U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C9H13NO2.ClH
Molecular Weight 203.666
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXEDRINE HYDROCHLORIDE

SMILES

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

InChI

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

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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
Quantitative and qualitative HPLC analysis of thermogenic weight loss products.
2004 Nov
Products containing bitter orange or synephrine: suspected cardiovascular adverse reactions.
2004 Oct 12
Exactly which synephrine alkaloids does Citrus aurantium (bitter orange) contain?
2005 Apr
Comment on Citrus aurantium Minireview.
2005 Feb
The presence of trace amines in postmortem cerebrospinal fluid in humans.
2005 May
Determination of ephedrine alkaloids in dietary supplement standard reference materials.
2005 May 15
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
Response of CEDIA amphetamines assay after a single dose of bitter orange.
2006 Apr
Metal content of ephedra-containing dietary supplements and select botanicals.
2006 Apr 1
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
Sensitive determination of synephrine by flow-injection chemiluminescence.
2006 Jan-Feb
Determination of octopamine, synephrine and tyramine in Citrus herbs by ionic liquid improved 'green' chromatography.
2006 Sep 1
Influence of microemulsion chirality on chromatographic figures of merit in EKC: results with novel three-chiral-component microemulsions and comparison with one- and two-chiral-component microemulsions.
2007 Aug
Two-chiral component microemulsion EKC - chiral surfactant and chiral oil. Part 2: diethyl tartrate.
2007 Aug
Effects of ingesting JavaFit Energy Extreme functional coffee on aerobic and anaerobic fitness markers in recreationally-active coffee consumers.
2007 Dec 8
Determination of synephrine in weight-loss products using high performance liquid chromatography with acidic potassium permanganate chemiluminescence detection.
2007 Jun 12
Chemiluminescence of synephrine based on the cerium(IV)-rhodamine B system.
2007 Mar-Apr
Simultaneous determination of flavonoid and alkaloid compounds in Citrus herbs by high-performance liquid chromatography-photodiode array detection-electrospray mass spectrometry.
2007 Oct 1
Fast high-performance liquid chromatography analysis of phenethylamine alkaloids in Citrus natural products on a pentafluorophenylpropyl stationary phase.
2007 Sep 21
Concentrations of p-synephrine in fruits and leaves of Citrus species (Rutaceae) and the acute toxicity testing of Citrus aurantium extract and p-synephrine.
2008 Aug
Effects of chemopreventive citrus phytochemicals on human P-glycoprotein and multidrug resistance protein 1.
2008 Dec 14
Vasospasm and stroke attributable to ephedra-free xenadrine: case report.
2008 Jul
Human pharmacology of a performance-enhancing dietary supplement under resting and exercise conditions.
2008 Jun
Selectivity and potential interference from phenolic compounds in chemiluminescence methods for the determination of synephrine.
2009 Mar-Apr
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 Fri Dec 15 15:19:08 GMT 2023
Edited
by admin
on Fri Dec 15 15:19:08 GMT 2023
Record UNII
EN5D1IH09S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OXEDRINE HYDROCHLORIDE
MART.   WHO-DD  
Common Name English
SYNEPHRINE HYDROCHLORIDE [MI]
Common Name English
SYNEPHRINE HYDROCHLORIDE
MI  
Common Name English
Oxedrine hydrochloride [WHO-DD]
Common Name English
OXEDRINE HYDROCHLORIDE [MART.]
Common Name English
OXEDRINE HCL
Common Name English
(RS)-1-(4-HYDROXYPHENYL)-2-(METHYLAMINO)ETHANOL HYDROCHLORIDE
Systematic Name English
Code System Code Type Description
SMS_ID
100000087306
Created by admin on Fri Dec 15 15:19:08 GMT 2023 , Edited by admin on Fri Dec 15 15:19:08 GMT 2023
PRIMARY
PUBCHEM
22302
Created by admin on Fri Dec 15 15:19:08 GMT 2023 , Edited by admin on Fri Dec 15 15:19:08 GMT 2023
PRIMARY
EPA CompTox
DTXSID70975251
Created by admin on Fri Dec 15 15:19:08 GMT 2023 , Edited by admin on Fri Dec 15 15:19:08 GMT 2023
PRIMARY
MERCK INDEX
m10412
Created by admin on Fri Dec 15 15:19:08 GMT 2023 , Edited by admin on Fri Dec 15 15:19:08 GMT 2023
PRIMARY Merck Index
CAS
5985-28-4
Created by admin on Fri Dec 15 15:19:08 GMT 2023 , Edited by admin on Fri Dec 15 15:19:08 GMT 2023
PRIMARY
WIKIPEDIA
Synephrine hydrochloride
Created by admin on Fri Dec 15 15:19:08 GMT 2023 , Edited by admin on Fri Dec 15 15:19:08 GMT 2023
PRIMARY
ECHA (EC/EINECS)
227-804-6
Created by admin on Fri Dec 15 15:19:08 GMT 2023 , Edited by admin on Fri Dec 15 15:19:08 GMT 2023
PRIMARY
FDA UNII
EN5D1IH09S
Created by admin on Fri Dec 15 15:19:08 GMT 2023 , Edited by admin on Fri Dec 15 15:19:08 GMT 2023
PRIMARY
EVMPD
SUB20984
Created by admin on Fri Dec 15 15:19:08 GMT 2023 , Edited by admin on Fri Dec 15 15:19:08 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE