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Showing Compound 2-Phenylethylamine (FDB010580)

Record Information
Version1.0
Creation date2010-04-08 22:09:12 UTC
Update date2020-09-17 15:30:49 UTC
Primary IDFDB010580
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Phenylethylamine
DescriptionPhenylethylamine (PEA) is an aromatic amine which has a constitutional isomer (+)-phenylethylamine (1-phenylethylamine), which has two stereoisomers: (R)-(+)-1-phenylethylamine and (S)-(-)-1-phenylethylamine. It is a strongly basic, colorless liquid at room temperature which is soluble in water, ethanol, and ether. Similar to other low-molecular-weight amines, it has a fishy odor. Upon exposure to air, it forms a solid carbonate salt with carbon dioxide. Phenylethylamines can be biosynthesized in mammals from the amino acid phenylalanine by enzymatic decarboxylation. Phenylethylamine is produced after microbial fermentation and is a metabolite of Bacillus, Enterococcus, Pseudomanas and Lactobacillus (PMID: 22953951; PMID: 17307265; PMID: 16630269) and has anti-microbial properties against pathogenic strains of E. coli. It is found in many foods such as chocolate. However, trace amounts from food are quickly metabolized by the enzyme monoamine oxidase (MAO-B) into phenylacetic acid, preventing significant concentrations from reaching the brain. In the human brain, phenylethylamine is a central nervous system stimulant that binds to the human trace amine-associated receptor 1 (hTAAR1) as an agonist (PMID 27424325). It is a precursor to the neurotransmitter phenylethanolamine. High levels of PEA have been found in the urine of schizophrenics, but it is not significantly elevated in the serum or CSF of schizophrenics (PMID: 7906896, PMID: 7360842). Urinary levels of PEA are significantly lower in children with attention deficit hyperactivity disorder (ADHD) (PMID: 12205654). Phenylethylamine is also a skin irritant and possible sensitizer. PEA is the primary compound found in carnivore urine (especially cat) that repels mice and rats. Quantitative HPLC analysis across 38 mammalian species has shown that PEA production in urine is especially high in carnivores, with some producing >3,000-fold more than herbivores (PMID: 21690383).
CAS Number64-04-0
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
BenzeneethanamineChEBI
beta-AminoethylbenzeneChEBI
beta-PhenethylamineChEBI
beta-PhenylethylamineChEBI
PhenethylamineChEBI
2-PhenylethylamineKegg
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-Phenylethylamine (acd/name 4.0)HMDB
b-PhenylaethylaminHMDB
Benzeneethanamine hydrochlorideHMDB
beta PhenethylamineHMDB
beta-PhenylaethylaminHMDB
Omega-phenylethylamineHMDB
PEAHMDB
Phenethylamine hydrochlorideHMDB
Polystyrene a-NH2HMDB
Phenethylamine hydrobromideHMDB
Phenethylamine tosylateHMDB
Phenethylamine conjugate acidHMDB
Phenethylamine sulfateHMDB
Phenethylamine, monolithium saltHMDB
2-Phenylethylammonium chlorideHMDB
Phenethylamine sulfate (2:1)HMDB
Phenethylamine, 15N-labeled CPDHMDB
Phenethylamine mesylateHMDB
Phenethylamine perchlorateHMDB
Phenethylamine, beta-(14)C-labeled CPDHMDB
Diphenethylamine sulfateHMDB
.omega.-phenylethylaminebiospider
βbiospider
β-aminoethylbenzenebiospider
β-phenethylaminebiospider
β-phenylaethylaminbiospider
β-phenylaethylamin (german)biospider
β-phenylethylaminebiospider
«omega»-phenylethylaminebiospider
1-Phenyl-2-amino-athan (GERMAN)biospider
1-Phenyl-2-aminoethane hydrochloridebiospider
1tnjbiospider
1utmbiospider
1utobiospider
2-phenyl-Ethanaminebiospider
2-Phenylethylamine hydrochloridebiospider
3-Methylbutanoic acidbiospider
B-phenethylaminebiospider
B-phenylaethylaminbiospider
B-phenylaethylamin (german)biospider
B-phenylethylaminebiospider
Benzeneethanamine, 9CIdb_source
Benzeneethanamine, hydrochloridebiospider
Beta phenethylaminebiospider
Beta-aminoethylbenzenebiospider
Beta-phenethylaminebiospider
Beta-phenylaethylaminbiospider
Beta-phenylethylaminebiospider
Ethanamine, 2-phenyl-biospider
Ethylamine, 2-phenyl-biospider
FEMA 3220db_source
Phenethylamine, βbiospider
Phenethylamine, 8CIdb_source
Phenethylamine, betabiospider
Phenethylamine, hydrochloridebiospider
Phenethylammonium chloridebiospider
Phenylethylaminebiospider
Polystyrene A-NH2biospider
Polystyrene A-NH2;biospider
β-aminoethylbenzeneGenerator
β-phenethylamineGenerator
β-phenylethylamineGenerator
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H11N
IUPAC name2-phenylethan-1-amine
InChI IdentifierInChI=1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2
InChI KeyBHHGXPLMPWCGHP-UHFFFAOYSA-N
Isomeric SMILESNCCC1=CC=CC=C1
Average Molecular Weight121.1796
Monoisotopic Molecular Weight121.089149357
Classification
Description 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.
