2004
)
0.32
" Efficient antitumor therapy can be attained with lower dosage of radiation along with these inhibitors and thus improving the survival rate of GBM patients with reduced side-effects from radiation."( Assessment of Radiation Resistance and Therapeutic Targeting of Cancer Stem Cells: A Raman Spectroscopic Study of Glioblastoma.
Arivazhagan, A; Kumar, S; Santhosh, V; Somasundaram, K; Umapathy, S; Visvanathan, A, 2018
)
0.48
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
morpholinesAny compound containing morpholine as part of its structure.
[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]

Pathways (3)

PathwayProteinsCompounds
phosphatidylcholine biosynthesis611
plasmalogen biosynthesis1024
phosphatidylcholine biosynthesis I816

Protein Targets (11)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, ATP-DEPENDENT DNA HELICASE Q1Homo sapiens (human)Potency10.00000.125919.1169125.8920AID2353
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency39.81070.011212.4002100.0000AID1030
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency28.22630.001530.607315,848.9004AID1224819; AID1224820
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency50.11870.035520.977089.1251AID504332
thioredoxin reductaseRattus norvegicus (Norway rat)Potency6.10270.100020.879379.4328AID488773; AID588453
GLS proteinHomo sapiens (human)Potency0.31620.35487.935539.8107AID624146
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency14.12540.011212.4002100.0000AID1030
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency19.95260.035520.977089.1251AID504332
flap endonuclease 1Homo sapiens (human)Potency18.88760.133725.412989.1251AID588795
ATP-dependent phosphofructokinaseTrypanosoma brucei brucei TREU927Potency33.80780.060110.745337.9330AID485368
[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)
Vesicular acetylcholine transporterHomo sapiens (human)IC50 (µMol)0.01200.01200.76803.0000AID255282
Choline kinase Plasmodium falciparum 3D7IC50 (µMol)250.00001.75001.75001.7500AID1498143
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (8)

Processvia Protein(s)Taxonomy
neurotransmitter transportVesicular acetylcholine transporterHomo sapiens (human)
positive regulation of acetylcholine secretion, neurotransmissionVesicular acetylcholine transporterHomo sapiens (human)
serotonin uptakeVesicular acetylcholine transporterHomo sapiens (human)
acetylcholine uptakeVesicular acetylcholine transporterHomo sapiens (human)
positive regulation of long-term synaptic potentiationVesicular acetylcholine transporterHomo sapiens (human)
proton transmembrane transportVesicular acetylcholine transporterHomo sapiens (human)
positive regulation of neuromuscular junction developmentVesicular acetylcholine transporterHomo sapiens (human)
chemical synaptic transmissionVesicular acetylcholine transporterHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
acetylcholine transmembrane transporter activityVesicular acetylcholine transporterHomo sapiens (human)
acetylcholine:proton antiporter activityVesicular acetylcholine transporterHomo sapiens (human)
protein bindingVesicular acetylcholine transporterHomo sapiens (human)
monoamine:proton antiporter activityVesicular acetylcholine transporterHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
plasma membraneVesicular acetylcholine transporterHomo sapiens (human)
clathrin-coated endocytic vesicle membraneVesicular acetylcholine transporterHomo sapiens (human)
synaptic vesicle membraneVesicular acetylcholine transporterHomo sapiens (human)
clathrin-sculpted acetylcholine transport vesicle membraneVesicular acetylcholine transporterHomo sapiens (human)
AP-1 adaptor complexVesicular acetylcholine transporterHomo sapiens (human)
AP-2 adaptor complexVesicular acetylcholine transporterHomo sapiens (human)
terminal boutonVesicular acetylcholine transporterHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (62)

Assay IDTitleYearJournalArticle
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
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.
AID1133592Toxicity in ip dosed CD-1 mouse assessed as SLUD syndrome1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Effect of sulfur substitution for the noncarbonyl oxygen in hemicholinium-3 and acetyl-seco-hemicholinium-3. Synthesis, biological activity, and structure-toxicity relationships.
AID1133587Toxicity in ip dosed CD-1 mouse assessed as mortality in presence of 0.2 mg/kg, ip neostigmine1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Effect of sulfur substitution for the noncarbonyl oxygen in hemicholinium-3 and acetyl-seco-hemicholinium-3. Synthesis, biological activity, and structure-toxicity relationships.
AID1133597Toxicity in ip dosed CD-1 mouse assessed as mortality1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Effect of sulfur substitution for the noncarbonyl oxygen in hemicholinium-3 and acetyl-seco-hemicholinium-3. Synthesis, biological activity, and structure-toxicity relationships.
AID1133589Toxicity in ip dosed CD-1 mouse assessed as mild to moderate ataxia1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Effect of sulfur substitution for the noncarbonyl oxygen in hemicholinium-3 and acetyl-seco-hemicholinium-3. Synthesis, biological activity, and structure-toxicity relationships.
AID1133594Toxicity in ip dosed CD-1 mouse assessed as cardiac contractions1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Effect of sulfur substitution for the noncarbonyl oxygen in hemicholinium-3 and acetyl-seco-hemicholinium-3. Synthesis, biological activity, and structure-toxicity relationships.
AID1133595Toxicity in ip dosed CD-1 mouse assessed as increase in peristalsis of the small intestine1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Effect of sulfur substitution for the noncarbonyl oxygen in hemicholinium-3 and acetyl-seco-hemicholinium-3. Synthesis, biological activity, and structure-toxicity relationships.
AID1133586Toxicity in ip dosed CD-1 mouse assessed as mortality in presence of 20 mg/kg, ip choline1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Effect of sulfur substitution for the noncarbonyl oxygen in hemicholinium-3 and acetyl-seco-hemicholinium-3. Synthesis, biological activity, and structure-toxicity relationships.
AID1133590Toxicity in ip dosed CD-1 mouse assessed as respiratory difficulties1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Effect of sulfur substitution for the noncarbonyl oxygen in hemicholinium-3 and acetyl-seco-hemicholinium-3. Synthesis, biological activity, and structure-toxicity relationships.
AID1133593Toxicity in ip dosed CD-1 mouse assessed as clonic convulsions1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Effect of sulfur substitution for the noncarbonyl oxygen in hemicholinium-3 and acetyl-seco-hemicholinium-3. Synthesis, biological activity, and structure-toxicity relationships.
AID255282Percent inhibition against Acetylcholine transporter at 1 uM2005Journal of medicinal chemistry, Nov-03, Volume: 48, Issue:22
2-n-Butyl-9-methyl-8-[1,2,3]triazol-2-yl-9H-purin-6-ylamine and analogues as A2A adenosine receptor antagonists. Design, synthesis, and pharmacological characterization.
AID1133591Toxicity in ip dosed CD-1 mouse assessed as loss of righting response1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Effect of sulfur substitution for the noncarbonyl oxygen in hemicholinium-3 and acetyl-seco-hemicholinium-3. Synthesis, biological activity, and structure-toxicity relationships.
AID1133588Toxicity in ip dosed CD-1 mouse assessed as exophthalmos1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Effect of sulfur substitution for the noncarbonyl oxygen in hemicholinium-3 and acetyl-seco-hemicholinium-3. Synthesis, biological activity, and structure-toxicity relationships.
AID1133596Toxicity in ip dosed CD-1 mouse assessed as excess fluids in lungs and peritoneal cavity1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Effect of sulfur substitution for the noncarbonyl oxygen in hemicholinium-3 and acetyl-seco-hemicholinium-3. Synthesis, biological activity, and structure-toxicity relationships.
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).
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.
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.
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.
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.
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.
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.
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.
AID588349qHTS for Inhibitors of ATXN expression: Validation of Cytotoxic Assay
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.
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.
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.
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.
AID588378qHTS for Inhibitors of ATXN expression: Validation
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.
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.
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.
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.
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.
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.
AID1498143Inhibition of Plasmodium falciparum 3D7 choline kinase expressed in Escherichia coli BL21(DE3) assessed as reduction in phosphocholine formation2018Bioorganic & medicinal chemistry letters, 08-01, Volume: 28, Issue:14
1,2-Diphenoxiethane salts as potent antiplasmodial agents.
AID1150505Toxicity in ip dosed Charles River CD-1 albino mouse assessed as mortality at >LD95 in presence of choline1976Journal of medicinal chemistry, Jun, Volume: 19, Issue:6
Synthesis and structure-toxicity relationships of three new stable analogues of acetyl-seco-hemicholinium-3.
AID52113Apparent Michaelis-Menten Constant (KM) for the acetylation of compound was calculated from Linewear-Burke plots by incubating for 10 minutes at 37 degrees Centigrade1984Journal of medicinal chemistry, Jun, Volume: 27, Issue:6
Acetylation of some novel hemicholinium compounds by soluble choline acetyltransferase: structure-activity relationships.
AID279808Inhibition of Plasmodium falciparum choline kinase at 50 uM in presence of 250 uM ATP2007Antimicrobial agents and chemotherapy, Feb, Volume: 51, Issue:2
Inhibition of Plasmodium falciparum choline kinase by hexadecyltrimethylammonium bromide: a possible antimalarial mechanism.
AID1150502Toxicity in ip dosed Charles River CD-1 albino mouse assessed as reduction of cardiac contraction1976Journal of medicinal chemistry, Jun, Volume: 19, Issue:6
Synthesis and structure-toxicity relationships of three new stable analogues of acetyl-seco-hemicholinium-3.
AID279792Inhibition of Plasmodium falciparum choline kinase at 50 uM in presence of 100 uM ATP2007Antimicrobial agents and chemotherapy, Feb, Volume: 51, Issue:2
Inhibition of Plasmodium falciparum choline kinase by hexadecyltrimethylammonium bromide: a possible antimalarial mechanism.
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.
AID194452In vitro inhibition of sodium-dependent high-affinity choline uptake activity (1 uM choline) at 1E-8 M concentration in the absence of thiosulfate1983Journal of medicinal chemistry, Jan, Volume: 26, Issue:1
Synthesis and biological activity of a 2-bromoethylamine (mustard) derivative of hemicholinium-3 and hemicholinium-15.
AID1150496Binding affinity to horse serum butyrylcholinesterase in water at pH 7.4 at 100 x 10'-5 M up to 6 hrs by UV-spectra analysis1976Journal of medicinal chemistry, Jun, Volume: 19, Issue:6
Synthesis and structure-toxicity relationships of three new stable analogues of acetyl-seco-hemicholinium-3.
AID279793Inhibition of Plasmodium falciparum choline kinase at 150 uM in presence of 100 uM ATP2007Antimicrobial agents and chemotherapy, Feb, Volume: 51, Issue:2
Inhibition of Plasmodium falciparum choline kinase by hexadecyltrimethylammonium bromide: a possible antimalarial mechanism.
AID51964Rate of acetylation of 13.0+/-1.1 umol compound by 1 g of choline acetyltransferase (ChAc) by incubating for 10 minutes at 37 degrees Centigrade1984Journal of medicinal chemistry, Jun, Volume: 27, Issue:6
Acetylation of some novel hemicholinium compounds by soluble choline acetyltransferase: structure-activity relationships.
AID194455In vitro inhibition of sodium-dependent high-affinity choline uptake activity (1 uM choline) at 5E-8 M concentration in the absence of thiosulfate1983Journal of medicinal chemistry, Jan, Volume: 26, Issue:1
Synthesis and biological activity of a 2-bromoethylamine (mustard) derivative of hemicholinium-3 and hemicholinium-15.
AID1150501Toxicity in ip dosed Charles River CD-1 albino mouse measured within 5 mins1976Journal of medicinal chemistry, Jun, Volume: 19, Issue:6
Synthesis and structure-toxicity relationships of three new stable analogues of acetyl-seco-hemicholinium-3.
AID86113Compound was tested in vitro for antiproliferative activity against human HT-29 cell line2000Bioorganic & medicinal chemistry letters, Apr-17, Volume: 10, Issue:8
QSAR of 1,1'-(1,2-ethylenebisbenzyl)bis(4-substitutedpyridinium) dibromides as choline kinase inhibitors: a different approach for antiproliferative drug design.
