• Bulletin of the Korean Chemical Society
• /
• v.24 no.11
• /
• pp.1641-1648
• /
• 2003

New and facile synthetic routes for preparation of optically active norephedrine, norpseudoephedrine and cathinone with high optical purities via double asymmetric induction by employing asymmetric reduction of 2-N-protected amino (or azido)-1-phenylpropanone and 2-methanesulfonyloxy-1-phenylpropanone with CBS-catalyzed-borane and $^dIpc_2BCl$ as chiral reducing agents are described.

• YAKHAK HOEJI
• /
• v.58 no.1
• /
• pp.53-57
• /
• 2014

In recent, the abuse of newly-emerging psychoactive drugs, ('designer drugs') is a rapidly increasing problem in Korean society. Quantitative-structure activity relationship (QSAR) is an alternative method to predict bioactivities of new abused compounds. In this study, cathinone-related new designer drugs, 4-methylbuphedrone and 4-methoxy-N,N-dimethylcathinone were tested for prediction of the bioactivity with QSAR model. The bioactivity of 4-methylbuphedrone and 4-methoxy-N,N-dimethylcathinone was similar to those of methylone. These results suggest that the prediction with QSAR model may provide scientific evidences for regulatory decision.

• Biomolecules & Therapeutics
• /
• v.25 no.2
• /
• pp.122-129
• /
• 2017

A diversity of synthetic cathinones has flooded the recreational drug marketplace worldwide. This variety is often a response to legal control actions for one specific compound (e.g. methcathinone) which has resulted in the emergence of closely related replacement. Based on recent trends, the nitrogen atom is one of the sites in the cathinone molecule being explored by designer type modifications. In this study, we designed and synthesized two new synthetic cathinones, (1) ${\alpha}-piperidinopropiophenone$ (PIPP) and (2) ${\alpha}-piperidinopentiothiophenone$ (PIVT), which have piperidine ring substituent on their nitrogen atom. Thereafter, we evaluated whether these two compounds have an abuse potential through the conditioned place preference (CPP) in mice and self-administration (SA) in rats. We also investigated whether the substances can induce locomotor sensitization in mice following 7 days daily injection and challenge. qRT-PCR analyses were conducted to determine their effects on dopamine-related genes in the striatum. PIPP (10 and 30 mg/kg) induced CPP in mice, but not PIVT. However, both synthetic cathinones were not self-administered by the rats and did not induce locomotor sensitization in mice. qRT-PCR analyses showed that PIPP, but not PIVT, reduced dopamine transporter gene expression in the striatum. These data indicate that PIPP, but not PIVT, has rewarding effects, which may be attributed to its ability to affect dopamine transporter gene expression. Altogether, this study suggests that PIPP may have abuse potential. Careful monitoring of this type of cathinone and related drugs are advocated.