U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C9H13NO2
Molecular Weight 167.205
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXEDRINE

SMILES

CNCC(O)C1=CC=C(O)C=C1

InChI

InChIKey=YRCWQPVGYLYSOX-UHFFFAOYSA-N
InChI=1S/C9H13NO2/c1-10-6-9(12)7-2-4-8(11)5-3-7/h2-5,9-12H,6H2,1H3

HIDE SMILES / InChI

Molecular Formula C9H13NO2
Molecular Weight 167.205
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

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 TargetPharmacologyConditionPotency
6.6 µM [EC50]
4.11 null [pKi]
4.44 null [pKi]
4.61 null [pKi]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Advantra Z

Cmax

ValueDoseCo-administeredAnalytePopulation
1.75 ng/mL
21 mg single, oral
OXEDRINE plasma
Homo sapiens
1.86 ng/mL
21 mg single, oral
OXEDRINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
427.9 ng × min/mL
21 mg single, oral
OXEDRINE plasma
Homo sapiens
466.4 ng × min/mL
21 mg single, oral
OXEDRINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2.56 h
21 mg single, oral
OXEDRINE plasma
Homo sapiens
2.64 h
21 mg single, oral
OXEDRINE plasma
Homo sapiens

Doses

AEs

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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
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
Record UNII
PEG5DP7434
Record Status Validated (UNII)
Record Version