P0884

Sigma-Aldrich

(±)-Propranolol hydrochloride

≥99% (TLC), powder

Synonym(s):
(±)-1-Isopropylamino-3-(1-naphthyloxy)-2-propanol hydrochloride, DL-Propranolol hydrochloride
Empirical Formula (Hill Notation):
C16H21NO2 · HCl
CAS Number:
Molecular Weight:
295.80
Beilstein/REAXYS Number:
4164259
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.

Quality Level

assay

≥99% (TLC)

form

powder

color

white

solubility

ethanol: 10 mg/mL
DMSO: <14.5 mg/mL
H2O: 50 mg/mL (dissolve with heat. Aqueous solutions are most stable at pH 3.0 and decompose rapidly at basic pH. Decomposition is accompanied by discoloration of the solution.)
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 8.0 mg/mL

originator

AstraZeneca

storage temp.

2-8°C

SMILES string

Cl.CC(C)NCC(O)COc1cccc2ccccc12

InChI

1S/C16H21NO2.ClH/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3-4-8-15(13)16;/h3-9,12,14,17-18H,10-11H2,1-2H3;1H

InChI key

ZMRUPTIKESYGQW-UHFFFAOYSA-N

Gene Information

human ... ADRB1(153), ADRB2(154), ADRB3(155), HTR1A(3350), HTR1B(3351), HTR1D(3352), HTR1E(3354), HTR1F(3355), HTR2A(3356), HTR2B(3357), HTR2C(3358)

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General description

Propranolol hydrochloride is easily soluble in ethanol and water.

Application

(±)-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

Packaging

1, 5, 25, 100 g in poly bottle

Biochem/physiol Actions

Propranolol hydrochloride is a β-adrenoceptor antagonist. Its action at β2 receptor results in bronchoconstriction. Due to its lipophilic nature, propranolol can penetrate to the central nervous system and has a negative effect. It serves as a 5-HT1/5-HT2 serotonin receptor antagonist. Propranolol hydrochloride is useful as an antihypertensive drug, cardiac depressant and also in the treatment of angina pectoris. It decreases the effect of stress and exercise on heart by reducing the rate of contraction and conduction of impulse. It is known to competitively block the action of catecholamines.

Features and Benefits

This compound is featured on the β-Adrenoceptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by AstraZeneca. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.
This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Caution

Shelf-life of the solid is at least four years if stored protected from the uptake of moisture.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Laxatives-Advances in Research and Application, 44-44 (2013)
Pharmaceutical Chemistry E-Book, 204-204 (2011)
Propranolol inhibition of beta-adrenergic receptor does not suppress pathologic neovascularization in oxygen-induced retinopathy
Chen J, et al.
Investigative Ophthalmology & Visual Science, 53(6), 2968-2977 (2012)
Y Y Tan et al.
Journal of autonomic pharmacology, 15(6), 421-436 (1995-12-01)
1. The effect of long-term treatment with the beta-adrenoceptor antagonists (--)-tertatolol and (--)-propranolol was studied. Sprague-Dawley rats were treated with either (--)-tertatolol (50 micrograms kg-1 hr-1), (--)-propranolol (250 micrograms kg-1 hr-1) or vehicle (1 mM HCl) for 14 days with...
Sabrina Mai-Yi Fan et al.
Proceedings of the National Academy of Sciences of the United States of America, 115(29), E6880-E6889 (2018-07-01)
Changes in external light patterns can alter cell activities in peripheral tissues through slow entrainment of the central clock in suprachiasmatic nucleus (SCN). It remains unclear whether cells in otherwise photo-insensitive tissues can achieve rapid responses to changes in external...
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