P0884

(±)-Propranolol hydrochloride

Name: (±)-Propranolol hydrochloride
Brand: SIGMA

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

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):

C₁₆H₂₁NO₂ · HCl

Número CAS:

318-98-9

Peso molecular:

295.80

NACRES:

NA.77

PubChem Substance ID:

24277796

UNSPSC Code:

12352200

EC Number:

206-268-7

MDL number:

MFCD00012558

Beilstein/REAXYS Number:

4164259

Nombre del producto

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

InChI key

ZMRUPTIKESYGQW-UHFFFAOYSA-N

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

SMILES string

Cl.CC(C)NCC(O)COc1cccc2ccccc12

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

Quality Level

200

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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Categorías relacionadas

Bioactive Small Molecules

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.

Disclaimer

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

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.

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.

pictograms

GHS07

signalword

Warning

hcodes

H302

pcodes

P264 - P270 - P301 + P312 + P330 - P501

Hazard Classifications

Acute Tox. 4 Oral

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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External light activates hair follicle stem cells through eyes via an ipRGC-SCN-sympathetic neural pathway.

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

Effects of occlusal disharmony on cardiac fibrosis, myocyte apoptosis and myocyte oxidative DNA damage in mice.

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

Laxatives-Advances in Research and Application, 44-44 (2013)

beta-Adrenoceptor regulation in rat heart, lung and skin after chronic treatment with (--)-tertatolol or (--)-propranolol.

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

Pharmaceutical Chemistry E-Book, 204-204 (2011)

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