4-Hydroxy-alpha-((methylamino)methyl)benzyl alcohol hydrochloride

Base Information

• Chemical Name: 4-Hydroxy-alpha-((methylamino)methyl)benzyl alcohol hydrochloride
• CAS No.: 5985-28-4
• Molecular Formula: C9H13NO2.HCl
• Molecular Weight: 203.669
• Hs Code.: 2922199090
• Mol file: 5985-28-4.mol

Synonyms:4-Hydroxy-alpha-((methylamino)methyl)benzyl alcohol hydrochloride;EINECS 227-804-6;p-Methylaminoethanol phenol hydrochloride;p-Methylaminoaethanolphenol hydrochlorid [German];l-1-p-Hydroxyphenyl-2-methylamino-1-ethanol hydrochloride;UNII-EN5D1IH09S;[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-methylazanium;chloride;p-Hydroxy-alpha-(methylaminomethyl)benzyl alcohol hydrochloride;EN5D1IH09S;Benzenemethanol, 4-hydroxy-alpha-((methylamino)methyl)-, hydrochloride;BENZYL ALCOHOL, p-HYDROXY-alpha-((METHYLAMINO)METHYL)-, HYDROCHLORIDE;p-Methylaminoaethanolphenol hydrochlorid;LS-43035

Chemical Property of 4-Hydroxy-alpha-((methylamino)methyl)benzyl alcohol hydrochloride

Chemical Property:

• Appearance/Colour: white powder
• Melting Point: 147-150oC
• Boiling Point: 341.1 °C at 760 mmHg
• Flash Point: 163.4 °C
• PSA: 52.49000
• LogP: 1.83790
• Storage Temp.: Refrigerator
• Solubility.: Methanol (Slightly), Water (Slightly)
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 203.0713064
• Heavy Atom Count: 13
• Complexity: 122

Purity/Quality:

99% ^*data from raw suppliers

rac-SynephrineHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[NH2+]CC(C1=CC=C(C=C1)O)O.[Cl-]
• 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.
• Uses: A α-adrenergic receptor agonist, vasoconstrictor.

Technology Process of 4-Hydroxy-alpha-((methylamino)methyl)benzyl alcohol hydrochloride

There total 2 articles about 4-Hydroxy-alpha-((methylamino)methyl)benzyl alcohol hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

→ (+/-)-Synephrine hydrochloride (5985-28-4)

Guidance literature:

Reference yield:

synephrine (532-80-9,582-84-3,614-35-7,94-07-5) → (+)p-synephrine hydrochloride (5985-28-4,14513-22-5,24940-67-8,61186-11-6)

Guidance literature:

Reference yield: 83.6%

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

Guidance literature:

In acetic acid; at 10 - 30 ℃; for 12h;

DOI:10.1016/S0006-2952(96)00661-2

upstream raw materials:

synephrine

Downstream raw materials:

2-(4-acetoxyphenyl)-2-chloro-N-methylethylammonium chloride

Refernces

• 1、 Midgley, John M.,Thonoor, Mohan C.,Drake, Alex F.,Williams, Clyde M.,Koziol, Anna E.,Palenik, Gus J.. "The Resolution and Absolute Configuration by X-Ray Crystallography of the Isomeric Octopamines and Synephrines". . p. 963 - 970. Retrieved 2007/10/02.