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S(−)-Propranolol hydrochloride (CAS 4199-10-4)

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Alternate Names:
(S)-1-Isopropylamino-3-(1-naphthyloxy)-2-propanol hydrochloride
Application:
S(−)-Propranolol hydrochloride is a β-adrenergic receptor antagonist
CAS Number:
4199-10-4
Purity:
≥95%
Molecular Weight:
295.80
Molecular Formula:
C16H21NO2•HCl
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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S(−)-Propranolol hydrochloride is a small molecule beta-AR (beta-adrenergic) receptor antagonist and the active isomer of (±)-Propranolol preparations. S(−)-Propranolol hydrochloride blocks the binding of epinephrine, norepinephrine, and other endogenous catecholamines to the beta-adrenergic receptor, impeding increases in cardiac flow velocity and general stimulation of the sympathetic nervous system signaled by association of these molecules to the beta-adrenergic receptor. In addition to blockade of agonist binding, antagonism of the beta-adrenergic receptor by S(−)-Propranolol hydrochloride produces negative chronotropic and inotropic action, effectively dampening the force and rate of cardiac contraction. These negative chronotropic and inotropic effects correlate to a demonstrated suppression of adrenaline-induced cardiac arrhythmia by S(−)-Propranolol hydrochloride. Suppression of beta-adrenergic receptor activation by S(−)-Propranolol hydrochloride has been widely exploited in counteracting situations sensitive to heightened cardiac activity including hypertension, angina pectoris, and cardiac ischemia. S(−)-Propranolol Hydrochloride is an inhibitor of SR-1A, SR-1B and SR-2C.


S(−)-Propranolol hydrochloride (CAS 4199-10-4) References

  1. Synthesis, stereoselective enzymatic hydrolysis, and skin permeation of diastereomeric propranolol ester prodrugs.  |  Udata, C., et al. 1999. J Pharm Sci. 88: 544-50. PMID: 10229647
  2. Stereospecific pharmacokinetics and pharmacodynamics of beta-adrenergic blockers in humans.  |  Mehvar, R. and Brocks, DR. 2001. J Pharm Pharm Sci. 4: 185-200. PMID: 11466176
  3. Solubility, metastable zone width, and racemic characterization of propranolol hydrochloride.  |  Wang, X., et al. 2002. Chirality. 14: 318-24. PMID: 11968072
  4. Inhibition of (-)-propranolol hydrochloride by its enantiomer in white mice.  |  Kuzeff, RM., et al. 2003. Forsch Komplementarmed Klass Naturheilkd. 10: 309-14. PMID: 14707479
  5. Inhibition of (-)-propranolol hydrochloride by its enantiomer in white mice--a placebo-controlled randomized study.  |  Kuzeff, RM., et al. 2004. Forsch Komplementarmed Klass Naturheilkd. 11: 14-9. PMID: 15004443
  6. Enantiospecific toxicity of the beta-blocker propranolol to Daphnia magna and Pimephales promelas.  |  Stanley, JK., et al. 2006. Environ Toxicol Chem. 25: 1780-6. PMID: 16833138
  7. Semipreparative enantiomer separation of propranolol hydrochloride by high-performance liquid chromatography using cellulose tris(3,5-Dimethylphenylcarbamate) chiral stationary phase.  |  Chen, L., et al. 2008. J Chromatogr Sci. 46: 767-71. PMID: 19007476
  8. Chiral interactions of the drug propranolol and α1-acid-glycoprotein at a micro liquid-liquid interface.  |  Lopes, P. and Kataky, R. 2012. Anal Chem. 84: 2299-304. PMID: 22250754
  9. Effects of (R)- and (S)-propranolol hydrochloride enantiomers on the resonance Rayleigh scattering spectra with erythrosine B as probe and their analytical applications.  |  Yang, J., et al. 2015. Talanta. 134: 754-760. PMID: 25618732
  10. Study on the removal of organic micropollutants from aqueous and ethanol solutions by HAP membranes with tunable hydrophilicity and hydrophobicity.  |  He, J., et al. 2017. Chemosphere. 174: 380-389. PMID: 28187384
  11. Novel chiral metal organic frameworks functionalized composites for facile preparation of optically pure propranolol hydrochlorides.  |  Ma, X., et al. 2019. J Pharm Biomed Anal. 172: 50-57. PMID: 31026772
  12. Optical isomers of propranolol.  |  Howe, R. and Shanks, RG. 1966. Nature. 210: 1336-8. PMID: 5963764
  13. Enantioseparation of beta-blockers labelled with a chiral fluorescent reagent, R (-)-DBD-PyNCS, by reversed-phase liquid chromatography.  |  Toyo'oka, T., et al. 1997. J Pharm Biomed Anal. 15: 1467-76. PMID: 9226577

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

S(−)-Propranolol hydrochloride, 100 mg

sc-200153
100 mg
$104.00