AID194456In vitro inhibition of sodium-dependent high-affinity choline uptake activity (1 uM choline) at 5E-8 M concentration in the presence of thiosulfate1983Journal of medicinal chemistry, Jan, Volume: 26, Issue:1
Synthesis and biological activity of a 2-bromoethylamine (mustard) derivative of hemicholinium-3 and hemicholinium-15.
AID1498146Antiplasmodial activity against Plasmodium falciparum 3D7 infected in human erythrocytes after 72 hrs by SYBR green 1-based fluorimetric assay2018Bioorganic & medicinal chemistry letters, 08-01, Volume: 28, Issue:14
1,2-Diphenoxiethane salts as potent antiplasmodial agents.
AID1150503Toxicity in ip dosed Charles River CD-1 albino mouse assessed as increase of peristalsis of small intestine1976Journal of medicinal chemistry, Jun, Volume: 19, Issue:6
Synthesis and structure-toxicity relationships of three new stable analogues of acetyl-seco-hemicholinium-3.
AID197722Na-dependent high-affinity choline uptake at 25 nM concentration for 15 min post wash preincubation time.1983Journal of medicinal chemistry, Jan, Volume: 26, Issue:1
Synthesis and biological activity of a 2-bromoethylamine (mustard) derivative of hemicholinium-3 and hemicholinium-15.
AID1150506Toxicity in ip dosed Charles River CD-1 albino mouse assessed as mortality at >LD95 in presence of neostigmine1976Journal of medicinal chemistry, Jun, Volume: 19, Issue:6
Synthesis and structure-toxicity relationships of three new stable analogues of acetyl-seco-hemicholinium-3.
AID1150495Binding affinity to bovine erythrocyte acetylcholinesterase in water at pH 7.4 at 100 x 10'-5 M up to 6 hrs by UV-spectra analysis1976Journal of medicinal chemistry, Jun, Volume: 19, Issue:6
Synthesis and structure-toxicity relationships of three new stable analogues of acetyl-seco-hemicholinium-3.
AID1498144Antiplasmodial activity against Plasmodium falciparum Dd2 infected in human erythrocytes after 48 hrs by picogreen-microfluorimetric assay2018Bioorganic & medicinal chemistry letters, 08-01, Volume: 28, Issue:14
1,2-Diphenoxiethane salts as potent antiplasmodial agents.
AID197721Na-dependent high-affinity choline uptake at 25 nM concentration for 0 min post wash pre-incubation time.1983Journal of medicinal chemistry, Jan, Volume: 26, Issue:1
Synthesis and biological activity of a 2-bromoethylamine (mustard) derivative of hemicholinium-3 and hemicholinium-15.
AID1498147Inhibition of Plasmodium falciparum choline kinase using [methyl-14C]choline as substrate assessed as reduction in rate of incorporation of 14C from [methyl-14C]choline into phosphocholine preincubated for 5 mins followed by substrate addition measured af2018Bioorganic & medicinal chemistry letters, 08-01, Volume: 28, Issue:14
1,2-Diphenoxiethane salts as potent antiplasmodial agents.
AID279809Inhibition of Plasmodium falciparum choline kinase at 150 uM in presence of 250 uM ATP2007Antimicrobial agents and chemotherapy, Feb, Volume: 51, Issue:2
Inhibition of Plasmodium falciparum choline kinase by hexadecyltrimethylammonium bromide: a possible antimalarial mechanism.
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.
AID1346901Human CHT (Choline transporter)2003Neurochemical research, Apr, Volume: 28, Issue:3-4
High-affinity choline transporter.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (955)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990614 (64.29)18.7374
1990's185 (19.37)18.2507
2000's102 (10.68)29.6817
2010's45 (4.71)24.3611
2020's9 (0.94)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 25.41

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 Index25.41 (24.57)
Research Supply Index3.00 (2.92)
Research Growth Index5.07 (4.65)
Search Engine Demand Index26.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (25.41)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.10%)5.53%
Trials0 (0.00%)5.53%
Reviews16 (1.66%)6.00%
Reviews1 (5.26%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other946 (98.23%)84.16%
Other18 (94.74%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]