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Sigma-Aldrich

(±)-Propranolol hydrochloride

≥99% (TLC), powder, β-adrenoceptor antagonist

Synonym(s):

(±)-1-Isopropylamino-3-(1-naphthyloxy)-2-propanol hydrochloride, DL-Propranolol hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C16H21NO2 · HCl
CAS Number:
318-98-9
Molecular Weight:
295.80
Beilstein/REAXYS Number:
4164259
EC Number:
206-268-7
MDL number:
MFCD00012558
UNSPSC Code:
12352200
PubChem Substance ID:
24277796
NACRES:
NA.77

product name

(±)-Propranolol hydrochloride, ≥99% (TLC), powder

assay

≥99% (TLC)

form

powder

color

white

solubility

ethanol: 10 mg/mL
DMSO: <14.5 mg/mL
H2O: 50 mg/mL
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.
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.

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

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 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 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.

Caution

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

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Yuka Yagisawa et al.
PloS one, 15(7), e0236547-e0236547 (2020-07-28)
Occlusal disharmony leads to morphological changes in the hippocampus and osteopenia of the lumbar vertebra and long bones in mice, and causes stress. Various types of stress are associated with increased incidence of cardiovascular disease, but the relationship between occlusal
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
Laxatives-Advances in Research and Application, 44-44 (2013)
Pharmaceutical Chemistry E-Book, 204-204 (2011)
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