Page last updated: 2024-11-05

3-phenylpropylamine

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

Description

3-phenylpropylamine : A phenylalkylamine that is benzene in which one of the hydrogens is substituted by a 3-aminopropyl group. [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 CID16259
CHEMBL ID276864
CHEBI ID45017
SCHEMBL ID52482
MeSH IDM0140351

Synonyms (66)

Synonym
EN300-20467
BB 0216505
NCIOPEN2_001106
nsc 87080
einecs 218-012-1
brn 2205526
3-phenylpropan-1-amine
propylamine, 3-phenyl-
1-amino-3-phenylpropane
.gamma.-phenylpropylamine
3-phenyl-1-propanamine
hydrocinnamylamine
3-phenylpropylamine
3-phenyl-n-propylamine
benzenepropanamine
nsc-87080
.gamma.-phenyl-n-propylamine
2038-57-5
nsc87080
3-phenyl-1-propylamine, 98%
DB04410
1TNK
3-phenyl-1-aminopropane
1UTL
3-phenylpropanamine
3-phenyl-1-propylamine
gamma-phenyl-n-propylamine
gamma-phenylpropylamine
inchi=1/c9h13n/c10-8-4-7-9-5-2-1-3-6-9/h1-3,5-6h,4,7-8,10h
bdbm50113826
STK825996
3-phenyl-propylamine
CHEMBL276864 ,
P0664
AKOS000120432
phenylpropylamine
p8326ez31p ,
4-12-00-02625 (beilstein handbook reference)
unii-p8326ez31p
FT-0616351
PS-5335
AB00940
S10208
SCHEMBL52482
propylamine, 3-phenyl
phenylpropyl amine
3-phenylpropylarnine
3-phenylproylamine
(3-phenylpropyl)amine
3-phenylpropyl-amine
1-phenyl-3-propylamine
3-aminopropylbenzene
3-phenyl propyl amine
3-phenyl-propyl-amine
mfcd00008224
gamma-aminopropylbenzene
DTXSID10174307
F2190-0400
?-aminopropylbenzene
J-013266
Q23978199
CHEBI:45017
5(6)-azidofluoresceindiacetate
SY049659
PD016298
Z104478312
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (3)

ClassDescription
phenylalkylamineAn arylalkylamine in which the aryl group is phenyl.
benzenesAny benzenoid aromatic compound consisting of the benzene skeleton and its substituted derivatives.
primary amino compoundA compound formally derived from ammonia by replacing one hydrogen atom by an organyl group.
[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 (26)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, TRYPSINBos taurus (cattle)Ki32,500.0000100.000011,466.000032,500.0000AID977610
Chain A, TRYPSINBos taurus (cattle)Ki32,500.0000100.000011,466.000032,500.0000AID977610
Chain A, TRYPSINBos taurus (cattle)Ki32,500.0000100.000011,466.000032,500.0000AID977610
Chain A, TRYPSINBos taurus (cattle)Ki32,500.0000100.000011,466.000032,500.0000AID977610
Chain A, TRYPSINBos taurus (cattle)Ki32,500.0000100.000011,466.000032,500.0000AID977610
Chain A, TRYPSINBos taurus (cattle)Ki32,500.0000100.000011,466.000032,500.0000AID977610
Cationic trypsinBos taurus (cattle)Ki32.50000.00001.07539.0000AID214878
[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)
5-hydroxytryptamine receptor 2CRattus norvegicus (Norway rat)Kd11.74900.00042.58328.5114AID6406
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)Kd11.74900.00012.62198.5114AID6406
5-hydroxytryptamine receptor 1ARattus norvegicus (Norway rat)Kd11.74900.00012.29338.5114AID6406
5-hydroxytryptamine receptor 1BRattus norvegicus (Norway rat)Kd11.74900.02342.74218.5114AID6406
5-hydroxytryptamine receptor 1DRattus norvegicus (Norway rat)Kd11.74900.02342.74218.5114AID6406
5-hydroxytryptamine receptor 1FRattus norvegicus (Norway rat)Kd11.74900.02342.74218.5114AID6406
5-hydroxytryptamine receptor 2BRattus norvegicus (Norway rat)Kd11.74900.00042.47358.5114AID6406
5-hydroxytryptamine receptor 6Rattus norvegicus (Norway rat)Kd11.74900.02342.74218.5114AID6406
5-hydroxytryptamine receptor 7 Rattus norvegicus (Norway rat)Kd11.74900.00012.70068.5114AID6406
5-hydroxytryptamine receptor 5ARattus norvegicus (Norway rat)Kd11.74900.02342.74218.5114AID6406
5-hydroxytryptamine receptor 5BRattus norvegicus (Norway rat)Kd11.74900.02342.74218.5114AID6406
5-hydroxytryptamine receptor 3ARattus norvegicus (Norway rat)Kd11.74900.00082.62148.5114AID6406
5-hydroxytryptamine receptor 4 Rattus norvegicus (Norway rat)Kd11.74900.02342.74218.5114AID6406
5-hydroxytryptamine receptor 3BRattus norvegicus (Norway rat)Kd11.74900.00082.62148.5114AID6406
[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 (10)

Processvia Protein(s)Taxonomy
proteolysisCationic trypsinBos taurus (cattle)
digestionCationic trypsinBos taurus (cattle)
dopamine catabolic processDopamine beta-hydroxylase Bos taurus (cattle)
norepinephrine biosynthetic processDopamine beta-hydroxylase Bos taurus (cattle)
catecholamine metabolic processAmine oxidase [flavin-containing] A Bos taurus (cattle)
inflammatory responseMembrane primary amine oxidaseHomo sapiens (human)
cell adhesionMembrane primary amine oxidaseHomo sapiens (human)
amine metabolic processMembrane primary amine oxidaseHomo sapiens (human)
response to antibioticMembrane primary amine oxidaseHomo sapiens (human)
negative regulation of primary amine oxidase activityMembrane primary amine oxidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (15)

Processvia Protein(s)Taxonomy
endopeptidase activityCationic trypsinBos taurus (cattle)
serine-type endopeptidase activityCationic trypsinBos taurus (cattle)
protein bindingCationic trypsinBos taurus (cattle)
metal ion bindingCationic trypsinBos taurus (cattle)
serpin family protein bindingCationic trypsinBos taurus (cattle)
dopamine beta-monooxygenase activityDopamine beta-hydroxylase Bos taurus (cattle)
copper ion bindingDopamine beta-hydroxylase Bos taurus (cattle)
L-ascorbic acid bindingDopamine beta-hydroxylase Bos taurus (cattle)
primary amine oxidase activityAmine oxidase [flavin-containing] A Bos taurus (cattle)
aliphatic amine oxidase activityAmine oxidase [flavin-containing] A Bos taurus (cattle)
monoamine oxidase activityAmine oxidase [flavin-containing] A Bos taurus (cattle)
primary amine oxidase activityAmine oxidase [flavin-containing] BBos taurus (cattle)
aliphatic amine oxidase activityAmine oxidase [flavin-containing] BBos taurus (cattle)
monoamine oxidase activityAmine oxidase [flavin-containing] BBos taurus (cattle)
copper ion bindingMembrane primary amine oxidaseHomo sapiens (human)
calcium ion bindingMembrane primary amine oxidaseHomo sapiens (human)
protein bindingMembrane primary amine oxidaseHomo sapiens (human)
primary amine oxidase activityMembrane primary amine oxidaseHomo sapiens (human)
identical protein bindingMembrane primary amine oxidaseHomo sapiens (human)
protein heterodimerization activityMembrane primary amine oxidaseHomo sapiens (human)
quinone bindingMembrane primary amine oxidaseHomo sapiens (human)
aliphatic amine oxidase activityMembrane primary amine oxidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (16)

Processvia Protein(s)Taxonomy
serine protease inhibitor complexCationic trypsinBos taurus (cattle)
extracellular spaceDopamine beta-hydroxylase Bos taurus (cattle)
transport vesicle membraneDopamine beta-hydroxylase Bos taurus (cattle)
chromaffin granule lumenDopamine beta-hydroxylase Bos taurus (cattle)
secretory granule lumenDopamine beta-hydroxylase Bos taurus (cattle)
chromaffin granule membraneDopamine beta-hydroxylase Bos taurus (cattle)
mitochondrial outer membraneAmine oxidase [flavin-containing] A Bos taurus (cattle)
mitochondrionAmine oxidase [flavin-containing] BBos taurus (cattle)
mitochondrial outer membraneAmine oxidase [flavin-containing] BBos taurus (cattle)
cytoplasmMembrane primary amine oxidaseHomo sapiens (human)
plasma membraneMembrane primary amine oxidaseHomo sapiens (human)
microvillusMembrane primary amine oxidaseHomo sapiens (human)
cell surfaceMembrane primary amine oxidaseHomo sapiens (human)
membraneMembrane primary amine oxidaseHomo sapiens (human)
early endosomeMembrane primary amine oxidaseHomo sapiens (human)
endoplasmic reticulumMembrane primary amine oxidaseHomo sapiens (human)
Golgi apparatusMembrane primary amine oxidaseHomo sapiens (human)
early endosomeMembrane primary amine oxidaseHomo sapiens (human)
plasma membraneMembrane primary amine oxidaseHomo sapiens (human)
endoplasmic reticulumMembrane primary amine oxidaseHomo sapiens (human)
Golgi apparatusMembrane primary amine oxidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (27)

