You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2006-05-22 14:17:32 UTC
Update Date2013-02-09 00:11:12 UTC
HMDB IDHMDB02017
Secondary Accession Numbers
  • HMDB02654
  • HMDB05942
  • HMDB06062
Metabolite Identification
Common Name1-Phenylethylamine
Description1-Phenylethylamine, or alpha-phenethylamine, is an amine. Individual enantiomers of this basic compound are useful for performing chiral resolution of acidic compounds by forming diastereomeric salts. -- Wikipedia.
Structure
Thumb
Synonyms
  1. (1-Aminoethyl)benzene
  2. 1-Amino-1-phenylethane
  3. 1-Fenylethylamin
  4. 1-Phenyl-1-ethanamine
  5. 1-Phenylethanamine
  6. 1-Phenylethylamine
  7. a-Aminoethylbenzene
  8. a-Methylbenzenemethanamine
  9. a-Methylbenzylamine
  10. a-Phenethylamine
  11. a-Phenylethylamine
  12. alpha-Aminoethylbenzene
  13. alpha-Methylbenzenemethanamine
  14. alpha-Methylbenzylamine
  15. alpha-Phenethylamine
  16. alpha-Phenylethylamine
  17. Sumine 2079
Chemical FormulaC8H11N
Average Molecular Weight121.1796
Monoisotopic Molecular Weight121.089149357
IUPAC Name1-phenylethan-1-amine
Traditional IUPAC Name1-phenylethylamine
CAS Registry Number98-84-0
SMILES
CC(N)C1=CC=CC=C1
InChI Identifier
InChI=1S/C8H11N/c1-7(9)8-5-3-2-4-6-8/h2-7H,9H2,1H3
InChI KeyRQEUFEKYXDPUSK-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassPhenylmethylamines
Sub ClassN/A
Other Descriptors
  • Organic Compounds
  • phenylethylamine(ChEBI)
Substituents
  • Primary Aliphatic Amine (Alkylamine)
Direct ParentPhenylmethylamines
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility42 mg/L at 20 °CNot Available
LogP1.49MEYLAN,WM & HOWARD,PH (1995)
Predicted Properties
PropertyValueSource
water solubility3.7 g/LALOGPS
logP1.36ALOGPS
logP1.52ChemAxon
logS-1.5ALOGPS
pKa (strongest basic)9.73ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count1ChemAxon
polar surface area26.02ChemAxon
rotatable bond count1ChemAxon
refractivity38.95ChemAxon
polarizability14.19ChemAxon
Spectra
SpectraGC-MSMS/MS
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.014 +/- 0.0065 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.14 +/- 0.027 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0070 +/- 0.002 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0071 +/- 0.0045 uMAdult (>18 years old)BothParkinson's disease details
Associated Disorders and Diseases
Disease References
Parkinson's disease
  1. Miura Y: Plasma beta-phenylethylamine in Parkinson's disease. Kurume Med J. 2000;47(4):267-72. Pubmed: 11197147
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022799
KNApSAcK IDNot Available
Chemspider ID7130
KEGG Compound IDC02455
BioCyc IDNot Available
BiGG ID45591
Wikipedia Link1-phenylethylamine
NuGOwiki LinkHMDB02017
Metagene LinkHMDB02017
METLIN ID3246
PubChem Compound7408
PDB IDNot Available
ChEBI ID670
References
Synthesis ReferenceLee, C. C.; Spinks, J. W. T. Rearrangement in the reaction between 2-phenylethylamine-1-C14 and nitrous acid. Canadian Journal of Chemistry (1953), 31 761-7.
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

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
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
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
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
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