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P8688

Sigma-Aldrich

(S)-(−)-Propranolol hydrochloride

≥98% (TLC), powder

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Synonym(s):
(S)-1-Isopropylamino-3-(1-naphthyloxy)-2-propanol hydrochloride
Linear Formula:
C10H7OCH2CH(OH)CH2NHCH(CH3)2·HCl
CAS Number:
4199-10-4
Molecular Weight:
295.80
Beilstein:
3574966
EC Number:
224-096-0
MDL number:
MFCD00064547
UNSPSC Code:
12352200
PubChem Substance ID:
24278657
NACRES:
NA.77

Quality Level

200

Assay

≥98% (TLC)

form

powder

optical activity

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

mp

193-195 °C (lit.)

solubility

ethanol: 10 mg/mL
DMSO: <14.5 mg/mL
H2O: 50 mg/mL (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[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

InChI key

ZMRUPTIKESYGQW-UQKRIMTDSA-N

Gene Information

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

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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)

Biochem/physiol Actions

(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

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 + H312 + H332

Hazard Classifications

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

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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Dietary Tryptophan Restriction Dose-Dependently Modulates Energy Balance, Gut Hormones, and Microbiota in Obesity-Prone Rats
Zapata RC, et al.
Obesity (Silver Spring, Md.), 26(4), 730-739 (2018)
Yee Yin Ho et al.
Food & function, 8(6), 2110-2114 (2017-05-18)
We found that intraduodenal administration of l-ornithine (l-Orn) stimulates growth hormone (GH) secretion in Wistar rats, and then investigated its mechanism. GH-releasing activity after intraduodenal administration of l-Orn was blocked by [d-Lys
Rizaldy C Zapata et al.
The Journal of nutritional biochemistry, 65, 115-127 (2019-01-28)
Moderate dietary protein restriction promotes hyperphagia and thermogenesis; however, little is known of whether these responses are due to restriction of the essential amino acids tryptophan and histidine. Here, we determined whether restriction of tryptophan and histidine alone recapitulate the
Matthew J Shepard et al.
Journal of neurosurgery, 1-9 (2018-12-01)
OBJECTIVEVon Hippel-Lindau disease (VHL) is a tumor predisposition syndrome characterized by CNS hemangioblastomas (HBs) and clear cell renal cell carcinomas (RCCs) due to hypoxia-inducible factor activation (pseudohypoxia). Because of the lack of effective medical therapies for VHL, HBs and RCCs
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)
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