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P8688

Sigma-Aldrich

(S)-(−)-Propranolol hydrochloride

≥98% (TLC), powder

Synonyme(s) :

(S)-1-Isopropylamino-3-(1-naphthyloxy)-2-propanol hydrochloride

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About This Item

Formule linéaire :
C10H7OCH2CH(OH)CH2NHCH(CH3)2·HCl
Numéro CAS:
4199-10-4
Poids moléculaire :
295.80
Numéro Beilstein :
3574966
Numéro CE :
224-096-0
Numéro MDL:
MFCD00064547
Code UNSPSC :
12352200
ID de substance PubChem :
24278657
Nomenclature NACRES :
NA.77

Niveau de qualité

200

Pureté

≥98% (TLC)

Forme

powder

Activité optique

[α]25/D −25.5°, c = 1.0 in ethanol(lit.)

Pf

193-195 °C (lit.)

Solubilité

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

Auteur

AstraZeneca

Température de stockage

2-8°C

Chaîne SMILES 

Cl[H].CC(C)NC[C@H](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/t14-;/m0./s1

Clé InChI

ZMRUPTIKESYGQW-UQKRIMTDSA-N

Informations sur le gène

human ... ADRB1(153) , ADRB2(154) , ADRB3(155) , HTR1A(3350) , HTR1B(3351) , HTR1D(3352) , HTR1E(3354) , HTR1F(3355)

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Description générale

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

(S)-(−)-Propranolol hydrochloride has been used:
  • as a non-selective β-blocker propranolol to inhibit the actions of epinephrine in mice
  • as a β1- and β2-aadrenergic receptor blocker in rat
  • as a medium supplement to investigate its effect on adipogenesis in hemangioma-derived stem cells (HemSC)

Actions biochimiques/physiologiques

(S)-(−)-Propranolol hydrochloride is biologically active enantiomer. It acts as β1 receptor antagonist in thalamocortical neurons. (S)-(−)-Propranolol hydrochloride elicits its inhibitory function on the β1 adrenoceptor in trigeminovascular pain pathway and serves as a preventive medicine in migraine.
Active β-adrenoceptor blocking enantiomer, as measured by inhibition of isoprenaline-induced tachycardia; Propranolol is also non-specific 5-HT1A, 5-HT1B and 5-HT1C serotonin receptor antagonist. The stereoselective association of mianserin and propranolol with the 5HT1A, 5HT1B and 5HT1C sites may prove useful in the characterization of these sites

Caractéristiques et avantages

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302 + H312 + H332

Classification des risques

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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Semipreparative enantiomer separation of propranolol hydrochloride by high-performance liquid chromatography using cellulose tris (3, 5-dimethylphenylcarbamate) chiral stationary phase
Chen L, et al.
Journal of Chromatographic Science, 46(9), 767-771 (2008)
Regulation of Hepatic Follistatin Expression at Rest and during Exercise in Mice
Peppler WT, et al.
Med Sci Sports Exerc. (2019)
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Journal of cardiovascular pharmacology, 25(2), 268-272 (1995-02-01)
All beta-adrenergic antagonists have an asymmetric carbon atom, and most commercially available beta-blockers consist of (R)- and (S)-enantiomers in a fixed 1:1-ratio. The drugs are believed to be contraindicated when peripheral vascular disease exists, presumably due to unopposed alpha-adrenergic vasoconstriction.
Propranolol modulates trigeminovascular responses in thalamic ventroposteromedial nucleus: a role in migraine?
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Brain, 128(1), 86-97 (2004)
G M Goodwin et al.
British journal of pharmacology, 84(3), 743-753 (1985-03-01)
Radioligand binding techniques have demonstrated the existence of 5-hydroxytryptamine (5-HT) binding subtypes: 5-HT2, 5-HT1A and 5-HT1B. These techniques have also indicated that certain drugs appear to show sub-type specificity: 8-hydroxy-2-(di-n-propylamino)tetralin(8-OH-DPAT), a 5-HT1A agonist; 5-methoxy-3(1,2,3,6-tetrahydropyridin-4-yl)1-H indole (RU 24969), a 5-HT1B agonist;
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