The alpha-ethyl phenethylamine derivative 1-(1,3-benzodioxol-5-yl)-2-butanamine was prepared. An asymmetric synthesis was used to prepare the enantiomers of this compound and the related alpha-methyl homologue (MDA). The racemates and enantiomers of both compounds were evaluated in the two-lever drug discrimination assay in rats trained to discriminate saline from 0.08 mg/kg of LSD tartrate. St...

The use of a supercritical carbon dioxide reaction medium for the determination of the (R)- and (S)-enantiomers of mandelic acid (MA) is proposed. The process involves a previous derivatization step under supercritical conditions by which the carboxyl group is esterified with methanol, then followed by acylation of the hydroxyl group in methyl MA with pentafluoropropionic anhydride in the absen...

Merrillianoid (1), a racemic neolignan possessing the characteristic benzo-2,7-dioxabicyclo[3.2.1]octane moiety, was isolated from the branches and leaves of Illicium merrillianum. Chiral separation of 1 gave two enantiomers (+)-1 and (-)-1. The structure of 1 was established by comprehensive spectroscopic analysis and single crystal X-ray diffraction. The absolute configurations of enantiomers...

Single crystal X-ray diffraction has been used as one of the common methods for the unambiguous determination of the absolute stereostructure of chiral molecules. However, this method is limited to molecules containing heavy atoms or to molecules with the possibility of functionalization with heavy elements or chiral internal references. Herein, we report the determination of the absolute stere...

A reversed-phase high-performance liquid chromatographic method for separation of the enantiomers of ketoprofen in formulations and in plasma matrices has been developed and optimized. A central composite design was used to develop response models and Derringer’s desirability function was then used for simultaneous optimization of chiral resolution and analysis time. This procedure enabled disc...

T he fundamentals of structure and stereochemistry have been considered in previous chapters in some detail. There are, however, practical aspects of stereochemistry that have not yet been mentioned, particularly with regard to chiral compounds. How, for instance, can a racemic mixture be separated into its component enantiomers (resolution); what methods can be used to establish the configurat...

2014 Microscopical, miscibility and X-ray studies establish the existence of two new mesophases in the two enantiomers of 1 (methyl)-heptyl terephthalidene bis amino cinnamate. In one of this two mesophases the two enantiomers do not exhibit a total miscibility range; while for the second the untwisted form observed with the racemic mixture has a higher temperature range of stability than the t...

Optically active isomers of N-methy1-2-(2-(2-(4-phenylpiperazino)ethoxy)phenyl)thiazolidine3-carboxamides(( + )-2 and(-)-2) have been synthesized and tested for positive inotropic activity. The racemic thiocarboxamide((•})-3) was resolved into the enantiomers(( + )-3 and(•E)-3) via the Land D-N-(2-naphthylsulfonyl)prolyl derivatives ((+ )-4 and (-)-4). Conversion of the thiocarboxamides (( + )-...

This paper describes the application of stereoselective antibodies as tailor-made chiral selectors for the separation of enantiomers in HPLC under isocratic conditions. Stereoselective monoclonal antibodies to D- and L-alpha-amino acids, raised against protein conjugates of p-amino-D- and L-phenylalanine, were immobilized on a synthetic high-flow-through support material and used for rapid enan...

Propafenone is an antiarrhythmic drug that produces a variable degree of P3-blockade in humans and is administered as a racemate. To examine the relative contribution of the individual enantiomers to pharmacologic effects seen during treatment with propafenone, we assessed the steady-state plasma concentrations of (+)-S-propafenone and (-)-R-propafenone in seven patients who were on long-term o...