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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:40 UTC
Update Date2020-11-09 23:16:37 UTC
HMDB IDHMDB0002182
Secondary Accession Numbers
  • HMDB02182
Metabolite Identification
Common NamePhenylephrine
DescriptionPhenylephrine, also known as mesaton or fenilefrina, 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. Outside of the human body,. Sulfate conjugation, primarily in the intestinal wall, and oxidative metabolism by monoamine oxidase (MAO) represent the principle routes of metabolism. Phenylephrine is a postsynaptic α1-receptor agonist with little effect on β-receptors of the heart. Stimulation of the α1-adrenergic receptors results in contraction arteriolar smooth muscle in the periphery. Three α1-receptor subtypes, which share approximately 75% homology in their transmembrane domains, have been identified: α1A (chromosome 8), α1B (chromosome 5), and α1D (chromosome 20). Phenylephrine is used as a decongestant, available as an oral medicine or as a nasal spray.
Structure
Data?1582752234
Synonyms
ValueSource
(-)-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
Chemical FormulaC9H13NO2
Average Molecular Weight167.205
Monoisotopic Molecular Weight167.094628665
IUPAC Name3-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol
Traditional Namephenylephrine
CAS Registry Number59-42-7
SMILES
CNC[C@H](O)C1=CC(O)=CC=C1
InChI Identifier
InChI=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
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.31HANSCH,C ET AL. (1995)
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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-b11a2a880d1683fa6caeSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-01b9-6900000000-bbdd210a846be116dbcdSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-b11a2a880d1683fa6caeSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01b9-6900000000-bbdd210a846be116dbcdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-3ea7ffd258ffba5a376aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-014i-4920000000-54a2b2a88914c83610f2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0udi-0900000000-d95a741ffcfe3f7bb7e9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0006-9800000000-7695881b36499169fb71Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-054o-9200000000-888fce606d860cd39be2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-edfcbc18ccdb6872b791Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-0900000000-15132688bbc7ac0be42fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-2900000000-34ccc7192518d4c14210Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00di-3900000000-e619f4210f81c11f61beSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00dl-6900000000-3178337a019ac9bf313dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0gb9-0900000000-e738818606836c1d6d1aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0udi-0900000000-36b72327f64f1355a502Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-052o-4900000000-935a9659fe39602b138dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-052f-9800000000-7d83555b537d6fec673bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-054o-9400000000-5ef2f6d1da57087e6ac7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-014i-0900000000-4a910a2109ba191b96e7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-edfcbc18ccdb6872b791Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-15132688bbc7ac0be42fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-2900000000-34ccc7192518d4c14210Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-3900000000-e8a5a4f1aae0796866a7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00dl-6900000000-3178337a019ac9bf313dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0900000000-8c4893aa69ea6a1ceecbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-0900000000-4406afb22d76646e2ef8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01c3-7900000000-56a2a2741d2166bf31bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-0cf5a5fa80f87facb9adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-2900000000-687762e0d4bf3efbffecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-140e96de62b4341791d9Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Adipose Tissue
  • Bladder
  • Brain
  • Kidney
  • Neuron
  • Prostate
  • Skeletal Muscle
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.3 (0.029-3.0) uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0019 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00388
Phenol Explorer Compound IDNot Available
FooDB IDFDB022891
KNApSAcK IDNot Available
Chemspider ID5818
KEGG Compound IDC07441
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenylephrine
METLIN ID699
PubChem Compound6041
PDB IDNot Available
ChEBI ID8093
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Kamiya A, Kawada T, Yamamoto K, Michikami D, Ariumi H, Miyamoto T, Uemura K, Sugimachi M, Sunagawa K: Muscle sympathetic nerve activity averaged over 1 minute parallels renal and cardiac sympathetic nerve activity in response to a forced baroreceptor pressure change. Circulation. 2005 Jul 19;112(3):384-6. Epub 2005 Jul 5. [PubMed:15998668 ]
  2. Thebault S, Zholos A, Enfissi A, Slomianny C, Dewailly E, Roudbaraki M, Parys J, Prevarskaya N: Receptor-operated Ca2+ entry mediated by TRPC3/TRPC6 proteins in rat prostate smooth muscle (PS1) cell line. J Cell Physiol. 2005 Jul;204(1):320-8. [PubMed:15672411 ]
  3. Rios JD, Horikawa Y, Chen LL, Kublin CL, Hodges RR, Dartt DA, Zoukhri D: Age-dependent alterations in mouse exorbital lacrimal gland structure, innervation and secretory response. Exp Eye Res. 2005 Apr;80(4):477-91. [PubMed:15781275 ]
  4. Gao YJ, Zeng ZH, Teoh K, Sharma AM, Abouzahr L, Cybulsky I, Lamy A, Semelhago L, Lee RM: Perivascular adipose tissue modulates vascular function in the human internal thoracic artery. J Thorac Cardiovasc Surg. 2005 Oct;130(4):1130-6. [PubMed:16214530 ]
  5. Gonzalez-Cadavid NF, Ryndin I, Vernet D, Magee TR, Rajfer J: Presence of NMDA receptor subunits in the male lower urogenital tract. J Androl. 2000 Jul-Aug;21(4):566-78. [PubMed:10901443 ]
  6. Grassi G, Dell'Oro R, Facchini A, Quarti Trevano F, Bolla GB, Mancia G: Effect of central and peripheral body fat distribution on sympathetic and baroreflex function in obese normotensives. J Hypertens. 2004 Dec;22(12):2363-9. [PubMed:15614031 ]
  7. Bouchelouche K, Andersen L, Alvarez S, Nordling J, Bouchelouche P: Increased contractile response to phenylephrine in detrusor of patients with bladder outlet obstruction: effect of the alpha1A and alpha1D-adrenergic receptor antagonist tamsulosin. J Urol. 2005 Feb;173(2):657-61. [PubMed:15643283 ]
  8. Boschmann M, Krupp G, Luft FC, Klaus S, Jordan J: In vivo response to alpha(1)-adrenoreceptor stimulation in human white adipose tissue. Obes Res. 2002 Jun;10(6):555-8. [PubMed:12055332 ]
  9. Chueh SC, Chern JW, Choong CM, Guh JH, Teng CM: Characterization of some novel alpha 1-adrenoceptor antagonists in human hyperplastic prostate. Eur J Pharmacol. 2002 Jun 7;445(1-2):125-31. [PubMed:12065203 ]
  10. Wang SY, Song Y, Xu M, Hao TP, Han QD, Zhang YY: [Redistribution of three alpha1-adrenergic receptor subtypes in the stably transfected HEK 293A cells upon agonist stimulation.]. Sheng Li Xue Bao. 2005 Aug 25;57(4):480-5. [PubMed:16094496 ]
  11. Guh JH, Hsieh CH, Teng CM: Investigation of the effects of some alkaloidal alpha1-adrenoceptor antagonists on human hyperplastic prostate. Eur J Pharmacol. 1999 Jun 25;374(3):503-10. [PubMed:10422796 ]
  12. Nomiya M, Yamaguchi O: A quantitative analysis of mRNA expression of alpha 1 and beta-adrenoceptor subtypes and their functional roles in human normal and obstructed bladders. J Urol. 2003 Aug;170(2 Pt 1):649-53. [PubMed:12853849 ]
  13. Lam KY, Yuen AP: Cancer of the larynx in Hong Kong: a clinico-pathological study. Eur J Surg Oncol. 1996 Apr;22(2):166-70. [PubMed:8608835 ]

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:
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 clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:
ADRA2B
Uniprot ID:
P18089
Molecular weight:
49953.1
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
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
Gene Name:
ADRA1B
Uniprot ID:
P35368
Molecular weight:
56835.4
General function:
Involved in nucleotide binding
Specific function:
May be a regulated effector of stress granule assembly. Phosphorylation-dependent sequence-specific endoribonuclease in vitro. Cleaves exclusively between cytosine and adenine and cleaves MYC mRNA preferentially at the 3'-UTR. ATP- and magnesium-dependent helicase. Unwinds preferentially partial DNA and RNA duplexes having a 17 bp annealed portion and either a hanging 3' tail or hanging tails at both 5'- and 3'-ends. Unwinds DNA/DNA, RNA/DNA, and RNA/RNA substrates with comparable efficiency. Acts unidirectionally by moving in the 5' to 3' direction along the bound single-stranded DNA.
Gene Name:
G3BP1
Uniprot ID:
Q13283
Molecular weight:
52164.045