Phenylpropanolamine (CED0006702)

Record Information
Version1.0
Creation Date2016-05-20 14:52:34 UTC
Update Date2026-05-14 16:37:31 UTC
Accession NumberCHEM015909
Identification
Common NamePhenylpropanolamine
ClassSmall Molecule
Description
Phenylpropanolamine is an organic compound with the chemical formula C9H13NO and an average molecular weight of 151.21 g/mol. Phenylpropanolamine belongs to the phenylpropanes, a subclass of benzene and substituted derivatives within the organic compounds. It is classified under the superclass of benzenoids. The compound has been identified in or released from 22 recorded sources across several categories. Within healthcare, pharmaceuticals, and veterinary products, it is found in nasal preparations. In the sector of food, food processing, and cookware, it is associated with the preparation of malt and fermentation processes for beer. Its presence is also recorded in building and construction materials, specifically tents or canopies, roofs, and fencing. Additionally, it is found in household cleaning and consumer products, including tobacco smoke filters, tobacco product cases, pipe accessories, other smoking requisites, and cigar cigarettes. It is further identified in electrical and electronic equipment, such as electrically stimulated smoking devices, electric switches, communication cables or conductors, antennas, fixed capacitors and their manufacture, and six other sources. Regarding its biological activity, phenylpropanolamine acts as an agonist, inhibitor, or partial agonist for seven recorded protein targets. These include the D(1A) dopamine receptor (DRD1), the Beta-1 adrenergic receptor (ADRB1), the Beta-2 adrenergic receptor (ADRB2), the Alpha-2A adrenergic receptor (ADRA2A), and three other proteins. The recorded route of exposure for this compound is oral.
Contaminant TypeNot Available
Chemical Structure
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 Mass151.206 g/mol
Monoisotopic Mass151.100 g/mol
CAS Registry Number14838-15-4
IUPAC Name(1S,2R)-2-amino-1-phenylpropan-1-ol
Traditional Namephenylpropanolamine
SMILESC[C@@H](N)[C@@H](O)C1=CC=CC=C1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 Area46.25 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
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-052f-9600000000-b39c5f4d78772cae806eNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-004i-6910000000-5f584053def735d7e242Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000j-0900000000-1599181977614a0d00ddNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05ox-4900000000-3ee623f48a8306bcaf2cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ugi-9600000000-afe25efb2c27bc61ad3aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00lr-1900000000-033f74cd4a3197c7510bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-6f806bd0a58cb073b571Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00lr-1900000000-67f5a63c6c4d589d1b96Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f89-0900000000-e5a6de9f258209c42ea3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0159-0900000000-983fa1b112e4d0fc78e1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-5900000000-94c2913c48414f6f2f68Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-9a4b3eaff66d145e5863Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zgi-2900000000-3c0efa3ebff61c0c1a7dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-057i-9800000000-430f9914117dd6db13e1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0900000000-bd416c91052a9169cf44Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-1900000000-72a0c1340e1e43018391Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9200000000-92f5cd8bb5a23727da79Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000x-9600000000-9d8b01ad2c9953ab2939Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00nf-7900000000-85ff14d88d237302bc5dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9000000000-7f166534dabf6f41827eNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
859.0Log mg/kg[480:1500]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
233BrushesPersonal care & cosmeticsNot Available
389Nasal preparationsHealthcare, pharmaceuticals & veterinary productsNot Available
496FencingBuilding & ConstructionNot Available
499RoofsBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
526LoudspeakersElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
533Sparking PlugsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
589Life BuoysMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Mandelate racemase structureClick to view 3D structureMandelate racemaseP11444Pseudomonas putidaPredicted (SEA)0.311397
Click to view 3D structureAlkaline ceramidase 2Q5QJU3HumansPredicted (SEA)2.17978
Click to view 3D structureSodium-dependent dopamine transporterP23977Rattus norvegicusPredicted (SEA)52.3925
Click to view 3D structureSodium-dependent serotonin transporterP31652Rattus norvegicusPredicted (SEA)113.66
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)325.332
Trace amine-associated receptor 1 structureClick to view 3D structureTrace amine-associated receptor 1Q96RJ0HumansPredicted (SEA)15.8034
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)160.292
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)186.06
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)259.627
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)351.1
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)272.083
Click to view 3D structureSigma non-opioid intracellular receptor 1Q60492Cavia porcellusPredicted (SEA)226.93
Glutamate receptor ionotropic, NMDA 2B structureClick to view 3D structureGlutamate receptor ionotropic, NMDA 2BQ13224HumansPredicted (SEA)24.8339
Click to view 3D structureSigma intracellular receptor 2Q5U3Y7Rattus norvegicusPredicted (SEA)122.457
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)1012.58
5-hydroxytryptamine receptor 6 structureClick to view 3D structure5-hydroxytryptamine receptor 6P50406HumansPredicted (SEA)283.76
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)457.598
Histone deacetylase 4 structureClick to view 3D structureHistone deacetylase 4P56524HumansPredicted (SEA)130.709
Histamine H1 receptor structureClick to view 3D structureHistamine H1 receptorP35367HumansPredicted (SEA)314.433
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)259.082
Click to view 3D structureKynureninaseP70712Rattus norvegicusPredicted (SEA)2.64687
Histone deacetylase 1 structureClick to view 3D structureHistone deacetylase 1Q13547HumansPredicted (SEA)469.119
Click to view 3D structure5-hydroxytryptamine receptor 2AP14842Rattus norvegicusPredicted (SEA)289.833
5-hydroxytryptamine receptor 7 structureClick to view 3D structure5-hydroxytryptamine receptor 7P34969HumansPredicted (SEA)359.586
Alpha-1A adrenergic receptor structureClick to view 3D structureAlpha-1A adrenergic receptorP35348HumansPredicted (SEA)270.915
Concentrations
Not Available
External Links
DrugBank IDDB00397
HMDB IDHMDB0001942
FooDB IDFDB022757
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID1846
PDB IDNot Available
Wikipedia LinkPhenylpropanolamine
Chemspider ID25082
ChEBI ID36
PubChem Compound ID26934
Kegg Compound IDC02343
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
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.
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.
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.
4. Fallis RJ, Fisher M: Cerebral vasculitis and hemorrhage associated with phenylpropanolamine. Neurology. 1985 Mar;35(3):405-7.
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.
6. Sullivan J, Abrams P: Pharmacological management of incontinence. Eur Urol. 1999;36 Suppl 1:89-95.