Propranolol hydrochloride

Base Information

• Chemical Name: Propranolol hydrochloride
• CAS No.: 318-98-9
• Deprecated CAS: 3506-09-0,146874-86-4,146874-86-4
• Molecular Formula: C16H21NO2^.HCl
• Molecular Weight: 295.809
• Hs Code.: 29221990
• European Community (EC) Number: 206-268-7
• NSC Number: 758950,91523
• UNII: F8A3652H1V
• DSSTox Substance ID: DTXSID3021198
• Wikidata: Q27108095
• NCI Thesaurus Code: C29382
• RXCUI: 82084
• ChEMBL ID: CHEMBL1671
• Mol file: 318-98-9.mol

Synonyms:1-(1-Naphthyloxy)-2-hydroxy-3-isopropylaminopropane hydrochloride;1-(Isopropylamino)-3-(1-naphthoxy)-propan-2-ol hydrochloride;DL-Propranolol hydrochloride;1-(Isopropylamino)-3-(1-naphthyloxy)-2-propanol hydrochloride;2-Propanol, 1-((1-methylethyl)amino)-3-(1-naphthalenyloxy)-, hydrochloride;1-(Isopropylamino)-3-(alpha-naphthoxy)-2-propanol hydrochloride;(2-Hydroxy-3-(naphthyloxy)propyl)isopropylammonium chloride;

Chemical Property of Propranolol hydrochloride

Chemical Property:

• Appearance/Colour: off-white to light-yellow cyrstalline solid
• Vapor Pressure: 2.48E-08mmHg at 25°C
• Melting Point: 163-165 ºC (lit.)
• Boiling Point: 434.9 ºC at 760 mmHg
• Flash Point: 216.8 ºC
• PSA: 41.49000
• LogP: 3.77040
• Storage Temp.: 2-8°C
• Solubility.: H2O: 50 mg/mL, clear, colorless
• Water Solubility.: SOLUBLE
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 295.1339066
• Heavy Atom Count: 20
• Complexity: 257

Purity/Quality:

99%, ^*data from raw suppliers

Propranolol hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi,T,F
• Statements: 22-39/23/24/25-23/24/25-11
• Safety Statements: 22-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)NCC(COC1=CC=CC2=CC=CC=C21)O.Cl
• Recent ClinicalTrials: Reconsolidation Therapy With Propranolol as a Treatment for Chronic Pain
• Recent EU Clinical Trials: Reconsolidation: a new intervention for traumatized healthcare workers.
• Uses: β?Adrenergic blocker. Antihypertensive; antianginal; antiarrhythmic (class II). For the prophylaxis of migraine Propranolol, a β-adrenergic blocker, is most commonly used to reduce blood pressure; treatment of over-active thyroid and some types of tremor; prevention of migraine headaches and some heart-rhythm problems; used to decrease the number of angina attacks (pain from an inadequate oxygen supply to the heart); used after a heart attack to prevent further damage to the heart. (±)-Propranolol hydrochloride has been used:to determine whether autonomic nervous system mediated the promotive effect on skin microcirculation in rat as a non-selective β- receptor blocker to reduce the arrhythmogenic events to study its effect on oxygen-induced retinopathy in mice
• Clinical Use: Beta-adrenoceptor blocker: Hypertension Phaeochromocytoma Angina Arrhythmias Anxiety Migraine prophylaxis
• Drug interactions: Potentially hazardous interactions with other drugs Anaesthetics: enhanced hypotensive effect; risk of bupivacaine toxicity increased. Analgesics: NSAIDs antagonise hypotensive effect. Anti-arrhythmics: increased risk of myocardial depression and bradycardia; increased risk of bradycardia, myocardial depression and AV block with amiodarone; concentration increased by propafenone and possibly dronedarone; increased risk of myocardial depression and bradycardia with flecainide; increased risk of lidocaine toxicity. Antibacterials: metabolism increased by rifampicin. Antidepressants: enhanced hypotensive effect with MAOIs; concentration increased by fluvoxamine; concentration of imipramine increased. Antihypertensives; enhanced hypotensive effect; increased risk of withdrawal hypertension with clonidine; increased risk of first dose hypotensive effect with post-synaptic alpha-blockers such as prazosin. Antimalarials: increased risk of bradycardia with mefloquine. Antipsychotics enhanced hypotensive effect with phenothiazines; concentration of both drugs increased with chlorpromazine. Calcium-channel blockers: increased risk of bradycardia and AV block with diltiazem; hypotension and heart failure possible with nifedipine and nisoldipine; asystole, severe hypotension and heart failure with verapamil. Cytotoxics: possible increased risk of bradycardia with crizotinib. Diuretics: enhanced hypotensive effect. Fingolimod: possibly increased risk of bradycardia. Moxisylyte: possible severe postural hypotension. Sympathomimetics: severe hypertension with adrenaline and noradrenaline and possibly with dobutamine.

Technology Process of Propranolol hydrochloride

There total 17 articles about Propranolol 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: 100.0%

isopropylamine (75-31-0) + (S)-(+)-1-chloro-3-(1-naphthyloxy)-2-propanol (132005-35-7) → (R)-propranolol hydrochloride (318-98-9,3506-09-0,4199-10-4,13071-11-9)

Guidance literature:

With sodium hydroxide; water; for 16h; Ambient temperature;

DOI:10.1021/jo00018a032

Reference yield: 99.92%

propranolol (525-66-6) → Inderal (318-98-9)

Guidance literature:

propranolol; With pyrographite; In ethanol; water; for 1.5h; Reflux;

With hydrogenchloride; In ethanol; water; at 10 - 30 ℃; for 18h; pH=1.5; Time;

Reference yield: 89.0%

<2R-(2α(R*),3aα,4α,7α,7aα)>-N-(1-Methylethyl)-3-(1-naphthoxy)-2-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>-1-propanamin → (R)-propranolol hydrochloride (318-98-9,3506-09-0,4199-10-4,13071-11-9)

Guidance literature:

With hydrogenchloride; In methanol; diethyl ether;

DOI:10.1007/BF00807429

upstream raw materials:

3-(1-naphthyloxy)-1,2-epoxypropane

isopropylamine

α-naphthol

1-bromo-3-(1-naphthalenyloxy)-2-propanone

Downstream raw materials:

propranolol

(S)-(-)-propanolol hydrochloride

(R)-propranolol hydrochloride

acetic acid methyl ester

Refernces

• 1、 -. "Preparation method of propranolol hydrochloride". Paragraph 0039-0053. . Retrieved 2021/04/03.
• 2、 -. "Substituted aromatic amino-alcohol compound, and preparation method and application thereof". Paragraph 0122-0125. . Retrieved 2019/01/05.