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Human Metabolome Database Version 3.5

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Showing metabocard for 1-Phenylethylamine (HMDB02017)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:32 -0600
Update Date 2013-02-08 17:11:12 -0700
HMDB ID HMDB02017
Secondary Accession Numbers
  • HMDB02654
  • HMDB05942
  • HMDB06062
Metabolite Identification
Common Name 1-Phenylethylamine
Description 1-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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C8H11N
Average Molecular Weight 121.1796
Monoisotopic Molecular Weight 121.089149357
IUPAC Name 1-phenylethan-1-amine
Traditional IUPAC Name 1-phenylethylamine
CAS Registry Number 98-84-0
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 Key RQEUFEKYXDPUSK-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Phenylmethylamines
Sub Class N/A
Other Descriptors
  • Organic Compounds
  • phenylethylamine(ChEBI)
Substituents
  • Primary Aliphatic Amine (Alkylamine)
Direct Parent Phenylmethylamines
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point < 25 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 42 mg/L at 20 °C Not Available
LogP 1.49 MEYLAN,WM & HOWARD,PH (1995)
Predicted Properties
Property Value Source
LogP 1.36 ALOGPS
LogP 1.52 ChemAxon
LogS -1.51 ALOGPS
pKa (strongest basic) 9.73 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 26.02 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 38.95 ChemAxon
Polarizability 14.19 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI RMU-6M)
MS/MS Spectrum CI-B (HITACHI M-80)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.014 +/- 0.0065 uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.14 +/- 0.027 uM Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
0.0070 +/- 0.002 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.0071 +/- 0.0045 uM Adult (>18 years old) Both Parkinson's disease Not Available
Associated Disorders and Diseases
Disease References
Parkinson's disease
  • Miura Y: Plasma beta-phenylethylamine in Parkinson's disease. Kurume Med J. 2000;47(4):267-72. Pubmed: 11197147 Link_out
    Associated OMIM IDs
    DrugBank ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB022799
    KNApSAcK ID Not Available
    Chemspider ID 7130 Link_out
    KEGG Compound ID C02455 Link_out
    BioCyc ID Not Available
    BiGG ID 45591 Link_out
    Wikipedia Link 1-phenylethylamine Link_out
    NuGOwiki Link HMDB02017 Link_out
    Metagene Link HMDB02017 Link_out
    METLIN ID 3246 Link_out
    PubChem Compound 7408 Link_out
    PDB ID Not Available
    ChEBI ID 670 Link_out
    References
    Synthesis Reference Lee, 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 References Not Available
    Enzymes
    Name: Amine oxidase [flavin-containing] B
    Reactions:
    • RCH2NHR' + H2O + O2 = RCHO + R'NH2 + H2O2 [RN:R01853]
    Gene Name: MAOB
    Uniprot ID: P27338 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Amine oxidase [flavin-containing] A
    Reactions:
    • RCH2NHR' + H2O + O2 = RCHO + R'NH2 + H2O2 [RN:R01853]
    Gene Name: MAOA
    Uniprot ID: P21397 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Aromatic-L-amino-acid decarboxylase
    Reactions:
    • (1) 3,4-dihydroxy-L-phenylalanine = dopamine + CO2 [RN:R02080]
    • (2) 5-hydroxy-L-tryptophan = 5-hydroxytryptamine + CO2 [RN:R02701]
    Gene Name: DDC
    Uniprot ID: P20711 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Membrane primary amine oxidase
    Reactions:
    • RCH2NH2 + H2O + O2 = RCHO + NH3 + H2O2 [RN:R01853]
    Gene Name: AOC3
    Uniprot ID: Q16853 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Retina-specific copper amine oxidase
    Reactions:
    • RCH2NH2 + H2O + O2 = RCHO + NH3 + H2O2 [RN:R01853]
    Gene Name: AOC2
    Uniprot ID: O75106 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA