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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-24 14:32:31 UTC
Update Date2021-10-13 04:44:18 UTC
HMDB IDHMDB0004826
Secondary Accession Numbers
  • HMDB04826
Metabolite Identification
Common Namep-Synephrine
Descriptionp-Synephrine, also known as (+/-)-synephrine or oxedrine, 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 has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make p-synephrine a potential biomarker for the consumption of these foods. p-Synephrine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on p-Synephrine.
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, MeSH
SympaethamineHMDB
SynephrineHMDB
SynephrinMeSH, HMDB
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

Adverse health effect

Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00043 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.45HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+137.18431661259
DarkChem[M-H]-134.08631661259
DeepCCS[M+H]+138.17430932474
DeepCCS[M-H]-134.34630932474
DeepCCS[M-2H]-171.97730932474
DeepCCS[M+Na]+147.51530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
p-SynephrineCNCC(O)C1=CC=C(O)C=C12705.8Standard polar33892256
p-SynephrineCNCC(O)C1=CC=C(O)C=C11613.1Standard non polar33892256
p-SynephrineCNCC(O)C1=CC=C(O)C=C11664.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
p-Synephrine,1TMS,isomer #1CNCC(O[Si](C)(C)C)C1=CC=C(O)C=C11708.7Semi standard non polar33892256
p-Synephrine,1TMS,isomer #2CNCC(O)C1=CC=C(O[Si](C)(C)C)C=C11653.8Semi standard non polar33892256
p-Synephrine,1TMS,isomer #3CN(CC(O)C1=CC=C(O)C=C1)[Si](C)(C)C1799.2Semi standard non polar33892256
p-Synephrine,2TMS,isomer #1CNCC(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C11608.6Semi standard non polar33892256
p-Synephrine,2TMS,isomer #2CN(CC(O[Si](C)(C)C)C1=CC=C(O)C=C1)[Si](C)(C)C1837.3Semi standard non polar33892256
p-Synephrine,2TMS,isomer #3CN(CC(O)C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C1816.5Semi standard non polar33892256
p-Synephrine,3TMS,isomer #1CN(CC(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C1777.0Semi standard non polar33892256
p-Synephrine,3TMS,isomer #1CN(CC(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C1806.7Standard non polar33892256
p-Synephrine,3TMS,isomer #1CN(CC(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C1848.5Standard polar33892256
p-Synephrine,1TBDMS,isomer #1CNCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C=C11950.5Semi standard non polar33892256
p-Synephrine,1TBDMS,isomer #2CNCC(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C11922.1Semi standard non polar33892256
p-Synephrine,1TBDMS,isomer #3CN(CC(O)C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C2020.4Semi standard non polar33892256
p-Synephrine,2TBDMS,isomer #1CNCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C12067.3Semi standard non polar33892256
p-Synephrine,2TBDMS,isomer #2CN(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C2310.0Semi standard non polar33892256
p-Synephrine,2TBDMS,isomer #3CN(CC(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2316.8Semi standard non polar33892256
p-Synephrine,3TBDMS,isomer #1CN(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2491.5Semi standard non polar33892256
p-Synephrine,3TBDMS,isomer #1CN(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2455.7Standard non polar33892256
p-Synephrine,3TBDMS,isomer #1CN(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2238.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - p-Synephrine GC-MS (3 TMS)splash10-014i-0900000000-e033087fd86dbd769b282014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Synephrine GC-MS (Non-derivatized)splash10-014i-0900000000-e033087fd86dbd769b282017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Synephrine GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-c295e3a3035d15a699ee2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Synephrine GC-EI-TOF (Non-derivatized)splash10-014i-2790000000-3975fb57a4851efa17dd2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Synephrine GC-EI-TOF (Non-derivatized)splash10-014i-1890000000-ddb8778ef0aef4591f0d2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Synephrine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-0b89ec1502bbf0bb18792017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Synephrine GC-MS (2 TMS) - 70eV, Positivesplash10-006x-9150000000-b5f2dbddba7baed4d7742017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Synephrine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Synephrine Linear Ion Trap , negative-QTOFsplash10-0002-0900000000-87218af459df32d035bb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Synephrine Linear Ion Trap , negative-QTOFsplash10-0002-0900000000-dd62606af13291e0de322017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Synephrine Linear Ion Trap , positive-QTOFsplash10-0udi-0900000000-279ae142a098a2d8cfbb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Synephrine Linear Ion Trap , positive-QTOFsplash10-0udi-0900000000-35c196c82d47f666eb5b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Synephrine 40V, Negative-QTOFsplash10-000x-9600000000-b52451ff9bd8a3887bba2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Synephrine 10V, Negative-QTOFsplash10-0002-0900000000-0c3a8e5c03a6dfd086672021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Synephrine 40V, Positive-QTOFsplash10-0a6r-9700000000-3f120631d0bab91d44b42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Synephrine 20V, Positive-QTOFsplash10-0k9l-3900000000-6c610eef126262adfcb62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Synephrine 35V, Positive-QTOFsplash10-0k9l-2900000000-5d02f910ae0ae85cd74f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Synephrine 10V, Positive-QTOFsplash10-0udi-0900000000-0e740a4914c01adc13312021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Synephrine 20V, Positive-QTOFsplash10-0f7c-3900000000-8999539f6d5a8d3758f02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Synephrine 10V, Positive-QTOFsplash10-0udi-0900000000-f4b3f4b27d9ca7224d4b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Synephrine 40V, Positive-QTOFsplash10-056r-9500000000-4ba94de2c8f5e98a4e2f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Synephrine 20V, Negative-QTOFsplash10-0a59-1900000000-4355e00e21057ebd01c92021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Synephrine 10V, Positive-QTOFsplash10-0uxr-0900000000-a8d55f47d1721c88e1422015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Synephrine 20V, Positive-QTOFsplash10-0uxr-0900000000-eb318fdbbcefb5c0f42b2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Synephrine 40V, Positive-QTOFsplash10-01c3-8900000000-750750ed3b7c777f89662015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Synephrine 10V, Negative-QTOFsplash10-014i-0900000000-73b64b38d378f6d409bc2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Synephrine 20V, Negative-QTOFsplash10-014j-2900000000-a2fc7c196d4cb2205cd22015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Synephrine 40V, Negative-QTOFsplash10-0006-9400000000-b3081d3e77cf948c0bab2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Synephrine 10V, Positive-QTOFsplash10-0udi-0900000000-59284684d3d1f5845efb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Synephrine 20V, Positive-QTOFsplash10-0q29-1900000000-eccd6882ea86aed6f8242021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Synephrine 40V, Positive-QTOFsplash10-0a4i-7900000000-2f829c6bfc720e5264532021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Synephrine 10V, Negative-QTOFsplash10-014i-1900000000-832cda2fe5651203ce372021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Synephrine 20V, Negative-QTOFsplash10-0avl-2900000000-6a789e30e9999b4391e72021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
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 IDFDB001397
KNApSAcK IDC00051735
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
MarkerDB IDMDB00000456
Good Scents IDrw1689541
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