Assay IDTitleYearJournalArticle
AID273097Activity of human SSAO measured as hydrogen peroxide production at 1 mM relative to benzylamine oxidation2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
New efficient substrates for semicarbazide-sensitive amine oxidase/VAP-1 enzyme: analysis by SARs and computational docking.
AID1548205Antibacterial activity against Acinetobacter baumannii ATCC 19606 assessed as bacterial growth inhibition at 32 ug/ml measured after 16 hrs by broth microdilution method2020Journal of medicinal chemistry, 04-23, Volume: 63, Issue:8
Synthesis and Antichlamydial Activity of Molecules Based on Dysregulators of Cylindrical Proteases.
AID1548207Antifungal activity against Cryptococcus neoformans var. grubii H99 ATCC 20882 assessed as fungal growth inhibition at 32 ug/ml measured after 16 hrs by broth microdilution method2020Journal of medicinal chemistry, 04-23, Volume: 63, Issue:8
Synthesis and Antichlamydial Activity of Molecules Based on Dysregulators of Cylindrical Proteases.
AID1548203Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 assessed as bacterial growth inhibition at 32 ug/ml measured after 16 hrs by broth microdilution method2020Journal of medicinal chemistry, 04-23, Volume: 63, Issue:8
Synthesis and Antichlamydial Activity of Molecules Based on Dysregulators of Cylindrical Proteases.
AID6406Affinity against 5-hydroxytryptamine receptors in rat fundus model1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Serotonin receptor affinities of psychoactive phenalkylamine analogues.
AID62282Kinetic parameter Km was measured for dopamine beta-monooxygenase1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
The enantiomeric specificity of the antihypertensive activity of 1-(phenylthio)-2-aminopropane, a synthetic substrate analogue for dopamine beta-monooxygenase.
AID231141Ratio of the kinetic parameter Kcat to the Km on substrate dopamine beta-hydrolase from bovine adrenals1984Journal of medicinal chemistry, Oct, Volume: 27, Issue:10
Antihypertensive activities of phenyl aminoethyl sulfides, a class of synthetic substrates for dopamine beta-hydroxylase.
AID231142Ratio of the kinetic parameter Kcat to the Km on substrate dopamine monoamine oxidase1984Journal of medicinal chemistry, Oct, Volume: 27, Issue:10
Antihypertensive activities of phenyl aminoethyl sulfides, a class of synthetic substrates for dopamine beta-hydroxylase.
AID1548201Antibacterial activity against Escherichia coli ATCC 25922 assessed as bacterial growth inhibition at 32 ug/ml measured after 16 hrs by broth microdilution method2020Journal of medicinal chemistry, 04-23, Volume: 63, Issue:8
Synthesis and Antichlamydial Activity of Molecules Based on Dysregulators of Cylindrical Proteases.
AID125213Compound was evaluated as substrate for monoamine oxidase (MAO) from bovine erythrocyte and the enzymatic kinetic constant was reported as Kcat1984Journal of medicinal chemistry, Oct, Volume: 27, Issue:10
Antihypertensive activities of phenyl aminoethyl sulfides, a class of synthetic substrates for dopamine beta-hydroxylase.
AID1548202Antibacterial activity against Escherichia coli K12 assessed as bacterial growth inhibition at 32 ug/ml measured after 16 hrs by broth microdilution method2020Journal of medicinal chemistry, 04-23, Volume: 63, Issue:8
Synthesis and Antichlamydial Activity of Molecules Based on Dysregulators of Cylindrical Proteases.
AID62142Compound was evaluated as substrate for Dopamine beta hydroxylase (DBH) from bovine adrenals and the enzymatic kinetic constant was reported as Km1984Journal of medicinal chemistry, Oct, Volume: 27, Issue:10
Antihypertensive activities of phenyl aminoethyl sulfides, a class of synthetic substrates for dopamine beta-hydroxylase.
AID61992Compound was evaluated as substrate for Dopamine beta hydroxylase (DBH) from bovine adrenals and the enzymatic kinetic constant was reported as Kcat1984Journal of medicinal chemistry, Oct, Volume: 27, Issue:10
Antihypertensive activities of phenyl aminoethyl sulfides, a class of synthetic substrates for dopamine beta-hydroxylase.
AID215916Binding affinity against trypsin2002Journal of medicinal chemistry, Jun-20, Volume: 45, Issue:13
SMall Molecule Growth 2001 (SMoG2001): an improved knowledge-based scoring function for protein-ligand interactions.
AID1548204Antibacterial activity against Klebsiella pneumoniae ATCC 700603 assessed as bacterial growth inhibition at 32 ug/ml measured after 16 hrs by broth microdilution method2020Journal of medicinal chemistry, 04-23, Volume: 63, Issue:8
Synthesis and Antichlamydial Activity of Molecules Based on Dysregulators of Cylindrical Proteases.
AID62284Kinetic parameter kcat was measured for dopamine beta-monooxygenase1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
The enantiomeric specificity of the antihypertensive activity of 1-(phenylthio)-2-aminopropane, a synthetic substrate analogue for dopamine beta-monooxygenase.
AID1548200Antibacterial activity against methicillin-resistant Staphylococcus aureus ATCC 43300 assessed as bacterial growth inhibition at 32 ug/ml measured after 16 hrs by broth microdilution method2020Journal of medicinal chemistry, 04-23, Volume: 63, Issue:8
Synthesis and Antichlamydial Activity of Molecules Based on Dysregulators of Cylindrical Proteases.
AID62283Kcat/Km value of the compound1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
The enantiomeric specificity of the antihypertensive activity of 1-(phenylthio)-2-aminopropane, a synthetic substrate analogue for dopamine beta-monooxygenase.
AID273099Binding affinity to human SSAO2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
New efficient substrates for semicarbazide-sensitive amine oxidase/VAP-1 enzyme: analysis by SARs and computational docking.
AID273100Binding affinity to mouse SSAO2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
New efficient substrates for semicarbazide-sensitive amine oxidase/VAP-1 enzyme: analysis by SARs and computational docking.
AID125217Compound was evaluated as substrate for monoamine oxidase (MAO) from bovine erythrocyte and the enzymatic kinetic constant was reported as Km1984Journal of medicinal chemistry, Oct, Volume: 27, Issue:10
Antihypertensive activities of phenyl aminoethyl sulfides, a class of synthetic substrates for dopamine beta-hydroxylase.
AID214878Binding affinity against bovine trypsin2002Journal of medicinal chemistry, Jun-06, Volume: 45, Issue:12
Simple, intuitive calculations of free energy of binding for protein-ligand complexes. 1. Models without explicit constrained water.
AID1548199Antibacterial activity against Staphylococcus aureus JE2 assessed as bacterial growth inhibition at 32 ug/ml measured after 16 hrs by broth microdilution method2020Journal of medicinal chemistry, 04-23, Volume: 63, Issue:8
Synthesis and Antichlamydial Activity of Molecules Based on Dysregulators of Cylindrical Proteases.
AID273098Activity of mouse SSAO measured as hydrogen peroxide production at 100 uM relative to benzylamine oxidation2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
New efficient substrates for semicarbazide-sensitive amine oxidase/VAP-1 enzyme: analysis by SARs and computational docking.
AID1548206Antifungal activity against Candida albicans ATCC 90028 assessed as fungal growth inhibition at 32 ug/ml measured after 16 hrs by broth microdilution method2020Journal of medicinal chemistry, 04-23, Volume: 63, Issue:8
Synthesis and Antichlamydial Activity of Molecules Based on Dysregulators of Cylindrical Proteases.
AID1811Experimentally measured binding affinity data derived from PDB1994Nature structural biology, Oct, Volume: 1, Issue:10
Prediction of new serine proteinase inhibitors.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB1994Nature structural biology, Oct, Volume: 1, Issue:10
Prediction of new serine proteinase inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (36.36)18.7374
1990's3 (27.27)18.2507
2000's3 (27.27)29.6817
2010's0 (0.00)24.3611
2020's1 (9.09)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 40.15

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index40.15 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.27 (4.65)
Search Engine Demand Index53.71 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (40.15)

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%
Other11 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]