P8688

(S)-(−)-Propranolol hydrochloride

≥98% (TLC), powder

• 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/REAXYS Number: 3574966
• EC Number: 224-096-0
• MDL number: MFCD00064547
• UNSPSC Code: 12352200
• PubChem Substance ID: 24278657
• NACRES: NA.77

Properties

• 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; 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)

Description

General description

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[1]
• as a β1- and β2-aadrenergic receptor blocker in rat[2]
• as a medium supplement to investigate its effect on adipogenesis in hemangioma-derived stem cells (HemSC)[3]

Biochem/physiol Actions

(S)-(−)-Propranolol hydrochloride is biologically active enantiomer.[4] 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.[5]

Active β-adrenoceptor blocking enantiomer, as measured by inhibition of isoprenaline-induced tachycardia; Propranolol is also non-specific 5-HT_1A, 5-HT_1B and 5-HT_1C serotonin receptor antagonist. The stereoselective association of mianserin and propranolol with the 5HT_1A, 5HT_1B and 5HT_1C 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.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302 + H312 + H332
• pcodes: P261 - P264 - P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312
• Hazard Classifications: Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - 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, Gloves