Page last updated: 2024-11-06

n-methyl-n-(1-methyl-4-pyrrolidino-2-butynyl)acetamide

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Description

N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide: RN given refers to parent cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID55005
CHEMBL ID310852
CHEBI ID125413
SCHEMBL ID3603670
MeSH IDM0116273

Synonyms (20)

Synonym
CHEMBL310852 ,
bm 5
acetamide, n-methyl-n-(1-methyl-4-(1-pyrrolidinyl)-2-butynyl)-
n-methyl-n-(1-methyl-4-(1-pyrrolidinyl)-2-butynyl)acetamide
brn 4183507
n-methyl-n-(1-methyl-4-pyrrolidino-2-butynyl)acetamide
CHEBI:125413
SCHEMBL3603670
n-methyl-n-(1-methyl-4-pyrrolidin-1-yl-but-2-ynyl)-acetamide
n-methyl-n-(1-methyl-4-pyrrolidin-1-yl-but-2-ynyl)-acetamide (r)
bdbm50004734
n-methyl-n-(1-methyl-4-pyrrolidin-1-yl-but-2-ynyl)-acetamide (s)
n-methyl-n-(1-methyl-4-pyrrolidin-1-yl-but-2-ynyl)-acetamide (bm 5)
83481-69-0
BRD-A52647795-001-01-9
n-methyl-n-(1-methyl-4-pyrrolidino-2-bu-tynyl)acetamide
Q27216030
n-methyl-n-[5-(1-pyrrolidinyl)pent-3-yn-2-yl]acetamide
DTXSID901003460
n-methyl-n-[5-(pyrrolidin-1-yl)pent-3-yn-2-yl]acetamide

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Gallamine caused parallel shifts to the right in the dose-response curves for inhibition of adenylate cyclase activity by the highly efficacious muscarinic agonist oxotremorine-M and the partial agonist Bm 5 [N-methyl-N-(1-methyl-4-pyrrolidino)-2-butynyl acetamide]."( Gallamine allosterically antagonizes muscarinic receptor-mediated inhibition of adenylate cyclase activity in the rat myocardium.
Ehlert, FJ, 1988
)
0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
N-alkylpyrrolidine
[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 (10)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Muscarinic acetylcholine receptor M2Homo sapiens (human)Ki0.33000.00000.690210.0000AID141401
Muscarinic acetylcholine receptor M4Homo sapiens (human)Ki0.33000.00000.79519.1201AID141401
Muscarinic acetylcholine receptor M1Rattus norvegicus (Norway rat)Ki0.04980.00010.579710.0000AID142216; AID142217; AID142223; AID142224
Muscarinic acetylcholine receptor M3Rattus norvegicus (Norway rat)Ki0.12550.00011.48339.1400AID142216; AID142217; AID142223; AID142224; AID142915
Muscarinic acetylcholine receptor M4Rattus norvegicus (Norway rat)Ki0.04980.00010.68688.2600AID142216; AID142217; AID142223; AID142224
Muscarinic acetylcholine receptor M5Rattus norvegicus (Norway rat)Ki0.04980.00010.66618.2600AID142216; AID142217; AID142223; AID142224
Muscarinic acetylcholine receptor M5Homo sapiens (human)Ki0.33000.00000.72926.9183AID141401
Muscarinic acetylcholine receptor M2Rattus norvegicus (Norway rat)Ki0.17090.00010.58908.2600AID101701; AID101704; AID142216; AID142217; AID142223; AID142224; AID142915
Muscarinic acetylcholine receptor M1Homo sapiens (human)Ki0.33000.00000.59729.1201AID141401
Muscarinic acetylcholine receptor M3Homo sapiens (human)Ki0.33000.00000.54057.7600AID141401
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (39)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathwayMuscarinic acetylcholine receptor M2Homo sapiens (human)
adenylate cyclase-modulating G protein-coupled receptor signaling pathwayMuscarinic acetylcholine receptor M2Homo sapiens (human)
phospholipase C-activating G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M2Homo sapiens (human)
G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M2Homo sapiens (human)
nervous system developmentMuscarinic acetylcholine receptor M2Homo sapiens (human)
regulation of heart contractionMuscarinic acetylcholine receptor M2Homo sapiens (human)
response to virusMuscarinic acetylcholine receptor M2Homo sapiens (human)
G protein-coupled serotonin receptor signaling pathwayMuscarinic acetylcholine receptor M2Homo sapiens (human)
presynaptic modulation of chemical synaptic transmissionMuscarinic acetylcholine receptor M2Homo sapiens (human)
regulation of smooth muscle contractionMuscarinic acetylcholine receptor M2Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M2Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerMuscarinic acetylcholine receptor M2Homo sapiens (human)
chemical synaptic transmissionMuscarinic acetylcholine receptor M2Homo sapiens (human)
signal transductionMuscarinic acetylcholine receptor M4Homo sapiens (human)
cell surface receptor signaling pathwayMuscarinic acetylcholine receptor M4Homo sapiens (human)
G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M4Homo sapiens (human)
regulation of locomotionMuscarinic acetylcholine receptor M4Homo sapiens (human)
G protein-coupled serotonin receptor signaling pathwayMuscarinic acetylcholine receptor M4Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M4Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerMuscarinic acetylcholine receptor M4Homo sapiens (human)
chemical synaptic transmissionMuscarinic acetylcholine receptor M4Homo sapiens (human)
gastric acid secretionMuscarinic acetylcholine receptor M5Homo sapiens (human)
G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M5Homo sapiens (human)
dopamine transportMuscarinic acetylcholine receptor M5Homo sapiens (human)
transmission of nerve impulseMuscarinic acetylcholine receptor M5Homo sapiens (human)
regulation of phosphatidylinositol dephosphorylationMuscarinic acetylcholine receptor M5Homo sapiens (human)
G protein-coupled serotonin receptor signaling pathwayMuscarinic acetylcholine receptor M5Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerMuscarinic acetylcholine receptor M5Homo sapiens (human)
chemical synaptic transmissionMuscarinic acetylcholine receptor M5Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M5Homo sapiens (human)
positive regulation of monoatomic ion transportMuscarinic acetylcholine receptor M1Homo sapiens (human)
signal transductionMuscarinic acetylcholine receptor M1Homo sapiens (human)
G protein-coupled receptor signaling pathwayMuscarinic acetylcholine receptor M1Homo sapiens (human)
protein kinase C-activating G protein-coupled receptor signaling pathwayMuscarinic acetylcholine receptor M1Homo sapiens (human)
phospholipase C-activating G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M1Homo sapiens (human)
G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M1Homo sapiens (human)
neuromuscular synaptic transmissionMuscarinic acetylcholine receptor M1Homo sapiens (human)
nervous system developmentMuscarinic acetylcholine receptor M1Homo sapiens (human)
regulation of locomotionMuscarinic acetylcholine receptor M1Homo sapiens (human)
saliva secretionMuscarinic acetylcholine receptor M1Homo sapiens (human)
cognitionMuscarinic acetylcholine receptor M1Homo sapiens (human)
regulation of postsynaptic membrane potentialMuscarinic acetylcholine receptor M1Homo sapiens (human)
regulation of glial cell proliferationMuscarinic acetylcholine receptor M1Homo sapiens (human)
positive regulation of intracellular protein transportMuscarinic acetylcholine receptor M1Homo sapiens (human)
G protein-coupled serotonin receptor signaling pathwayMuscarinic acetylcholine receptor M1Homo sapiens (human)
postsynaptic modulation of chemical synaptic transmissionMuscarinic acetylcholine receptor M1Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerMuscarinic acetylcholine receptor M1Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M1Homo sapiens (human)
chemical synaptic transmissionMuscarinic acetylcholine receptor M1Homo sapiens (human)
calcium-mediated signalingMuscarinic acetylcholine receptor M3Homo sapiens (human)
regulation of monoatomic ion transmembrane transporter activityMuscarinic acetylcholine receptor M3Homo sapiens (human)
smooth muscle contractionMuscarinic acetylcholine receptor M3Homo sapiens (human)
signal transductionMuscarinic acetylcholine receptor M3Homo sapiens (human)
G protein-coupled receptor signaling pathwayMuscarinic acetylcholine receptor M3Homo sapiens (human)
phospholipase C-activating G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M3Homo sapiens (human)
G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M3Homo sapiens (human)
synaptic transmission, cholinergicMuscarinic acetylcholine receptor M3Homo sapiens (human)
nervous system developmentMuscarinic acetylcholine receptor M3Homo sapiens (human)
positive regulation of insulin secretionMuscarinic acetylcholine receptor M3Homo sapiens (human)
protein modification processMuscarinic acetylcholine receptor M3Homo sapiens (human)
positive regulation of smooth muscle contractionMuscarinic acetylcholine receptor M3Homo sapiens (human)
saliva secretionMuscarinic acetylcholine receptor M3Homo sapiens (human)
acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M3Homo sapiens (human)
G protein-coupled serotonin receptor signaling pathwayMuscarinic acetylcholine receptor M3Homo sapiens (human)
ion channel modulating, G protein-coupled receptor signaling pathwayMuscarinic acetylcholine receptor M3Homo sapiens (human)
ligand-gated ion channel signaling pathwayMuscarinic acetylcholine receptor M3Homo sapiens (human)
regulation of smooth muscle contractionMuscarinic acetylcholine receptor M3Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerMuscarinic acetylcholine receptor M3Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M3Homo sapiens (human)
chemical synaptic transmissionMuscarinic acetylcholine receptor M3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
G protein-coupled acetylcholine receptor activityMuscarinic acetylcholine receptor M2Homo sapiens (human)
arrestin family protein bindingMuscarinic acetylcholine receptor M2Homo sapiens (human)
G protein-coupled serotonin receptor activityMuscarinic acetylcholine receptor M2Homo sapiens (human)
G protein-coupled serotonin receptor activityMuscarinic acetylcholine receptor M4Homo sapiens (human)
G protein-coupled acetylcholine receptor activityMuscarinic acetylcholine receptor M4Homo sapiens (human)
phosphatidylinositol phospholipase C activityMuscarinic acetylcholine receptor M5Homo sapiens (human)
protein bindingMuscarinic acetylcholine receptor M5Homo sapiens (human)
G protein-coupled acetylcholine receptor activityMuscarinic acetylcholine receptor M5Homo sapiens (human)
G protein-coupled serotonin receptor activityMuscarinic acetylcholine receptor M5Homo sapiens (human)
phosphatidylinositol phospholipase C activityMuscarinic acetylcholine receptor M1Homo sapiens (human)
protein bindingMuscarinic acetylcholine receptor M1Homo sapiens (human)
G protein-coupled acetylcholine receptor activityMuscarinic acetylcholine receptor M1Homo sapiens (human)
G protein-coupled serotonin receptor activityMuscarinic acetylcholine receptor M1Homo sapiens (human)
phosphatidylinositol phospholipase C activityMuscarinic acetylcholine receptor M3Homo sapiens (human)
protein bindingMuscarinic acetylcholine receptor M3Homo sapiens (human)
G protein-coupled acetylcholine receptor activityMuscarinic acetylcholine receptor M3Homo sapiens (human)
signaling receptor activityMuscarinic acetylcholine receptor M3Homo sapiens (human)
acetylcholine bindingMuscarinic acetylcholine receptor M3Homo sapiens (human)
