Enantioseparation of amfepramone (rac-diethylpropion): Preparative separation of the enantiomers and enantioselective analysis

Mey, Boris; Paulus, Hanns; Lamparter, Erich; Blaschke, Gottfried

doi:10.1002/(sici)1520-636x(1999)11:10<772::aid-chir6>3.0.co;2-e

Cited by 16 publications

(10 citation statements)

References 28 publications

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“…Methylamine would be produced at the same time. A similar reaction was observed in the previous study [14], where 1,2-propanedione and diethylamine were identified as the degradation products of N,N-diethylcathinone.…”

Section: Identification Of the Degradation Products Of 4-mmc And Its supporting

confidence: 88%

“…4(f), was also observed. Other cathinone derivatives such as N,N-diethylcathinone (diethylpropion) [13,14] and cathinone [15] gave 1-phenyl-1,2-propanedione as a degradation product. However, propiophenone [14] and diphenylpyrazine [15], reported as degradation products of other cathinone derivatives, were not detected.…”

Section: Effects Of Antioxidants On the Stability Of 4-mmc In Alkalinmentioning

confidence: 99%

See 1 more Smart Citation

Degradation pathways of 4-methylmethcathinone in alkaline solution and stability of methcathinone analogs in various pH solutions

Tsujikawa

Mikuma

Kuwayama

et al. 2012

Forensic Science International

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Section: Identification Of the Degradation Products Of 4-mmc And Its supporting

confidence: 88%

Section: Effects Of Antioxidants On the Stability Of 4-mmc In Alkalinmentioning

confidence: 99%

Degradation pathways of 4-methylmethcathinone in alkaline solution and stability of methcathinone analogs in various pH solutions

Tsujikawa

Mikuma

Kuwayama

et al. 2012

Forensic Science International

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“…A possible explanation for this may be that there was competition between the alcohol and the solute to bind with the CSP. [26][27][28] Different alcohols had different abilities to bind with CSP. Alcohol with a weak polarity could bind with the CSP weakly, resulting in a longer retention of the analytes.…”

Section: Influence Of the Type Of The Alcohol In Mobile Phase On The mentioning

confidence: 99%

Normal-Phase HPLC Enantioseparation of Novel Chiral Metal Tetrahedrane-type Clusters on an Amylose-based Chiral Stationary Phase

Wang

Zhao

et al. 2005

ANAL. SCI.

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IntroductionIn recent years, the synthesis of chiral tetrahedrane-type clusters has been extensively studied, and various types have become accessible, [1][2][3][4][5][6][7][8][9][10] which are a kind of organometallic compounds receiving greatly growing interest due to their potential application to asymmetric reaction catalysts. [11][12][13][14] Using a framework chirality cluster as an asymmetric reaction catalyst would not only bring a basic conceptual breakthrough in asymmetric catalysis, in which the most asymmetric induction originates from the central or planar chirality of the P or N ligand, but would also extend the methodology in the designs of new chiral catalysts. The major remaining problem is to separate them into enantiomers. The traditional method for enantioseparation was to change the chiral clusters into diastereoisomers by column chromatography (CC) or thin-layer chromatography (TLC), even though it was time-consuming and inefficient. 15 Furthermore, the auxiliary optically active group could not be removed without destroying of the cluster 16 after enantioseparation.HPLC is one of the efficient techniques for enantioseparation, which requires mild separation conditions. If the tetrahedral cluster enantiomers could be separated directly without derivatization by HPLC on a chiral stationary phase (CSP), destruction of the cluster would be avoided. There are various types of chiral stationary phases presently available, among which polysaccharide-based CSPs have been proved to be quite versatile. A wide variety of enantiomeric compounds, including chiral aromatic alcohols, enantiomeric amides, pyriproxyfen, and amino alcohols, have been separated on these CSPs. 17During the past two years, our laboratory has paid great attention to the enantioseparation of chiral tetrahedrane-type metal clusters, and some satisfactory results have been obtained. So far, several CSPs have been prepared and applied to the enantioseparation these compounds, and more than 50 pairs chiral tetralhedrane-type clusters have been successfully resolved up to now. These CSPs included ATPC-coated SiO2, 18 CDMPC-coated SiO2, [19][20][21]22 where CDMPC means cellulose tris(3,5-dimethylphenylcarbamate) and ATPC means amylose tris(phenylcarbamate). It was found that the chiral stationary phases based on traditional silica were superior to those ZrO2-based chromatographic stationary phases; moreover, the cellulose-based and amylose-based chiral stationary phases have very broad and complementary enantiorecognition properties. 23 In the present work, the enantioseparation of novel chiral tetrahedrane-type clusters was achieved with amylose tris(3,5-dimethylphenylcarbamate) as a chiral stationary phase. The retention factors (k′), separation factors (α), and the resolutions (Rs) under different mobile phases were compared. The effect of a structural variation of the solutes on their enantioseparation was also investigated. Until now, the direct enantioseparation of chiral tetrahedrane-type clusters on amylose ADMPC-CSP has not b...

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“…Most of the recent publications are focused on the enantioseparation and quantitative analysis of chiral drugs using various CDs. HP-b-CD was used for quantitative analysis of the enantiomers of amfepramone [276]. CE was used as a complementary technique to HPLC to determine enantiomeric impurity.…”

Section: Applications Of Chiral Ce To Pharmaceutical Analysismentioning

confidence: 99%

Recent developments in chiral capillary electrophoresis and applications of this technique to pharmaceutical and biomedical analysis

Ahmad

2001

Electrophoresis

186

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This paper provides an overview of the current status of chiral capillary electrophoresis (CE). The emphasis is placed on the application of CE in chiral separation of various racemic compounds. During the last two years about 280 papers, several review articles, and two entire issues, edited by S. Fanali (Electrophoresis 1999, 20, 2577-2798, and H. Nishi and S. Terabe (J. Chromatogr. A 2000, 879, 1-471.) have been devoted to chiral CE. Enantiomeric separations of various compounds, e.g., pharmaceuticals, drug candidates, drugs and related metabolites in biological fluids, amino acids, di- and tri peptides, pesticides and fungicides, have been performed using different chiral selectors. Native and derivatized cyclodextrins continue to be the most widely used chiral selectors. Other chiral selectors such as natural and synthetic chiral micelles, crown ethers, chiral ligands, proteins, oligo- and polysaccharides, and macrocyclic antibiotics have also been applied to chiral CE separations.

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Enantioseparation of amfepramone (rac-diethylpropion): Preparative separation of the enantiomers and enantioselective analysis

Cited by 16 publications

References 28 publications

Degradation pathways of 4-methylmethcathinone in alkaline solution and stability of methcathinone analogs in various pH solutions

Degradation pathways of 4-methylmethcathinone in alkaline solution and stability of methcathinone analogs in various pH solutions

Normal-Phase HPLC Enantioseparation of Novel Chiral Metal Tetrahedrane-type Clusters on an Amylose-based Chiral Stationary Phase

Recent developments in chiral capillary electrophoresis and applications of this technique to pharmaceutical and biomedical analysis

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