Synephrine hydrochloride
Synephrine hydrochloride Basic information
- Product Name:
- Synephrine hydrochloride
- Synonyms:
-
- 1-(4-Hydroxyphenyl)-2-(methylamino)-ethanol hydrochloride
- 4-hydroxy-alpha-((methylamino)methyl)-benzenemethanohydrochloride
- l-1-p-hydroxyphenyl-2-methylamino-1-ethanolhydrochloride
- p-hydroxy-alpha-((methylamino)methyl)-benzylalcohohydrochloride
- p-hydroxy-alpha-(methylaminomethyl)benzylalcoholhydrochloride
- p-methylaminoaethanolphenolhydrochlorid
- SYNEPHRINE HCL
- SYNEPHRINE HYDROCHLORIDE
- CAS:
- 5985-28-4
- MF:
- C9H14ClNO2
- MW:
- 203.67
- EINECS:
- 227-804-6
- Product Categories:
-
- Amines
- Inhibitors
- Intermediates & Fine Chemicals
- Pharmaceuticals
- 5985-28-4
- Mol File:
- 5985-28-4.mol
Synephrine hydrochloride Chemical Properties
- Melting point:
- 147-150°C
- storage temp.
- Refrigerator
- solubility
- Methanol (Slightly), Water (Slightly)
- form
- Solid
- color
- Off-White to Pale Beige
- 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)
Synephrine hydrochloride Usage And Synthesis
Description
(±)-Synephrine is an alkaloid with vasoconstrictor and metabolic activities. It binds to α1A-, α2A-, and α2C-adrenergic receptors (ARs; Kis = 78, 36.7, and 24.4 μM, respectively). (±)-Synephrine is an agonist of α1A-ARs in HEK293 cells (EC50 = 4 μM in a reporter assay) but not in CHO cells expressing α2A- or α2C-AR. It also acts as an antagonist of α1A-, α2A-, and α2C-ARs, inhibiting L-phenylephrine-induced activation of α1A-AR in HEK293 cells and activation of α2A- and α2C-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.
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