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Showing Compound Synephrine (FDB001397)

Record Information
Version1.0
Creation date2010-04-08 22:04:57 UTC
Update date2018-05-28 23:05:53 UTC
Primary IDFDB001397
Secondary Accession Numbers
  • FDB007966
Chemical Information
FooDB NameSynephrine
DescriptionSynephrine (or oxedrine) is a drug commonly used for weight loss. While its effectiveness is widely debated, synephrine has gained significant popularity as an alternative to ephedrine, a related substance which has been made illegal or restricted in many countries due to its use as a precursor in the illicit manufacture of methamphetamine. Products containing bitter orange or synephrine: suspected cardiovascular adverse reactions [citation needed]. Synephrine is derived primarily from the fruit of Citrus aurantium, a relatively small citrus tree, of which several of its more common names include Bitter Orange, Sour Orange, and Zhi shi.; There has been some confusion surrounding synephrine and phenylephrine (neosynephrine), one of its positional isomers. The chemicals are similar in structure; the only difference is the location of the aromatic hydroxyl group. In synephrine, the hydroxyl is at the para position, whereas, in neosynephrine, it is at the meta position. Each compound has differing biological properties.; p-Synephrine is an endogenous amine in plasma, in variable levels with a tendency to be higher in hypertensive patients (PMID 8255371).
CAS Number94-07-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(+/-)-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
α-(4-hydroxyphenyl)ethyl alcoholbiospider
1-(p-Hydroxyphenyl)-2-methylaminoethanoldb_source
4-Hydroxy-a-[(methylamino)methyl]benzenemethanol, 9CIdb_source
Ethaphenedb_source
Oxedrine, BANdb_source
p-(a-Hydroxy-b-methylaminoethyl)phenoldb_source
Sympatholdb_source
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
Chemical FormulaC9H13NO2
IUPAC name4-[1-hydroxy-2-(methylamino)ethyl]phenol
InChI IdentifierInChI=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
Isomeric SMILESCNCC(O)C1=CC=C(O)C=C1
Average Molecular Weight167.205
Monoisotopic Molecular Weight167.094628665
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 64.65%; H 7.84%; N 8.38%; O 19.14%DFC
Melting Point184.5 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP-0.45HANSCH,C ET AL. (1995)
Experimental pKa8.9
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSSynephrine, 3 TMS, GC-MS Spectrumsplash10-014i-0900000000-e033087fd86dbd769b28Spectrum
GC-MSSynephrine, non-derivatized, GC-MS Spectrumsplash10-014i-0900000000-e033087fd86dbd769b28Spectrum
GC-MSSynephrine, non-derivatized, GC-MS Spectrumsplash10-014i-0900000000-c295e3a3035d15a699eeSpectrum
GC-MSSynephrine, non-derivatized, GC-MS Spectrumsplash10-014i-2790000000-3975fb57a4851efa17ddSpectrum
GC-MSSynephrine, non-derivatized, GC-MS Spectrumsplash10-014i-1890000000-ddb8778ef0aef4591f0dSpectrum
Predicted GC-MSSynephrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9200000000-0b89ec1502bbf0bb1879Spectrum
Predicted GC-MSSynephrine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006x-9150000000-b5f2dbddba7baed4d774Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-0900000000-87218af459df32d035bbSpectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-0900000000-dd62606af13291e0de32Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0900000000-279ae142a098a2d8cfbbSpectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0900000000-35c196c82d47f666eb5bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0900000000-a8d55f47d1721c88e142Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-0900000000-eb318fdbbcefb5c0f42bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01c3-8900000000-750750ed3b7c777f8966Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-73b64b38d378f6d409bcSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-2900000000-a2fc7c196d4cb2205cd2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-b3081d3e77cf948c0babSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC04548
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI ID29081
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBZZ90-X:BZZ90-X
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDSynephrine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference