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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-24 14:32:31 UTC
Update Date2020-02-26 21:25:15 UTC
HMDB IDHMDB0004826
Secondary Accession Numbers
  • HMDB04826
Metabolite Identification
Common Namep-Synephrine
Descriptionp-Synephrine, also known as (+/-)-synephrine or sympatol, belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. p-Synephrine is a drug. p-Synephrine is a very strong basic compound (based on its pKa). Outside of the human body, p-synephrine has been detected, but not quantified in, several different foods, such as citrus, fruits, lemons, mandarin orange (clementine, tangerine), and sweet oranges. This could make p-synephrine a potential biomarker for the consumption of these foods.
Structure
Data?1582752315
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
(+)-p-SynephrineHMDB
(+)-SynephrineHMDB
(+)-[(Methylamino)methyl]-benzenemethanoHMDB
AnaleptinHMDB
ParasympatolHMDB
SimpalonHMDB
SimpatolHMDB
SympaethaminHMDB
SympaethamineHMDB
SynephrineHMDB
SynephrinHMDB
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-014i-0900000000-e033087fd86dbd769b28Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-0900000000-e033087fd86dbd769b28Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-c295e3a3035d15a699eeSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-2790000000-3975fb57a4851efa17ddSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-1890000000-ddb8778ef0aef4591f0dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-0b89ec1502bbf0bb1879Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-006x-9150000000-b5f2dbddba7baed4d774Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-0900000000-87218af459df32d035bbSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-0900000000-dd62606af13291e0de32Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0900000000-279ae142a098a2d8cfbbSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0900000000-35c196c82d47f666eb5bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0900000000-a8d55f47d1721c88e142Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-0900000000-eb318fdbbcefb5c0f42bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01c3-8900000000-750750ed3b7c777f8966Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-73b64b38d378f6d409bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-2900000000-a2fc7c196d4cb2205cd2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-b3081d3e77cf948c0babSpectrum
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
FooDB IDFDB000709
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
Food Biomarker OntologyNot Available
VMH IDNot Available
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