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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
[Studies on chemical constituents from the flower of Citrus aurantium].
2001 Dec
Characterization of antidepressant-like effects of p-synephrine stereoisomers.
2001 Jul
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
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
Electrical storm: case series and review of management.
2003 Sep
Ephedra-free is not danger-free.
2003 Sep 19
[Determination of synephrine and N-methyltyramine in Pericarpium Citri Reticulatae viride by HPLC].
2004 Jun
Quantitative and qualitative HPLC analysis of thermogenic weight loss products.
2004 Nov
Safety and efficacy of citrus aurantium for weight loss.
2004 Nov 15
Contributions of biochemistry to the pathogenesis of primary headaches.
2004 Oct
Products containing bitter orange or synephrine: suspected cardiovascular adverse reactions.
2004 Oct 12
Ischemic stroke associated with use of an ephedra-free dietary supplement containing synephrine.
2005 Apr
Exactly which synephrine alkaloids does Citrus aurantium (bitter orange) contain?
2005 Apr
Nitrogen metabolism components as a tool to discriminate between organic and conventional citrus fruits.
2005 Apr 6
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
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
Analysis of ephedra-free labeled dietary supplements sold in the San Francisco Bay area in 2003.
2006
Blood pressure and heart rate effects following a single dose of bitter orange.
2006 Jan
A rapid and simple procedure for the determination of synephrine in dietary supplements by gas chromatography-mass spectrometry.
2006 Jun 16
Thermogenic effect from nutritionally enriched coffee consumption.
2006 Jun 5
Applications of LC-MS in the study of the uptake, distribution, metabolism and excretion of bioactive polyphenols from dietary supplements.
2006 Mar 27
Metabolic and physiological effects of ingesting extracts of bitter orange, green tea and guarana at rest and during treadmill walking in overweight males.
2006 May
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 three chemical components in Fructus aurantii immaturus].
2006 Sep
Determination of octopamine, synephrine and tyramine in Citrus herbs by ionic liquid improved 'green' chromatography.
2006 Sep 1
Trace amine-associated receptor 1-Family archetype or iconoclast?
2007 Dec
Effects of ingesting JavaFit Energy Extreme functional coffee on aerobic and anaerobic fitness markers in recreationally-active coffee consumers.
2007 Dec 8
Detection and validated quantification of nine herbal phenalkylamines and methcathinone in human blood plasma by LC-MS/MS with electrospray ionization.
2007 Feb
Chemiluminescence of synephrine based on the cerium(IV)-rhodamine B system.
2007 Mar-Apr
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
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
Simultaneous determination of flavonoid and alkaloid compounds in Citrus herbs by high-performance liquid chromatography-photodiode array detection-electrospray mass spectrometry.
2007 Oct 1
Effects of chemopreventive citrus phytochemicals on human P-glycoprotein and multidrug resistance protein 1.
2008 Dec 14
Citrus aurantium--beware of the bitter orange.
2008 Jul
Vasospasm and stroke attributable to ephedra-free xenadrine: case report.
2008 Jul
Certification of standard reference materials containing bitter orange.
2008 Jul
Coronary spasm and thrombosis in a bodybuilder using a nutritional supplement containing synephrine, octopamine, tyramine and caffeine.
2008 May
Synephrine content of juice from Satsuma mandarins (Citrus unshiu Marcovitch).
2008 Oct 8
Determination of ephedrine alkaloids in Ephedra natural products using HPLC on a pentafluorophenylpropyl stationary phase.
2008 Sep 29
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 18:57:08 GMT 2023
Edited
by admin
on Fri Dec 15 18:57:08 GMT 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 Fri Dec 15 18:57:08 GMT 2023 , Edited by admin on Fri Dec 15 18:57:08 GMT 2023
WHO-VATC QS01GA06
Created by admin on Fri Dec 15 18:57:08 GMT 2023 , Edited by admin on Fri Dec 15 18:57:08 GMT 2023
WHO-ATC S01GA56
Created by admin on Fri Dec 15 18:57:08 GMT 2023 , Edited by admin on Fri Dec 15 18:57:08 GMT 2023
DSLD 2287 (Number of products:206)
Created by admin on Fri Dec 15 18:57:08 GMT 2023 , Edited by admin on Fri Dec 15 18:57:08 GMT 2023
WHO-VATC QC01CA08
Created by admin on Fri Dec 15 18:57:08 GMT 2023 , Edited by admin on Fri Dec 15 18:57:08 GMT 2023
WHO-ATC C01CA08
Created by admin on Fri Dec 15 18:57:08 GMT 2023 , Edited by admin on Fri Dec 15 18:57:08 GMT 2023
WHO-VATC QS01GA56
Created by admin on Fri Dec 15 18:57:08 GMT 2023 , Edited by admin on Fri Dec 15 18:57:08 GMT 2023
WHO-VATC QS01FB90
Created by admin on Fri Dec 15 18:57:08 GMT 2023 , Edited by admin on Fri Dec 15 18:57:08 GMT 2023
Code System Code Type Description
PUBCHEM
7172
Created by admin on Fri Dec 15 18:57:08 GMT 2023 , Edited by admin on Fri Dec 15 18:57:08 GMT 2023
PRIMARY
MESH
D013578
Created by admin on Fri Dec 15 18:57:08 GMT 2023 , Edited by admin on Fri Dec 15 18:57:08 GMT 2023
PRIMARY
RS_ITEM_NUM
1642609
Created by admin on Fri Dec 15 18:57:08 GMT 2023 , Edited by admin on Fri Dec 15 18:57:08 GMT 2023
PRIMARY
ChEMBL
CHEMBL33720
Created by admin on Fri Dec 15 18:57:08 GMT 2023 , Edited by admin on Fri Dec 15 18:57:08 GMT 2023
PRIMARY
WIKIPEDIA
SYNEPHRINE
Created by admin on Fri Dec 15 18:57:08 GMT 2023 , Edited by admin on Fri Dec 15 18:57:08 GMT 2023
PRIMARY
MERCK INDEX
m10412
Created by admin on Fri Dec 15 18:57:08 GMT 2023 , Edited by admin on Fri Dec 15 18:57:08 GMT 2023
PRIMARY Merck Index
NSC
170956
Created by admin on Fri Dec 15 18:57:08 GMT 2023 , Edited by admin on Fri Dec 15 18:57:08 GMT 2023
PRIMARY
RXCUI
10288
Created by admin on Fri Dec 15 18:57:08 GMT 2023 , Edited by admin on Fri Dec 15 18:57:08 GMT 2023
PRIMARY RxNorm
CHEBI
29081
Created by admin on Fri Dec 15 18:57:08 GMT 2023 , Edited by admin on Fri Dec 15 18:57:08 GMT 2023
PRIMARY
ECHA (EC/EINECS)
202-300-9
Created by admin on Fri Dec 15 18:57:08 GMT 2023 , Edited by admin on Fri Dec 15 18:57:08 GMT 2023
PRIMARY
EPA CompTox
DTXSID0030588
Created by admin on Fri Dec 15 18:57:08 GMT 2023 , Edited by admin on Fri Dec 15 18:57:08 GMT 2023
PRIMARY
EVMPD
SUB14726MIG
Created by admin on Fri Dec 15 18:57:08 GMT 2023 , Edited by admin on Fri Dec 15 18:57:08 GMT 2023
PRIMARY
NSC
166285
Created by admin on Fri Dec 15 18:57:08 GMT 2023 , Edited by admin on Fri Dec 15 18:57:08 GMT 2023
PRIMARY
SMS_ID
100000088818
Created by admin on Fri Dec 15 18:57:08 GMT 2023 , Edited by admin on Fri Dec 15 18:57:08 GMT 2023
PRIMARY
CAS
94-07-5
Created by admin on Fri Dec 15 18:57:08 GMT 2023 , Edited by admin on Fri Dec 15 18:57:08 GMT 2023
PRIMARY
DRUG BANK
DB09203
Created by admin on Fri Dec 15 18:57:08 GMT 2023 , Edited by admin on Fri Dec 15 18:57:08 GMT 2023
PRIMARY
CHEBI
58606
Created by admin on Fri Dec 15 18:57:08 GMT 2023 , Edited by admin on Fri Dec 15 18:57:08 GMT 2023
PRIMARY
FDA UNII
PEG5DP7434
Created by admin on Fri Dec 15 18:57:08 GMT 2023 , Edited by admin on Fri Dec 15 18:57:08 GMT 2023
PRIMARY
DRUG CENTRAL
3577
Created by admin on Fri Dec 15 18:57:08 GMT 2023 , Edited by admin on Fri Dec 15 18:57:08 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY