ChemicalBook Product Catalog Biochemical Engineering Inhibitors Neuronal Signaling Adrenergic Receptor agonists Synephrine hydrochloride

Synephrine hydrochloride

Product NameSynephrine hydrochloride
CAS5985-28-4
MFC9H14ClNO2
MW203.67
EINECS227-804-6
MOL File5985-28-4.mol

Chemical Properties

Melting point	147-150°C
storage temp.	Refrigerator
solubility	Methanol (Slightly), Water (Slightly)
form	Solid
color	Off-White to Pale Beige
Cosmetics Ingredients Functions	ANTIOXIDANT SKIN CONDITIONING HAIR CONDITIONING
InChI	InChI=1S/C9H13NO2.ClH/c1-10-6-9(12)7-2-4-8(11)5-3-7;/h2-5,9-12H,6H2,1H3;1H
InChIKey	COTCEGYSNTWJQV-UHFFFAOYSA-N
SMILES	C1(=CC=C(O)C=C1)C(O)CNC.Cl
LogP	-0.030 (est)
CAS DataBase Reference	5985-28-4(CAS DataBase Reference)

Safety Information

HS Code

2922498590

Usage And Synthesis

Description

(±)-Synephrine is an alkaloid with vasoconstrictor and metabolic activities. It binds to α_1A-, α_2A-, and α_2C-adrenergic receptors (ARs; K_is = 78, 36.7, and 24.4 μM, respectively). (±)-Synephrine is an agonist of α_1A-ARs in HEK293 cells (EC₅₀ = 4 μM in a reporter assay) but not in CHO cells expressing α_2A- or α_2C-AR. It also acts as an antagonist of α_1A-, α_2A-, and α_2C-ARs, inhibiting L-phenylephrine-induced activation of α_1A-AR in HEK293 cells and activation of α_2A- and α_2C-ARs induced by the α₂-AR agonist medetomidine in CHO cells (IC₅₀s = 12.8, 26, and 27.3 μM, respectively, in reporter assays). (±)-Synephrine induces contractions in isolated rabbit aortic rings (EC₅₀ = 6.2 μg/ml) and increases ligation-induced mean arterial pressure in rats when administered at a dose of 2 mg/kg per day. It induces lipolysis in isolated rat and human adipocytes when used at concentrations of 100 and 1,000 μg/ml. (±)-Synephrine (50 μM) increases phosphorylation of Akt and AMP-activated protein kinase (AMPK) and translocation of Glut4 to the plasma membrane, as well as increases insulin-induced glucose consumption in L6 muscle cells when used at concentrations ranging from 25 to 200 μM.

Chemical Properties

Pale Beige Solid

Uses

A α-adrenergic receptor agonist, vasoconstrictor.

References

[1] YI-TSAU HUANG . Fructus aurantii reduced portal pressure in portal hypertensive rats[J]. Life sciences, 1995, 57 22: Pages 2011-2020. DOI: 10.1016/0024-3205(95)02195-o
[2] JOSEP MERCADER. Isopropylnorsynephrine is a stronger lipolytic agent in human adipocytes than synephrine and other amines present in Citrus aurantium.[J]. Journal of physiology and biochemistry, 2011, 67 3: 443-452. DOI: 10.1007/s13105-011-0078-2
[3] NA-YOUNG HONG. p-Synephrine stimulates glucose consumption via AMPK in L6 skeletal muscle cells[J]. Biochemical and biophysical research communications, 2012, 418 4: Pages 720-724. DOI: 10.1016/j.bbrc.2012.01.085
[4] GUOYI MA. Effects of synephrine and beta-phenethylamine on human alpha-adrenoceptor subtypes.[J]. Planta medica, 2010, 76 10: 981-986. DOI: 10.1055/s-0029-1240884
[5] J A BEVAN J V O. Relative sensitivity of some large blood vessels of the rabbit to sympathomimetic amines.[J]. Journal of Pharmacology and Experimental Therapeutics, 1965, 150 3: 370-374.