Synephrine

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Synephrine
Accession Number
DB09203
Type
Small Molecule
Groups
Experimental
Description

Synephrine, or, more specifically, p-synephrine, is an alkaloid, occurring naturally in some plants and animals, and also in approved drugs products as its m-substituted analog known as neo-synephrine. p-synephrine (or formerly Sympatol and oxedrine [BAN]) and m-synephrine are known for their longer acting adrenergic effects compared to norepinephrine.

There has been some confusion about the biological effects of synephrine because of the similarity of this un-prefixed name to the names m-synephrine, Meta-synephrine and Neosynephrine, all of which refer to a related drug and naturally-occurring amine more commonly known as phenylephrine. Although there are chemical and pharmacological similarities between synephrine and phenylephrine, they are nevertheless different substances.

Structure
Thumb
Synonyms
  • (±)-Synephrine
  • Oxedrine
  • p-synephrine
International/Other Brands
Sympatol
Categories
UNII
PEG5DP7434
CAS number
94-07-5
Weight
Average: 167.205
Monoisotopic: 167.094628665
Chemical Formula
C9H13NO2
InChI Key
YRCWQPVGYLYSOX-UHFFFAOYSA-N
InChI
InChI=1S/C9H13NO2/c1-10-6-9(12)7-2-4-8(11)5-3-7/h2-5,9-12H,6H2,1H3
IUPAC Name
4-[1-hydroxy-2-(methylamino)ethyl]phenol
SMILES
CNCC(O)C1=CC=C(O)C=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAlpha-1 adrenergic receptorsNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Synephrine.Approved, Investigational
AcemetacinThe therapeutic efficacy of Acemetacin can be decreased when used in combination with Synephrine.Approved, Experimental, Investigational
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Synephrine.Approved, Investigational
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Synephrine.Approved, Illicit, Investigational
AtomoxetineAtomoxetine may increase the hypertensive activities of Synephrine.Approved
BenzphetamineThe risk or severity of adverse effects can be increased when Benzphetamine is combined with Synephrine.Approved, Illicit
Benzylpenicilloyl PolylysineSynephrine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BromocriptineBromocriptine may increase the hypertensive and vasoconstricting activities of Synephrine.Approved, Investigational
BucindololThe risk or severity of adverse effects can be increased when Synephrine is combined with Bucindolol.Investigational
BunazosinBunazosin may decrease the vasoconstricting activities of Synephrine.Investigational
CabergolineCabergoline may increase the hypertensive and vasoconstricting activities of Synephrine.Approved
Calcium carbimideThe risk or severity of adverse effects can be increased when Calcium carbimide is combined with Synephrine.Approved, Withdrawn
CarvedilolCarvedilol may decrease the vasoconstricting activities of Synephrine.Approved, Investigational
CeliprololThe risk or severity of adverse effects can be increased when Celiprolol is combined with Synephrine.Approved, Investigational
ChlorphentermineThe risk or severity of adverse effects can be increased when Chlorphentermine is combined with Synephrine.Illicit, Withdrawn
ClenbuterolThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Synephrine.Approved, Investigational, Vet Approved
DesvenlafaxineDesvenlafaxine may increase the tachycardic activities of Synephrine.Approved, Investigational
DihydroergotamineDihydroergotamine may increase the hypertensive and vasoconstricting activities of Synephrine.Approved, Investigational
DobutamineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Synephrine.Approved
DopamineThe risk or severity of adverse effects can be increased when Dopamine is combined with Synephrine.Approved
DoxazosinDoxazosin may decrease the vasoconstricting activities of Synephrine.Approved
DoxofyllineThe risk or severity of adverse effects can be increased when Synephrine is combined with Doxofylline.Approved, Investigational
DronabinolDronabinol may increase the tachycardic activities of Synephrine.Approved, Illicit
DuloxetineDuloxetine may increase the tachycardic activities of Synephrine.Approved
EpanololThe risk or severity of adverse effects can be increased when Synephrine is combined with Epanolol.Experimental
EphedrineThe risk or severity of adverse effects can be increased when Ephedrine is combined with Synephrine.Approved
EpinephrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Synephrine.Approved, Vet Approved
Ergoloid mesylateErgoloid mesylate may increase the hypertensive and vasoconstricting activities of Synephrine.Approved
ErgonovineErgonovine may increase the hypertensive and vasoconstricting activities of Synephrine.Approved
ErgotamineErgotamine may increase the hypertensive and vasoconstricting activities of Synephrine.Approved
EtilefrineThe risk or severity of adverse effects can be increased when Etilefrine is combined with Synephrine.Withdrawn
FenoterolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Synephrine.Approved, Investigational
FenozoloneThe risk or severity of adverse effects can be increased when Synephrine is combined with Fenozolone.Experimental
HyaluronidaseHyaluronidase may increase the vasoconstricting activities of Synephrine.Approved, Investigational
HydroxyamphetamineThe risk or severity of adverse effects can be increased when Synephrine is combined with Hydroxyamphetamine.Approved
IndoraminIndoramin may decrease the vasoconstricting activities of Synephrine.Withdrawn
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Synephrine.Approved, Investigational
IsoprenalineThe risk or severity of adverse effects can be increased when Isoprenaline is combined with Synephrine.Approved, Investigational
IsoxsuprineThe risk or severity of adverse effects can be increased when Isoxsuprine is combined with Synephrine.Approved, Withdrawn
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Synephrine.Approved
LacidipineSynephrine may increase the hypotensive activities of Lacidipine.Approved, Investigational
LevomilnacipranLevomilnacipran may increase the tachycardic activities of Synephrine.Approved, Investigational
LinezolidLinezolid may increase the hypertensive activities of Synephrine.Approved, Investigational
LorpiprazoleThe therapeutic efficacy of Synephrine can be increased when used in combination with Lorpiprazole.Approved
MefenorexThe risk or severity of adverse effects can be increased when Synephrine is combined with Mefenorex.Experimental
MephentermineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Synephrine.Approved
MetaraminolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Synephrine.Approved, Investigational
MethamphetamineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Synephrine.Approved, Illicit
MethoxamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Synephrine.Approved, Investigational
MethylergometrineMethylergometrine may increase the hypertensive and vasoconstricting activities of Synephrine.Approved
MidodrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Synephrine.Approved
MilnacipranMilnacipran may increase the tachycardic activities of Synephrine.Approved, Investigational
NabiloneNabilone may increase the tachycardic activities of Synephrine.Approved, Investigational
NorepinephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Synephrine.Approved
NylidrinThe risk or severity of adverse effects can be increased when Nylidrin is combined with Synephrine.Approved
OrciprenalineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Synephrine.Approved
OxymetazolineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Synephrine.Approved, Investigational
Patent BlueThe therapeutic efficacy of Synephrine can be decreased when used in combination with Patent Blue.Approved
PhenmetrazineThe risk or severity of adverse effects can be increased when Phenmetrazine is combined with Synephrine.Approved, Illicit
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Synephrine.Approved, Illicit
PhenylephrineThe risk or severity of adverse effects can be increased when Phenylephrine is combined with Synephrine.Approved
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Synephrine.Approved, Vet Approved, Withdrawn
PrazosinPrazosin may decrease the vasoconstricting activities of Synephrine.Approved
PrenalterolThe risk or severity of adverse effects can be increased when Synephrine is combined with Prenalterol.Experimental
ProcaterolThe risk or severity of adverse effects can be increased when Procaterol is combined with Synephrine.Approved, Investigational
PseudoephedrineThe risk or severity of adverse effects can be increased when Synephrine is combined with Pseudoephedrine.Approved
RacepinephrineThe risk or severity of adverse effects can be increased when Synephrine is combined with Racepinephrine.Approved
RitodrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Synephrine.Approved, Investigational
SilodosinSilodosin may decrease the vasoconstricting activities of Synephrine.Approved
SpironolactoneSpironolactone may decrease the vasoconstricting activities of Synephrine.Approved
TamsulosinTamsulosin may decrease the vasoconstricting activities of Synephrine.Approved, Investigational
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Synephrine.Approved
TerazosinTerazosin may decrease the vasoconstricting activities of Synephrine.Approved
TerbutalineThe risk or severity of adverse effects can be increased when Terbutaline is combined with Synephrine.Approved
TetryzolineThe risk or severity of adverse effects can be increased when Tetryzoline is combined with Synephrine.Approved
TramazolineThe risk or severity of adverse effects can be increased when Synephrine is combined with Tramazoline.Investigational
TretoquinolThe risk or severity of adverse effects can be increased when Synephrine is combined with Tretoquinol.Experimental
TrimazosinTrimazosin may decrease the vasoconstricting activities of Synephrine.Experimental
TyramineThe risk or severity of adverse effects can be increased when Tyramine is combined with Synephrine.Investigational, Nutraceutical
UrapidilUrapidil may decrease the vasoconstricting activities of Synephrine.Investigational
VenlafaxineVenlafaxine may increase the tachycardic activities of Synephrine.Approved
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0004826
KEGG Drug
D07148
KEGG Compound
C04548
PubChem Compound
7172
PubChem Substance
310265111
ChemSpider
6904
ChEBI
29081
ChEMBL
CHEMBL33720
Wikipedia
Synephrine
ATC Codes
C01CA08 — OxedrineS01GA06 — OxedrineS01GA56 — Oxedrine, combinations

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility18.6 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.25 m3·mol-1ChemAxon
Polarizability18.23 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-014i-0900000000-e033087fd86dbd769b28
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-014i-0900000000-e033087fd86dbd769b28
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-0900000000-c295e3a3035d15a699ee
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-2790000000-3975fb57a4851efa17dd
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-1890000000-ddb8778ef0aef4591f0d
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uxr-0900000000-a8d55f47d1721c88e142
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uxr-0900000000-eb318fdbbcefb5c0f42b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01c3-8900000000-750750ed3b7c777f8966
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0900000000-73b64b38d378f6d409bc
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014j-2900000000-a2fc7c196d4cb2205cd2
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9400000000-b3081d3e77cf948c0bab
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0002-0900000000-87218af459df32d035bb
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0002-0900000000-dd62606af13291e0de32
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0udi-0900000000-279ae142a098a2d8cfbb
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0udi-0900000000-35c196c82d47f666eb5b

Taxonomy

Description
This compound belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that a unsubstituted at the 2-position.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenols
Sub Class
1-hydroxy-2-unsubstituted benzenoids
Direct Parent
1-hydroxy-2-unsubstituted benzenoids
Alternative Parents
Aralkylamines / Benzene and substituted derivatives / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Organopnictogen compounds / Hydrocarbon derivatives / Aromatic alcohols
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
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
phenols, ethanolamines, phenethylamine alkaloid (CHEBI:29081)

Targets

Kind
Protein group
Organism
Human
Pharmacological action
Unknown
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...

Components:
References
  1. Huang YT, Lin HC, Chang YY, Yang YY, Lee SD, Hong CY: Hemodynamic effects of synephrine treatment in portal hypertensive rats. Jpn J Pharmacol. 2001 Feb;85(2):183-8. [PubMed:11286401]

Drug created on October 19, 2015 12:45 / Updated on May 01, 2018 23:57