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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-04-06 16:22:10 UTC
Update Date2020-11-09 23:18:35 UTC
HMDB IDHMDB0012275
Secondary Accession Numbers
  • HMDB0060276
  • HMDB12275
  • HMDB60276
Metabolite Identification
Common NamePhenylethylamine
DescriptionPhenethylamine (PEA) 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 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 (a trace amine). Phenethylamine can be 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 (into phenylacetic acid), preventing significant concentrations from reaching the brain. Phenylethylamine 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 ). It has been found that PEA is the primary compound found in carnivore (especially cat) urine that leads to rodent (mouse and rat) avoidance. In other words, phenylethylamine is useful for scaring off rodent pests. Quantitative HPLC analysis across 38 mammalian species has shown that PEA production in urine is especially enhanced in carnivores, with some producing >3,000-fold more than herbivores (PMID: 21690383 ). Phenethylamine has been found to be a metabolite of Bacillus, Enterococcus and Lactobacillus (PMID: 22953951 ; PMID: 17307265 ; PMID: 16630269 ).
Structure
Data?1582753036
Synonyms
ValueSource
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
Chemical FormulaC8H11N
Average Molecular Weight121.1796
Monoisotopic Molecular Weight121.089149357
IUPAC Name2-phenylethan-1-amine
Traditional Name2-phenylethylamine
CAS Registry Number64-04-0
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
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:

Physical Properties
StateSolid
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0udi-3900000000-c931498c67dbf88820eeSpectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00dr-5900000000-d15a3c803d2534e366d8Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-7713ab7346491f1f5f42Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-94774bbd6283b4a26a51Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0abc-5900000000-724c680a9564ac27f7eeSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-5ba434a8565ec0014b6bSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-053r-9000000000-f312ab6fe99f8eca86e7Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-3900000000-c931498c67dbf88820eeSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00dr-5900000000-d15a3c803d2534e366d8Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dr-4900000000-4c37abb4c50d5582d87cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001l-9100000000-3e2562db471b8bb298d2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-95c5a1366bba1014e2aaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0ab9-0900000000-5ad03d29c0ff6167539cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-0900000000-1b25fe0d03af3ce715baSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-056r-7900000000-a6478bab1f5bd04c7329Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9100000000-abdacae4bceb2048614fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9000000000-d61f8f9b0d593297d010Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0ab9-0900000000-e3d2be06e661bac2f739Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-0900000000-fc4c40ae6333ed1f04f6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-056r-7900000000-f25cc18055d08500ec9dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9100000000-0e8ece94eaa349e6fd21Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0uk9-2900000000-272fff4a446fcf053de8Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-e833e9ebdd0584ee9cffSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-f51c34f8fd6e67925a52Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-162188a06251a43ccc54Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-162188a06251a43ccc54Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-2a12817c62551d9dee50Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-ac8b555024a8bbc5e78bSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-926231c14695be35af04Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-c5e8005c53eaf96bc957Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0900000000-10a3aff16ce06e5488bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-c8186da6e772bfd9759cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9500000000-2745e56fb8603507394bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-b746d7d1eb593614d234Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1900000000-f4ada8157d6dde803051Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufu-9500000000-54d2d2a1b68d878200b8Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-bf5d1e8f4a14683bd0aaSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00-0.030 uMAdult (>18 years old)BothNormal details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified10 +/- 10 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.011 (0.003-0.067) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBulimia Nervosa details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn disease
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis
details
UrineDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothADHD (Attention Defict Hyperactivity Disorder) details
UrineDetected and Quantified0.028 +/- 0.038 umol/mmol creatinineChildren (1-13 years old)BothAutism details
Associated Disorders and Diseases
Disease References
Bulimia nervosa
  1. Davis BA, Kennedy SH, D'Souza J, Durden DA, Goldbloom DS, Boulton AA: Correlations of plasma and urinary phenylacetic acid and phenylethylamine concentrations with eating behavior and mood rating scores in brofaromine-treated women with bulimia nervosa. J Psychiatry Neurosci. 1994 Jul;19(4):282-8. [PubMed:7918350 ]
Crohn's disease
  1. Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
Ulcerative colitis
  1. Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
Minimal brain dysfunction
  1. Kusaga A, Yamashita Y, Koeda T, Hiratani M, Kaneko M, Yamada S, Matsuishi T: Increased urine phenylethylamine after methylphenidate treatment in children with ADHD. Ann Neurol. 2002 Sep;52(3):372-4. [PubMed:12205654 ]
Autism
  1. Kusaga A, Yamashita Y, Koeda T, Hiratani M, Kaneko M, Yamada S, Matsuishi T: Increased urine phenylethylamine after methylphenidate treatment in children with ADHD. Ann Neurol. 2002 Sep;52(3):372-4. [PubMed:12205654 ]
Associated OMIM IDs
DrugBank IDDB04325
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDPEAMN
MarkerDB ID
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 ]
  2. O'Reilly RL, Davis BA: Phenylethylamine and schizophrenia. Prog Neuropsychopharmacol Biol Psychiatry. 1994 Jan;18(1):63-75. [PubMed:7906896 ]
  3. Potkin SG, Wyatt RJ, Karoum F: Phenylethylamine (PEA) and phenylacetic acid (PAA) in the urine of chronic schizophrenic patients and controls. Psychopharmacol Bull. 1980 Jan;16(1):52-4. [PubMed:7360842 ]
  4. Kusaga A, Yamashita Y, Koeda T, Hiratani M, Kaneko M, Yamada S, Matsuishi T: Increased urine phenylethylamine after methylphenidate treatment in children with ADHD. Ann Neurol. 2002 Sep;52(3):372-4. [PubMed:12205654 ]
  5. Ferrero DM, Lemon JK, Fluegge D, Pashkovski SL, Korzan WJ, Datta SR, Spehr M, Fendt M, Liberles SD: Detection and avoidance of a carnivore odor by prey. Proc Natl Acad Sci U S A. 2011 Jul 5;108(27):11235-40. doi: 10.1073/pnas.1103317108. Epub 2011 Jun 20. [PubMed:21690383 ]
  6. Kim B, Byun BY, Mah JH: Biogenic amine formation and bacterial contribution in Natto products. Food Chem. 2012 Dec 1;135(3):2005-11. doi: 10.1016/j.foodchem.2012.06.091. Epub 2012 Jul 3. [PubMed:22953951 ]
  7. Landete JM, Pardo I, Ferrer S: Tyramine and phenylethylamine production among lactic acid bacteria isolated from wine. Int J Food Microbiol. 2007 Apr 20;115(3):364-8. doi: 10.1016/j.ijfoodmicro.2006.10.051. Epub 2007 Jan 18. [PubMed:17307265 ]
  8. Marcobal A, de las Rivas B, Munoz R: First genetic characterization of a bacterial beta-phenylethylamine biosynthetic enzyme in Enterococcus faecium RM58. FEMS Microbiol Lett. 2006 May;258(1):144-9. doi: 10.1111/j.1574-6968.2006.00206.x. [PubMed:16630269 ]

Enzymes

General function:
Involved in N-acetyltransferase activity
Specific function:
Controls the night/day rhythm of melatonin production in the pineal gland. Catalyzes the N-acetylation of serotonin into N-acetylserotonin, the penultimate step in the synthesis of melatonin.
Gene Name:
AANAT
Uniprot ID:
Q16613
Molecular weight:
23343.8
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
Reactions
Phenylethylamine + Oxygen + Water → Phenylacetaldehyde + Ammonia + Hydrogen peroxidedetails
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
Reactions
Phenylethylamine + Oxygen + Water → Phenylacetaldehyde + Ammonia + Hydrogen peroxidedetails
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
Reactions
L-Phenylalanine → Phenylethylamine + Carbon dioxidedetails
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
Reactions
Phenylethylamine + Oxygen + Water → Phenylacetaldehyde + Ammonia + Hydrogen peroxidedetails
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
Reactions
Phenylethylamine + Oxygen + Water → Phenylacetaldehyde + Ammonia + Hydrogen peroxidedetails
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for trace amines, including beta- phenylethylamine (b-PEA), p-tyramine (p-TYR), octopamine and tryptamine, with highest affinity for b-PEA and p-TYR. Unresponsive to classical biogenic amines, such as epinephrine and histamine and only partially activated by dopamine and serotonine. Trace amines are biogenic amines present in very low levels in mammalian tissues. Although some trace amines have clearly defined roles as neurotransmitters in invertebrates, the extent to which they function as true neurotransmitters in vertebrates has remained speculative. Trace amines are likely to be involved in a variety of physiological functions that have yet to be fully understood. The signal transduced by this receptor is mediated by the G(s)-class of G-proteins which activate adenylate cyclase
Gene Name:
TAAR1
Uniprot ID:
Q96RJ0
Molecular weight:
39091.3