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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-09 21:15:22 UTC
Update Date2017-12-07 16:40:51 UTC
HMDB IDHMDB0060276
Secondary Accession Numbers
  • HMDB60276
Metabolite Identification
Common Name2-Phenylethanaminium
DescriptionPhenylethylamine, also known as beta-phenethylamine or benzeneethanamine, belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine. Phenylethylamine is slightly soluble (in water) and a very strong basic compound (based on its pKa). Phenylethylamine has been detected in multiple biofluids, such as urine and blood. Phenylethylamine exists in all eukaryotes, ranging from yeast to humans. Phenylethylamine is also a parent compound for other transformation products, including but not limited to, 3,4-dimethoxyphenylethylamine, 4-methoxyphenylethylamine, and 3-{(3E)-4-hydroxy-6-oxo-3-[(2-phenylethyl)imino]cyclohexa-1,4-dien-1-yl}-L-alanine.
Structure
Thumb
Synonyms
ValueSource
BenzeneethanamineChEBI
beta-AminoethylbenzeneChEBI
beta-PhenethylamineChEBI
beta-PhenylethylamineChEBI
PhenethylamineChEBI
b-AminoethylbenzeneGenerator
β-aminoethylbenzeneGenerator
b-PhenethylamineGenerator
β-phenethylamineGenerator
b-PhenylethylamineGenerator
β-phenylethylamineGenerator
(2-Aminoethyl)benzeneHMDB
(2-Aminoethyl)polystyreneHMDB
1-amino-2-PhenylethaneHMDB
1-PhenethylamineHMDB
1-Phenyl-2-amino-athanHMDB
1-Phenyl-2-aminoethaneHMDB
1TNJHMDB
1UtmHMDB
1UtoHMDB
2-amino-1-PhenylethaneHMDB
2-amino-FenylethanHMDB
2-FenylethylaminHMDB
2-PhenethylamineHMDB
2-Phenyl-ethanamineHMDB
2-PhenylethanamineHMDB
2-Phenylethanamine (acd/name 4.0)HMDB
2-PhenylethylamineHMDB
2-Phenylethylamine (acd/name 4.0)HMDB
b-PhenylaethylaminHMDB
Benzeneethanamine hydrochlorideHMDB
beta PhenethylamineHMDB
beta-PhenylaethylaminHMDB
Omega-phenylethylamineHMDB
PEAHMDB
Phenethylamine hydrochlorideHMDB
Polystyrene a-NH2HMDB
Phenethylamine hydrobromideMeSH
Phenethylamine tosylateMeSH
Phenethylamine conjugate acidMeSH
Phenethylamine sulfateMeSH
Phenethylamine, monolithium saltMeSH
2-Phenylethylammonium chlorideMeSH
Phenethylamine sulfate (2:1)MeSH
Phenethylamine, 15N-labeled CPDMeSH
Phenethylamine mesylateMeSH
Phenethylamine perchlorateMeSH
Phenethylamine, beta-(14)C-labeled CPDMeSH
Chemical FormulaC8H11N
Average Molecular Weight121.1796
Monoisotopic Molecular Weight121.089149357
IUPAC Name2-phenylethan-1-amine
Traditional Name2-phenylethylamine
CAS Registry NumberNot Available
SMILES
NCCC1=CC=CC=C1
InChI Identifier
InChI=1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2
InChI KeyBHHGXPLMPWCGHP-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenethylamines. These are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentPhenethylamines
Alternative Parents
Substituents
  • Phenethylamine
  • 2-arylethylamine
  • Aralkylamine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Role

Industrial application:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.19 g/LALOGPS
logP1.41ALOGPS
logP1.39ChemAxon
logS-1.7ALOGPS
pKa (Strongest Basic)9.79ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.29 m³·mol⁻¹ChemAxon
Polarizability14.35 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0udi-3900000000-c931498c67dbf88820eeView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00dr-5900000000-d15a3c803d2534e366d8View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-7713ab7346491f1f5f42View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-94774bbd6283b4a26a51View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0abc-5900000000-724c680a9564ac27f7eeView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-5ba434a8565ec0014b6bView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-053r-9000000000-f312ab6fe99f8eca86e7View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-3900000000-c931498c67dbf88820eeView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00dr-5900000000-d15a3c803d2534e366d8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dr-4900000000-4c37abb4c50d5582d87cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001l-9100000000-3e2562db471b8bb298d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-95c5a1366bba1014e2aaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0ab9-0900000000-5ad03d29c0ff6167539cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-0900000000-1b25fe0d03af3ce715baView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-056r-7900000000-a6478bab1f5bd04c7329View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9100000000-abdacae4bceb2048614fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9000000000-d61f8f9b0d593297d010View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0ab9-0900000000-e3d2be06e661bac2f739View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-0900000000-fc4c40ae6333ed1f04f6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-056r-7900000000-f25cc18055d08500ec9dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9100000000-0e8ece94eaa349e6fd21View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0uk9-2900000000-272fff4a446fcf053de8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-e833e9ebdd0584ee9cffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-f51c34f8fd6e67925a52View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-162188a06251a43ccc54View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-162188a06251a43ccc54View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-2a12817c62551d9dee50View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-ac8b555024a8bbc5e78bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-926231c14695be35af04View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-c5e8005c53eaf96bc957View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0900000000-10a3aff16ce06e5488bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-c8186da6e772bfd9759cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9500000000-2745e56fb8603507394bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-b746d7d1eb593614d234View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1900000000-f4ada8157d6dde803051View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufu-9500000000-54d2d2a1b68d878200b8View in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-bf5d1e8f4a14683bd0aaView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010580
KNApSAcK IDC00001426
Chemspider ID13856352
KEGG Compound IDC05332
BioCyc IDPHENYLETHYLAMINE
BiGG IDNot Available
Wikipedia Link2-phenylethylamine
METLIN IDNot Available
PubChem Compound1001
PDB IDNot Available
ChEBI ID18397
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]