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Human Metabolome Database Version 3.5

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Showing metabocard for Phenylpropanolamine (HMDB01942)

Record Information
Version 3.5
Creation Date 2006-05-18 03:09:22 -0600
Update Date 2013-02-08 17:11:04 -0700
HMDB ID HMDB01942
Secondary Accession Numbers
  • HMDB05002
Metabolite Identification
Common Name Phenylpropanolamine
Description Phenylpropanolamine is a sympathomimetic that acts mainly by causing release of norepinephrine but also has direct agonist activity at some adrenergic receptors. It is most commonly used as a nasal vasoconstrictor and an appetite depressant. -- Pubchem.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. DL-Norephedrine
  2. DL-Phenylpropanolamine
  3. Hydriatine
  4. L-NOREPHEDRINE
  5. L-Phenyl Propanolamine
  6. Mucorama
  7. Nobese
  8. Norephedrine
  9. Obestat
  10. Phenylpropanolamine
  11. Prestwick_388
  12. Propadrine
Chemical Formula C9H13NO
Average Molecular Weight 151.2056
Monoisotopic Molecular Weight 151.099714043
IUPAC Name (1S,2R)-2-amino-1-phenylpropan-1-ol
Traditional IUPAC Name phenylpropanolamine
CAS Registry Number 154-41-6
SMILES C[C@@H](N)[C@@H](O)C1=CC=CC=C1
InChI Identifier InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m1/s1
InChI Key DLNKOYKMWOXYQA-VXNVDRBHSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Phenethylamines
Sub Class Amphetamines and Derivatives
Other Descriptors
  • Organic Compounds
Substituents
  • 1,2 Aminoalcohol
  • Benzyl Alcohol Derivative
  • Primary Aliphatic Amine (Alkylamine)
  • Secondary Alcohol
Direct Parent Amphetamines and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Drug
Biofunction Not Available
Application Not Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 194 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 733 mg/mL Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 20.6 g/L ALOGPS
LogP 0.57 ALOGPS
LogP 0.89 ChemAxon
LogS -0.87 ALOGPS
pKa (strongest acidic) 13.9 ChemAxon
pKa (strongest basic) 9.37 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 46.25 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 44.91 ChemAxon
Polarizability 16.98 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
2.0 (0.005-5.0) uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022757
KNApSAcK ID Not Available
Chemspider ID 25082 Link_out
KEGG Compound ID C02343 Link_out
BioCyc ID 4-P-PANTHETHEINE Link_out
BiGG ID Not Available
Wikipedia Link Phenylpropanolamine Link_out
NuGOwiki Link HMDB01942 Link_out
Metagene Link HMDB01942 Link_out
METLIN ID 1846 Link_out
PubChem Compound 26934 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Ho TS, Pedersen-Bjergaard S, Rasmussen KE: Experiences with carrier-mediated transport in liquid-phase microextraction. J Chromatogr Sci. 2006 Jun;44(6):308-16. Pubmed: 16884585 Link_out
  2. Stockley CS, Wing LM, Miners JO: Stereospecific high-performance liquid chromatographic assay for the enantiomers of phenylpropanolamine in human plasma. Ther Drug Monit. 1991 Jul;13(4):332-8. Pubmed: 1780966 Link_out
  3. Dowse R, Haigh JM, Kanfer I: Determination of phenylpropanolamine in serum and urine by high-performance liquid chromatography. J Pharm Sci. 1983 Sep;72(9):1018-20. Pubmed: 6631684 Link_out
  4. Fallis RJ, Fisher M: Cerebral vasculitis and hemorrhage associated with phenylpropanolamine. Neurology. 1985 Mar;35(3):405-7. Pubmed: 3974900 Link_out
  5. Swain RA, Harsha DM, Baenziger J, Saywell RM Jr: Do pseudoephedrine or phenylpropanolamine improve maximum oxygen uptake and time to exhaustion? Clin J Sport Med. 1997 Jul;7(3):168-73. Pubmed: 9262882 Link_out
  6. Sullivan J, Abrams P: Pharmacological management of incontinence. Eur Urol. 1999;36 Suppl 1:89-95. Pubmed: 10393480 Link_out
Enzymes
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: Alpha-2A adrenergic receptor
Reactions:
    Gene Name: ADRA2A
    Uniprot ID: P08913 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Alpha-1A adrenergic receptor
    Reactions:
      Gene Name: ADRA1A
      Uniprot ID: P35348 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA