26328-11-0

Basic information

• Product Name: S(-)-PINDOLOL
• Synonyms: L-PINDOLOL;(S)-1-(1H-INDOL-4-YLOXY)-3-[(1-METHYLETHYL)AMINO]-2-PROPANOL;S(-)-PINDOLOL;(-)-PINDOLOL B-ADRENERGIC BLOCKING;2-Propanol, 1-(1H-indol-4-yloxy)-3-[(1-methylethyl)amino]-, (2S)- (9CI);2-Propanol, 1-(1H-indol-4-yloxy)-3-[(1-methylethyl)amino]-, (S)-;(2S)-1-(1H-Indole-4-yloxy)-3-(isopropylamino)propane-2-ol;(S)-1-(1H-Indole-4-yloxy)-3-[(1-methylethyl)amino]-2-propanol
• CAS NO: 26328-11-0
• Molecular Formula: C₁₄H₂₀N₂O₂
• Molecular Weight: 248.32
• Product Categories: Adrenergics;Antagonists;Neurotransmitters
• Mol File: 26328-11-0.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 457.1 °C at 760 mmHg
• Flash Point: 230.3 °C
• Appearance: white/solid
• Density: 1.152 g/cm³
• Vapor Pressure: 3.77E-09mmHg at 25°C
• Refractive Index: 1.596
• Storage Temp.: Desiccate at +4°C
• Solubility: 0.1 M NaOH: 0.2 mg/mL
• PKA: 13.94±0.20(Predicted)
• CAS DataBase Reference: S(-)-PINDOLOL(CAS DataBase Reference)
• NIST Chemistry Reference: S(-)-PINDOLOL(26328-11-0)
• EPA Substance Registry System: S(-)-PINDOLOL(26328-11-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 26328-11-0(Hazardous Substances Data)

Usage

Biological Activity

5-HT 1A/1B ? receptor antagonist, with roughly equal affinity for each subtype. A partial agonist at mouse and human β 3 -adrenoceptors. More active enantiomer of pindolol (1-(1H-Indol-4-yloxy)-3-[(1-methylethyl)amino]-2-propanol ).

InChI:InChI=1/C14H20N2O2/c1-10(2)16-8-11(17)9-18-14-5-3-4-13-12(14)6-7-15-13/h3-7,10-11,15-17H,8-9H2,1-2H3/t11-/m0/s1

Upstream product

• 13523-86-9 1-(1H-indol-4-yloxy)-3-(isopropylamino)-2-propanol 
• 68430-36-4 <5S>-3-isopropyl-5-(4-indolyloxymethyl)-oxazolidin-2-one 
• 144024-36-2 (S)-(-)-1-<1-(4-methylphenyl)sulfonyl-4-indolyloxy>-3-(2-propylamino)-2-propanol 
• 75-31-0 isopropylamine 
• 67-64-1 acetone 
• 160319-71-1 (S)-4-(2-hydroxy-3-nitropropoxy)indole 
• 2380-94-1 1H-indol-4-ol 
• 115314-14-2 (2s)-(+)-glycidyl 3-nitrobenzenesulfonate 
• 119373-62-5 4-(formylmethoxy)indole 
• 61212-32-6 rac-3-(4-indolyloxy)propane-1,2-diol 
• 41274-09-3 (R)-3-tosyloxy-1,2-propanediol 
• 144024-34-0 (R)-(-)-3-<1-(4-methylphenyl)sulfonyl-4-indolyloxy>-1-<(4-methylphenyl)sulfonyloxy>-2-propanol 
• 68430-29-5 (S)-5-hydroxymethyl-3-(methylethyl)oxazolidinone 
• 68430-28-4 ((S)-2,3-Dihydroxy-propyl)-isopropyl-carbamic acid ethyl ester 

Downstream Products

• 174509-44-5 S-pindolol benzoate 

Relevant articles and documents

Enantioselective hydrogenation of dehydro-amino acid derivatives using pindophos-rhodium as chiral catalyst

The enantiomers of PINDOPHOS, the aminophosphine phosphinite derivative of the commercial β-blocker Pindolol, were prepared and used as ligands in the rhodium catalyzed asymmetric hydrogenation of non-proteinogenic amino acid precursors. The isolated (R)- and (S)-configured rhodium complexes are highly active catalysts leading to (L)- or (D)-amino acids. Enantiomeric excesses between 92 and 95% ee could be realized. The newly obtained amino acid derivatives were fully characterized by NMR spectroscopy.

Synthesis and crystal structure of (S)-pindolol

Racemic 3-(4-indolyloxy)-1,2-propanediol 2 has been effectively resolved into (S)- and (R)-enantiomers by a preferential crystallization procedure. Non-racemic (S)-2 was converted into (S)-4-(2,3-epoxypropoxy)-1H-indole (S)-4 via a Mitsunobu reaction and then into (S)-pindolol (S)-1. The crystalline (S)-1 was studied by single crystal X-ray diffraction. A large number of symmetry independent molecules (Z' = 6) led to a weakening of the system of strong intermolecular hydrogen bonds, which combined with a loose packing (PI = 64.6%), may be the cause of the abnormally low melting point of (S)-1 as compared with rac-1.

Preparation of a novel hydroxypropyl-γ-cyclodextrin functionalized monolith for separation of chiral drugs in capillary electrochromatography

In this study, a novel hydroxypropyl-γ-cyclodextrin (HP-γ-CD) functionalized monolithic capillary column was prepared by one-pot sequential strategy and used for chiral separation in capillary electrochromatography for the first time. In one pot, GMA-HP-γ-CD as functional monomer was allowed to be formed via the ring opening reaction between HP-γ-CD and glycidyl methacrylate (GMA) catalyzed by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and then copolymerized directly with ethylene dimethacrylate (EDMA) and 2-acrylamido-2-methyl propane sulfonic acid (AMPS) in the presence of porogenic solvents via thermally initiated free radical polymerization. The preparation conditions of monoliths were optimized. Enantiomer separations of six chiral drugs including pindolol, clorprenaline, tulobuterol, clenbuterol, propranolol, and tropicamide were achieved on the monolith. Among them, pindolol, clorprenaline, and tropicamide were baseline separated with resolution values of 1.62, 1.73, and 1.55, respectively. The mechanism of enantiomer separation was discussed by comparison of the HP-γ-CD and HP-β-CD functionalized monoliths.

Enantioselective potential of polysaccharide-based chiral stationary phases in supercritical fluid chromatography

The enantioselective potential of two polysaccharide-based chiral stationary phases for analysis of chiral structurally diverse biologically active compounds was evaluated in supercritical fluid chromatography using a set of 52 analytes. The chiral selectors immobilized on 2.5?μm silica particles were tris-(3,5-dimethylphenylcarmabate) derivatives of cellulose or amylose. The influence of the polysaccharide backbone, different organic modifiers, and different mobile phase additives on retention and enantioseparation was monitored. Conditions for fast baseline enantioseparation were found for the majority of the compounds. The success rate of baseline and partial enantioseparation with cellulose-based chiral stationary phase was 51.9% and 15.4%, respectively. Using amylose-based chiral stationary phase we obtained 76.9% of baseline enantioseparations and 9.6% of partial enantioseparations of the tested compounds. The best results on cellulose-based chiral stationary phase were achieved particularly with propane-2-ol and a mixture of isopropylamine and trifluoroacetic acid as organic modifier and additive to CO2, respectively. Methanol and basic additive isopropylamine were preferred on amylose-based chiral stationary phase. The complementary enantioselectivity of the cellulose- and amylose-based chiral stationary phases allows separation of the majority of the tested structurally different compounds. Separation systems were found to be directly applicable for analyses of biologically active compounds of interest.