Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C9H13NO2 |
| Molecular Weight | 167.205 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CNC[C@@H](O)C1=CC=C(O)C=C1
InChI
InChIKey=YRCWQPVGYLYSOX-SECBINFHSA-N
InChI=1S/C9H13NO2/c1-10-6-9(12)7-2-4-8(11)5-3-7/h2-5,9-12H,6H2,1H3/t9-/m1/s1
| Molecular Formula | C9H13NO2 |
| Molecular Weight | 167.205 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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. | 2009-01 |
|
| Effects of chemopreventive citrus phytochemicals on human P-glycoprotein and multidrug resistance protein 1. | 2008-12-14 |
|
| Synephrine content of juice from Satsuma mandarins (Citrus unshiu Marcovitch). | 2008-10-08 |
|
| Determination of ephedrine alkaloids in Ephedra natural products using HPLC on a pentafluorophenylpropyl stationary phase. | 2008-09-29 |
|
| Selectivity and potential interference from phenolic compounds in chemiluminescence methods for the determination of synephrine. | 2008-09-13 |
|
| Concentrations of p-synephrine in fruits and leaves of Citrus species (Rutaceae) and the acute toxicity testing of Citrus aurantium extract and p-synephrine. | 2008-08 |
|
| Citrus aurantium--beware of the bitter orange. | 2008-07 |
|
| Vasospasm and stroke attributable to ephedra-free xenadrine: case report. | 2008-07 |
|
| Sensitive determination of norepinephrine, synephrine, and isoproterenol by capillary electrophoresis with indirect electrochemiluminescence detection. | 2008-07 |
|
| Certification of standard reference materials containing bitter orange. | 2008-07 |
|
| Human pharmacology of a performance-enhancing dietary supplement under resting and exercise conditions. | 2008-06 |
|
| Coronary spasm and thrombosis in a bodybuilder using a nutritional supplement containing synephrine, octopamine, tyramine and caffeine. | 2008-05 |
|
| In vitro anticholinesterase activity of various alkaloids. | 2007-12-12 |
|
| Effects of ingesting JavaFit Energy Extreme functional coffee on aerobic and anaerobic fitness markers in recreationally-active coffee consumers. | 2007-12-08 |
|
| Lipolysis induced by segment wall extract from Satsuma mandarin orange (Citrus unshu Mark). | 2007-12 |
|
| Trace amine-associated receptor 1-Family archetype or iconoclast? | 2007-12 |
|
| Mass spectrometric determination of the predominant adrenergic protoalkaloids in bitter orange (Citrus aurantium). | 2007-11-28 |
|
| Simultaneous determination of flavonoid and alkaloid compounds in Citrus herbs by high-performance liquid chromatography-photodiode array detection-electrospray mass spectrometry. | 2007-10-01 |
|
| Temperature effects on the enantioselectivity of basic analytes in capillary EKC using sulfated beta-CDs as chiral selectors. | 2007-10 |
|
| Fast high-performance liquid chromatography analysis of phenethylamine alkaloids in Citrus natural products on a pentafluorophenylpropyl stationary phase. | 2007-09-21 |
|
| Determination of bitter orange alkaloids in dietary supplement Standard Reference Materials by liquid chromatography with atmospheric-pressure ionization mass spectrometry. | 2007-09 |
|
| Chromatographic and electrophoretic methods for the analysis of phenethylamine [corrected] alkaloids in Citrus aurantium. | 2007-08-17 |
|
| 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. | 2007-08 |
|
| Two-chiral component microemulsion EKC - chiral surfactant and chiral oil. Part 2: diethyl tartrate. | 2007-08 |
|
| Determination of Bitter Orange alkaloids in dietary supplements standard reference materials by liquid chromatography with ultraviolet absorbance and fluorescence detection. | 2007-07-13 |
|
| Simultaneous analysis of adrenergic amines and flavonoids in citrus peel jams and fruit juices by liquid chromatography: part 2. | 2007-06-22 |
|
| Determination of synephrine in weight-loss products using high performance liquid chromatography with acidic potassium permanganate chemiluminescence detection. | 2007-06-12 |
|
| A case of severe exercise-induced rhabdomyolysis associated with a weight-loss dietary supplement. | 2007-06 |
|
| Two-chiral-component microemulsion electrokinetic chromatography-chiral surfactant and chiral oil: part 1. dibutyl tartrate. | 2007-06 |
|
| Biochemistry of neuromodulation in primary headaches: focus on anomalies of tyrosine metabolism. | 2007-05 |
|
| Determination of synephrine in bitter orange raw materials, extracts, and dietary supplements by liquid chromatography with ultraviolet detection: single-laboratory validation. | 2007-03-22 |
|
| Detection and validated quantification of nine herbal phenalkylamines and methcathinone in human blood plasma by LC-MS/MS with electrospray ionization. | 2007-02 |
|
| Anti-inflammatory effects and mechanisms of the ethanol extract of Evodia rutaecarpa and its bioactive components on neutrophils and microglial cells. | 2007-01-26 |
|
| Evaluation of the stimulant content of dietary supplements marketed as "ephedra-free". | 2007 |
|
| Reporting associations between dietary supplements and adverse events. | 2006-12 |
|
| Chemical and biological comparisons on Evodia with two related species of different locations and conditions. | 2006-11-24 |
|
| Chemiluminescence of synephrine based on the cerium(IV)-rhodamine B system. | 2006-11-08 |
|
| 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. | 2006-11 |
|
| Consumption of dietary supplements containing Citrus aurantium (bitter orange)--2004 California Behavioral Risk Factor Surveillance Survey (BRFSS). | 2006-10 |
|
| Determination of octopamine, synephrine and tyramine in Citrus herbs by ionic liquid improved 'green' chromatography. | 2006-09-01 |
|
| [Determination of three chemical components in Fructus aurantii immaturus]. | 2006-09 |
|
| Strategies for enantioseparations of catecholamines and structurally related compounds by capillary zone electrophoresis using sulfated beta-cyclodextrins as chiral selectors. | 2006-09 |
|
| Abnormal platelet trace amine profiles in migraine with and without aura. | 2006-08 |
|
| A rapid and simple procedure for the determination of synephrine in dietary supplements by gas chromatography-mass spectrometry. | 2006-06-16 |
|
| Thermogenic effect from nutritionally enriched coffee consumption. | 2006-06-05 |
|
| Metal content of ephedra-containing dietary supplements and select botanicals. | 2006-04-01 |
|
| Response of CEDIA amphetamines assay after a single dose of bitter orange. | 2006-04 |
|
| Variant angina associated with bitter orange in a dietary supplement. | 2006-04 |
|
| Development and validation of HPLC methods for the analysis of phenethylamine and indoloquinazoline alkaloids in Evodia species. | 2006-03 |
|
| Analysis of ephedra-free labeled dietary supplements sold in the San Francisco Bay area in 2003. | 2006 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 22:15:58 GMT 2025
by
admin
on
Mon Mar 31 22:15:58 GMT 2025
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| Record UNII |
73SNV1H5Y5
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| Record Status |
Validated (UNII)
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| Record Version |
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Preferred Name | English | ||
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DTXSID70904723
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667452
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73SNV1H5Y5
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33016
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532-80-9
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