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
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
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 | ( + / - ) |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/21904645Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21904645
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 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25262941 |
6.6 µM [EC50] | ||
Target ID: CHEMBL229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20217639 |
4.11 null [pKi] | ||
Target ID: CHEMBL1867 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20217639 |
4.44 null [pKi] | ||
Target ID: CHEMBL1916 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20217639 |
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 |
---|---|---|
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
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT01423019
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20217639
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
Edited
Thu Jul 06 02:07:01 UTC 2023
by
admin
on
Thu Jul 06 02:07:01 UTC 2023
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Record UNII |
PEG5DP7434
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
S01GA06
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WHO-VATC |
QS01GA06
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WHO-ATC |
S01GA56
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DSLD |
2287 (Number of products:206)
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WHO-VATC |
QC01CA08
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WHO-ATC |
C01CA08
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WHO-VATC |
QS01GA56
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WHO-VATC |
QS01FB90
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7172
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D013578
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1642609
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CHEMBL33720
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SYNEPHRINE
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M10412
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170956
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10288
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29081
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202-300-9
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DTXSID0030588
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SUB14726MIG
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94-07-5
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DB09203
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58606
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PEG5DP7434
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3577
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> AGONIST | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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ACTIVE MOIETY |