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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-18 09:09:22 UTC
Update Date2021-09-14 15:19:01 UTC
HMDB IDHMDB0001942
Secondary Accession Numbers
  • HMDB0005002
  • HMDB01942
  • HMDB05002
Metabolite Identification
Common NamePhenylpropanolamine
DescriptionPhenylpropanolamine, also known as D-norephedrine, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. Phenylpropanolamine is a drug which is used for the treatment of nasal congestion, control of urinary incontinence, priapism and obesity. Based on a literature review a significant number of articles have been published on Phenylpropanolamine.
Structure
Data?1582752218
Synonyms
ValueSource
D-NorephedrineKegg
NorephedrineKegg
DL-NorephedrineHMDB
DL-PhenylpropanolamineHMDB
HydriatineHMDB
L-NOREPHEDRINEHMDB
L-Phenyl propanolamineHMDB
MucoramaHMDB
NobeseHMDB
ObestatHMDB
Prestwick_388HMDB
PropadrineHMDB
Phenylpropanolamine hydrochlorideMeSH, HMDB
PropagestMeSH, HMDB
DexatrimMeSH, HMDB
Hydrochloride, phenylpropanolamineMeSH, HMDB
ProlamineMeSH, HMDB
PhenylpropanolamineMeSH
Triaminic DMMeSH, HMDB
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
Description Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropanes
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point194 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility733 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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 Area46.25 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.91 m³·mol⁻¹ChemAxon
Polarizability16.98 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.52631661259
DarkChem[M-H]-132.63231661259
AllCCS[M+H]+134.78132859911
AllCCS[M-H]-133.68132859911
DeepCCS[M+H]+140.82430932474
DeepCCS[M-H]-138.42830932474
DeepCCS[M-2H]-171.91430932474
DeepCCS[M+Na]+146.73630932474
AllCCS[M+H]+134.832859911
AllCCS[M+H-H2O]+130.332859911
AllCCS[M+NH4]+138.932859911
AllCCS[M+Na]+140.132859911
AllCCS[M-H]-133.732859911
AllCCS[M+Na-2H]-135.132859911
AllCCS[M+HCOO]-136.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PhenylpropanolamineC[C@@H](N)[C@@H](O)C1=CC=CC=C12288.6Standard polar33892256
PhenylpropanolamineC[C@@H](N)[C@@H](O)C1=CC=CC=C11284.5Standard non polar33892256
PhenylpropanolamineC[C@@H](N)[C@@H](O)C1=CC=CC=C11356.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phenylpropanolamine,1TMS,isomer #1C[C@@H](N)[C@@H](O[Si](C)(C)C)C1=CC=CC=C11402.6Semi standard non polar33892256
Phenylpropanolamine,1TMS,isomer #2C[C@@H](N[Si](C)(C)C)[C@@H](O)C1=CC=CC=C11454.6Semi standard non polar33892256
Phenylpropanolamine,2TMS,isomer #1C[C@@H](N[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=CC=CC=C11504.5Semi standard non polar33892256
Phenylpropanolamine,2TMS,isomer #1C[C@@H](N[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=CC=CC=C11532.3Standard non polar33892256
Phenylpropanolamine,2TMS,isomer #1C[C@@H](N[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=CC=CC=C11698.4Standard polar33892256
Phenylpropanolamine,2TMS,isomer #2C[C@H]([C@@H](O)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1640.6Semi standard non polar33892256
Phenylpropanolamine,2TMS,isomer #2C[C@H]([C@@H](O)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1637.0Standard non polar33892256
Phenylpropanolamine,2TMS,isomer #2C[C@H]([C@@H](O)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1901.4Standard polar33892256
Phenylpropanolamine,3TMS,isomer #1C[C@H]([C@@H](O[Si](C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1726.6Semi standard non polar33892256
Phenylpropanolamine,3TMS,isomer #1C[C@H]([C@@H](O[Si](C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1667.0Standard non polar33892256
Phenylpropanolamine,3TMS,isomer #1C[C@H]([C@@H](O[Si](C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1721.4Standard polar33892256
Phenylpropanolamine,1TBDMS,isomer #1C[C@@H](N)[C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C11651.7Semi standard non polar33892256
Phenylpropanolamine,1TBDMS,isomer #2C[C@@H](N[Si](C)(C)C(C)(C)C)[C@@H](O)C1=CC=CC=C11708.4Semi standard non polar33892256
Phenylpropanolamine,2TBDMS,isomer #1C[C@@H](N[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C11939.3Semi standard non polar33892256
Phenylpropanolamine,2TBDMS,isomer #1C[C@@H](N[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C11933.4Standard non polar33892256
Phenylpropanolamine,2TBDMS,isomer #1C[C@@H](N[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C12006.4Standard polar33892256
Phenylpropanolamine,2TBDMS,isomer #2C[C@H]([C@@H](O)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2081.2Semi standard non polar33892256
Phenylpropanolamine,2TBDMS,isomer #2C[C@H]([C@@H](O)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2049.8Standard non polar33892256
Phenylpropanolamine,2TBDMS,isomer #2C[C@H]([C@@H](O)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2115.2Standard polar33892256
Phenylpropanolamine,3TBDMS,isomer #1C[C@H]([C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2362.2Semi standard non polar33892256
Phenylpropanolamine,3TBDMS,isomer #1C[C@H]([C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2263.2Standard non polar33892256
Phenylpropanolamine,3TBDMS,isomer #1C[C@H]([C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2092.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Phenylpropanolamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9600000000-b39c5f4d78772cae806e2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenylpropanolamine GC-MS (1 TMS) - 70eV, Positivesplash10-004i-6910000000-5f584053def735d7e2422017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenylpropanolamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenylpropanolamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenylpropanolamine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000j-0900000000-1599181977614a0d00dd2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenylpropanolamine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-05ox-4900000000-3ee623f48a8306bcaf2c2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenylpropanolamine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0ugi-9600000000-afe25efb2c27bc61ad3a2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenylpropanolamine LC-ESI-QTOF , positive-QTOFsplash10-00lr-1900000000-033f74cd4a3197c7510b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenylpropanolamine Linear Ion Trap , positive-QTOFsplash10-001i-0900000000-6f806bd0a58cb073b5712017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenylpropanolamine -1V, Positive-QTOFsplash10-00lr-1900000000-67f5a63c6c4d589d1b962021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropanolamine 10V, Positive-QTOFsplash10-0f89-0900000000-e5a6de9f258209c42ea32017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropanolamine 20V, Positive-QTOFsplash10-0159-0900000000-983fa1b112e4d0fc78e12017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropanolamine 40V, Positive-QTOFsplash10-014i-5900000000-94c2913c48414f6f2f682017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropanolamine 10V, Negative-QTOFsplash10-0udi-0900000000-9a4b3eaff66d145e58632017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropanolamine 20V, Negative-QTOFsplash10-0zgi-2900000000-3c0efa3ebff61c0c1a7d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropanolamine 40V, Negative-QTOFsplash10-057i-9800000000-430f9914117dd6db13e12017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropanolamine 10V, Positive-QTOFsplash10-001i-0900000000-bd416c91052a9169cf442021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropanolamine 20V, Positive-QTOFsplash10-014i-1900000000-72a0c1340e1e430183912021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropanolamine 40V, Positive-QTOFsplash10-0006-9200000000-92f5cd8bb5a23727da792021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropanolamine 10V, Negative-QTOFsplash10-000x-9600000000-9d8b01ad2c9953ab29392021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropanolamine 20V, Negative-QTOFsplash10-00nf-7900000000-85ff14d88d237302bc5d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylpropanolamine 40V, Negative-QTOFsplash10-004i-9000000000-7f166534dabf6f41827e2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.0 (0.005-5.0) uMAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00397
Phenol Explorer Compound IDNot Available
FooDB IDFDB022757
KNApSAcK IDNot Available
Chemspider ID25082
KEGG Compound IDC02343
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenylpropanolamine
METLIN ID1846
PubChem Compound26934
PDB IDNot Available
ChEBI ID36
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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