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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-24 14:32:31 UTC
Update Date2019-01-11 19:18:12 UTC
HMDB IDHMDB0004826
Secondary Accession Numbers
  • HMDB04826
Metabolite Identification
Common Namep-Synephrine
Descriptionp-Synephrine is an endogenous amine in plasma, in variable levels with a tendency to be higher in hypertensive patients (PMID 8255371 ).
Structure
Data?1547234292
Synonyms
ValueSource
(+/-)-synephrineChEBI
1-(4-Hydroxyphenyl)-2-(methylamino)ethanolChEBI
1-(4-Hydroxyphenyl)-2-methylaminoethanolChEBI
4-Hydroxy-alpha-[(methylamino)methyl]benzenemethanolChEBI
beta-Methylamino-alpha-(4-hydroxyphenyl)ethyl alcoholChEBI
OxedrineChEBI
p-Hydroxy-alpha-[(methylamino)methyl]benzyl alcoholChEBI
SympatolChEBI
-SynephrineKegg
4-Hydroxy-a-[(methylamino)methyl]benzenemethanolGenerator
4-Hydroxy-α-[(methylamino)methyl]benzenemethanolGenerator
b-Methylamino-a-(4-hydroxyphenyl)ethyl alcoholGenerator
Β-methylamino-α-(4-hydroxyphenyl)ethyl alcoholGenerator
p-Hydroxy-a-[(methylamino)methyl]benzyl alcoholGenerator
p-Hydroxy-α-[(methylamino)methyl]benzyl alcoholGenerator
SympaethaminMeSH
SynephrinMeSH
(+)-P-SynephrineHMDB
(+)-SynephrineHMDB
(+)-[(methylamino)Methyl]-benzenemethanoHMDB
AnaleptinHMDB
ParasympatolHMDB
SimpalonHMDB
SimpatolHMDB
SympaethamineHMDB
SynephrineHMDB
Chemical FormulaC9H13NO2
Average Molecular Weight167.205
Monoisotopic Molecular Weight167.094628665
IUPAC Name4-[1-hydroxy-2-(methylamino)ethyl]phenol
Traditional Namesynephrine
CAS Registry Number94-07-5
SMILES
CNCC(O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C9H13NO2/c1-10-6-9(12)7-2-4-8(11)5-3-7/h2-5,9-12H,6H2,1H3
InChI KeyYRCWQPVGYLYSOX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class1-hydroxy-2-unsubstituted benzenoids
Direct Parent1-hydroxy-2-unsubstituted benzenoids
Alternative Parents
Substituents
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Monocyclic benzene moiety
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Organic oxygen compound
  • Aromatic alcohol
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.45HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility18.6 g/LALOGPS
logP-0.62ALOGPS
logP-0.071ChemAxon
logS-0.95ALOGPS
pKa (Strongest Acidic)9.76ChemAxon
pKa (Strongest Basic)9.15ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area52.49 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.25 m³·mol⁻¹ChemAxon
Polarizability18.23 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-014i-0900000000-e033087fd86dbd769b28JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-0900000000-e033087fd86dbd769b28JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-c295e3a3035d15a699eeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-2790000000-3975fb57a4851efa17ddJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-1890000000-ddb8778ef0aef4591f0dJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-0b89ec1502bbf0bb1879JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-006x-9150000000-b5f2dbddba7baed4d774JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-0900000000-87218af459df32d035bbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-0900000000-dd62606af13291e0de32JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0900000000-279ae142a098a2d8cfbbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0900000000-35c196c82d47f666eb5bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0900000000-a8d55f47d1721c88e142JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-0900000000-eb318fdbbcefb5c0f42bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01c3-8900000000-750750ed3b7c777f8966JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-73b64b38d378f6d409bcJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-2900000000-a2fc7c196d4cb2205cd2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-b3081d3e77cf948c0babJSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00034 +/- 0.0001 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.017 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0107 (0.00440-0.017) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0009 +/- 0.0004 uMAdult (>18 years old)BothHypertension details
Associated Disorders and Diseases
Disease References
Hypertension
  1. Andrew R, Best SA, Watson DG, Midgley JM, Reid JL, Squire IB: Analysis of biogenic amines in plasma of hypertensive patients and a control group. Neurochem Res. 1993 Nov;18(11):1179-82. [PubMed:8255371 ]
Associated OMIM IDs
DrugBank IDDB09203
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001397
KNApSAcK IDNot Available
Chemspider ID6904
KEGG Compound IDC04548
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSynephrine
METLIN ID7088
PubChem Compound7172
PDB IDNot Available
ChEBI ID29081
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Andrew R, Watson DG, Best SA, Midgley JM, Wenlong H, Petty RK: The determination of hydroxydopamines and other trace amines in the urine of parkinsonian patients and normal controls. Neurochem Res. 1993 Nov;18(11):1175-7. [PubMed:8255370 ]
  2. Andrew R, Best SA, Watson DG, Midgley JM, Reid JL, Squire IB: Analysis of biogenic amines in plasma of hypertensive patients and a control group. Neurochem Res. 1993 Nov;18(11):1179-82. [PubMed:8255371 ]

Enzymes

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