Page last updated: 2024-11-05

n-phenethylpiperidine

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

Cross-References

ID SourceID
PubMed CID9513
CHEMBL ID75228
SCHEMBL ID917609
MeSH IDM0534843

Synonyms (39)

Synonym
nsc-122975
n-phenethylpiperidine
1-phenethyl-piperidine
CHEMBL75228 ,
1-phenethylpiperidine
piperidine, 1-(2-phenylethyl)-
6949-43-5
ac927
332-14-9
brn 0137585
einecs 206-362-8
1-piperidino-2-phenyl-aethan [german]
piperidine, 1-phenethyl-
1-(2-phenylethyl)piperidine
n-(2-phenylethyl)piperidine
fmp-199
ai3-11531
1-piperidino-2-phenylethane
bdbm50109389
inchi=1/c13h19n/c1-3-7-13(8-4-1)9-12-14-10-5-2-6-11-14/h1,3-4,7-8h,2,5-6,9-12h2
dbdvakghpzjlth-uhfffaoysa-
NCGC00184305-01
NCGC00184305-02
unii-5ty7c52m7f
5ty7c52m7f ,
5-20-02-00064 (beilstein handbook reference)
1-piperidino-2-phenyl-aethan
AKOS006242111
phenethylpiperidine
DTXSID5059822
SCHEMBL917609
1-(2-phenylethyl)piperidine #
J-505048
n-boc-3-ethylpyrrolidine-
AS-57452
A866821
CS-0451167
EN300-8588965
Z137504398
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (8)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Alpha-1B adrenergic receptorRattus norvegicus (Norway rat)Ki7.50000.00010.949010.0000AID35286
Amine oxidase [flavin-containing] AHomo sapiens (human)IC50 (µMol)757.30000.00002.37899.7700AID641830
Amine oxidase [flavin-containing] AHomo sapiens (human)Ki1,901.20000.00192.379710.0000AID641835; AID641922
Alpha-1D adrenergic receptorRattus norvegicus (Norway rat)Ki7.50000.00000.575110.0000AID35286
Amine oxidase [flavin-containing] BHomo sapiens (human)IC50 (µMol)761.50000.00001.89149.5700AID641831
5-hydroxytryptamine receptor 3ARattus norvegicus (Norway rat)Ki0.70000.00020.484110.0000AID5897
Alpha-1A adrenergic receptorRattus norvegicus (Norway rat)Ki7.50000.00000.965010.0000AID35286
5-hydroxytryptamine receptor 3BRattus norvegicus (Norway rat)Ki0.70000.00020.502310.0000AID5897
Sigma non-opioid intracellular receptor 1Rattus norvegicus (Norway rat)Ki0.08850.00030.26715.0700AID204284
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (15)

Processvia Protein(s)Taxonomy
biogenic amine metabolic processAmine oxidase [flavin-containing] AHomo sapiens (human)
positive regulation of signal transductionAmine oxidase [flavin-containing] AHomo sapiens (human)
dopamine catabolic processAmine oxidase [flavin-containing] AHomo sapiens (human)
response to xenobiotic stimulusAmine oxidase [flavin-containing] BHomo sapiens (human)
response to toxic substanceAmine oxidase [flavin-containing] BHomo sapiens (human)
response to aluminum ionAmine oxidase [flavin-containing] BHomo sapiens (human)
response to selenium ionAmine oxidase [flavin-containing] BHomo sapiens (human)
negative regulation of serotonin secretionAmine oxidase [flavin-containing] BHomo sapiens (human)
phenylethylamine catabolic processAmine oxidase [flavin-containing] BHomo sapiens (human)
substantia nigra developmentAmine oxidase [flavin-containing] BHomo sapiens (human)
response to lipopolysaccharideAmine oxidase [flavin-containing] BHomo sapiens (human)
dopamine catabolic processAmine oxidase [flavin-containing] BHomo sapiens (human)
response to ethanolAmine oxidase [flavin-containing] BHomo sapiens (human)
positive regulation of dopamine metabolic processAmine oxidase [flavin-containing] BHomo sapiens (human)
hydrogen peroxide biosynthetic processAmine oxidase [flavin-containing] BHomo sapiens (human)
response to corticosteroneAmine oxidase [flavin-containing] BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
protein bindingAmine oxidase [flavin-containing] AHomo sapiens (human)
primary amine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
aliphatic amine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
monoamine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
flavin adenine dinucleotide bindingAmine oxidase [flavin-containing] AHomo sapiens (human)
protein bindingAmine oxidase [flavin-containing] BHomo sapiens (human)
primary amine oxidase activityAmine oxidase [flavin-containing] BHomo sapiens (human)
electron transfer activityAmine oxidase [flavin-containing] BHomo sapiens (human)
identical protein bindingAmine oxidase [flavin-containing] BHomo sapiens (human)
aliphatic amine oxidase activityAmine oxidase [flavin-containing] BHomo sapiens (human)
monoamine oxidase activityAmine oxidase [flavin-containing] BHomo sapiens (human)
flavin adenine dinucleotide bindingAmine oxidase [flavin-containing] BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
mitochondrionAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrial outer membraneAmine oxidase [flavin-containing] AHomo sapiens (human)
cytosolAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] BHomo sapiens (human)
mitochondrial envelopeAmine oxidase [flavin-containing] BHomo sapiens (human)
mitochondrial outer membraneAmine oxidase [flavin-containing] BHomo sapiens (human)
dendriteAmine oxidase [flavin-containing] BHomo sapiens (human)
neuronal cell bodyAmine oxidase [flavin-containing] BHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (34)

