Human Metabolome Database Version 3.5

Showing metabocard for Phenylpropanolamine (HMDB01942)

Record Information
Version 3.5
Creation Date 2006-05-18 03:09:22 -0600
Update Date 2013-06-12 13:29:27 -0600
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 | PDB | 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
  • Drug metabolite
Biofunction
  • Waste products
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
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
2.0 (0.005-5.0) uM Adult (>18 years old) Both Normal
Urine Expected but not Quantified
Not Applicable Not Available Not Available Normal
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID DBMET00540 Link_out
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 C07911 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: Not Available
Gene Name: MAOA
Uniprot ID: P21397 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-2A adrenergic receptor
Reactions: Not Available
Gene Name: ADRA2A
Uniprot ID: P08913 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-1A adrenergic receptor
Reactions: Not Available
Gene Name: ADRA1A
Uniprot ID: P35348 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA