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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:47 UTC
HMDB IDHMDB01065
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Hydroxyphenethylamine
DescriptionSimple amine found in the brain. It may be modulator of sympathetic functions. Its derivatives are adrenergic agonists and antagonists. It is also used in chemical industry.
Structure
Thumb
Synonyms
ValueSource
2-amino-1-PhenylethanolChEBI
2-Hydroxy-2-phenylethylamineChEBI
2-HydroxyphenethylamineChEBI
2-Phenyl-2-hydroxyethylamineChEBI
alpha-(Aminomethyl)benzyl alcoholChEBI
beta-Hydroxy-beta-phenylethylamineChEBI
beta-HydroxyphenethylamineChEBI
beta-PhenethanolamineChEBI
beta-PhenylethanolamineChEBI
BisnorephedrineChEBI
PhenethanolamineChEBI
a-(Aminomethyl)benzyl alcoholGenerator
α-(aminomethyl)benzyl alcoholGenerator
b-Hydroxy-b-phenylethylamineGenerator
β-hydroxy-β-phenylethylamineGenerator
b-HydroxyphenethylamineGenerator
β-hydroxyphenethylamineGenerator
b-PhenethanolamineGenerator
β-phenethanolamineGenerator
b-PhenylethanolamineGenerator
β-phenylethanolamineGenerator
2-amino-1-Phenyl-1-ethanolHMDB
2-amino-1-Phenylethanol-1HMDB
beta-Hydroxy-beta-phenyl-ethylamineHMDB
beta-Hydroxy-phenethylamineHMDB
beta-HydroxyphenylethylamineHMDB
DL-beta-Phenyl-beta-hydroxyethylamineHMDB
HydroxyethylamineHMDB
Chemical FormulaC8H11NO
Average Molecular Weight137.179
Monoisotopic Molecular Weight137.084063979
IUPAC Name2-amino-1-phenylethan-1-ol
Traditional Nameβ phenylethanolamine
CAS Registry Number7568-93-6
SMILES
NCC(O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C8H11NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H,6,9H2
InChI KeyInChIKey=ULSIYEODSMZIPX-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassAmines
Sub ClassAralkylamines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary amine
  • Organooxygen compound
  • Primary aliphatic amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Tyrosine metabolism
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point56.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility45.8 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility21.4 mg/mLALOGPS
logP0.31ALOGPS
logP0.47ChemAxon
logS-0.81ALOGPS
pKa (Strongest Acidic)14.13ChemAxon
pKa (Strongest Basic)9.13ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.25 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.49 m3·mol-1ChemAxon
Polarizability15.18 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0000900000-548706c8c2ce9f09a548View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-0900000000-c3f1f0f273348db1d32dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-6900000000-bdb37afcb3284184bb38View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
Tissue Location
  • Testes
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00033 +/- 0.00023 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0052 +/- 0.0016 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00052 +/- 0.00052 uMAdult (>18 years old)BothCirrhosis details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022404
KNApSAcK IDNot Available
Chemspider ID975
KEGG Compound IDC02735
BioCyc IDPHENYLETHANOLAMINE
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01065
Metagene LinkHMDB01065
METLIN ID59
PubChem Compound1000
PDB IDNot Available
ChEBI ID16343
References
Synthesis ReferenceYe, Qizhuang. Syntheses of conformationally defined analogs of tyramine and phenylethanolamine and their biological evaluations at central dopamine receptors and the active site of phenylethanolamine N-methyltransferase. (1988), 152 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Buller KM, Hamlin AS, Osborne PB: Dissection of peripheral and central endogenous opioid modulation of systemic interleukin-1beta responses using c-fos expression in the rat brain. Neuropharmacology. 2005 Aug;49(2):230-42. [15993445 ]
  2. Davidoff MS, Ungefroren H, Middendorff R, Koeva Y, Bakalska M, Atanassova N, Holstein AF, Jezek D, Pusch W, Muller D: Catecholamine-synthesizing enzymes in the adult and prenatal human testis. Histochem Cell Biol. 2005 Sep;124(3-4):313-23. Epub 2005 Oct 28. [16052322 ]
  3. Evinger MJ, Mathew E, Cikos S, Powers JF, Lee YS, Sheikh S, Ross RA, Tischler AS: Nicotine stimulates expression of the PNMT gene through a novel promoter sequence. J Mol Neurosci. 2005;26(1):39-55. [15968085 ]
  4. Gee CL, Nourse A, Hsin AY, Wu Q, Tyndall JD, Grunewald GL, McLeish MJ, Martin JL: Disulfide-linked dimers of human adrenaline synthesizing enzyme PNMT are catalytically active. Biochim Biophys Acta. 2005 Jun 15;1750(1):82-92. Epub 2005 Apr 2. [15893506 ]

Enzymes

General function:
Involved in methyltransferase activity
Specific function:
Converts noradrenaline to adrenaline.
Gene Name:
PNMT
Uniprot ID:
P11086
Molecular weight:
30854.745
Reactions
S-Adenosylmethionine + 2-Hydroxyphenethylamine → S-Adenosylhomocysteine + N-Methylphenylethanolaminedetails