Synephrine

Description

Epigallocatechin gallate (EGCG), a diester of epigallocatechin and gallic acid, is a polyphenol dietary supplement that is purported to have benefits to human immune function. (Catechins such as EGCG belong to the class of compounds known as flavonoids.) Naturally occurring EGCG is most commonly found in tea leaves, especially in green tea.
p-Synephrine, or simply synephrine, is a dietary supplement that was originally extracted from various orange species. It exists as two optical isomers; the one shown here is the more common (R)- (or?D-) enantiomer. It is a positional isomer of?m-synephrine, also called neosynephrine or phenylephrine. Both molecules are decongestants and vasodilators.
ECGC and?p-synephrine are two of many substances found in sports nutrition products.?But evidence for the efficacy of these products is hard to come by.?Most clinical studies on sports supplements have 12 or fewer participants, so the data obtained must be very strong to be statistically significant.
Another downside of sports nutrition products is that they may pose health dangers. For example, ephedra, with a structure similar to that of?p-synephrine, was banned by the US Food and Drug Administration because it raises blood pressure.

Chemical properties

Synephrine, also known as Analeptin or p-synephrine, is naturally occurring alkaloid. It is an off-white to beige powder that is derived from the fruit of small citrus trees (Citrus aurantium). It is soluble in water, insoluble in ether, almost insoluble in chloroform, ether. Synephrine is related structurally to endogenous neurotransmitters (adrenaline and noradrenaline), and acts on several adrenergic and serotonergic receptors.

The Uses of Synephrine

(±)-Synephrine has been used as an alkaloid to investigate its in vitro antiviral, antibacterial, antifungal and cytotoxicity activities.

What are the applications of Application

(±)-Synephrine is an α-adrenergic receptor agonist

Definition

ChEBI: Synephrine is a phenethylamine alkaloid that is 4-(2-aminoethyl)phenol substituted by a hydroxy group at position 1 and a methyl group at the amino nitrogen. It has a role as a plant metabolite and an alpha-adrenergic agonist. It is a phenethylamine alkaloid, a member of phenols and a member of ethanolamines. It is a conjugate base of a synephrinium.

What are the applications of Application

Synephrine is a α-adrenergic receptor agonist, vasoconstrictor that has been reported to have thermogenic properties. Therefore, it is widely used as a dietary supplement to enhance energy and promote weight loss. It is reported that the (-)-form of synephrine has more potent than that of the (+)-form. (The product is for research purpose only.)

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 1045, 1949 DOI: 10.1021/ja01171a079

General Description

Synephrine is a sympathomimetic amine from the plant?Citrus aurantium and is identified as a major active component of dietary supplements.

Biochem/physiol Actions

Synephrine is naturally found in citrus plants belonging to the Rutaceae family. It is a sympathomimetic alkaloid. Synephrine has 3 isomeric forms, such as m-synephrine, p-synephrine and o-synephrine. It exhibits β-adrenergic properties.