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Details

Stereochemistry RACEMIC
Molecular Formula 2C9H13NO2.H2O4S
Molecular Weight 432.4903
Optical Activity ( + / - )
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXEDRINE SULFATE

SMILES

CNCC(c1ccc(cc1)O)O.CNCC(c1ccc(cc1)O)O.OS(=O)(=O)O

InChI

InChIKey=KCIXZGUJCYKCKY-UHFFFAOYSA-N
InChI=1S/2C9H13NO2.H2O4S/c2*1-10-6-9(12)7-2-4-8(11)5-3-7;1-5(2,3)4/h2*2-5,9-12H,6H2,1H3;(H2,1,2,3,4)

HIDE SMILES / InChI

Molecular Formula C9H13NO2
Molecular Weight 167.2054
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula H2O4S
Molecular Weight 98.0796
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Reactions of amino alcohols in superacid: the direct observation of dicationic intermediates and their application in synthesis.
2001 Aug 23
Screening for endogenous substrates reveals that CYP2D6 is a 5-methoxyindolethylamine O-demethylase.
2003 Jun
Moderate weight-lowering effect of octopamine treatment in obese Zucker rats.
2003 Sep
Electrical storm: case series and review of management.
2003 Sep
Safety and efficacy of citrus aurantium for weight loss.
2004 Nov 15
Products containing bitter orange or synephrine: suspected cardiovascular adverse reactions.
2004 Oct 12
Citrus aurantium, an ingredient of dietary supplements marketed for weight loss: current status of clinical and basic research.
2004 Sep
A rapid liquid chromatography electrospray ionization mass spectrometry(n) method for evaluation of synephrine in Citrus aurantium L. samples.
2005 Dec 28
Molecular mechanisms of toxicity of important food-borne phytotoxins.
2005 Feb
Anti-obese action of raspberry ketone.
2005 May 27
Response of CEDIA amphetamines assay after a single dose of bitter orange.
2006 Apr
Citrus aurantium and synephrine alkaloids in the treatment of overweight and obesity: an update.
2006 Feb
Blood pressure and heart rate effects following a single dose of bitter orange.
2006 Jan
An isotopically labeled internal standard liquid chromatography-tandem mass spectrometry method for determination of ephedrine alkaloids and synephrine in dietary supplements.
2006 Jan 25
Thermogenic effect from nutritionally enriched coffee consumption.
2006 Jun 5
Strategies for enantioseparations of catecholamines and structurally related compounds by capillary zone electrophoresis using sulfated beta-cyclodextrins as chiral selectors.
2006 Sep
Trace amine-associated receptor 1-Family archetype or iconoclast?
2007 Dec
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 synephrine in bitter orange raw materials, extracts, and dietary supplements by liquid chromatography with ultraviolet detection: single-laboratory validation.
2007 Jan-Feb
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
Two-chiral-component microemulsion electrokinetic chromatography-chiral surfactant and chiral oil: part 1. dibutyl tartrate.
2007 Jun
Chemiluminescence of synephrine based on the cerium(IV)-rhodamine B system.
2007 Mar-Apr
Mass spectrometric determination of the predominant adrenergic protoalkaloids in bitter orange (Citrus aurantium).
2007 Nov 28
Temperature effects on the enantioselectivity of basic analytes in capillary EKC using sulfated beta-CDs as chiral selectors.
2007 Oct
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
Coronary spasm and thrombosis in a bodybuilder using a nutritional supplement containing synephrine, octopamine, tyramine and caffeine.
2008 May
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 Sat Jun 26 09:53:28 UTC 2021
Edited
by admin
on Sat Jun 26 09:53:28 UTC 2021
Record UNII
QC6316150O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OXEDRINE SULFATE
WHO-DD  
Common Name English
P-SYNEPHRINE SULFATE
Common Name English
(RS)-1-(4-HYDROXYPHENYL)-2-(METHYLAMINO)ETHANOL HEMISULFATE
Systematic Name English
4-(1-HYDROXY-2-(METHYLAMINO)ETHYL)PHENOL HEMISULFATE
Systematic Name English
DL-SYNEPHRINE SULFATE
Common Name English
SYNEPHRINE SULFATE
Common Name English
(+/-)-SYNEPHRINE SULFATE
Common Name English
SYNEPHRIN SULFATE
Common Name English
OXEDRINE SULFATE [WHO-DD]
Common Name English
.BETA.-METHYLAMINO-.ALPHA.-(4-HYDROXYPHENYL)ETHYL ALCOHOL HEMISULFATE
Common Name English
Code System Code Type Description
PUBCHEM
139033144
Created by admin on Sat Jun 26 09:53:28 UTC 2021 , Edited by admin on Sat Jun 26 09:53:28 UTC 2021
PRIMARY
EVMPD
SUB03565MIG
Created by admin on Sat Jun 26 09:53:28 UTC 2021 , Edited by admin on Sat Jun 26 09:53:28 UTC 2021
PRIMARY
FDA UNII
QC6316150O
Created by admin on Sat Jun 26 09:53:28 UTC 2021 , Edited by admin on Sat Jun 26 09:53:28 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY