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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H13NO2
Molecular Weight 167.205
Optical Activity ( - )
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
Vasospasm and stroke attributable to ephedra-free xenadrine: case report.
2008-07
Certification of standard reference materials containing bitter orange.
2008-07
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
Lipolysis induced by segment wall extract from Satsuma mandarin orange (Citrus unshu Mark).
2007-12
Mass spectrometric determination of the predominant adrenergic protoalkaloids in bitter orange (Citrus aurantium).
2007-11-28
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
A case of severe exercise-induced rhabdomyolysis associated with a weight-loss dietary supplement.
2007-06
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
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
Metabolic and physiological effects of ingesting extracts of bitter orange, green tea and guarana at rest and during treadmill walking in overweight males.
2006-05
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
A rapid liquid chromatography electrospray ionization mass spectrometry(n) method for evaluation of synephrine in Citrus aurantium L. samples.
2005-12-28
Rational method development strategies on a fluorinated liquid chromatography stationary phase: mobile phase ion concentration and temperature effects on the separation of ephedrine alkaloids.
2005-11-18
Sensitive determination of synephrine by flow-injection chemiluminescence.
2005-08-16
Determination of ephedrine alkaloids in dietary supplement standard reference materials.
2005-05-15
Enantioselective LC analysis of synephrine in natural products on a protein-based chiral stationary phase.
2005-04-29
Quantitative and qualitative HPLC analysis of thermogenic weight loss products.
2004-11
Ephedra-free is not danger-free.
2003-09-19
HPLC electrochemical detection of trace amines in human plasma and platelets and expression of mRNA transcripts of trace amine receptors in circulating leukocytes.
2003-07-31
Screening for endogenous substrates reveals that CYP2D6 is a 5-methoxyindolethylamine O-demethylase.
2003-06
Determination of adrenergic agonists from extracts and herbal products of Citrus aurantium L. var. amara by LC.
2002-08-01
Seville (sour) orange juice: synephrine content and cardiovascular effects in normotensive adults.
2001-10
Selective inhibition of adenylyl cyclase by octopamine via a human cloned alpha 2A-adrenoceptor.
1997-09
Determination of p-hydroxymandelic acid enantiomers in urine by high-performance liquid chromatography with electrochemical detection.
1997-06
Determination of synephrine enantiomers in food and conjugated synephrine in urine by high-performance liquid chromatography with electrochemical detection.
1996-03-15
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 Mon Mar 31 22:15:58 GMT 2025
Edited
by admin
on Mon Mar 31 22:15:58 GMT 2025
Record UNII
Y276ILP9M0
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
(-)-OXEDRINE
Preferred 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 Mon Mar 31 22:15:58 GMT 2025 , Edited by admin on Mon Mar 31 22:15:58 GMT 2025
PRIMARY
CHEBI
63694
Created by admin on Mon Mar 31 22:15:58 GMT 2025 , Edited by admin on Mon Mar 31 22:15:58 GMT 2025
PRIMARY
CAS
614-35-7
Created by admin on Mon Mar 31 22:15:58 GMT 2025 , Edited by admin on Mon Mar 31 22:15:58 GMT 2025
PRIMARY
CHEBI
119
Created by admin on Mon Mar 31 22:15:58 GMT 2025 , Edited by admin on Mon Mar 31 22:15:58 GMT 2025
PRIMARY
PUBCHEM
854067
Created by admin on Mon Mar 31 22:15:58 GMT 2025 , Edited by admin on Mon Mar 31 22:15:58 GMT 2025
PRIMARY