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Record Information
Version3.6
Creation Date2006-05-18 09:09:22 UTC
Update Date2013-06-12 19:29:27 UTC
HMDB IDHMDB01942
Secondary Accession Numbers
  • HMDB05002
Metabolite Identification
Common NamePhenylpropanolamine
DescriptionPhenylpropanolamine 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
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 FormulaC9H13NO
Average Molecular Weight151.2056
Monoisotopic Molecular Weight151.099714043
IUPAC Name(1S,2R)-2-amino-1-phenylpropan-1-ol
Traditional IUPAC Namephenylpropanolamine
CAS Registry Number154-41-6
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 KeyDLNKOYKMWOXYQA-VXNVDRBHSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassPhenethylamines
Sub ClassAmphetamines and Derivatives
Other Descriptors
  • Organic Compounds
Substituents
  • 1,2 Aminoalcohol
  • Benzyl Alcohol Derivative
  • Primary Aliphatic Amine (Alkylamine)
  • Secondary Alcohol
Direct ParentAmphetamines and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Drug
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point194 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility733 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility20.6 g/LALOGPS
logP0.57ALOGPS
logP0.89ChemAxon
logS-0.87ALOGPS
pKa (strongest acidic)13.9ChemAxon
pKa (strongest basic)9.37ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count2ChemAxon
polar surface area46.25ChemAxon
rotatable bond count2ChemAxon
refractivity44.91ChemAxon
polarizability16.98ChemAxon
Spectra
SpectraMS/MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.0 (0.005-5.0) uMAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00540
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022757
KNApSAcK IDNot Available
Chemspider ID25082
KEGG Compound IDC07911
BioCyc ID4-P-PANTHETHEINE
BiGG IDNot Available
Wikipedia LinkPhenylpropanolamine
NuGOwiki LinkHMDB01942
Metagene LinkHMDB01942
METLIN ID1846
PubChem Compound26934
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot 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
  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
  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
  4. Fallis RJ, Fisher M: Cerebral vasculitis and hemorrhage associated with phenylpropanolamine. Neurology. 1985 Mar;35(3):405-7. Pubmed: 3974900
  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
  6. Sullivan J, Abrams P: Pharmacological management of incontinence. Eur Urol. 1999;36 Suppl 1:89-95. Pubmed: 10393480

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. 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 G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular weight:
51486.0