Page last updated: 2024-12-08

n-methyl-n-(1-phenyl-2-(1-pyrrolidinyl)ethyl)phenylacetamide

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Description

N-methyl-N-(1-phenyl-2-(1-pyrrolidinyl)ethyl)phenylacetamide: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID190901
CHEMBL ID94734
SCHEMBL ID8061918
MeSH IDM0235410

Synonyms (24)

Synonym
CHEMBL94734 ,
n-methyl-2-phenyl-n-((s)-1-phenyl-2-pyrrolidin-1-yl-ethyl)-acetamide
bdbm50039966
1-[(s)-2-(methyl-phenylacetyl-amino)-2-phenyl-ethyl]-pyrrolidinium
tocris-0783
NCGC00024789-01
mppepa
NCGC00024789-02
157947-87-0
n-methyl-2-phenyl-n-[(1s)-1-phenyl-2-pyrrolidin-1-ylethyl]acetamide
0g3rs2p5hf ,
n-methyl-n-(1-phenyl-2-(1-pyrrolidinyl)ethyl)phenylacetamide
unii-0g3rs2p5hf
SCHEMBL8061918
n-methyl-n-(1-phenyl-2-(1-pyrrolidinyl)ethyl)benzeneacetamide, (s)-
benzeneacetamide, n-methyl-n-((1s)-1-phenyl-2-(1-pyrrolidinyl)ethyl)-
benzeneacetamide, n-methyl-n-(1-phenyl-2-(1-pyrrolidinyl)ethyl)-, (s)-
n-methyl-n-((1s)-1-phenyl-2-(1-pyrrolidinyl)ethyl)benzeneacetamide
DTXSID90935832
n-methyl-2-phenyl-n-[1-phenyl-2-(pyrrolidin-1-yl)ethyl]acetamide
n-mppp
Q27236737
(s)-n-methyl-n-(1-phenyl-2-(1-pyrrolidinyl)ethyl)benzeneacetamide
PD071360
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (24)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency7.94330.003245.467312,589.2998AID2517
thyroid stimulating hormone receptorHomo sapiens (human)Potency31.62280.001318.074339.8107AID926; AID938
cytochrome P450 2D6 isoform 1Homo sapiens (human)Potency3.16230.00207.533739.8107AID891
cytochrome P450 2C19 precursorHomo sapiens (human)Potency12.58930.00255.840031.6228AID899
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency12.58930.031610.279239.8107AID884; AID885
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Inositol monophosphatase 1Rattus norvegicus (Norway rat)Potency14.12541.000010.475628.1838AID1457
GABA theta subunitRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
[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)
Cytochrome P450 2D6Homo sapiens (human)IC50 (µMol)0.04600.00002.015110.0000AID241920
Kappa-type opioid receptorHomo sapiens (human)Ki0.00580.00000.362410.0000AID238876
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Kappa-type opioid receptorHomo sapiens (human)EC50 (µMol)0.05000.00000.22448.9900AID240265
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (46)

