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Record Information
Version3.6
Creation Date2006-05-18 09:09:22 UTC
Update Date2017-08-16 03:50:08 UTC
HMDB IDHMDB0001942
Secondary Accession Numbers
  • HMDB01942
  • 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
ValueSource
D-NorephedrineKegg
NorephedrineKegg
DL-NorephedrineHMDB
DL-PhenylpropanolamineHMDB
HydriatineHMDB
L-NOREPHEDRINEHMDB
L-Phenyl propanolamineHMDB
MucoramaHMDB
NobeseHMDB
ObestatHMDB
Prestwick_388HMDB
PropadrineHMDB
Phenylpropanolamine hydrochlorideMeSH
PropagestMeSH
DexatrimMeSH
Hydrochloride, phenylpropanolamineMeSH
ProlamineMeSH
Chemical FormulaC9H13NO
Average Molecular Weight151.2056
Monoisotopic Molecular Weight151.099714043
IUPAC Name(1S,2R)-2-amino-1-phenylpropan-1-ol
Traditional Namephenylpropanolamine
CAS Registry Number14838-15-4
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
DescriptionThis compound belongs to the class of chemical entities known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentPhenylpropanes
Alternative Parents
Substituents
  • Phenylpropane
  • Aralkylamine
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organopnictogen compound
  • Primary amine
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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 mg/mLALOGPS
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 Area46.25 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.91 m3·mol-1ChemAxon
Polarizability16.98 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)splash10-000j-0900000000-1599181977614a0d00ddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05ox-4900000000-3ee623f48a8306bcaf2cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0ugi-9600000000-afe25efb2c27bc61ad3aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00lr-1900000000-033f74cd4a3197c7510bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0900000000-6f806bd0a58cb073b571View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
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 Quantified Not AvailableNot AvailableNormal
    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 LinkHMDB0001942
    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 Jul;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