Dexpropranolol

Base Information

• Chemical Name: Dexpropranolol
• CAS No.: 5051-22-9
• Molecular Formula: C₁₆H₂₁NO₂
• Molecular Weight: 259.348
• Hs Code.: 2933990090
• European Community (EC) Number: 225-749-2
• UNII: PG6KY07UD7
• DSSTox Substance ID: DTXSID3045304
• Nikkaji Number: J8.801C
• Wikidata: Q27088458
• NCI Thesaurus Code: C77944
• Pharos Ligand ID: ABUWF4KLMWKM
• Metabolomics Workbench ID: 53405
• ChEMBL ID: CHEMBL275742
• Mol file: 5051-22-9.mol

Synonyms:Anaprilin;Anapriline;Avlocardyl;AY 20694;AY-20694;AY20694;Betadren;Dexpropranolol;Dociton;Hydrochloride, Propranolol;Inderal;Obsidan;Obzidan;Propanolol;Propranolol;Propranolol Hydrochloride;Rexigen

Chemical Property of Dexpropranolol

Chemical Property:

• Vapor Pressure: 2.48E-08mmHg at 25°C
• Melting Point: 96 °C
• Refractive Index: 1.58
• Boiling Point: 434.9 °C at 760 mmHg
• PKA: pKa 9.53±0.01(H2O,t=25±0.5,I=0.15(KCl))(Approximate)
• Flash Point: 216.8 °C
• PSA: 41.49000
• Density: 1.093 g/cm³
• LogP: 3.77040
• Storage Temp.: Store at RT
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 259.157228913
• Heavy Atom Count: 19
• Complexity: 257

Purity/Quality:

95-99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)NCC(COC1=CC=CC2=CC=CC=C21)O
• Isomeric SMILES: CC(C)NC[C@H](COC1=CC=CC2=CC=CC=C21)O
• Uses: Propranolol has been studied most carefully in experiments and in clinics. It is used for ventricular tachycardia, arrhythmia caused by digitalis drug overdose, or as a result of thyrotoxosis or excess catecholamine activity. Despite the fact that there are a number of β-adrenoblockers, propranolol is considered the first choice of drugs although other blockers of calcium blockers can be just as effective. Propranolol is used for treating hypertension, angina pectoris, supraventricular arrhythmia, ventricular tachycardia, migraines, hypertrophic subaortal stenosis, and pheochromocytosis. It is used following a myocardial infraction. Propranolol is used in treating arterial hypertonicity, angina, extrasystole, superventricular arrhythmia, ventricular tachycardia, migraines, hypertrophic subaortic stenosis, and pheochromocytoma. It also is used in the postanginal phase of myocardial infarctions.
• Indications: Propranolol slows heart rate, increases the effective refractory period of atrioventricular ganglia, suppresses automatism of heart cells, and reduces excitability and contractibility of the myocardium. It is used for supraventricular and ventricular arrhythmias.
• Clinical Use: Currently, R(+)-PROPRANOLOL HCL is approved for use inthe United States for hypertension, cardiac arrhythmias,angina pectoris, postmyocardial infarction, hypertrophiccardiomyopathy, pheochromocytoma, migraine prophylaxis,and essential tremor. In addition, because of its highlipophilicity (log P=3.10) and thus its ability to penetratethe CNS, propranolol has found use in treating anxiety andis under investigation for the treatment of a variety of otherconditions, including schizophrenia, alcohol withdrawalsyndrome, and aggressive behavior.

Technology Process of Dexpropranolol

There total 58 articles about Dexpropranolol 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: 95.0%

(S)-(+)-1-chloro-2-acetoxy-3-(1-naphthyloxy)propane (132076-77-8) + isopropylamine (75-31-0) → (R)-propranolol (525-66-6,4199-09-1,5051-22-9,13013-17-7)

Guidance literature:

With sodium hydroxide; In isopropyl alcohol; at 20 ℃; for 1h;

DOI:10.1016/j.bmcl.2004.05.084

Reference yield: 93.0%

C26H41NO4Si (228704-16-3) → (R)-propranolol (525-66-6,4199-09-1,5051-22-9,13013-17-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/jo990272o

Reference yield: 90.0%

[(R)-2-Benzyloxy-3-(naphthalen-1-yloxy)-propyl]-isopropyl-amine → (R)-propranolol (525-66-6,4199-09-1,5051-22-9,13013-17-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 24h; Ambient temperature;

DOI:10.1016/0957-4166(96)00337-0

upstream raw materials:

propranolol

α-naphthol

(R)-3-(1-naphthyloxy)-1,2-propanediol

isopropylamine

Refernces

• 1、 Shuang, Yazhou,Liao, Yuqin,Wang, Hui,Wang, Yuanxing,Li, Laisheng. "Preparation and evaluation of a triazole-bridged bis(β-cyclodextrin)–bonded chiral stationary phase for HPLC". . p. 168 - 184. Retrieved 2019/11/25.
• 2、 Zhao, Baojing,Li, Lan,Wang, Yuting,Zhou, Zhiming. "Preparation of polar group derivative β-cyclodextrin bonded hydride silica chiral stationary phases and their chromatography separation performances". . p. 643 - 649. Retrieved 2018/11/27.