UCIBIO-REQUIMTE, Laboratório de Toxicologia, Departamento de Ciências Biológicas, Faculdade de Farmácia, Universidade do Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal; Laboratório de Química Orgânica e Farmacêutica, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal.
ICBAS, Instituto de Ciências Biomédicas de Abel Salazar, Universidade do Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal; Centro Interdisciplinar de Investigação Marinha e Ambiental (CIIMAR), Universidade do Porto, Avenida General Norton de Matos, 4450-208 Matosinhos, Portugal.
J Chromatogr B Analyt Technol Biomed Life Sci. 2018 Nov 15;1100-1101:158-164. doi: 10.1016/j.jchromb.2018.10.002. Epub 2018 Oct 15.
The enantioresolution of pentedrone and methylone was carried out at a multi-milligram scale by liquid chromatography on a Chiralpak AS® 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.
五亚甲基二氧吡咯戊酮和 3,4-亚甲基二氧甲基苯丙胺的对映体拆分是在 Chiralpak AS®固定相上通过液相色谱在毫克级规模上进行的。使用该柱可实现优异的对映体拆分，能够收集到高纯度的对映体级分，对映体过量值高于 98%。五亚甲基二氧吡咯戊酮对映体的总回收率达到 72%，3,4-亚甲基二氧甲基苯丙胺的总回收率达到 80%。此外，首次通过电子圆二色性（ECD）光谱法，并借助理论计算，确定了这两种苯丙胺类兴奋剂对映体的绝对构型，结果为 (+)‑(S)和 (-)‑(R)-五亚甲基二氧吡咯戊酮，以及 (-)‑(S)和 (+)‑(R)-3,4-亚甲基二氧甲基苯丙胺。