Assay IDTitleYearJournalArticle
AID738297Antagonist activity at sigma 2 receptor in human MCF7 cells assessed as effect on bradykinin-triggered Ca2+ response at 10 uM pretreated for 10 mins measured every 5 secs by fluorescence analysis2013Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7
Investigation of σ receptors agonist/antagonist activity through N-(6-methoxytetralin-1-yl)- and N-(6-methoxynaphthalen-1-yl)alkyl derivatives of polymethylpiperidines.
AID641927Inhibition of human recombinant MAOA expressed in insect cells assessed as oxidation of kynuramine substrate at 2 mM measured after additional enzyme added after 120 mins incubation2011Bioorganic & medicinal chemistry, Dec-15, Volume: 19, Issue:24
Time-dependent slowly-reversible inhibition of monoamine oxidase A by N-substituted 1,2,3,6-tetrahydropyridines.
AID231644Binding affinity ratio of sigma 1 receptor to that of sigma 2 receptor2004Journal of medicinal chemistry, Apr-22, Volume: 47, Issue:9
4-(tetralin-1-yl)- and 4-(naphthalen-1-yl)alkyl derivatives of 1-cyclohexylpiperazine as sigma receptor ligands with agonist sigma2 activity.
AID765139Displacement of [3H](+)-pentazocine from sigma 1 receptor in rat brain homogenates after 120 mins by liquid scintillation counting2013Bioorganic & medicinal chemistry, Sep-01, Volume: 21, Issue:17
Effect of ring-constrained phenylpropyloxyethylamines on sigma receptors.
AID256864Percentage inhibition of rat C6 glioma cell proliferation mediated by sigma 1 receptor at 50 uM2005Journal of medicinal chemistry, Dec-29, Volume: 48, Issue:26
Methyl substitution on the piperidine ring of N-[omega-(6-methoxynaphthalen-1-yl)alkyl] derivatives as a probe for selective binding and activity at the sigma(1) receptor.
AID77183Inhibition of electrically stimulated contractions of the isolated guinea pig badder at 30 uM.2004Journal of medicinal chemistry, Apr-22, Volume: 47, Issue:9
4-(tetralin-1-yl)- and 4-(naphthalen-1-yl)alkyl derivatives of 1-cyclohexylpiperazine as sigma receptor ligands with agonist sigma2 activity.
AID203682In vitro binding affinity at opioid sigma-1 receptor in guinea pig brain membranes by (+)-[3H]pentazocine displacement.2004Journal of medicinal chemistry, Apr-22, Volume: 47, Issue:9
4-(tetralin-1-yl)- and 4-(naphthalen-1-yl)alkyl derivatives of 1-cyclohexylpiperazine as sigma receptor ligands with agonist sigma2 activity.
AID641841Inhibition of human recombinant MAOA expressed in insect cells assessed as oxidation of kynuramine substrate at 2 mM measured after additional substrate added after 90 mins incubation2011Bioorganic & medicinal chemistry, Dec-15, Volume: 19, Issue:24
Time-dependent slowly-reversible inhibition of monoamine oxidase A by N-substituted 1,2,3,6-tetrahydropyridines.
AID641835Competitive inhibition of human recombinant MAO-A assessed as dissociation constant for enzyme-inhibitor complex by Lineweaver-Burk plot analysis2011Bioorganic & medicinal chemistry, Dec-15, Volume: 19, Issue:24
Time-dependent slowly-reversible inhibition of monoamine oxidase A by N-substituted 1,2,3,6-tetrahydropyridines.
AID738302Antiproliferative activity against human MCF7 cells transfected with human sigma1 receptor after 48 hrs by MTT assay2013Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7
Investigation of σ receptors agonist/antagonist activity through N-(6-methoxytetralin-1-yl)- and N-(6-methoxynaphthalen-1-yl)alkyl derivatives of polymethylpiperidines.
AID641832Selectivity index, ratio of IC50 for human recombinant MAOB to IC50 for human recombinant MAOA2011Bioorganic & medicinal chemistry, Dec-15, Volume: 19, Issue:24
Time-dependent slowly-reversible inhibition of monoamine oxidase A by N-substituted 1,2,3,6-tetrahydropyridines.