Processvia Protein(s)Taxonomy
xenobiotic metabolic processCytochrome P450 2D6Homo sapiens (human)
steroid metabolic processCytochrome P450 2D6Homo sapiens (human)
cholesterol metabolic processCytochrome P450 2D6Homo sapiens (human)
estrogen metabolic processCytochrome P450 2D6Homo sapiens (human)
coumarin metabolic processCytochrome P450 2D6Homo sapiens (human)
alkaloid metabolic processCytochrome P450 2D6Homo sapiens (human)
alkaloid catabolic processCytochrome P450 2D6Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 2D6Homo sapiens (human)
isoquinoline alkaloid metabolic processCytochrome P450 2D6Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 2D6Homo sapiens (human)
retinol metabolic processCytochrome P450 2D6Homo sapiens (human)
long-chain fatty acid biosynthetic processCytochrome P450 2D6Homo sapiens (human)
negative regulation of bindingCytochrome P450 2D6Homo sapiens (human)
oxidative demethylationCytochrome P450 2D6Homo sapiens (human)
negative regulation of cellular organofluorine metabolic processCytochrome P450 2D6Homo sapiens (human)
arachidonic acid metabolic processCytochrome P450 2D6Homo sapiens (human)
immune responseKappa-type opioid receptorHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwayKappa-type opioid receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayKappa-type opioid receptorHomo sapiens (human)
chemical synaptic transmissionKappa-type opioid receptorHomo sapiens (human)
sensory perceptionKappa-type opioid receptorHomo sapiens (human)
locomotory behaviorKappa-type opioid receptorHomo sapiens (human)
sensory perception of painKappa-type opioid receptorHomo sapiens (human)
adenylate cyclase-inhibiting opioid receptor signaling pathwayKappa-type opioid receptorHomo sapiens (human)
response to insulinKappa-type opioid receptorHomo sapiens (human)
positive regulation of dopamine secretionKappa-type opioid receptorHomo sapiens (human)
negative regulation of luteinizing hormone secretionKappa-type opioid receptorHomo sapiens (human)
response to nicotineKappa-type opioid receptorHomo sapiens (human)
G protein-coupled opioid receptor signaling pathwayKappa-type opioid receptorHomo sapiens (human)
maternal behaviorKappa-type opioid receptorHomo sapiens (human)
eating behaviorKappa-type opioid receptorHomo sapiens (human)
response to estrogenKappa-type opioid receptorHomo sapiens (human)
estrous cycleKappa-type opioid receptorHomo sapiens (human)
response to ethanolKappa-type opioid receptorHomo sapiens (human)
regulation of saliva secretionKappa-type opioid receptorHomo sapiens (human)
behavioral response to cocaineKappa-type opioid receptorHomo sapiens (human)
sensory perception of temperature stimulusKappa-type opioid receptorHomo sapiens (human)
defense response to virusKappa-type opioid receptorHomo sapiens (human)
cellular response to lipopolysaccharideKappa-type opioid receptorHomo sapiens (human)
cellular response to glucose stimulusKappa-type opioid receptorHomo sapiens (human)
positive regulation of p38MAPK cascadeKappa-type opioid receptorHomo sapiens (human)
positive regulation of potassium ion transmembrane transportKappa-type opioid receptorHomo sapiens (human)
response to acrylamideKappa-type opioid receptorHomo sapiens (human)
positive regulation of eating behaviorKappa-type opioid receptorHomo sapiens (human)
conditioned place preferenceKappa-type opioid receptorHomo sapiens (human)
neuropeptide signaling pathwayKappa-type opioid receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (13)

Processvia Protein(s)Taxonomy
monooxygenase activityCytochrome P450 2D6Homo sapiens (human)
iron ion bindingCytochrome P450 2D6Homo sapiens (human)
oxidoreductase activityCytochrome P450 2D6Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygenCytochrome P450 2D6Homo sapiens (human)
heme bindingCytochrome P450 2D6Homo sapiens (human)
anandamide 8,9 epoxidase activityCytochrome P450 2D6Homo sapiens (human)
anandamide 11,12 epoxidase activityCytochrome P450 2D6Homo sapiens (human)
anandamide 14,15 epoxidase activityCytochrome P450 2D6Homo sapiens (human)
G protein-coupled opioid receptor activityKappa-type opioid receptorHomo sapiens (human)
protein bindingKappa-type opioid receptorHomo sapiens (human)
receptor serine/threonine kinase bindingKappa-type opioid receptorHomo sapiens (human)
dynorphin receptor activityKappa-type opioid receptorHomo sapiens (human)
neuropeptide bindingKappa-type opioid receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (18)

Processvia Protein(s)Taxonomy
mitochondrionCytochrome P450 2D6Homo sapiens (human)
endoplasmic reticulumCytochrome P450 2D6Homo sapiens (human)
endoplasmic reticulum membraneCytochrome P450 2D6Homo sapiens (human)
cytoplasmCytochrome P450 2D6Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 2D6Homo sapiens (human)
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
nucleoplasmKappa-type opioid receptorHomo sapiens (human)
mitochondrionKappa-type opioid receptorHomo sapiens (human)
cytosolKappa-type opioid receptorHomo sapiens (human)
plasma membraneKappa-type opioid receptorHomo sapiens (human)
membraneKappa-type opioid receptorHomo sapiens (human)
sarcoplasmic reticulumKappa-type opioid receptorHomo sapiens (human)
T-tubuleKappa-type opioid receptorHomo sapiens (human)
dendriteKappa-type opioid receptorHomo sapiens (human)
synaptic vesicle membraneKappa-type opioid receptorHomo sapiens (human)
presynaptic membraneKappa-type opioid receptorHomo sapiens (human)
perikaryonKappa-type opioid receptorHomo sapiens (human)
axon terminusKappa-type opioid receptorHomo sapiens (human)
postsynaptic membraneKappa-type opioid receptorHomo sapiens (human)
plasma membraneKappa-type opioid receptorHomo sapiens (human)
neuron projectionKappa-type opioid receptorHomo sapiens (human)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (21)