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
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 79.29%; H 9.15%; N 11.56%DFC
Melting Point-60 oC
Boiling PointBp7 70-71°DFC
Experimental Water SolubilityNot Available
Experimental logP1.41HANSCH,C ET AL. (1995)
Experimental pKa9.83
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd244 0.96DFC
Refractive Indexn25D 1.5290DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-bf5d1e8f4a14683bd0aaSpectrum
GC-MS2-Phenylethylamine, 1 TMS, GC-MS Spectrumsplash10-0udi-3900000000-c931498c67dbf88820eeSpectrum
GC-MS2-Phenylethylamine, 2 TMS, GC-MS Spectrumsplash10-00dr-5900000000-d15a3c803d2534e366d8Spectrum
GC-MS2-Phenylethylamine, non-derivatized, GC-MS Spectrumsplash10-001i-9000000000-7713ab7346491f1f5f42Spectrum
GC-MS2-Phenylethylamine, non-derivatized, GC-MS Spectrumsplash10-001i-9000000000-94774bbd6283b4a26a51Spectrum
GC-MS2-Phenylethylamine, non-derivatized, GC-MS Spectrumsplash10-0abc-5900000000-724c680a9564ac27f7eeSpectrum
GC-MS2-Phenylethylamine, non-derivatized, GC-MS Spectrumsplash10-001i-9000000000-5ba434a8565ec0014b6bSpectrum
GC-MS2-Phenylethylamine, non-derivatized, GC-MS Spectrumsplash10-053r-9000000000-f312ab6fe99f8eca86e7Spectrum
GC-MS2-Phenylethylamine, non-derivatized, GC-MS Spectrumsplash10-0udi-3900000000-c931498c67dbf88820eeSpectrum
GC-MS2-Phenylethylamine, non-derivatized, GC-MS Spectrumsplash10-00dr-5900000000-d15a3c803d2534e366d8Spectrum
GC-MS2-Phenylethylamine, non-derivatized, GC-MS Spectrumsplash10-00dr-4900000000-4c37abb4c50d5582d87cSpectrum
Predicted GC-MS2-Phenylethylamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001l-9100000000-3e2562db471b8bb298d2Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-95c5a1366bba1014e2aaSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0ab9-0900000000-5ad03d29c0ff6167539cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-0900000000-1b25fe0d03af3ce715baSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-056r-7900000000-a6478bab1f5bd04c7329Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9100000000-abdacae4bceb2048614fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9000000000-d61f8f9b0d593297d010Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0ab9-0900000000-e3d2be06e661bac2f739Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-0900000000-fc4c40ae6333ed1f04f6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-056r-7900000000-f25cc18055d08500ec9dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9100000000-0e8ece94eaa349e6fd21Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0uk9-2900000000-272fff4a446fcf053de8Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-e833e9ebdd0584ee9cffSpectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-f51c34f8fd6e67925a52Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-162188a06251a43ccc54Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-162188a06251a43ccc54Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-2a12817c62551d9dee50Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-ac8b555024a8bbc5e78bSpectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-926231c14695be35af04Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-c5e8005c53eaf96bc957Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0900000000-10a3aff16ce06e5488bbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-c8186da6e772bfd9759cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9500000000-2745e56fb8603507394bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-b746d7d1eb593614d234Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1900000000-f4ada8157d6dde803051Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufu-9500000000-54d2d2a1b68d878200b8Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
ChemSpider ID13856352
ChEMBL IDCHEMBL610
KEGG Compound IDC05332
Pubchem Compound ID1001
Pubchem Substance IDNot Available
ChEBI ID18397
Phenol-Explorer IDNot Available
DrugBank IDDB04325
HMDB IDHMDB12275
CRC / DFC (Dictionary of Food Compounds) IDFFC18-E:FFC18-E
EAFUS ID2958
Dr. Duke ID2-PHENYLETHYL-AMINE|BETA-PHENYLETHYLAMINE|PHENETHYLAMINE|PHENYLETHYLAMINE
BIGG IDNot Available
KNApSAcK IDC00001426
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1035561
SuperScent IDNot Available
Wikipedia ID2-Phenylethylamine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti depressant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
central nervous system stimulant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
irritantDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
Enzymes
NameGene NameUniProt ID
Aromatic-L-amino-acid decarboxylaseDDCP20711
Serotonin N-acetyltransferaseAANATQ16613
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
ammoniacal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fishy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.