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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:32 UTC
Update Date2023-02-21 17:16:03 UTC
HMDB IDHMDB0002017
Secondary Accession Numbers
  • HMDB0002654
  • HMDB0005942
  • HMDB0006062
  • HMDB02017
  • HMDB02654
  • HMDB05942
  • HMDB06062
Metabolite Identification
Common Name1-Phenylethylamine
Description1-Phenylethylamine, also known as a-aminoethylbenzene or a-methylbenzylamine, belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group. 1-Phenylethylamine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 1-phenylethylamine a potential biomarker for the consumption of these foods. 1-Phenylethylamine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 1-Phenylethylamine.
Structure
Data?1676999763
Synonyms
ValueSource
1-Amino-1-phenylethaneChEBI
1-PhenethylamineChEBI
alpha-AminoethylbenzeneChEBI
alpha-MethylbenzenemethanamineChEBI
alpha-MethylbenzylamineChEBI
alpha-PhenylethylamineChEBI
a-AminoethylbenzeneGenerator
Α-aminoethylbenzeneGenerator
a-MethylbenzenemethanamineGenerator
Α-methylbenzenemethanamineGenerator
a-MethylbenzylamineGenerator
Α-methylbenzylamineGenerator
a-PhenylethylamineGenerator
Α-phenylethylamineGenerator
1-Phenethylamine hydrochlorideMeSH
1-Phenethylamine hydrochloride, (+-)-isomerMeSH
1-Phenethylamine, (+-)-isomerMeSH
1-Phenethylamine, (R)-isomerMeSH
1-Phenethylamine, (S)-isomerMeSH
(1-Aminoethyl)benzeneHMDB
1-FenylethylaminHMDB
1-Phenyl-1-ethanamineHMDB
1-PhenylethanamineHMDB
a-PhenethylamineHMDB
alpha-PhenethylamineHMDB
Sumine 2079HMDB
Chemical FormulaC8H11N
Average Molecular Weight121.1796
Monoisotopic Molecular Weight121.089149357
IUPAC Name1-phenylethan-1-amine
Traditional Name(+/-)-α-methylbenzylamine
CAS Registry Number98-84-0
SMILES
CC(N)C1=CC=CC=C1
InChI Identifier
InChI=1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3
InChI KeyRQEUFEKYXDPUSK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary aliphatic amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility42 mg/L at 20 °CNot Available
LogP1.49MEYLAN,WM & HOWARD,PH (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.7 g/LALOGPS
logP1.36ALOGPS
logP1.52ChemAxon
logS-1.5ALOGPS
pKa (Strongest Basic)9.73ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.95 m³·mol⁻¹ChemAxon
Polarizability14.19 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+124.72431661259
DarkChem[M-H]-121.03531661259
DeepCCS[M+H]+126.34330932474
DeepCCS[M-H]-123.16130932474
DeepCCS[M-2H]-160.12530932474
DeepCCS[M+Na]+135.24830932474
AllCCS[M+H]+125.332859911
AllCCS[M+H-H2O]+120.432859911
AllCCS[M+NH4]+129.832859911
AllCCS[M+Na]+131.132859911
AllCCS[M-H]-125.932859911
AllCCS[M+Na-2H]-128.132859911
AllCCS[M+HCOO]-130.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-PhenylethylamineCC(N)C1=CC=CC=C11502.7Standard polar33892256
1-PhenylethylamineCC(N)C1=CC=CC=C11009.0Standard non polar33892256
1-PhenylethylamineCC(N)C1=CC=CC=C11061.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-Phenylethylamine,1TMS,isomer #1CC(N[Si](C)(C)C)C1=CC=CC=C11232.4Semi standard non polar33892256
1-Phenylethylamine,1TMS,isomer #1CC(N[Si](C)(C)C)C1=CC=CC=C11213.5Standard non polar33892256
1-Phenylethylamine,1TMS,isomer #1CC(N[Si](C)(C)C)C1=CC=CC=C11483.4Standard polar33892256
1-Phenylethylamine,2TMS,isomer #1CC(C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1442.9Semi standard non polar33892256
1-Phenylethylamine,2TMS,isomer #1CC(C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1390.5Standard non polar33892256
1-Phenylethylamine,2TMS,isomer #1CC(C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1554.1Standard polar33892256
1-Phenylethylamine,1TBDMS,isomer #1CC(N[Si](C)(C)C(C)(C)C)C1=CC=CC=C11454.6Semi standard non polar33892256
1-Phenylethylamine,1TBDMS,isomer #1CC(N[Si](C)(C)C(C)(C)C)C1=CC=CC=C11440.1Standard non polar33892256
1-Phenylethylamine,1TBDMS,isomer #1CC(N[Si](C)(C)C(C)(C)C)C1=CC=CC=C11664.7Standard polar33892256
1-Phenylethylamine,2TBDMS,isomer #1CC(C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1836.9Semi standard non polar33892256
1-Phenylethylamine,2TBDMS,isomer #1CC(C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1816.8Standard non polar33892256
1-Phenylethylamine,2TBDMS,isomer #1CC(C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1809.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 1-Phenylethylamine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0a4i-0900000000-135bdaa3f3418b3597652014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Phenylethylamine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-004i-0900000000-2a4fe768d40a2f4f0d722014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Phenylethylamine EI-B (Non-derivatized)splash10-0a6r-9700000000-2e29a83dd23d9c59dd092017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Phenylethylamine CI-B (Non-derivatized)splash10-0a4i-1900000000-f1e9aac2f4bed1fdabac2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Phenylethylamine EI-B (Non-derivatized)splash10-0a4i-0900000000-c24ecc231eb7dac647e52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Phenylethylamine