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-VIFPVBQESA-N
InChI=1S/C9H13NO2/c1-10-6-9(12)7-2-4-8(11)5-3-7/h2-5,9-12H,6H2,1H3/t9-/m0/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 |
Oxedrine (-)- is an inactive enantiomer of alkaloid oxedrine (synephrine). Oxedrine (-)- was detected in orange juice and marmalade. It may thus possibly be formed during production using citrus fruits. The natural alkaloid synephrine exists only as (+)-synephrine, whereas synthetically produced synephrine exists as a 50/50 racemic mixture of (-)/(+)-synephrine. Following ingestion of (+)-oxedrine, it is postulated that chiral inversion occurs, resulting in inversion to oxedrine (-)- in urine. Epinephrine analogs such as propadrine and oxedrine (-)- counteracted the biological action of epinephrine.
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
Determination of synephrine enantiomers in food and conjugated synephrine in urine by high-performance liquid chromatography with electrochemical detection. | 1996 Mar 15 |
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Determination of p-hydroxymandelic acid enantiomers in urine by high-performance liquid chromatography with electrochemical detection. | 1997 Jun |
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Selective inhibition of adenylyl cyclase by octopamine via a human cloned alpha 2A-adrenoceptor. | 1997 Sep |
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Seville (sour) orange juice: synephrine content and cardiovascular effects in normotensive adults. | 2001 Oct |
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Determination of adrenergic agonists from extracts and herbal products of Citrus aurantium L. var. amara by LC. | 2002 Aug 1 |
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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 |
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Screening for endogenous substrates reveals that CYP2D6 is a 5-methoxyindolethylamine O-demethylase. | 2003 Jun |
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Ephedra-free is not danger-free. | 2003 Sep 19 |
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Quantitative and qualitative HPLC analysis of thermogenic weight loss products. | 2004 Nov |
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Enantioselective LC analysis of synephrine in natural products on a protein-based chiral stationary phase. | 2005 Apr 29 |
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A rapid liquid chromatography electrospray ionization mass spectrometry(n) method for evaluation of synephrine in Citrus aurantium L. samples. | 2005 Dec 28 |
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Determination of ephedrine alkaloids in dietary supplement standard reference materials. | 2005 May 15 |
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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 |
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Response of CEDIA amphetamines assay after a single dose of bitter orange. | 2006 Apr |
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Metal content of ephedra-containing dietary supplements and select botanicals. | 2006 Apr 1 |
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Abnormal platelet trace amine profiles in migraine with and without aura. | 2006 Aug |
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Sensitive determination of synephrine by flow-injection chemiluminescence. | 2006 Jan-Feb |
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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 |
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Strategies for enantioseparations of catecholamines and structurally related compounds by capillary zone electrophoresis using sulfated beta-cyclodextrins as chiral selectors. | 2006 Sep |
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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 |
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Chromatographic and electrophoretic methods for the analysis of phenethylamine [corrected] alkaloids in Citrus aurantium. | 2007 Aug 17 |
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Lipolysis induced by segment wall extract from Satsuma mandarin orange (Citrus unshu Mark). | 2007 Dec |
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Detection and validated quantification of nine herbal phenalkylamines and methcathinone in human blood plasma by LC-MS/MS with electrospray ionization. | 2007 Feb |
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Determination of synephrine in bitter orange raw materials, extracts, and dietary supplements by liquid chromatography with ultraviolet detection: single-laboratory validation. | 2007 Jan-Feb |
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A case of severe exercise-induced rhabdomyolysis associated with a weight-loss dietary supplement. | 2007 Jun |
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Mass spectrometric determination of the predominant adrenergic protoalkaloids in bitter orange (Citrus aurantium). | 2007 Nov 28 |
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In vitro anticholinesterase activity of various alkaloids. | 2007 Sep-Oct |
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Vasospasm and stroke attributable to ephedra-free xenadrine: case report. | 2008 Jul |
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Certification of standard reference materials containing bitter orange. | 2008 Jul |
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Coronary spasm and thrombosis in a bodybuilder using a nutritional supplement containing synephrine, octopamine, tyramine and caffeine. | 2008 May |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 08:42:48 GMT 2023
by
admin
on
Sat Dec 16 08:42:48 GMT 2023
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Record UNII |
Y276ILP9M0
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Record Status |
Validated (UNII)
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Record Version |
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