Multi-milligram resolution and determination of absolute configuration of pentedrone and methylone enantiomers

被引：24

作者：

Silva, Barbara ^{[1
,2
]}

Pereira, Jose A. ^{[3
,4
]}

Cravo, Sara ^{[2
,4
]}

Araujo, Ana Margarida ^{[1
]}

Fernandes, Carla ^{[2
,4
]}

Pinto, Madalena M. M. ^{[2
,4
]}

de Pinho, Paula Guedes ^{[1
]}

Remiao, Fernando ^{[1
]}

机构：

[1] Univ Porto, Fac Farm, Dept Ciencias Biol, UCIBIO REQUIMTE,Lab Toxicol, Rua Jorge Viterbo Ferreira 228, P-4050313 Porto, Portugal

[2] Univ Porto, Fac Farm, Dept Ciencias Quim, Lab Quim Organ & Farmaceut, Rua Jorge Viterbo Ferreira 228, P-4050313 Porto, Portugal

[3] Univ Porto, ICBAS, Rua Jorge Viterbo Ferreira 228, P-4050313 Porto, Portugal

[4] Univ Porto, Ctr Interdisciplinar Invest Marinha & Ambiental C, Ave Gen Norton de Matos, P-4450208 Matosinhos, Portugal

来源：

JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES | 2018年 / 1100卷

关键词：

Multi-milligram enantioresolution; Polysaccharide-based stationary phase; Absolute configuration; Synthetic cathinones; Pentedrone; Methylone; PERFORMANCE LIQUID-CHROMATOGRAPHY; BETA-KETO AMPHETAMINES; CHIRAL RECOGNITION MECHANISM; DOPAMINERGIC SH-SY5Y CELLS; PSYCHOACTIVE SUBSTANCES; SYNTHETIC CATHINONES; STATIONARY PHASES; 3,4-METHYLENEDIOXYPYROVALERONE MDPV; DERIVATIVES; RATS;

D O I：

10.1016/j.jchromb.2018.10.002

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

The enantioresolution of pentedrone and methylone was carried out at a multi-milligram scale by liquid chromatography on a Chiralpak AS (R) stationary phase. The excellent enantioresolution using this column allowed to collect highly pure enantiomeric fractions, achieving enantiomeric ratios higher than 98%. An overall recovery of 72% was achieved for pentedrone enantiomers and 80% for methylone. Furthermore, the absolute configuration of the enantiomers of both cathinones was determined for the first time by electronic circular dichroism (ECD) spectroscopy, with the aid of theoretical calculations, as (+)-(S) and (-)-(R)-pentedrone, and (-)-(S) and (+)-(R)-methylone.

引用

页码：158 / 164

页数：7

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