Synephrine HCl

Alias: Sympatol; Synephrine HCl; oxedrine
Cat No.:V1139 Purity: ≥98%
Synephrine HCl (Sympatol; oxedrine), the hydrochloride salt of synephrine which is a naturally occuring protoalkaloid extracted from bitter orange and other citrus species, is commonly used for weight loss.
Synephrine HCl Chemical Structure CAS No.: 5985-28-4
Product category: Adrenergic Receptor
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10g
25g
Other Sizes

Other Forms of Synephrine HCl:

  • Synephrine
  • Synephrine tartrate
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Synephrine HCl (Sympatol; oxedrine), the hydrochloride salt of synephrine which is a naturally occuring protoalkaloid extracted from bitter orange and other citrus species, is commonly used for weight loss. Synephrine has also been widely used as an alternative to ephedrine. Products that contain synephrine or bitter orange may cause negative cardiovascular reactions. Regardless of insulin-stimulated PI3 kinase-Akt activity in L6 skeletal muscle cells, synephrine can promote glucose consumption (Glut4-dependent glucose uptake) by upregulating AMPK activity.

Biological Activity I Assay Protocols (From Reference)
Targets
β adrenergic receptor
ln Vitro
Synephrine (0.1-30 μM) exhibits strong vasoconstrictive effects on isolated rat aortas in a dose-dependent manner that is significantly inhibited by pretreatment with ketanserin, prazosin, and BRL15572, but not by pretreatment with SB216641 and propranolol. This suggests that synephrine acts via serotonergic 5-HT(1D) receptors, adrenergic alpha(1)-receptors, and adrenergic alpha(1)-receptors.[2] Synephrine is the only partial agonist of the α1A-AR subtype that is stably expressed in HEK 293 cells, with an EC50 of 4 µM and a maximal response at 100 µM equal to 55.3% of the L-phenylephrine maximum, despite the fact that the Ki values of Synephrine, 1R, 2S-norephedrine, and β-phenethylamine are the same for all three subtypes. Synephrine may function as an antagonist rather than an agonist of the pre-synaptic α(2A)- and α(2C)-AR subtypes found in nerve terminals, according to functional studies on the α2A- and α2C-AR subtypes that are stably expressed in CHO cells. However, synephrine's antagonist activity is less than its partial agonist potency.[3] In a dose-dependent manner, synephrine (~100 μM) treatment raises basal glucose consumption over the control by up to 50% without compromising the viability of L6 skeletal muscle cells. When basal or insulin-stimulated lactic acid production and glucose consumption are combined, synephrine dramatically increases both of these processes. In addition, synephrine-induced glucose consumption and the translocation of Glut4 from the cytoplasm to the plasma membrane are responsive to AMPK inhibition but not PI3 kinase inhibition. Synephrine treatment stimulates the phosphorylation of AMPK but not Akt.[4]
ln Vivo
Eight days of administration of Synephrine (1 mg/kg per 12 hours) significantly reduces the portal tributary blood flow, portal venous pressure, and cardiac index in both PVL and BDL rats, and improves the hyperdynamic state in portal hypertensive rats induced by either partial portal vein ligation (PVL) or bile duct ligation (BDL).[1]
Animal Protocol
Dissolved in 0.1 N HCl; 1 mg/kg per 12 hours; Oral gavage
Male Sprague-Dawley rats with portal hypertension (with or without cirrhosis) induced by bile duct ligation or partial portal vein ligation
References

[1]. Jpn J Pharmacol . 2001 Feb;85(2):183-8.

[2]. J Pharmacol Sci . 2009 Sep;111(1):73-81.

[3]. Planta Med . 2010 Jul;76(10):981-6.

[4]. Biochem Biophys Res Commun . 2012 Feb 24;418(4):720-4.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C9H14CLNO2
Molecular Weight
203.67
Exact Mass
203.07
Elemental Analysis
C, 53.08; H, 6.93; Cl, 17.41; N, 6.88; O, 15.71
CAS #
5985-28-4
Related CAS #
Synephrine; 94-07-5; Synephrine hemitartrate; 16589-24-5
Appearance
Solid powder
SMILES
CNCC(C1=CC=C(C=C1)O)O.Cl
InChi Key
COTCEGYSNTWJQV-UHFFFAOYSA-N
InChi Code
InChI=1S/C9H13NO2.ClH/c1-10-6-9(12)7-2-4-8(11)5-3-7;/h2-5,9-12H,6H2,1H3;1H
Chemical Name
4-[1-hydroxy-2-(methylamino)ethyl]phenol;hydrochloride
Synonyms
Sympatol; Synephrine HCl; oxedrine
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: ~14 mg/mL (~68.7 mM)
Water: ~41 mg/mL (~201.3 mM)
Ethanol: ~4 mg/mL (~19.6 mM)
Solubility (In Vivo)
Saline: 30 mg/mL
 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.9099 mL 24.5495 mL 49.0990 mL
5 mM 0.9820 mL 4.9099 mL 9.8198 mL
10 mM 0.4910 mL 2.4550 mL 4.9099 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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