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Record Information
Version3.6
Creation Date2006-08-24 14:32:31 UTC
Update Date2013-05-29 19:41:09 UTC
HMDB IDHMDB04826
Secondary Accession NumbersNone
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
Thumb
Synonyms
  1. (+)-p-Synephrine
  2. (+)-Synephrine
  3. (+)-[(methylamino)methyl]-Benzenemethano
  4. Analeptin
  5. Oxedrine
  6. Parasympatol
  7. Simpalon
  8. Simpatol
  9. Sympaethamin
  10. Sympaethamine
  11. Sympatol
  12. Synephrine
Chemical FormulaC9H13NO2
Average Molecular Weight167.205
Monoisotopic Molecular Weight167.094628665
IUPAC Name4-[1-hydroxy-2-(methylamino)ethyl]phenol
Traditional IUPAC 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
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassPhenethylamines
Sub ClassN/A
Other Descriptors
  • Organic Compounds
  • ethanolamines(ChEBI)
Substituents
  • 1,2 Aminoalcohol
  • Benzyl Alcohol Derivative
  • Phenol
  • Phenol Derivative
  • Secondary Alcohol
  • Secondary Aliphatic Amine (Dialkylamine)
Direct ParentPhenethylamines
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 area52.49ChemAxon
rotatable bond count3ChemAxon
refractivity47.25ChemAxon
polarizability18.23ChemAxon
Spectra
SpectraGC-MS
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
BiofluidStatusValueAgeSexConditionReferenceDetails
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 IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB000709
KNApSAcK IDNot Available
Chemspider ID6904
KEGG Compound IDC04548
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04826
Metagene LinkHMDB04826
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