Record Information
Version1.0
Creation date2011-09-21 00:21:12 UTC
Update date2015-10-09 22:31:29 UTC
Primary IDFDB022891
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePhenylephrine
DescriptionPhenylephrine, also known as mesaton or m-sympathol, belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position. Phenylephrine is a very strong basic compound (based on its pKa). Phenylephrine is a bitter tasting compound.
CAS Number59-42-7
Structure
Thumb
Synonyms
SynonymSource
(-)-m-Hydroxy-alpha-(methylaminomethyl)benzyl alcoholChEBI
FenilefrinaChEBI
L-(3-Hydroxyphenyl)-N-methylethanolamineChEBI
PhenylephrinumChEBI
R(-)-PhenylephrineChEBI
Phenylephrine minimsKegg
(-)-m-Hydroxy-a-(methylaminomethyl)benzyl alcoholGenerator
(-)-m-Hydroxy-α-(methylaminomethyl)benzyl alcoholGenerator
AdrianolHMDB
Ak-dilateHMDB
Ak-nefrinHMDB
Alcon efrinHMDB
Alconefrin nasal drops 12HMDB
Alconefrin nasal drops 25HMDB
Alconefrin nasal drops 50HMDB
Alconefrin nasal spray 25HMDB
BiomydrinHMDB
DilatairHMDB
DionephrineHMDB
DoktorsHMDB
DurationHMDB
I-phrineHMDB
IsophrimHMDB
IsophrinHMDB
Isopto frinHMDB
m-MethylaminoethanolphenolHMDB
m-OxedrineHMDB
m-SympatholHMDB
m-SympatolHMDB
m-SynephrineHMDB
MesatonHMDB
MesatoneHMDB
MesatonumHMDB
MetaoxedrinHMDB
MetaoxedrineHMDB
MetaoxedrinumHMDB
MetasympatolHMDB
MetasynephrineHMDB
MezatonHMDB
Minims phenylephrineHMDB
MydfrinHMDB
Neo-synephrineHMDB
Neo-synephrine nasal dropsHMDB
Neo-synephrine nasal jellyHMDB
Neo-synephrine nasal sprayHMDB
Neo-synephrine pediatric nasal dropsHMDB
NeofrinHMDB
NeophrynHMDB
NeosynephrineHMDB
NostrilHMDB
Nostril spray pumpHMDB
Nostril spray pump mildHMDB
Ocu-phrin sterile eye dropsHMDB
Ocu-phrin sterile ophthalmic solutionHMDB
OcugestrinHMDB
PhenopticHMDB
PrefrinHMDB
Prefrin liquifilmHMDB
Pyracort DHMDB
R(-)-MezatonHMDB
Relief eye drops for red eyesHMDB
RhinallHMDB
SpersaphrineHMDB
Vicks sinexHMDB
VisadronHMDB
Neo synephrineHMDB
Phenylephrine tannateHMDB
Tannate, phenylephrineHMDB
(R)-3-Hydroxy-alpha-((methylamino)methyl)benzenemethanolHMDB
Phenylephrine hydrochlorideHMDB
Ak-Dilatehmdb
Ak-Nefrinhmdb
Alconefrin Nasal Drops 12hmdb
Alconefrin Nasal Drops 25hmdb
Alconefrin Nasal Drops 50hmdb
Alconefrin Nasal Spray 25hmdb
I-Phrinehmdb
Isopto Frinhmdb
Minims Phenylephrinehmdb
Neo-Synephrinehmdb
Neo-Synephrine Nasal Dropshmdb
Neo-Synephrine Nasal Jellyhmdb
Neo-Synephrine Nasal Sprayhmdb
Neo-Synephrine Pediatric Nasal Dropshmdb
Nostril Spray Pumphmdb
Nostril Spray Pump Mildhmdb
Ocu-Phrin Sterile Eye Dropshmdb
Ocu-Phrin Sterile Ophthalmic Solutionhmdb
Prefrin Liquifilmhmdb
Relief Eye Drops for Red Eyeshmdb
Vicks Sinexhmdb
Predicted Properties
PropertyValueSource
Water Solubility22 g/LALOGPS
logP-0.69ALOGPS
logP-0.07ChemAxon
logS-0.88ALOGPS
pKa (Strongest Acidic)9.07ChemAxon
pKa (Strongest Basic)9.69ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area52.49 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.25 m³·mol⁻¹ChemAxon
Polarizability18.2 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC9H13NO2
IUPAC name3-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol
InChI IdentifierInChI=1S/C9H13NO2/c1-10-6-9(12)7-3-2-4-8(11)5-7/h2-5,9-12H,6H2,1H3/t9-/m0/s1
InChI KeySONNWYBIRXJNDC-VIFPVBQESA-N
Isomeric SMILESCNC[C@H](O)C1=CC(O)=CC=C1
Average Molecular Weight167.205
Monoisotopic Molecular Weight167.094628665
Classification
Description belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class1-hydroxy-4-unsubstituted benzenoids
Direct Parent1-hydroxy-4-unsubstituted benzenoids
Alternative Parents
Substituents
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Monocyclic benzene moiety
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Secondary aliphatic amine
  • Secondary amine
  • Alcohol
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-014i-0900000000-b11a2a880d1683fa6caeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-01b9-6900000000-bbdd210a846be116dbcdJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-b11a2a880d1683fa6caeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01b9-6900000000-bbdd210a846be116dbcdJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-3ea7ffd258ffba5a376aJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-014i-4920000000-54a2b2a88914c83610f2JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0udi-0900000000-d95a741ffcfe3f7bb7e9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0006-9800000000-7695881b36499169fb71JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-054o-9200000000-888fce606d860cd39be2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-edfcbc18ccdb6872b791JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-0900000000-15132688bbc7ac0be42fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-2900000000-34ccc7192518d4c14210JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00di-3900000000-e619f4210f81c11f61beJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00dl-6900000000-3178337a019ac9bf313dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0gb9-0900000000-e738818606836c1d6d1aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0udi-0900000000-36b72327f64f1355a502JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-052o-4900000000-935a9659fe39602b138dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-052f-9800000000-7d83555b537d6fec673bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-054o-9400000000-5ef2f6d1da57087e6ac7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-014i-0900000000-4a910a2109ba191b96e7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-edfcbc18ccdb6872b791JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-15132688bbc7ac0be42fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-2900000000-34ccc7192518d4c14210JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-3900000000-e8a5a4f1aae0796866a7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00dl-6900000000-3178337a019ac9bf313dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0900000000-8c4893aa69ea6a1ceecbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-0900000000-4406afb22d76646e2ef8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01c3-7900000000-56a2a2741d2166bf31bcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-0cf5a5fa80f87facb9adJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-2900000000-687762e0d4bf3efbffecJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-140e96de62b4341791d9JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID5818
ChEMBL IDCHEMBL1215
KEGG Compound IDC07441
Pubchem Compound ID6041
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB00388
HMDB IDHMDB02182
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPhenylephrine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Alpha-2A adrenergic receptorADRA2AP08913
Alpha-2B adrenergic receptorADRA2BP18089
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference