5985-28-4

Basic information

• Product Name: Synephrine hydrochloride
• Synonyms: 1-(4-Hydroxyphenyl)-2-(methylamino)-ethanol hydrochloride;SYNEPHRINE HCL;SYNEPHRINE HYDROCHLORIDE;N-METHYL OCTOPAMINE HCL;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
• CAS NO: 5985-28-4
• Molecular Formula: C₉H₁₃NO₂*ClH
• Molecular Weight: 203.67
• EINECS: 227-804-6
• Product Categories: Amines;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 5985-28-4.mol
• Article Data: 2

Chemical Properties

• Melting Point: 147-150°C
• Boiling Point: 341.1 °C at 760 mmHg
• Flash Point: 163.4 °C
• Appearance: white powder
• Storage Temp.: Refrigerator
• Solubility: Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: Synephrine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Synephrine hydrochloride(5985-28-4)
• EPA Substance Registry System: Synephrine hydrochloride(5985-28-4)

Safety Data

• Hazardous Substances Data: 5985-28-4(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/C9H13NO2.ClH/c1-10-6-9(12)7-2-4-8(11)5-3-7;/h2-5,9-12H,6H2,1H3;1H

Synthetic route

(+/-)-Synephrine hydrochloride (5985-28-4) + acetyl chloride (75-36-5) → 2-(4-acetoxyphenyl)-2-chloro-N-methylethylammonium chloride (14593-25-0)

Conditions	Yield
In acetic acid at 10 - 30℃; for 12h;	83.6%

hydrogenchloride (7647-01-0) + (+/-)-Synephrine hydrochloride (5985-28-4) + acetic acid (64-19-7) + acetyl chloride (75-36-5) → 4-acetoxy-1-<1-chloro-2-methylamino-ethyl>-benzene hydrochloride

cucurbit[6]uril decahydrate + (+/-)-Synephrine hydrochloride (5985-28-4) → C36H36N24O12*2C9H13NO2*14H2O*2Cl(1-)*2H(1+)

Conditions	Yield
Stage #1: cucurbit[6]uril decahydrate With magnesium(II) chloride hexahydrate; water Heating; Stage #2: (+/-)-Synephrine hydrochloride for 48h;

Upstream product

• 532-80-9 synephrine 

Downstream Products

• 14593-25-0 2-(4-acetoxyphenyl)-2-chloro-N-methylethylammonium chloride 

Relevant articles and documents

Synthesis and uses of synephrine derivatives

The present invention discloses a novel syntheses of synephrine, its derivatives, and the salts of the foregoing, including their intermediates. One or more of the substituents of the nitrogen atom of the synephrine is/are modified to produce the derivatives. The synephrine derivatives and their salts are useful for treating animals for diseases, conditions, or disorders modulated by β3-adrenergic receptor. They are preferably used as fat breakdown agents and/or weight loss agents.