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Details

Stereochemistry RACEMIC
Molecular Formula C9H13NO2
Molecular Weight 167.205
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXEDRINE

SMILES

CNCC(O)C1=CC=C(O)C=C1

InChI

InChIKey=YRCWQPVGYLYSOX-UHFFFAOYSA-N
InChI=1S/C9H13NO2/c1-10-6-9(12)7-2-4-8(11)5-3-7/h2-5,9-12H,6H2,1H3

HIDE SMILES / InChI

Molecular Formula C9H13NO2
Molecular Weight 167.205
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: The description was created based on several sources, including https://www.drugs.com/international/oxedrine.html | https://clinicaltrials.gov/ct2/show/NCT01423019 | https://www.ncbi.nlm.nih.gov/pubmed/20217639

Oxedrine (Sympatol, p-synephrine) is a naturally occurring alkaloid molecule first appeared in Europe towards the end of the 1920s being sold as a drug under the brand name Sympatol. Oxedrine was then being prescribed as a remedy for a number of respiratory conditions, which include asthma, whooping cough, colds, and hay fever. More recently, synephrine gained popularity as a weight loss aid and it has become a favored component in the more popular brands of weight loss supplement stacks. This popularity can be attributed in part to the ban imposed on ephedra, to which it shares similar mechanisms of action. Most, if not all of the synephrine being sold as a dietary supplement is extracted and synthesized from the Citrus aurantium plant, more commonly known as bitter orange. Just like ephedrine, synephrine has vasoconstrictive abilities, although at a lesser potency compared to ephedrine. There is no mention of synephrine in editions of Drill's Pharmacology in Medicine later than the 3rd, nor is there any reference to synephrine in the 2012 Physicians' Desk Reference, nor in the current FDA "Orange Book". One current reference source describes synephrine as a vasoconstrictor that has been given to hypotensive patients, orally or by injection, in doses of 20–100 mg.

Originator

Sources: Archiv fuer Experimentelle Pathologie und Pharmakologie (1927), 124, 231-44.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
6.6 µM [EC50]
4.11 null [pKi]
4.44 null [pKi]
4.61 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Advantra Z

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.75 ng/mL
21 mg single, oral
dose: 21 mg
route of administration: Oral
experiment type: SINGLE
co-administered: CAFFEINE
OXEDRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.86 ng/mL
21 mg single, oral
dose: 21 mg
route of administration: Oral
experiment type: SINGLE
co-administered: CAFFEINE
OXEDRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
427.9 ng × min/mL
21 mg single, oral
dose: 21 mg
route of administration: Oral
experiment type: SINGLE
co-administered: CAFFEINE
OXEDRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
466.4 ng × min/mL
21 mg single, oral
dose: 21 mg
route of administration: Oral
experiment type: SINGLE
co-administered: CAFFEINE
OXEDRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.56 h
21 mg single, oral
dose: 21 mg
route of administration: Oral
experiment type: SINGLE
co-administered: CAFFEINE
OXEDRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2.64 h
21 mg single, oral
dose: 21 mg
route of administration: Oral
experiment type: SINGLE
co-administered: CAFFEINE
OXEDRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
100 mg single, oral
Studied dose
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources: Page: p.5
healthy, 22.3 ± 1.6
n = 12
Health Status: healthy
Age Group: 22.3 ± 1.6
Sex: M
Population Size: 12
Sources: Page: p.5
100 mg 1 times / day multiple, oral
Studied dose
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Co-administed with::
caffeine, p.o(400 mg, q.d, 2 weeks)
Sources: Page: p.11
healthy, 27
n = 1
Disc. AE: Ventricular fibrillation...
AEs leading to
discontinuation/dose reduction:
Ventricular fibrillation
Sources: Page: p.11
AEs

AEs

AESignificanceDosePopulation
Ventricular fibrillation Disc. AE
100 mg 1 times / day multiple, oral
Studied dose
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Co-administed with::
caffeine, p.o(400 mg, q.d, 2 weeks)
Sources: Page: p.11
healthy, 27
n = 1
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Synthesis of lipids in the fat body of Gryllus bimaculatus: age-dependency and regulation by adipokinetic hormone.
2001 Aug
Reactions of amino alcohols in superacid: the direct observation of dicationic intermediates and their application in synthesis.
2001 Aug 23
[Studies on chemical constituents from the flower of Citrus aurantium].
2001 Dec
Hemodynamic effects of synephrine treatment in portal hypertensive rats.
2001 Feb
Characterization of antidepressant-like effects of p-synephrine stereoisomers.
2001 Jul
Seville (sour) orange juice: synephrine content and cardiovascular effects in normotensive adults.
2001 Oct
Determination of adrenergic agonists from extracts and herbal products of Citrus aurantium L. var. amara by LC.
2002 Aug 1
Determination of hesperidin and synephrine in Pericarpium Citri Reticulatae by capillary electrophoresis with electrochemical detection.
2002 Jun
Octopaminergic agonists for the cockroach neuronal octopamine receptor.
2003
HPLC electrochemical detection of trace amines in human plasma and platelets and expression of mRNA transcripts of trace amine receptors in circulating leukocytes.
2003 Jul 31
Screening for endogenous substrates reveals that CYP2D6 is a 5-methoxyindolethylamine O-demethylase.
2003 Jun
Biological activities of the shrub Salsola tuberculatiformis Botsch.: contraceptive or stress alleviator?
2003 Jun
Elusive amines and primary headaches: historical background and prospectives.
2003 May
Electrical storm: case series and review of management.
2003 Sep
Determination of ephedrine alkaloids and synephrine in dietary supplements by column-switching cation exchange high-performance liquid chromatography with scanning-wavelength ultraviolet and fluorescence detection.
2003 Sep 10
Ephedra-free is not danger-free.
2003 Sep 19
Bitter orange weight loss products may not be safe.
2004 Dec
Synephrine is not Neo-Synephrine.
2004 Dec
Characterization studies and cytotoxicity assays of Pt(II) and Pd(II) dithiocarbamate complexes by means of FT-IR, NMR spectroscopy and mass spectrometry.
2004 Jun
Safety and efficacy of citrus aurantium for weight loss.
2004 Nov 15
Enantioselective LC analysis of synephrine in natural products on a protein-based chiral stationary phase.
2005 Apr 29
A rapid liquid chromatography electrospray ionization mass spectrometry(n) method for evaluation of synephrine in Citrus aurantium L. samples.
2005 Dec 28
Comment on Citrus aurantium Minireview.
2005 Feb
Molecular mechanisms of toxicity of important food-borne phytotoxins.
2005 Feb
Determination of ephedrine alkaloids in dietary supplement standard reference materials.
2005 May 15
Anti-obese action of raspberry ketone.
2005 May 27
Rational method development strategies on a fluorinated liquid chromatography stationary phase: mobile phase ion concentration and temperature effects on the separation of ephedrine alkaloids.
2005 Nov 18
Hemodynamic effects of ephedra-free weight-loss supplements in humans.
2005 Sep
Variant angina associated with bitter orange in a dietary supplement.
2006 Apr
Abnormal platelet trace amine profiles in migraine with and without aura.
2006 Aug
Blood pressure and heart rate effects following a single dose of bitter orange.
2006 Jan
Quantitative and qualitative analysis of flavonoid markers in Frucus aurantii of different geographical origin by capillary electrophoresis with electrochemical detection.
2006 Jan 18
Sensitive determination of synephrine by flow-injection chemiluminescence.
2006 Jan-Feb
A rapid and simple procedure for the determination of synephrine in dietary supplements by gas chromatography-mass spectrometry.
2006 Jun 16
A new method for fabrication of an integrated indium tin oxide electrode on electrophoresis microchips with amperometric detection and its application for determination of synephrine and hesperidin in pericarpium citri reticulatae.
2006 Nov
Determination of octopamine, synephrine and tyramine in Citrus herbs by ionic liquid improved 'green' chromatography.
2006 Sep 1
Evaluation of the stimulant content of dietary supplements marketed as "ephedra-free".
2007
Two-chiral component microemulsion EKC - chiral surfactant and chiral oil. Part 2: diethyl tartrate.
2007 Aug
Chromatographic and electrophoretic methods for the analysis of phenethylamine [corrected] alkaloids in Citrus aurantium.
2007 Aug 17
Anti-inflammatory effects and mechanisms of the ethanol extract of Evodia rutaecarpa and its bioactive components on neutrophils and microglial cells.
2007 Jan 26
Determination of Bitter Orange alkaloids in dietary supplements standard reference materials by liquid chromatography with ultraviolet absorbance and fluorescence detection.
2007 Jul 13
A case of severe exercise-induced rhabdomyolysis associated with a weight-loss dietary supplement.
2007 Jun
Determination of synephrine in weight-loss products using high performance liquid chromatography with acidic potassium permanganate chemiluminescence detection.
2007 Jun 12
Biochemistry of neuromodulation in primary headaches: focus on anomalies of tyrosine metabolism.
2007 May
Simultaneous analysis of adrenergic amines and flavonoids in citrus peel jams and fruit juices by liquid chromatography: part 2.
2007 May-Jun
Determination of bitter orange alkaloids in dietary supplement Standard Reference Materials by liquid chromatography with atmospheric-pressure ionization mass spectrometry.
2007 Sep
Fast high-performance liquid chromatography analysis of phenethylamine alkaloids in Citrus natural products on a pentafluorophenylpropyl stationary phase.
2007 Sep 21
Human pharmacology of a performance-enhancing dietary supplement under resting and exercise conditions.
2008 Jun
Coronary spasm and thrombosis in a bodybuilder using a nutritional supplement containing synephrine, octopamine, tyramine and caffeine.
2008 May
Screening for in vivo (anti)estrogenic activity of ephedrine and p-synephrine and their natural sources Ephedra sinica Stapf. (Ephedraceae) and Citrus aurantium L. (Rutaceae) in rats.
2009 Jan
Patents

Patents

Sample Use Guides

Two capsules are taken twice daily, 20-30 minutes before breakfast and evening meals. Two capsules contain a total of 50 mg p-synephrine.
Route of Administration: Oral
HEK293 cells stably expressing the α1A-AR were transfected with the TRE‑LUC plasmid (40 μg/mL) using electroporation (70msec, single pulse, 150 volts). The transfected cells were seeded at a density of 50000 cells/well in microtiter plates (Cultureplate®; Packard) in 200 μL media and allowed to grow for 24 h with incubation at 37°C (5% CO2). After 24 h, the cells were treated with various drug concentrations for 20 h, which was found to be optimum during time-course analyses performed earlier. When antagonist studies were performed, the compounds (Oxedrine 1nM-1mM) were added 15min prior to the addition of the agonist L-phenylephrine. Following drug exposures, the cells were lysed, and luciferase activity was measured using the Luclite assay kit
Substance Class Chemical
Created
by admin
on Thu Jul 06 02:07:01 UTC 2023
Edited
by admin
on Thu Jul 06 02:07:01 UTC 2023
Record UNII
PEG5DP7434
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OXEDRINE
MART.   WHO-DD  
Common Name English
PARASYMPATOL
Brand Name English
(±)-OXEDRINE
Common Name English
P-SYNEPHRINE
Common Name English
DL-SYNEPHRINE
Common Name English
ANALEPTIN
Common Name English
(±)-SYNEPHRINE
Common Name English
SYNTHENATE
Brand Name English
(RS)-1-(4-HYDROXYPHENYL)-2-(METHYLAMINO)ETHANOL
Systematic Name English
ETHAPHENE
Common Name English
BENZENEMETHANOL, 4-HYDROXY-.ALPHA.-((METHYLAMINO)METHYL)-
Systematic Name English
SIMPALON
Brand Name English
NSC-170956
Code English
ADVANTRA Z
Brand Name English
NSC-166285
Code English
Oxedrine [WHO-DD]
Common Name English
SYNEPHRINE [MI]
Common Name English
SYNEPHRIN
Common Name English
SYNEPHRINE
INCI   MI  
INCI  
Official Name English
S-38537-9
Code English
OXEDRINE [USP IMPURITY]
Common Name English
SYNEPHRINE [USP-RS]
Common Name English
SYNEPHRINE [INCI]
Common Name English
OXEDRINE [MART.]
Common Name English
Classification Tree Code System Code
WHO-ATC S01GA06
Created by admin on Thu Jul 06 02:07:01 UTC 2023 , Edited by admin on Thu Jul 06 02:07:01 UTC 2023
WHO-VATC QS01GA06
Created by admin on Thu Jul 06 02:07:01 UTC 2023 , Edited by admin on Thu Jul 06 02:07:01 UTC 2023
WHO-ATC S01GA56
Created by admin on Thu Jul 06 02:07:01 UTC 2023 , Edited by admin on Thu Jul 06 02:07:01 UTC 2023
DSLD 2287 (Number of products:206)
Created by admin on Thu Jul 06 02:07:01 UTC 2023 , Edited by admin on Thu Jul 06 02:07:01 UTC 2023
WHO-VATC QC01CA08
Created by admin on Thu Jul 06 02:07:01 UTC 2023 , Edited by admin on Thu Jul 06 02:07:01 UTC 2023
WHO-ATC C01CA08
Created by admin on Thu Jul 06 02:07:01 UTC 2023 , Edited by admin on Thu Jul 06 02:07:01 UTC 2023
WHO-VATC QS01GA56
Created by admin on Thu Jul 06 02:07:01 UTC 2023 , Edited by admin on Thu Jul 06 02:07:01 UTC 2023
WHO-VATC QS01FB90
Created by admin on Thu Jul 06 02:07:01 UTC 2023 , Edited by admin on Thu Jul 06 02:07:01 UTC 2023
Code System Code Type Description
PUBCHEM
7172
Created by admin on Thu Jul 06 02:07:01 UTC 2023 , Edited by admin on Thu Jul 06 02:07:01 UTC 2023
PRIMARY
MESH
D013578
Created by admin on Thu Jul 06 02:07:01 UTC 2023 , Edited by admin on Thu Jul 06 02:07:01 UTC 2023
PRIMARY
RS_ITEM_NUM
1642609
Created by admin on Thu Jul 06 02:07:01 UTC 2023 , Edited by admin on Thu Jul 06 02:07:01 UTC 2023
PRIMARY
ChEMBL
CHEMBL33720
Created by admin on Thu Jul 06 02:07:01 UTC 2023 , Edited by admin on Thu Jul 06 02:07:01 UTC 2023
PRIMARY
WIKIPEDIA
SYNEPHRINE
Created by admin on Thu Jul 06 02:07:01 UTC 2023 , Edited by admin on Thu Jul 06 02:07:01 UTC 2023
PRIMARY
MERCK INDEX
M10412
Created by admin on Thu Jul 06 02:07:01 UTC 2023 , Edited by admin on Thu Jul 06 02:07:01 UTC 2023
PRIMARY Merck Index
NSC
170956
Created by admin on Thu Jul 06 02:07:01 UTC 2023 , Edited by admin on Thu Jul 06 02:07:01 UTC 2023
PRIMARY
RXCUI
10288
Created by admin on Thu Jul 06 02:07:01 UTC 2023 , Edited by admin on Thu Jul 06 02:07:01 UTC 2023
PRIMARY RxNorm
CHEBI
29081
Created by admin on Thu Jul 06 02:07:01 UTC 2023 , Edited by admin on Thu Jul 06 02:07:01 UTC 2023
PRIMARY
ECHA (EC/EINECS)
202-300-9
Created by admin on Thu Jul 06 02:07:01 UTC 2023 , Edited by admin on Thu Jul 06 02:07:01 UTC 2023
PRIMARY
EPA CompTox
DTXSID0030588
Created by admin on Thu Jul 06 02:07:01 UTC 2023 , Edited by admin on Thu Jul 06 02:07:01 UTC 2023
PRIMARY
EVMPD
SUB14726MIG
Created by admin on Thu Jul 06 02:07:01 UTC 2023 , Edited by admin on Thu Jul 06 02:07:01 UTC 2023
PRIMARY
NSC
166285
Created by admin on Thu Jul 06 02:07:01 UTC 2023 , Edited by admin on Thu Jul 06 02:07:01 UTC 2023
PRIMARY
SMS_ID
100000088818
Created by admin on Thu Jul 06 02:07:01 UTC 2023 , Edited by admin on Thu Jul 06 02:07:01 UTC 2023
PRIMARY
CAS
94-07-5
Created by admin on Thu Jul 06 02:07:01 UTC 2023 , Edited by admin on Thu Jul 06 02:07:01 UTC 2023
PRIMARY
DRUG BANK
DB09203
Created by admin on Thu Jul 06 02:07:01 UTC 2023 , Edited by admin on Thu Jul 06 02:07:01 UTC 2023
PRIMARY
CHEBI
58606
Created by admin on Thu Jul 06 02:07:01 UTC 2023 , Edited by admin on Thu Jul 06 02:07:01 UTC 2023
PRIMARY
FDA UNII
PEG5DP7434
Created by admin on Thu Jul 06 02:07:01 UTC 2023 , Edited by admin on Thu Jul 06 02:07:01 UTC 2023
PRIMARY
DRUG CENTRAL
3577
Created by admin on Thu Jul 06 02:07:01 UTC 2023 , Edited by admin on Thu Jul 06 02:07:01 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
SALT/SOLVATE -> PARENT
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PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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ACTIVE MOIETY