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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
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not 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
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-bf5d1e8f4a14683bd0aa2015-03-01View Spectrum
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
Predicted GC-MS2-Phenylethylamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-95c5a1366bba1014e2aa2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0ab9-0900000000-5ad03d29c0ff6167539c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-0900000000-1b25fe0d03af3ce715ba2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-056r-7900000000-a6478bab1f5bd04c73292017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9100000000-abdacae4bceb2048614f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9000000000-d61f8f9b0d593297d0102017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0ab9-0900000000-e3d2be06e661bac2f7392017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-0900000000-fc4c40ae6333ed1f04f62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-056r-7900000000-f25cc18055d08500ec9d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9100000000-0e8ece94eaa349e6fd212017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0uk9-2900000000-272fff4a446fcf053de82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-e833e9ebdd0584ee9cff2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-f51c34f8fd6e67925a522017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-162188a06251a43ccc542017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-162188a06251a43ccc542017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-2a12817c62551d9dee502017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-ac8b555024a8bbc5e78b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-926231c14695be35af042017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-c5e8005c53eaf96bc9572017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-6f9e6a6eb6c2ac8f45312017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-1900000000-aeb026a07351a147ae192017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-3900000000-a6c6357f047322c4efe12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a6r-6900000000-0a32d01e2dda19a78c832017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-056r-9600000000-be832e76b1211d35978c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-004i-9400000000-ab97002137a57a7802bc2017-09-14View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
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.