Synephrine hydrochloride CAS#: 5985-28-4

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Synephrine hydrochloride

Basic information Safety Supplier Related

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

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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)

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Safety Information

HS Code: 2922498590

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Synephrine hydrochloride Usage And Synthesis

Description

(±)-Synephrine is an alkaloid with vasoconstrictor and metabolic activities. It binds to α_1A-, α_2A-, and α_2C-adrenergic receptors (ARs; K_is = 78, 36.7, and 24.4 μM, respectively). (±)-Synephrine is an agonist of α_1A-ARs in HEK293 cells (EC₅₀ = 4 μM in a reporter assay) but not in CHO cells expressing α_2A- or α_2C-AR. It also acts as an antagonist of α_1A-, α_2A-, and α_2C-ARs, inhibiting L-phenylephrine-induced activation of α_1A-AR in HEK293 cells and activation of α_2A- and α_2C-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.

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