5985-28-4

Usage

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 academic research and scientific papers

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.

The Resolution and Absolute Configuration by X-Ray Crystallography of the Isomeric Octopamines and Synephrines

Racemates of the naturally occuring biogenic amines, o-, m-, and p-octopamine and p-synephrine, have been resolved by the preparation of suitable diastereomeric salts with antipodes of appropriate organic acids.The circular dichroism (c.d.) curves of (-)-m-octopamine hydrochloride and (-)-m-synephrine hydrochloride were superimposable and of opposite sign to those of the corresponding (-)-p-derivatives.X-ray crystallography of the (-)-3-bromocamphor-8-sulphonate salt of (-)-p-synephrine confirmed (for the first time by direct means in this series of compounds) that the absolute configuration of (-)-p-synephrine is R.It is concluded from the c.d. data that the absolute configuration of (-)-p-octopamine is also R.