G protein-coupled serotonin receptor activityMuscarinic acetylcholine receptor M3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (18)

Processvia Protein(s)Taxonomy
plasma membraneMuscarinic acetylcholine receptor M2Homo sapiens (human)
membraneMuscarinic acetylcholine receptor M2Homo sapiens (human)
clathrin-coated endocytic vesicle membraneMuscarinic acetylcholine receptor M2Homo sapiens (human)
asymmetric synapseMuscarinic acetylcholine receptor M2Homo sapiens (human)
symmetric synapseMuscarinic acetylcholine receptor M2Homo sapiens (human)
presynaptic membraneMuscarinic acetylcholine receptor M2Homo sapiens (human)
neuronal cell bodyMuscarinic acetylcholine receptor M2Homo sapiens (human)
axon terminusMuscarinic acetylcholine receptor M2Homo sapiens (human)
postsynaptic membraneMuscarinic acetylcholine receptor M2Homo sapiens (human)
glutamatergic synapseMuscarinic acetylcholine receptor M2Homo sapiens (human)
cholinergic synapseMuscarinic acetylcholine receptor M2Homo sapiens (human)
plasma membraneMuscarinic acetylcholine receptor M2Homo sapiens (human)
synapseMuscarinic acetylcholine receptor M2Homo sapiens (human)
dendriteMuscarinic acetylcholine receptor M2Homo sapiens (human)
plasma membraneMuscarinic acetylcholine receptor M4Homo sapiens (human)
postsynaptic membraneMuscarinic acetylcholine receptor M4Homo sapiens (human)
dendriteMuscarinic acetylcholine receptor M4Homo sapiens (human)
plasma membraneMuscarinic acetylcholine receptor M4Homo sapiens (human)
synapseMuscarinic acetylcholine receptor M4Homo sapiens (human)
plasma membraneMuscarinic acetylcholine receptor M5Homo sapiens (human)
postsynaptic membraneMuscarinic acetylcholine receptor M5Homo sapiens (human)
dendriteMuscarinic acetylcholine receptor M5Homo sapiens (human)
plasma membraneMuscarinic acetylcholine receptor M5Homo sapiens (human)
synapseMuscarinic acetylcholine receptor M5Homo sapiens (human)
plasma membraneMuscarinic acetylcholine receptor M1Homo sapiens (human)
membraneMuscarinic acetylcholine receptor M1Homo sapiens (human)
presynaptic membraneMuscarinic acetylcholine receptor M1Homo sapiens (human)
axon terminusMuscarinic acetylcholine receptor M1Homo sapiens (human)
Schaffer collateral - CA1 synapseMuscarinic acetylcholine receptor M1Homo sapiens (human)
postsynaptic density membraneMuscarinic acetylcholine receptor M1Homo sapiens (human)
glutamatergic synapseMuscarinic acetylcholine receptor M1Homo sapiens (human)
cholinergic synapseMuscarinic acetylcholine receptor M1Homo sapiens (human)
synapseMuscarinic acetylcholine receptor M1Homo sapiens (human)
dendriteMuscarinic acetylcholine receptor M1Homo sapiens (human)
plasma membraneMuscarinic acetylcholine receptor M1Homo sapiens (human)
endoplasmic reticulum membraneMuscarinic acetylcholine receptor M3Homo sapiens (human)
plasma membraneMuscarinic acetylcholine receptor M3Homo sapiens (human)
basal plasma membraneMuscarinic acetylcholine receptor M3Homo sapiens (human)
basolateral plasma membraneMuscarinic acetylcholine receptor M3Homo sapiens (human)
postsynaptic membraneMuscarinic acetylcholine receptor M3Homo sapiens (human)
synapseMuscarinic acetylcholine receptor M3Homo sapiens (human)
plasma membraneMuscarinic acetylcholine receptor M3Homo sapiens (human)
dendriteMuscarinic acetylcholine receptor M3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (60)

Assay IDTitleYearJournalArticle
AID142216Binding activity to muscarinic acetylcholine receptor in rat heart, assayed using [3H]QNB as a radioligand in the presence of Gpp(NH)p.1990Journal of medicinal chemistry, Dec, Volume: 33, Issue:12
Chemical and biochemical studies of 2-propynylpyrrolidine derivatives. Restricted-rotation analogues of N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM-5).
AID142224Binding affinity to muscarinic acetylcholine receptor was determined in presence of [3H]QNB radioligand (in vitro)1991Journal of medicinal chemistry, Aug, Volume: 34, Issue:8
Cholinergic activity of acetylenic imidazoles and related compounds.
AID75763Equilibrium dissociation constant of the compound-receptor complex was determined by its ability to antagonize carbachol-induced contractions in the ileum (spasmolytic activity)1989Journal of medicinal chemistry, Apr, Volume: 32, Issue:4
Conformationally restricted analogues of the muscarinic agent N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide.
AID101701Tested for binding affinity to [3H]QNB and GppNHp radiolabeled muscarinic M2 receptor in rat heart1993Journal of medicinal chemistry, Nov-12, Volume: 36, Issue:23
The synthesis and biochemical pharmacology of enantiomerically pure methylated oxotremorine derivatives.
AID116740Acute toxicity administered intraperitoneally to mice1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
5-Methyl-2-pyrrolidone analogues of oxotremorine as selective muscarinic agonists.
AID73717Concentration that elicits 50% of its own maximum contractile response in guinea pig ileum1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
5-Methyl-2-pyrrolidone analogues of oxotremorine as selective muscarinic agonists.
AID141198Relative efficacies determined with oxotremorine as the reference in guinea pig ileum, as a measure of muscarinic acetylcholine receptor M3 agonistic activity1992Journal of medicinal chemistry, Aug-21, Volume: 35, Issue:17
Urea and 2-imidazolidone derivatives of the muscarinic agents oxotremorine and N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide.
AID101703Binding affinity at [3H]QNB radiolabeled muscarinic M2 receptor in rat cortex.1993Journal of medicinal chemistry, Nov-12, Volume: 36, Issue:23
The synthesis and biochemical pharmacology of enantiomerically pure methylated oxotremorine derivatives.
AID75759Maximum contractile response relative to that elicited by carbachol in guinea pig ileum1989Journal of medicinal chemistry, Apr, Volume: 32, Issue:4
Conformationally restricted analogues of the muscarinic agent N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide.
AID73719Concentration that elicits 50% of its own maximum contractile response, in guinea pig ileum1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
Derivatives of the muscarinic agent N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide.
AID123417Antimuscarinic activity in intact mice was determined as the dose required to double the dose of oxotremorine inducing a predetermined tremor intensity.1989Journal of medicinal chemistry, Apr, Volume: 32, Issue:4
Conformationally restricted analogues of the muscarinic agent N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide.
AID141401Binding affinity was determined using [3H]-NMS for Muscarinic acetylcholine receptor in SK-N-SH neuroblastoma cells1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Functionalized congener approach for the design of novel muscarinic agents. Synthesis and pharmacological evaluation of N-methyl-N-[4-(1-pyrrolidinyl)-2-butynyl] amides.
AID142214Binding activity to the muscarinic acetylcholine receptor in rat cortex, assayed using [3H]PZ as a radioligand.1990Journal of medicinal chemistry, Dec, Volume: 33, Issue:12
Chemical and biochemical studies of 2-propynylpyrrolidine derivatives. Restricted-rotation analogues of N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM-5).
AID142915Muscarinic acetylcholine receptor binding affinity was determined using [3H]NMS for NG108-15 neuroblastoma cells1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Functionalized congener approach for the design of novel muscarinic agents. Synthesis and pharmacological evaluation of N-methyl-N-[4-(1-pyrrolidinyl)-2-butynyl] amides.
AID142223Binding affinity to muscarinic acetylcholine receptor was determined in presence of [3H]OXO-M radioligand (in vitro)1991Journal of medicinal chemistry, Aug, Volume: 34, Issue:8
Cholinergic activity of acetylenic imidazoles and related compounds.
AID142231Compound was tested for the concentration that inhibited the specific binding of (-)-[3H]-NMS to muscarinic receptor in the rat cerebral cortex.1989Journal of medicinal chemistry, Apr, Volume: 32, Issue:4
Conformationally restricted analogues of the muscarinic agent N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide.
AID77637Equilibrium dissociation constant muscarinic receptor complex, measured in guinea pig ileum1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
Derivatives of the muscarinic agent N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide.
AID228329Ratio of Ki value for QNB to that of Ki value for Oxo-M.1991Journal of medicinal chemistry, Aug, Volume: 34, Issue:8
Cholinergic activity of acetylenic imidazoles and related compounds.
AID142021Binding affinity at muscarinic acetylcholine receptor M4 from NG108-15 cell line in presence of [3H]-NMS1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Functionalized congener approach for the design of novel muscarinic agents. Synthesis and pharmacological evaluation of N-methyl-N-[4-(1-pyrrolidinyl)-2-butynyl] amides.
AID113326ED50 value as cholinergic agonism by measuring lacrimation in mice (in vivo)1991Journal of medicinal chemistry, Aug, Volume: 34, Issue:8
Cholinergic activity of acetylenic imidazoles and related compounds.
AID114480Central muscarinic activity administered intraperitoneally to mice, expressed as hypothermia1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
5-Methyl-2-pyrrolidone analogues of oxotremorine as selective muscarinic agonists.
AID230678Ratio of [3H]QNB+GppNHp/[3H]-QNB1993Journal of medicinal chemistry, Nov-12, Volume: 36, Issue:23
The synthesis and biochemical pharmacology of enantiomerically pure methylated oxotremorine derivatives.
AID142232Displacement of [3H]3-quinuclidinyl benzilate ([3H]-QNB) from muscarinic acetylcholine receptor of rat cerebral cortex1992Journal of medicinal chemistry, Aug-21, Volume: 35, Issue:17
Urea and 2-imidazolidone derivatives of the muscarinic agents oxotremorine and N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide.
AID142213Binding activity to the muscarinic acetylcholine receptor in rat cortex, assayed using [3H]CD as a radioligand.1990Journal of medicinal chemistry, Dec, Volume: 33, Issue:12
Chemical and biochemical studies of 2-propynylpyrrolidine derivatives. Restricted-rotation analogues of N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM-5).
AID113330ED50 value determined as oxotremorine antagonism by measuring salivation in mice (in vivo)1991Journal of medicinal chemistry, Aug, Volume: 34, Issue:8
Cholinergic activity of acetylenic imidazoles and related compounds.
AID104025Binding affinity at [3H]PZ radiolabeled muscarinic M1 receptor in rat cortex.1993Journal of medicinal chemistry, Nov-12, Volume: 36, Issue:23
The synthesis and biochemical pharmacology of enantiomerically pure methylated oxotremorine derivatives.
AID141330Percent increase in [3H]myo-inositol at muscarinic acetylcholine receptor M3 from SK-N-SH human neuroblastoma cells1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Functionalized congener approach for the design of novel muscarinic agents. Synthesis and pharmacological evaluation of N-methyl-N-[4-(1-pyrrolidinyl)-2-butynyl] amides.
AID114040Muscarinic activity administered intraperitoneally to mice, expressed as salivation1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
5-Methyl-2-pyrrolidone analogues of oxotremorine as selective muscarinic agonists.
AID142215Binding activity against Muscarinic acetylcholine receptor in rat cortex, using [3H]QNB as a radioligand.1990Journal of medicinal chemistry, Dec, Volume: 33, Issue:12
Chemical and biochemical studies of 2-propynylpyrrolidine derivatives. Restricted-rotation analogues of N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM-5).
AID77365Efficacy relative to that of carbachol1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
5-Methyl-2-pyrrolidone analogues of oxotremorine as selective muscarinic agonists.
AID77702Maximum contractile response relative to that elicited by carbachol was measured in guinea pig ileum1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
5-Methyl-2-pyrrolidone analogues of oxotremorine as selective muscarinic agonists.
AID113327ED50 value as cholinergic agonist by measuring salivation in mice (in vivo)1991Journal of medicinal chemistry, Aug, Volume: 34, Issue:8
Cholinergic activity of acetylenic imidazoles and related compounds.
AID77639Equilibrium dissociation constant receptor complex, measured in guinea pig urinary bladder1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
5-Methyl-2-pyrrolidone analogues of oxotremorine as selective muscarinic agonists.
AID77638Equilibrium dissociation constant receptor complex, measured in guinea pig ileum1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
5-Methyl-2-pyrrolidone analogues of oxotremorine as selective muscarinic agonists.
AID231029Muscarinic 1 receptor agonistic activity as the selectivity ratio of Ki against [3H]-QNB+ Gpp(NH)p to that of [3H]PZ1990Journal of medicinal chemistry, Dec, Volume: 33, Issue:12
Chemical and biochemical studies of 2-propynylpyrrolidine derivatives. Restricted-rotation analogues of N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM-5).
AID124472Antimuscarinic activity on the intact mice.(Dose required to double the dose of oxotremorine inducing a predetermined tremor intensity.)1992Journal of medicinal chemistry, Jan-24, Volume: 35, Issue:2
Phenyl-substituted analogues of oxotremorine as muscarinic antagonists.
AID112394Tremorolytic activity administered intraperitoneally to mice1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
5-Methyl-2-pyrrolidone analogues of oxotremorine as selective muscarinic agonists.
AID123418Dose required to double the dose of oxotremorine inducing a predetermined (grade 2) tremor intensity in mice1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
Derivatives of the muscarinic agent N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide.
AID101704Binding affinity at [3H]QNB radiolabeled muscarinic M2 receptor in rat heart.1993Journal of medicinal chemistry, Nov-12, Volume: 36, Issue:23
The synthesis and biochemical pharmacology of enantiomerically pure methylated oxotremorine derivatives.
AID142227Inhibition of [3H]N-methylscopolamine binding to muscarinic acetylcholine receptor of rat cerebral cortex.1992Journal of medicinal chemistry, Jan-24, Volume: 35, Issue:2
Phenyl-substituted analogues of oxotremorine as muscarinic antagonists.
AID113329ED50 value determined as oxotremorine antagonism by measuring lacrimation in mice (in vivo)1991Journal of medicinal chemistry, Aug, Volume: 34, Issue:8
Cholinergic activity of acetylenic imidazoles and related compounds.
AID141065Muscarinic acetylcholine receptor M3 agonistic/antagonistic activity in guinea pig ileum1992Journal of medicinal chemistry, Aug-21, Volume: 35, Issue:17
Urea and 2-imidazolidone derivatives of the muscarinic agents oxotremorine and N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide.
AID142020Percent inhibition against muscarinic acetylcholine receptor M4 from NG108-15 cell line1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Functionalized congener approach for the design of novel muscarinic agents. Synthesis and pharmacological evaluation of N-methyl-N-[4-(1-pyrrolidinyl)-2-butynyl] amides.
AID231028Muscarinic 1 receptor agonistic activity as the selectivity ratio of Ki against [3H]-QNB to that of [3H]PZ1990Journal of medicinal chemistry, Dec, Volume: 33, Issue:12
Chemical and biochemical studies of 2-propynylpyrrolidine derivatives. Restricted-rotation analogues of N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM-5).
AID141075Dissociation constant for complex with muscarinic acetylcholine receptor M3 of guinea pig ileum1992Journal of medicinal chemistry, Aug-21, Volume: 35, Issue:17
Urea and 2-imidazolidone derivatives of the muscarinic agents oxotremorine and N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide.
AID101700Binding affinity at [3H]CD radiolabeled muscarinic M2 receptor in rat cortex.1993Journal of medicinal chemistry, Nov-12, Volume: 36, Issue:23
The synthesis and biochemical pharmacology of enantiomerically pure methylated oxotremorine derivatives.
AID114478Central muscarinic activity administered intraperitoneally to mice, expressed as analgesia1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
5-Methyl-2-pyrrolidone analogues of oxotremorine as selective muscarinic agonists.
AID231030Muscarinic 2 receptor agonistic activity was determined as the selectivity ratio of Ki against [3H]QNB+ Gpp(NH)p to that of [3H]QNB1990Journal of medicinal chemistry, Dec, Volume: 33, Issue:12
Chemical and biochemical studies of 2-propynylpyrrolidine derivatives. Restricted-rotation analogues of N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM-5).
AID77367Efficacy relative to that of carbachol, measured in guinea pig ileum1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
Derivatives of the muscarinic agent N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide.
AID231701Relative [3H]QNB and [3H]-CD binding to muscarinic M2 receptor1993Journal of medicinal chemistry, Nov-12, Volume: 36, Issue:23
The synthesis and biochemical pharmacology of enantiomerically pure methylated oxotremorine derivatives.
AID77704Maximum contractile response relative to that elicited by carbachol, in guinea pig ileum1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
Derivatives of the muscarinic agent N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide.
AID142217Binding activity to muscarinic acetylcholine receptor in rat heart, assayed using [3H]-QNB as a radioligand.1990Journal of medicinal chemistry, Dec, Volume: 33, Issue:12
Chemical and biochemical studies of 2-propynylpyrrolidine derivatives. Restricted-rotation analogues of N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM-5).
AID113331ED50 value determined as oxotremorine antagonism by measuring tremors in mice (in vivo)1991Journal of medicinal chemistry, Aug, Volume: 34, Issue:8
Cholinergic activity of acetylenic imidazoles and related compounds.
AID141066Maximum contractile response relative to carbachol (E max) in guinea pig ileum as muscarinic acetylcholine receptor M3 agonistic/antagonistic activity1992Journal of medicinal chemistry, Aug-21, Volume: 35, Issue:17
Urea and 2-imidazolidone derivatives of the muscarinic agents oxotremorine and N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide.
AID142894The agonist ratio as the ratio of Ki against [3H]QNB to that of [3H]-CD1990Journal of medicinal chemistry, Dec, Volume: 33, Issue:12
Chemical and biochemical studies of 2-propynylpyrrolidine derivatives. Restricted-rotation analogues of N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM-5).
AID141333Percent binding affinity at muscarinic acetylcholine receptor M3 from SK-N-SH human neuroblastoma cells in presence of [3H]NMS1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Functionalized congener approach for the design of novel muscarinic agents. Synthesis and pharmacological evaluation of N-methyl-N-[4-(1-pyrrolidinyl)-2-butynyl] amides.
AID75758In vitro effective concentration required to agonise oxotremorine-induced tremors in guinea pig ileum.1989Journal of medicinal chemistry, Apr, Volume: 32, Issue:4
Conformationally restricted analogues of the muscarinic agent N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide.
AID113328ED50 value as cholinergic agonist by measuring tremors in mice (in vivo)1991Journal of medicinal chemistry, Aug, Volume: 34, Issue:8
Cholinergic activity of acetylenic imidazoles and related compounds.
AID141145Determination of dissociation constant from antimuscarinic activity on isolated guinea pig ileum.1992Journal of medicinal chemistry, Jan-24, Volume: 35, Issue:2
Phenyl-substituted analogues of oxotremorine as muscarinic antagonists.
AID77703Maximum contractile response relative to that elicited by carbachol was measured in guinea pig urinary bladder1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
5-Methyl-2-pyrrolidone analogues of oxotremorine as selective muscarinic agonists.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (21)

TimeframeStudies, This Drug (%)All Drugs %
pre-199011 (52.38)18.7374
1990's9 (42.86)18.2507
2000's1 (4.76)29.6817
2010's0 (0.00)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: 11.30

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 Index11.30 (24.57)
Research Supply Index3.14 (2.92)
Research Growth Index4.43 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.30)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (4.76%)5.53%
Reviews1 (4.76%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other19 (90.48%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]