EI-B (Non-derivatized)splash10-004i-0900000000-18cd62e45ebef721cf152017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Phenylethylamine GC-EI-TOF (Non-derivatized)splash10-0a4i-0900000000-135bdaa3f3418b3597652017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Phenylethylamine GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-2a4fe768d40a2f4f0d722017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Phenylethylamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9800000000-034169b06cf971ea0de82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Phenylethylamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Phenylethylamine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-00di-2900000000-3c3e1297242c1758bc622012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Phenylethylamine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-004i-9000000000-8c3a3f7f817d09e21f602012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Phenylethylamine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0fb9-9000000000-b504746c5cd545cd988e2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Phenylethylamine EI-B (HITACHI RMU-6M) , Positive-QTOFsplash10-0a6r-9700000000-fc38e120d18302f980be2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Phenylethylamine CI-B (HITACHI M-80) , Positive-QTOFsplash10-0a4i-1900000000-4fdd915024cb2a9a7b772012-08-31HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Phenylethylamine 10V, Positive-QTOFsplash10-05fr-0900000000-c9d262cb8c31aebbb5872017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Phenylethylamine 20V, Positive-QTOFsplash10-05fr-1900000000-8d9a32725dd560f528602017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Phenylethylamine 40V, Positive-QTOFsplash10-0a4i-9700000000-bcd17c3f76f1c23076152017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Phenylethylamine 10V, Negative-QTOFsplash10-00di-0900000000-6f5156a9d2c3dbf44ab92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Phenylethylamine 20V, Negative-QTOFsplash10-00di-1900000000-6932727e42783d1676462017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Phenylethylamine 40V, Negative-QTOFsplash10-0fb9-9700000000-9cf44cfe1d047fdb41b12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Phenylethylamine 10V, Positive-QTOFsplash10-0a4i-0900000000-fc018ed650092a395b412021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Phenylethylamine 20V, Positive-QTOFsplash10-0a4i-3900000000-2aa99a22eb9f39dac2b92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Phenylethylamine 40V, Positive-QTOFsplash10-0fb9-9100000000-629c5c80f9234239b0e52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Phenylethylamine 10V, Negative-QTOFsplash10-00b9-9500000000-78913b21b862b88a1d2c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Phenylethylamine 20V, Negative-QTOFsplash10-00b9-9800000000-71e91c4128b31c54279f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Phenylethylamine 40V, Negative-QTOFsplash10-004i-9100000000-68857a4c8c09a31f092a2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.014 +/- 0.0065 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.14 +/- 0.027 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0070 +/- 0.002 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0071 +/- 0.0045 uMAdult (>18 years old)BothParkinson's disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Parkinson's disease
  1. Miura Y: Plasma beta-phenylethylamine in Parkinson's disease. Kurume Med J. 2000;47(4):267-72. [PubMed:11197147 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022799
KNApSAcK IDNot Available
Chemspider ID7130
KEGG Compound IDC02455
BioCyc IDNot Available
BiGG ID45591
Wikipedia Link1-Phenylethylamine
METLIN ID3246
PubChem Compound7408
PDB IDNot Available
ChEBI ID670
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceLee, C. C.; Spinks, J. W. T. Rearrangement in the reaction between 2-phenylethylamine-1-C14 and nitrous acid. Canadian Journal of Chemistry (1953), 31 761-7.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Miura Y: Plasma beta-phenylethylamine in Parkinson's disease. Kurume Med J. 2000;47(4):267-72. [PubMed:11197147 ]
  2. Samonina-Kosicka J, Kanska M: Mechanistic studies of reactions catalysed by diamine oxidase using isotope effects. Isotopes Environ Health Stud. 2013;49(3):357-64. doi: 10.1080/10256016.2013.825612. [PubMed:24117430 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:
DDC
Uniprot ID:
P20711
Molecular weight:
53893.755
General function:
Involved in copper ion binding
Specific function:
Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity. May play a role in adipogenesis.
Gene Name:
AOC3
Uniprot ID:
Q16853
Molecular weight:
84621.27
General function:
Involved in copper ion binding
Specific function:
Has a monoamine oxidase activity with substrate specificity for 2-phenylethylamine and tryptamine. May play a role in adipogenesis. May be a critical modulator of signal transmission in retina.
Gene Name:
AOC2
Uniprot ID:
O75106
Molecular weight:
80515.11