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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
Structure of OXEDRINE, (-)-

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

HIDE SMILES / InChI

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

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Determination of synephrine enantiomers in food and conjugated synephrine in urine by high-performance liquid chromatography with electrochemical detection.
1996 Mar 15
Determination of p-hydroxymandelic acid enantiomers in urine by high-performance liquid chromatography with electrochemical detection.
1997 Jun
Selective inhibition of adenylyl cyclase by octopamine via a human cloned alpha 2A-adrenoceptor.
1997 Sep
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
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
Ephedra-free is not danger-free.
2003 Sep 19
Quantitative and qualitative HPLC analysis of thermogenic weight loss products.
2004 Nov
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
Determination of ephedrine alkaloids in dietary supplement standard reference materials.
2005 May 15
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
Response of CEDIA amphetamines assay after a single dose of bitter orange.
2006 Apr
Metal content of ephedra-containing dietary supplements and select botanicals.
2006 Apr 1
Abnormal platelet trace amine profiles in migraine with and without aura.
2006 Aug
Sensitive determination of synephrine by flow-injection chemiluminescence.
2006 Jan-Feb
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
Strategies for enantioseparations of catecholamines and structurally related compounds by capillary zone electrophoresis using sulfated beta-cyclodextrins as chiral selectors.
2006 Sep
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
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
Detection and validated quantification of nine herbal phenalkylamines and methcathinone in human blood plasma by LC-MS/MS with electrospray ionization.
2007 Feb
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
Mass spectrometric determination of the predominant adrenergic protoalkaloids in bitter orange (Citrus aurantium).
2007 Nov 28
In vitro anticholinesterase activity of various alkaloids.
2007 Sep-Oct
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
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:42:48 GMT 2023
Edited
by admin
on Sat Dec 16 08:42:48 GMT 2023
Record UNII
Y276ILP9M0
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OXEDRINE, (-)-
Common Name English
(-)-OXEDRINE
Common Name English
L-SYNEPHRINE
Common Name English
BENZENEMETHANOL, 4-HYDROXY-.ALPHA.-((METHYLAMINO)METHYL)-, (.ALPHA.R)-
Systematic Name English
(R)-SYNEPHRINE
Common Name English
(-)-SYNEPHRINE
Common Name English
Code System Code Type Description
FDA UNII
Y276ILP9M0
Created by admin on Sat Dec 16 08:42:48 GMT 2023 , Edited by admin on Sat Dec 16 08:42:48 GMT 2023
PRIMARY
CHEBI
63694
Created by admin on Sat Dec 16 08:42:48 GMT 2023 , Edited by admin on Sat Dec 16 08:42:48 GMT 2023
PRIMARY
CAS
614-35-7
Created by admin on Sat Dec 16 08:42:48 GMT 2023 , Edited by admin on Sat Dec 16 08:42:48 GMT 2023
PRIMARY
CHEBI
119
Created by admin on Sat Dec 16 08:42:48 GMT 2023 , Edited by admin on Sat Dec 16 08:42:48 GMT 2023
PRIMARY
PUBCHEM
854067
Created by admin on Sat Dec 16 08:42:48 GMT 2023 , Edited by admin on Sat Dec 16 08:42:48 GMT 2023
PRIMARY