Record Information
Version1.0
Creation date2010-04-08 22:09:12 UTC
Update date2019-11-27 17:16:28 UTC
Primary IDFDB010580
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Phenylethylamine
DescriptionPresent in cooked cabbage, cheeses, sherry, wine, processed lean fish, cocoa, raw cauliflower, raw beetroot and raw radish. Flavouring ingredient D-Phenylalanine increases the brain content of phenylethylamine. Phenylethylamine has been shown at least indirectly to satisfy the four main criteria required to demonstrate that a neuroamine sustains mood and that its deficit can be responsible for depression. Antidepressant drug therapy is an indirect (pharmacological) "replacement" of brain phenylethylamine. Phenethylamine is an aromatic amine, which is a colorless liquid at room temperature. It 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. Phenethylamine is strongly basic and forms a stable crystalline hydrochloride salt with a melting point of 217 oC. Phenethylamine is also a skin irritant and possible sensitizer.; Phenethylamine (PEA) is a natural monoamine alkaloid, trace amine, and psychoactive drug with stimulant effects. In the mammalian central nervous system, phenethylamine is believed to function as a neuromodulator or neurotransmitter. It is biosynthesized from the amino acid phenylalanine by enzymatic decarboxylation. Besides mammals, phenethylamine is found in many other organisms and foods such as chocolate, especially after microbial fermentation. It is sold as a dietary supplement for purported mood and weight loss-related therapeutic benefits; however, orally ingested phenethylamine is usually inactive on account of extensive first-pass metabolism by monoamine oxidase (MAO) into phenylacetic acid, preventing significant concentrations from reaching the brain.; Phenethylamine is an aromatic amine, which is a colorless liquid at room temperature. It 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. Phenethylamine is strongly basic and forms a stable crystalline hydrochloride salt with a melting point of 217 °C. Phenethylamine is also a skin irritant and possible sensitizer.; Phenethylamine, or 2-phenylethylamine, is an alkaloid and monoamine. Phenethylamine also has a constitutional isomer (+)-phenylethylamine (1-phenylethylamine), which has two stereoisomers: (R)-(+)-1-phenylethylamine and (S)-(-)-1-phenylethylamine. In the human brain, 2-phenethylamine is believed to function as a neuromodulator or neurotransmitter (trace amine). Phenethylamine is a natural compound biosynthesized from the amino acid phenylalanine by enzymatic decarboxylation. It is also found in many foods such as chocolate, especially after microbial fermentation. However trace amounts from food are quickly metabolized by the enzyme MAO-B, preventing significant concentrations from reaching the brain.; Phenylethylamine is a precursor to the neurotransmitter phenylethanolamine.
CAS Number64-04-0
Structure
Thumb
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 sulfateMeSH
.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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
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
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.