AID348122Displacement of [3H](+)-pentazocine from sigma 1 receptor in guinea pig brain membrane without cerebellum2008Journal of medicinal chemistry, Dec-11, Volume: 51, Issue:23
Novel 4-(4-aryl)cyclohexyl-1-(2-pyridyl)piperazines as Delta(8)-Delta(7) sterol isomerase (emopamil binding protein) selective ligands with antiproliferative activity.
AID1420180Cytotoxicity against human SH-SY5Y cells at 50 uM after 48 hrs by MTT assay2018Bioorganic & medicinal chemistry letters, 10-15, Volume: 28, Issue:19
New piperidine-based derivatives as sigma receptor ligands. Synthesis and pharmacological evaluation.
AID348128Cytotoxicity against human PC3 cells assessed as LDH release at 100 uM after 24 hrs relative to untreated control2008Journal of medicinal chemistry, Dec-11, Volume: 51, Issue:23
Novel 4-(4-aryl)cyclohexyl-1-(2-pyridyl)piperazines as Delta(8)-Delta(7) sterol isomerase (emopamil binding protein) selective ligands with antiproliferative activity.
AID641830Inhibition of human recombinant MAOA expressed in insect cells using kynuramine substrate after 60 mins2011Bioorganic & medicinal chemistry, Dec-15, Volume: 19, Issue:24
Time-dependent slowly-reversible inhibition of monoamine oxidase A by N-substituted 1,2,3,6-tetrahydropyridines.
AID349266Displacement of [3H]ditolylguanidine from sigma 2 opioid receptor in rat brain cerebellum2008European journal of medicinal chemistry, Jun, Volume: 43, Issue:6
Nitrile analogs of meperidine as high affinity and selective sigma-1 receptor ligands.
AID641922Competitive inhibition of human recombinant MAO-A assessed as dissociation constant for enzyme-inhibitor-substrate complex by Lineweaver-Burk plot analysis2011Bioorganic & medicinal chemistry, Dec-15, Volume: 19, Issue:24
Time-dependent slowly-reversible inhibition of monoamine oxidase A by N-substituted 1,2,3,6-tetrahydropyridines.
AID348121Displacement of [3H](-)-(S)-emopamil from EBP in guinea pig liver membrane2008Journal of medicinal chemistry, Dec-11, Volume: 51, Issue:23
Novel 4-(4-aryl)cyclohexyl-1-(2-pyridyl)piperazines as Delta(8)-Delta(7) sterol isomerase (emopamil binding protein) selective ligands with antiproliferative activity.
AID204284Binding affinity for sigma-1 receptor by displacing [3H]-(+) pentazocine2002Bioorganic & medicinal chemistry letters, Feb-11, Volume: 12, Issue:3
N-arylalkylpiperidines as high-affinity sigma-1 and sigma-2 receptor ligands: phenylpropylamines as potential leads for selective sigma-2 agents.
AID348123Displacement of [3H]-DTG from sigma 2-type opioid receptor in rat liver membrane in presence of (+)-pentazocine2008Journal of medicinal chemistry, Dec-11, Volume: 51, Issue:23
Novel 4-(4-aryl)cyclohexyl-1-(2-pyridyl)piperazines as Delta(8)-Delta(7) sterol isomerase (emopamil binding protein) selective ligands with antiproliferative activity.
AID765138Displacement of [3H]di-o-tolylguanidine from sigma 2 receptor in rat brain homogenates after 120 mins by liquid scintillation counting2013Bioorganic & medicinal chemistry, Sep-01, Volume: 21, Issue:17
Effect of ring-constrained phenylpropyloxyethylamines on sigma receptors.
AID1420188Cytotoxicity against human PANC1 cells at 50 uM after 48 hrs by MTT assay2018Bioorganic & medicinal chemistry letters, 10-15, Volume: 28, Issue:19
New piperidine-based derivatives as sigma receptor ligands. Synthesis and pharmacological evaluation.
AID348127Selectivity ratio of Ki for sigma 2 receptor in rat liver membrane to Ki for EBP in guinea pig liver membrane2008Journal of medicinal chemistry, Dec-11, Volume: 51, Issue:23
