Details
| Stereochemistry | RACEMIC |
| Molecular Formula | 2C9H13NO2.H2O4S |
| Molecular Weight | 432.489 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OS(O)(=O)=O.CNCC(O)C1=CC=C(O)C=C1.CNCC(O)C2=CC=C(O)C=C2
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)
DescriptionCurator'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
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
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1075144 |
6.6 µM [EC50] | ||
Target ID: CHEMBL229 |
4.11 null [pKi] | ||
Target ID: CHEMBL1867 |
4.44 null [pKi] | ||
Target ID: CHEMBL1916 |
4.61 null [pKi] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Advantra Z Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.75 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18341680/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18341680/ |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
427.9 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18341680/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18341680/ |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.56 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18341680/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18341680/ |
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
| Dose | Population | Adverse 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 Health Status: healthy Age Group: 27 Sex: F Population Size: 1 Sources: Page: p.11 |
Disc. AE: Ventricular fibrillation... AEs leading to discontinuation/dose reduction: Ventricular fibrillation Sources: Page: p.11 |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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 Health Status: healthy Age Group: 27 Sex: F Population Size: 1 Sources: Page: p.11 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| A rapid liquid chromatography electrospray ionization mass spectrometry(n) method for evaluation of synephrine in Citrus aurantium L. samples. | 2005 Dec 28 |
|
| Simultaneous quantification of adrenergic amines and flavonoids in C. aurantium, various Citrus species, and dietary supplements by liquid chromatography. | 2005 Nov-Dec |
|
| 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 |
|
| Citrus aurantium and synephrine alkaloids in the treatment of overweight and obesity: an update. | 2006 Feb |
|
| An isotopically labeled internal standard liquid chromatography-tandem mass spectrometry method for determination of ephedrine alkaloids and synephrine in dietary supplements. | 2006 Jan 25 |
|
| 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 |
|
| Development and validation of HPLC methods for the analysis of phenethylamine and indoloquinazoline alkaloids in Evodia species. | 2006 Mar |
|
| Acute tubular necrosis associated with chromium picolinate-containing dietary supplement. | 2006 Mar |
|
| 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 |
|
| Chemical and biological comparisons on Evodia with two related species of different locations and conditions. | 2006 Nov 24 |
|
| Consumption of dietary supplements containing Citrus aurantium (bitter orange)--2004 California Behavioral Risk Factor Surveillance Survey (BRFSS). | 2006 Oct |
|
| [Determination of three chemical components in Fructus aurantii immaturus]. | 2006 Sep |
|
| Strategies for enantioseparations of catecholamines and structurally related compounds by capillary zone electrophoresis using sulfated beta-cyclodextrins as chiral selectors. | 2006 Sep |
|
| 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 |
|
| 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 |
|
| Chromatographic and electrophoretic methods for the analysis of phenethylamine [corrected] alkaloids in Citrus aurantium. | 2007 Aug 17 |
|
| Lipolysis induced by segment wall extract from Satsuma mandarin orange (Citrus unshu Mark). | 2007 Dec |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| In vitro anticholinesterase activity of various alkaloids. | 2007 Sep-Oct |
|
| 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 |
|
| Citrus aurantium--beware of the bitter orange. | 2008 Jul |
|
| Vasospasm and stroke attributable to ephedra-free xenadrine: case report. | 2008 Jul |
|
| Sensitive determination of norepinephrine, synephrine, and isoproterenol by capillary electrophoresis with indirect electrochemiluminescence detection. | 2008 Jul |
|
| Certification of standard reference materials containing bitter orange. | 2008 Jul |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Selectivity and potential interference from phenolic compounds in chemiluminescence methods for the determination of synephrine. | 2009 Mar-Apr |
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
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139033144
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SUB03565MIG
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100000085487
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QC6316150O
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ACTIVE MOIETY
SUBSTANCE RECORD
