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
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
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 | ( + / - ) |
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 |
---|---|---|
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 |
|
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 |
|
Moderate weight-lowering effect of octopamine treatment in obese Zucker rats. | 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 |
|
Synephrine is not Neo-Synephrine. | 2004 Dec |
|
Possible association of acute lateral-wall myocardial infarction and bitter orange supplement. | 2004 May |
|
Elevated levels of circulating trace amines in primary headaches. | 2004 May 25 |
|
Quantitative and qualitative HPLC analysis of thermogenic weight loss products. | 2004 Nov |
|
Contributions of biochemistry to the pathogenesis of primary headaches. | 2004 Oct |
|
Citrus aurantium, an ingredient of dietary supplements marketed for weight loss: current status of clinical and basic research. | 2004 Sep |
|
Ischemic stroke associated with use of an ephedra-free dietary supplement containing synephrine. | 2005 Apr |
|
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 |
|
Molecular mechanisms of toxicity of important food-borne phytotoxins. | 2005 Feb |
|
Hemodynamic effects of ephedra-free weight-loss supplements in humans. | 2005 Sep |
|
Reporting associations between dietary supplements and adverse events. | 2006 Dec |
|
Quantitative and qualitative analysis of flavonoid markers in Frucus aurantii of different geographical origin by capillary electrophoresis with electrochemical detection. | 2006 Jan 18 |
|
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 |
|
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 |
|
[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 |
|
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 |
|
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 synephrine in bitter orange raw materials, extracts, and dietary supplements by liquid chromatography with ultraviolet detection: single-laboratory validation. | 2007 Jan-Feb |
|
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 |
|
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 |
|
Determination of bitter orange alkaloids in dietary supplement Standard Reference Materials by liquid chromatography with atmospheric-pressure ionization mass spectrometry. | 2007 Sep |
|
In vitro anticholinesterase activity of various alkaloids. | 2007 Sep-Oct |
|
Citrus aurantium--beware of the bitter orange. | 2008 Jul |
|
Sensitive determination of norepinephrine, synephrine, and isoproterenol by capillary electrophoresis with indirect electrochemiluminescence detection. | 2008 Jul |
|
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 |
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 15:19:08 UTC 2023
by
admin
on
Fri Dec 15 15:19:08 UTC 2023
|
Record UNII |
EN5D1IH09S
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
100000087306
Created by
admin on Fri Dec 15 15:19:08 UTC 2023 , Edited by admin on Fri Dec 15 15:19:08 UTC 2023
|
PRIMARY | |||
|
22302
Created by
admin on Fri Dec 15 15:19:08 UTC 2023 , Edited by admin on Fri Dec 15 15:19:08 UTC 2023
|
PRIMARY | |||
|
DTXSID70975251
Created by
admin on Fri Dec 15 15:19:08 UTC 2023 , Edited by admin on Fri Dec 15 15:19:08 UTC 2023
|
PRIMARY | |||
|
m10412
Created by
admin on Fri Dec 15 15:19:08 UTC 2023 , Edited by admin on Fri Dec 15 15:19:08 UTC 2023
|
PRIMARY | Merck Index | ||
|
5985-28-4
Created by
admin on Fri Dec 15 15:19:08 UTC 2023 , Edited by admin on Fri Dec 15 15:19:08 UTC 2023
|
PRIMARY | |||
|
Synephrine hydrochloride
Created by
admin on Fri Dec 15 15:19:08 UTC 2023 , Edited by admin on Fri Dec 15 15:19:08 UTC 2023
|
PRIMARY | |||
|
227-804-6
Created by
admin on Fri Dec 15 15:19:08 UTC 2023 , Edited by admin on Fri Dec 15 15:19:08 UTC 2023
|
PRIMARY | |||
|
EN5D1IH09S
Created by
admin on Fri Dec 15 15:19:08 UTC 2023 , Edited by admin on Fri Dec 15 15:19:08 UTC 2023
|
PRIMARY | |||
|
SUB20984
Created by
admin on Fri Dec 15 15:19:08 UTC 2023 , Edited by admin on Fri Dec 15 15:19:08 UTC 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> SALT/SOLVATE |