Assay IDTitleYearJournalArticle
AID148729Compound was tested for the change in the Opioid receptor kappa 1 binding affinity (Ki(mut)/Ki(wild) for I294K point mutations.1998Journal of medicinal chemistry, Nov-19, Volume: 41, Issue:24
Conformational analysis and automated receptor docking of selective arylacetamide-based kappa-opioid agonists.
AID238876Inhibitory constant against human Opioid receptor kappa using [3H]diprenorphine as radio ligand2005Bioorganic & medicinal chemistry letters, May-16, Volume: 15, Issue:10
Arylacetamide kappa opioid receptor agonists with reduced cytochrome P450 2D6 inhibitory activity.
AID148691Tested for inhibitory concentration against [3H]U-69593 binding at sites of kappa-opioid receptor in guinea pig brain membrane1994Journal of medicinal chemistry, Sep-02, Volume: 37, Issue:18
Isothiocyanate-substituted kappa-selective opioid receptor ligands derived from N-methyl-N-[(1S)-1-phenyl-2-(1-pyrrolidinyl)ethyl] phenylacetamide.
AID243692Percent inhibition against human Opioid receptor mu 1 using [3H]diprenorphine as radio ligand2005Bioorganic & medicinal chemistry letters, May-16, Volume: 15, Issue:10
Arylacetamide kappa opioid receptor agonists with reduced cytochrome P450 2D6 inhibitory activity.
AID149749Tested for inhibitory concentration against [3H]DPDPE binding at sites of delta-opioid receptor in guinea pig brain membrane1994Journal of medicinal chemistry, Sep-02, Volume: 37, Issue:18
Isothiocyanate-substituted kappa-selective opioid receptor ligands derived from N-methyl-N-[(1S)-1-phenyl-2-(1-pyrrolidinyl)ethyl] phenylacetamide.
AID241920Inhibition of cytochrome P450 2D6 was determined using MAMC (7-methoxy-4-aminomethyl-coumarin) as substrate2005Bioorganic & medicinal chemistry letters, May-16, Volume: 15, Issue:10
Arylacetamide kappa opioid receptor agonists with reduced cytochrome P450 2D6 inhibitory activity.
AID148725Compound was tested for the change in the Opioid receptor kappa 1 binding affinity (Ki(mut)/Ki(wild) for E297A point mutations.1998Journal of medicinal chemistry, Nov-19, Volume: 41, Issue:24
Conformational analysis and automated receptor docking of selective arylacetamide-based kappa-opioid agonists.
AID141489Tested for inhibitory concentration against [3H]DAMGO binding at sites of mu-opioid receptor in guinea pig brain membrane1994Journal of medicinal chemistry, Sep-02, Volume: 37, Issue:18
Isothiocyanate-substituted kappa-selective opioid receptor ligands derived from N-methyl-N-[(1S)-1-phenyl-2-(1-pyrrolidinyl)ethyl] phenylacetamide.
AID148620Tested for inhibitory concentration against [3H]bremazocine binding to total sites of opioid receptor in guinea pig brain membrane1994Journal of medicinal chemistry, Sep-02, Volume: 37, Issue:18
Isothiocyanate-substituted kappa-selective opioid receptor ligands derived from N-methyl-N-[(1S)-1-phenyl-2-(1-pyrrolidinyl)ethyl] phenylacetamide.
AID240265Agonist activity assessed by ability to stimulate [35S]GTP gammaS binding to opioid receptor kappa in human membranes2005Bioorganic & medicinal chemistry letters, May-16, Volume: 15, Issue:10
Arylacetamide kappa opioid receptor agonists with reduced cytochrome P450 2D6 inhibitory activity.
AID148726Compound was tested for the change in the Opioid receptor kappa 1 binding affinity (Ki(mut)/Ki(wild) for G319V point mutations.1998Journal of medicinal chemistry, Nov-19, Volume: 41, Issue:24
Conformational analysis and automated receptor docking of selective arylacetamide-based kappa-opioid agonists.
AID148268Tested for percentage specific binding of compound at 10 nM against [3H]U-69593 on washed kappa-opioid receptor binding site1994Journal of medicinal chemistry, Sep-02, Volume: 37, Issue:18
Isothiocyanate-substituted kappa-selective opioid receptor ligands derived from N-methyl-N-[(1S)-1-phenyl-2-(1-pyrrolidinyl)ethyl] phenylacetamide.
AID148727Compound was tested for the change in the Opioid receptor kappa 1 binding affinity (Ki(mut)/Ki(wild) for H291A point mutations.1998Journal of medicinal chemistry, Nov-19, Volume: 41, Issue:24
Conformational analysis and automated receptor docking of selective arylacetamide-based kappa-opioid agonists.
AID148266Tested for percentage specific binding of compound at 10 nM against [3H]U-69593 on kappa-opioid receptor binding site protected with 1 uM naloxone1994Journal of medicinal chemistry, Sep-02, Volume: 37, Issue:18
Isothiocyanate-substituted kappa-selective opioid receptor ligands derived from N-methyl-N-[(1S)-1-phenyl-2-(1-pyrrolidinyl)ethyl] phenylacetamide.
AID148267Tested for percentage specific binding of compound at 10 nM against [3H]U-69593 on unwashed kappa-opioid receptor binding site1994Journal of medicinal chemistry, Sep-02, Volume: 37, Issue:18
Isothiocyanate-substituted kappa-selective opioid receptor ligands derived from N-methyl-N-[(1S)-1-phenyl-2-(1-pyrrolidinyl)ethyl] phenylacetamide.
AID148723Compound was tested for the change in the Opioid receptor kappa 1 binding affinity (Ki(mut)/Ki(wild) for D138A point mutations.1998Journal of medicinal chemistry, Nov-19, Volume: 41, Issue:24
Conformational analysis and automated receptor docking of selective arylacetamide-based kappa-opioid agonists.
AID243720Percent inhibition against human Opioid receptor delta 1 using [3H]diprenorphine as radio ligand2005Bioorganic & medicinal chemistry letters, May-16, Volume: 15, Issue:10
Arylacetamide kappa opioid receptor agonists with reduced cytochrome P450 2D6 inhibitory activity.
AID148728Compound was tested for the change in the Opioid receptor kappa 1 binding affinity (Ki(mut)/Ki(wild) for I294A point mutations.1998Journal of medicinal chemistry, Nov-19, Volume: 41, Issue:24
Conformational analysis and automated receptor docking of selective arylacetamide-based kappa-opioid agonists.
AID148720Compound was tested for the change in the Opioid receptor kappa 1 binding affinity (Ki(mut)/Ki(wild) for A298H point mutations.1998Journal of medicinal chemistry, Nov-19, Volume: 41, Issue:24
Conformational analysis and automated receptor docking of selective arylacetamide-based kappa-opioid agonists.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (40.00)18.2507
2000's1 (20.00)29.6817
2010's0 (0.00)24.3611
2020's2 (40.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.94

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 Index12.94 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.73 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.94)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]