Novel 4-(4-aryl)cyclohexyl-1-(2-pyridyl)piperazines as Delta(8)-Delta(7) sterol isomerase (emopamil binding protein) selective ligands with antiproliferative activity.
AID765137Selectivity ratio of Ki for sigma 2 receptor in rat brain homogenates to Ki for sigma 1 receptor in rat brain homogenates2013Bioorganic & medicinal chemistry, Sep-01, Volume: 21, Issue:17
Effect of ring-constrained phenylpropyloxyethylamines on sigma receptors.
AID203825In vitro binding affinity at opioid sigma-2 receptor in rat liver membranes by [3H]-DTG displacement in the presence of 1 uM (+)-pentazocine.2004Journal of medicinal chemistry, Apr-22, Volume: 47, Issue:9
4-(tetralin-1-yl)- and 4-(naphthalen-1-yl)alkyl derivatives of 1-cyclohexylpiperazine as sigma receptor ligands with agonist sigma2 activity.
AID348126Selectivity ratio of Ki for sigma 1 receptor in guinea pig brain membrane without cerebellum to Ki for EBP in guinea pig liver membrane2008Journal of medicinal chemistry, Dec-11, Volume: 51, Issue:23
Novel 4-(4-aryl)cyclohexyl-1-(2-pyridyl)piperazines as Delta(8)-Delta(7) sterol isomerase (emopamil binding protein) selective ligands with antiproliferative activity.
AID349265Displacement of [3H](+)-pentazocine from sigma 1 opioid receptor in rat brain cerebellum2008European journal of medicinal chemistry, Jun, Volume: 43, Issue:6
Nitrile analogs of meperidine as high affinity and selective sigma-1 receptor ligands.
AID35286In vitro binding affinity at alpha-1 adrenergic receptor in rat cortex by [3H]prazosin displacement.2004Journal of medicinal chemistry, Apr-22, Volume: 47, Issue:9
4-(tetralin-1-yl)- and 4-(naphthalen-1-yl)alkyl derivatives of 1-cyclohexylpiperazine as sigma receptor ligands with agonist sigma2 activity.
AID738303Antiproliferative activity against human MCF7 cells after 48 hrs by MTT assay2013Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7
Investigation of σ receptors agonist/antagonist activity through N-(6-methoxytetralin-1-yl)- and N-(6-methoxynaphthalen-1-yl)alkyl derivatives of polymethylpiperidines.
AID349267Selectivity ratio of Ki for rat sigma 2 opioid receptor to Ki for rat sigma 1 opioid receptor2008European journal of medicinal chemistry, Jun, Volume: 43, Issue:6
Nitrile analogs of meperidine as high affinity and selective sigma-1 receptor ligands.
AID641831Inhibition of human recombinant MAOB expressed in insect cells using benzylamine hydrochloride as substrate after 30 mins2011Bioorganic & medicinal chemistry, Dec-15, Volume: 19, Issue:24
Time-dependent slowly-reversible inhibition of monoamine oxidase A by N-substituted 1,2,3,6-tetrahydropyridines.
AID204308Binding affinity for sigma-2 receptor by displacing [3H]DTG in presence of dextrallorphan2002Bioorganic & medicinal chemistry letters, Feb-11, Volume: 12, Issue:3
N-arylalkylpiperidines as high-affinity sigma-1 and sigma-2 receptor ligands: phenylpropylamines as potential leads for selective sigma-2 agents.
AID5897In vitro binding affinity at serotonin 5-hydroxytryptamine 3 receptor in rat cortex by [3H]granisetron displacement.2004Journal of medicinal chemistry, Apr-22, Volume: 47, Issue:9
4-(tetralin-1-yl)- and 4-(naphthalen-1-yl)alkyl derivatives of 1-cyclohexylpiperazine as sigma receptor ligands with agonist sigma2 activity.
AID348125Antiproliferative activity against human PC3 cells expressing EBP at 100 uM after 48 hrs by MTT assay2008Journal of medicinal chemistry, Dec-11, Volume: 51, Issue:23
Novel 4-(4-aryl)cyclohexyl-1-(2-pyridyl)piperazines as Delta(8)-Delta(7) sterol isomerase (emopamil binding protein) selective ligands with antiproliferative activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's5 (55.56)29.6817
2010's4 (44.44)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]