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P8688 Sigma-Aldrich

(S)-(−)-Propranolol hydrochloride

≥98% (TLC), powder

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

  • CAS Number 4199-10-4

  • Linear Formula C10H7OCH2CH(OH)CH2NHCH(CH3)2·HCl

  • Molecular Weight 295.80

  •  Beilstein/REAXYS Number 3574966

  •  EC Number 224-096-0

  •  MDL number MFCD00064547

  •  PubChem Substance ID 24278657

  •  NACRES NA.77

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Properties

Related Categories Adrenergics, Adrenergics - Antagonists, Antagonists- Adrenergics, Approved Therapeutics/Drug Candidates, AstraZeneca,
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)

Description

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)

Packaging

100, 500 mg in glass bottle

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.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

HPLC Analysis of Propranolol Enantiomers on Astec® CHIROBIOTIC® TAG

From our library of Articles, Sigma-Aldrich presents HPLC Analysis of Propranolol Enantiomers on Astec® CHIROBIOTIC® TAG
Keywords: Antihypertensives, Chromatography, High performance liquid chromatography, Pharmaceutical

Peer-Reviewed Papers
15

References

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