Page last updated: 2024-11-04

4-diphenylacetoxy-1,1-dimethylpiperidinium

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

Description

4-diphenylacetoxy-1,1-dimethylpiperidinium: muscarinic receptor antagonist; RN given refers to parent cpd; do not confuse abbreviation 4-DAMP with a similar cpd which does not contain dimethyl groups [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

4-DAMP(1+) : A quaternary ammonium salt obtained by formal methylation of the tertiary amino function of 4-diphenylacetoxy-N-methylpiperidine. [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 CID1734
CHEMBL ID76897
CHEMBL ID168067
CHEBI ID73467
SCHEMBL ID2730650
MeSH IDM0125170

Synonyms (41)

Synonym
CHEMBL76897 ,
gtpl307
(1,1-dimethylpiperidin-1-ium-4-yl) 2,2-di(phenyl)acetate
NCGC00015304-01
lopac-d-104
NCGC00024611-01
tocris-0482
LOPAC0_000407
NCGC00163244-01
4-diphenylacetoxy-1,1-dimethylpiperidinium
NCGC00024611-02
L023947
NCGC00015304-04
81405-11-0
chebi:73467 ,
CHEMBL168067 ,
acetic acid 4-[(4-acetoxy-phenyl)-pyridin-2-yl-methyl]-phenyl ester
bdbm50176065
4-diphenylacetoxy-1,1-dimethyl-piperidinium; iodide
CCG-204500
106458-69-9
NCGC00015304-03
NCGC00015304-02
unii-t2c393vhb9
t2c393vhb9 ,
4-(2,2-diphenylacetoxy)-1,1-dimethylpiperidinium
4-damp(1+)
n,n-dimethyl-4-(diphenylacetoxy)piperidinium
SCHEMBL2730650
DTXSID70231086
Q27073759
1,1-dimethyl-4-diphenylacetoxypiperidinium ion
4-((2,2-diphenylacetyl)oxy)-1,1-dimethylpiperidinium
piperidinium, 4-((diphenylacetyl)oxy)-1,1-dimethyl-
piperidinium, 4-((2,2-diphenylacetyl)oxy)-1,1-dimethyl-
NCGC00015304-09
NCGC00015304-08
[3h]4-damp
gtpl11497
(1,1-dimethylpiperidin-1-ium-4-yl) 2,2-diphenylacetate,bromide
2-p-cyanophenyl-1,3-dithiolane

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" All these antagonists caused a concentration-dependent rightward shift of the dose-response curve for carbachol-stimulated amylase release without altering the maximal response."( Characterization of muscarinic receptor subtypes on rat pancreatic acini: pharmacological identification by secretory responses and binding studies.
Kashima, K; Kataoka, K; Kato, M; Kuriyama, K; Ohkuma, S, 1992
)
0.28
" The muscarinic antagonists pirenzepine, (+-)-5,11-dihydro-11-[[[2-[2-((dipropylamino)methyl)-1-piperidinyl] ethyl]amino]-carbonyl]-6H-pyrido(2,3-b)(1,4)-benzodiazepin-6-one (AF-DX 384), 11-[[4-[4-(diethylamino)butyl]-1-piperidinyl]acetyl]-5,11-dihydro- 6H-pyrido(2,3-b)(1,4)-benzodiazepin-6-one (AQ-RA 741), p-fluorohexahydro-sila-difenidol (p-F-HHSiD), 4-diphenylacetoxy-N-methylpiperidine methiodide (4-DAMP) and (R)- and (S)-hexahydro-difenidol [(R)-HHD, (S)-HHD] shifted the muscarine, methacholine or carbachol dose-response curve to the right in a competitive manner."( Characterization of muscarinic receptors mediating vasodilation in guinea-pig ileum submucosal arterioles by the use of computer-assisted videomicroscopy.
Bungardt, E; Feifel, R; Lambrecht, G; Moser, U; Mutschler, E; Surprenant, A; Tacke, R; Vockert, E, 1992
)
0.28
" Log ID50s calculated for the antagonists from the dose-response curves were found to correlate significantly with the log Kis of the antagonists for the muscarinic M3 receptor subtype."( Pressor response to posterior hypothalamic administration of carbachol is mediated by muscarinic M3 receptor.
Martin, JR, 1992
)
0.28
" Low concentrations of pirenzepine (10(-8) M), produced a rightward shift in the dose-response curve to McN, without inhibiting responses to carbachol."( Functional subtyping of muscarinic receptors on canine esophageal mucosa.
Donoff, B; Lad, R; Rangachari, PK, 1991
)
0.28
" Alinidine (10(-6) M) shifted the dose-response curves of acetylcholine and carbachol to the right, but it did not affect those for isosorbide dinitrate, isoproterenol and adenosine."( Anti-muscarinic effect of alinidine on acetylcholine-induced vasodilation in isolated and perfused dog coronary arteries.
Chiba, S; Furukawa, Y; Nakane, T, 1991
)
0.28
" Dose-response curves were constructed, and the IC50s determined for 4-diphenylacetoxy-N-methylpiperidine methiodide (4-DAMP), pirenzepine (PRZ) and 11-2[[2-[(diethylamino)methyl]-1-piperidinyl]acetyl]-5,11,-dihydro- 6H-pyrido[2,3-b] [1,4]benzodiazepin-6-one (AF-DX 116) were 72 nM, 385 nM, and 24 microM, respectively."( Activation of the pharmacologically defined M3 muscarinic receptor depolarizes hippocampal pyramidal cells.
Alger, BE; Pitler, TA, 1990
)
0.28
" All the antagonists shifted the methacholine dose-response curve to the right in a parallel and concentration-dependent fashion, yielding Schild plots with slopes not significantly different from unity."( Characterization of the muscarinic receptor subtype involved in phosphoinositide metabolism in bovine tracheal smooth muscle.
Elzinga, CR; Meurs, H; Roffel, AF; Zaagsma, J, 1990
)
0.28
" 4-DAMP (10(-9) to 10(-6) M) caused a progressive parallel rightward shift in the acetylcholine dose-response curve without a change in maximal amylase release."( Muscarinic receptor subtypes on rat pancreatic acini: secretion and binding studies.
Louie, DS; Owyang, C, 1986
)
0.27
" 4-DAMP, atropine, and pirenzepine caused a progressive parallel rightward shift in the dose-response curve of pancreatic secretion for bethanechol."( Subtypes of muscarinic receptors in pancreatic exocrine secretion in anesthetized dog.
Chiba, S; Haruta, K; Homma, N; Horiuchi, A; Iwatsuki, K; Yonekura, H, 1989
)
0.28
" Atropine caused a dose-dependent rightward shift in the dose-response curves of inhibitory and excitatory effects of the two muscarinic agonists."( Pharmacologic identification, activation and antagonism of two muscarine receptor subtypes in the lower esophageal sphincter.
Gilbert, R; Goyal, RK; Rattan, S, 1984
)
0.27
" Oxotremorine generated dose-response curves that were similar in both the circular and longitudinal vectors and intermediate to those previously reported for carbachol and aceclidine."( The effect of muscarinic agonists and selective receptor subtype antagonists on the contractile response of the isolated rhesus monkey ciliary muscle.
Gabelt, BT; Kaufman, PL; Poyer, JF, 1994
)
0.29
" In experiment 1, steers were dosed with 0, 25, or 50 micrograms."( Effects of slaframine and 4-diphenylacetoxy-N-methylpiperidine methiodide (4DAMP) on pancreatic exocrine secretion in the bovine.
Croom, WJ; Hagler, WM; Harmon, DL; Krehbiel, CR; St Jean, G; Walker, JA, 1994
)
0.29
"1 microM), shifted the dose-response curve for muscarine-induced adrenaline secretion to the right."( Muscarinic receptor subtypes mediating catecholamine secretion and increase in intracellular Ca2+ concentration in adrenal chromaffin cells of the guinea pig.
Asano, T; Ito, S; Nakazato, Y; Ohta, T; Otsuguro, K, 1995
)
0.29
" Dose-response curves were constructed using the putatively selective antagonists pirenzepine (M1), gallamine (M2) and 4-DAMP (M3: 4-diphenyl-acetoxy-N-methylpiperidine) and compared with the non-selective blocker, atropine."( Functional characterization of peripheral muscarinic subtypes in anesthetized cats.
Koss, MC, 1997
)
0.3
" Our results indicated that acute exercise induced the following effects: (1) the dose-response curves of ACh and CLO shifted to the left; (2) the high-affinity M3 binding sites increased in number but not in affinity; (3) the alpha2 binding sites decreased in number but increased in affinity."( Acute exercise enhances receptor-mediated endothelium-dependent vasodilation by receptor upregulation.
Chen, H; Cheng, L; Hsu, L; Jen, CJ; Lin, MT; Yang, C, 1999
)
0.3
" That some patients still yielded to acute organophosphate poisoning despite repeated dosing of atropine suggests that cellular mechanisms that are independent of muscarinic receptor activation may also be engaged in organophosphate poisoning."( Muscarinic receptor-independent activation of cyclic adenosine monophosphate-dependent protein kinase in rostral ventrolateral medulla underlies the sympathoexcitatory phase of cardiovascular responses during mevinphos intoxication in the rat.
Chan, SH; Chang, AY; Tsai, CY; Wu, CH, 2007
)
0.34
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
cholinergic antagonistAny drug that binds to but does not activate cholinergic receptors, thereby blocking the actions of acetylcholine or cholinergic agonists.
muscarinic antagonistA drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
[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
quaternary ammonium ionA derivative of ammonium, NH4(+), in which all four of the hydrogens bonded to nitrogen have been replaced with univalent (usually organyl) groups.
[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 (14)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency44.66840.003245.467312,589.2998AID2517
Chain A, HADH2 proteinHomo sapiens (human)Potency7.94330.025120.237639.8107AID886
Chain B, HADH2 proteinHomo sapiens (human)Potency7.94330.025120.237639.8107AID886
ATAD5 protein, partialHomo sapiens (human)Potency2.90810.004110.890331.5287AID493107
regulator of G-protein signaling 4Homo sapiens (human)Potency0.16820.531815.435837.6858AID504845
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency6.70160.035520.977089.1251AID504332
cytochrome P450 2D6 isoform 1Homo sapiens (human)Potency39.81070.00207.533739.8107AID891
cytochrome P450 2C9 precursorHomo sapiens (human)Potency39.81070.00636.904339.8107AID883
D(1A) dopamine receptorHomo sapiens (human)Potency0.25930.02245.944922.3872AID488982
serine/threonine-protein kinase mTOR isoform 1Homo sapiens (human)Potency2.07490.00378.618923.2809AID2668
histone acetyltransferase KAT2A isoform 1Homo sapiens (human)Potency29.90330.251215.843239.8107AID504327
muscarinic acetylcholine receptor M1Rattus norvegicus (Norway rat)Potency0.01350.00106.000935.4813AID943; AID944
lethal factor (plasmid)Bacillus anthracis str. A2012Potency12.58930.020010.786931.6228AID912
Histamine H2 receptorCavia porcellus (domestic guinea pig)Potency39.81070.00638.235039.8107AID883
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (31)

Assay IDTitleYearJournalArticle
AID1345511Rat M5 receptor (Acetylcholine receptors (muscarinic))1992Life sciences, , Volume: 51, Issue:12
Cloning of the rat M3, M4 and M5 muscarinic acetylcholine receptor genes by the polymerase chain reaction (PCR) and the pharmacological characterization of the expressed genes.
AID1345465Human M4 receptor (Acetylcholine receptors (muscarinic))1991The Journal of pharmacology and experimental therapeutics, Feb, Volume: 256, Issue:2
Antagonist binding profiles of five cloned human muscarinic receptor subtypes.
AID1345286Human M1 receptor (Acetylcholine receptors (muscarinic))1991The Journal of pharmacology and experimental therapeutics, Feb, Volume: 256, Issue:2
Antagonist binding profiles of five cloned human muscarinic receptor subtypes.
AID1345699Rat M3 receptor (Acetylcholine receptors (muscarinic))1992Life sciences, , Volume: 51, Issue:12
Cloning of the rat M3, M4 and M5 muscarinic acetylcholine receptor genes by the polymerase chain reaction (PCR) and the pharmacological characterization of the expressed genes.
AID1345364Rat M2 receptor (Acetylcholine receptors (muscarinic))1998The Journal of pharmacology and experimental therapeutics, Feb, Volume: 284, Issue:2
Pharmacological comparison of the cloned human and rat M2 muscarinic receptor genes expressed in the murine fibroblast (B82) cell line.
AID1345364Rat M2 receptor (Acetylcholine receptors (muscarinic))1992Life sciences, , Volume: 51, Issue:12
Cloning of the rat M3, M4 and M5 muscarinic acetylcholine receptor genes by the polymerase chain reaction (PCR) and the pharmacological characterization of the expressed genes.
AID1345326Human M2 receptor (Acetylcholine receptors (muscarinic))1998The Journal of pharmacology and experimental therapeutics, Feb, Volume: 284, Issue:2
Pharmacological comparison of the cloned human and rat M2 muscarinic receptor genes expressed in the murine fibroblast (B82) cell line.
AID1345343Human M3 receptor (Acetylcholine receptors (muscarinic))1991The Journal of pharmacology and experimental therapeutics, Feb, Volume: 256, Issue:2
Antagonist binding profiles of five cloned human muscarinic receptor subtypes.
AID1345543Human M5 receptor (Acetylcholine receptors (muscarinic))1991The Journal of pharmacology and experimental therapeutics, Feb, Volume: 256, Issue:2
Antagonist binding profiles of five cloned human muscarinic receptor subtypes.
AID1345435Rat M4 receptor (Acetylcholine receptors (muscarinic))1992Life sciences, , Volume: 51, Issue:12
Cloning of the rat M3, M4 and M5 muscarinic acetylcholine receptor genes by the polymerase chain reaction (PCR) and the pharmacological characterization of the expressed genes.
AID1345189Rat M1 receptor (Acetylcholine receptors (muscarinic))1992Life sciences, , Volume: 51, Issue:12
Cloning of the rat M3, M4 and M5 muscarinic acetylcholine receptor genes by the polymerase chain reaction (PCR) and the pharmacological characterization of the expressed genes.
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.
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.
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.
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.
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.
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.
AID588349qHTS for Inhibitors of ATXN expression: Validation of Cytotoxic Assay
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.
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.
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.
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.
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.
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.
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.
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.
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.
AID588378qHTS for Inhibitors of ATXN expression: Validation
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 (433)

TimeframeStudies, This Drug (%)All Drugs %
pre-199030 (6.93)18.7374
1990's213 (49.19)18.2507
2000's132 (30.48)29.6817
2010's51 (11.78)24.3611
2020's7 (1.62)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 9.05

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 Index9.05 (24.57)
Research Supply Index6.10 (2.92)
Research Growth Index5.15 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (9.05)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.22%)5.53%
Reviews4 (0.90%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other441 (98.88%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]