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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-04-06 16:22:10 UTC
Update Date2017-10-23 19:06:02 UTC
HMDB IDHMDB0012275
Secondary Accession Numbers
  • HMDB12275
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 ).
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 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
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
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

Biological Location:

  Biofluid and excreta:

Source:

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
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
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00-0.030 uMAdult (>18 years old)BothNormal details
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected but not Quantified Children (1-13 years old)BothNormal details
    UrineDetected but not Quantified Adult (>18 years old)BothNormal details
    UrineDetected and Quantified0.011 (0.003-0.067) umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    BloodDetected but not Quantified Adult (>18 years old)BothBulimia Nervosa details
    UrineDetected but not Quantified Children (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 ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDDB04325
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB010580
    KNApSAcK IDC00001426
    Chemspider ID13856352
    KEGG Compound IDC05332
    BioCyc IDPHENYLETHYLAMINE
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem Compound1001
    PDB IDNot Available
    ChEBI ID18397
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Not Available
    General References
    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 ]
    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. 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 ]

    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