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 hydrochloride, also known as (±)-Synephrine, is an alkaloid with vasoconstrictor and metabolic activities. It is a pale beige solid that binds to α1A-, α2A-, and α2C-adrenergic receptors (ARs) and exhibits both agonist and antagonist properties. Synephrine hydrochloride is known for its ability to induce contractions in isolated aortic rings, increase mean arterial pressure, and promote lipolysis in adipocytes.

Uses

Used in Pharmaceutical Industry:
Synephrine hydrochloride is used as an α-adrenergic receptor agonist and vasoconstrictor for its ability to induce contractions in isolated aortic rings and increase mean arterial pressure in rats. This makes it a valuable compound for the development of medications targeting cardiovascular conditions.
Used in Metabolic Applications:
Synephrine hydrochloride is used as a metabolic activator for its ability to induce lipolysis in isolated rat and human adipocytes. It also increases phosphorylation of Akt and AMP-activated protein kinase (AMPK) and translocation of Glut4 to the plasma membrane, which can enhance insulin-induced glucose consumption in muscle cells. This makes it a potential candidate for the development of treatments for metabolic disorders and obesity.
Used in Research and Development:
Synephrine hydrochloride is used as a research compound for studying the effects of adrenergic receptor agonists and antagonists on various physiological processes. Its dual agonist and antagonist properties make it a valuable tool for understanding the complex interactions between these receptors and their roles in health and disease.

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.