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 |
|
[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 |
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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
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
Fri Dec 15 18:57:08 GMT 2023
by
admin
on
Fri Dec 15 18:57:08 GMT 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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S01GA06
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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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C01CA08
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QS01GA56
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QS01FB90
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D013578
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SYNEPHRINE
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m10412
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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 |
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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ACTIVE MOIETY |
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