81882-39-5Relevant academic research and scientific papers
Determination of the chiral status of different novel psychoactive substance classes by capillary electrophoresis and β-cyclodextrin derivatives
H?gele, Johannes S.,Hubner, Eva-Maria,Schmid, Martin G.
, p. 1191 - 1207 (2020)
Besides the abuse of well-known illicit drugs, consumers discovered new synthetic compounds with similar effects but minor alterations in their chemical structure. Originally, these so-called novel psychoactive substances (NPS) have been created to circumvent law of prosecution because of illicit drug abuse. During the past decade, such compounds came up in generations, the most popular compound was a synthetic cathinone derivative named mephedrone. Cathinones are structurally related to amphetamines; to date, more than 120 completely new derivatives have been synthesized and are traded via the Internet. Cathinones possess a chiral center; however, only little is known about the pharmacology of their enantiomers. However, NPS comprise further chiral compound classes such as amphetamine derivatives, ketamines, 2-(aminopropyl)benzofurans, and phenidines. In continuation of our project, a cheap and easy-to-perform chiral capillary zone electrophoresis method for enantioseparation of cathinones presented previously was extended to the aforementioned compound classes. Enantioresolution was achieved by simply adding native β-cyclodextrin, acetyl-β-cyclodextrin, 2-hydroxypropyl-β-cyclodextrin, or carboxymethyl-β-cyclodextrin as chiral selector additives to the background electrolyte. Fifty-one chiral NPS served as analytes mainly purchased from online vendors via the Internet. Using 10 mM of the aforementioned β-cyclodextrins in a 10 mM sodium phosphate buffer (pH 2.5), overall, 50 of 51 NPS were resolved. However, chiral separation ability of the selectors differed depending on the analyte. Additionally, simultaneous enantioseparations, the determination of enantiomeric migration orders of selected analytes, and a repeatability study were performed successfully. It was proven that all separated NPS were traded as racemic mixtures.
Catalytic Enantioselective Synthesis of N-C Axially Chiral Mebroqualone and Its Derivatives through Reductive Asymmetric Desymmetrization
Hirai, Motohiro,Terada, Shumpei,Yoshida, Hiroaki,Ebine, Kenki,Hirata, Tomoaki,Kitagawa, Osamu
, p. 5700 - 5703 (2016/11/17)
In the presence of (R)-DTBM-SEGPHOS-Pd(OAc)2 catalyst, treatment of various 3-(2,6-dibromophenyl)quinazolin-4-ones with NaBH4 gave optically active N-C axially chiral quinazolinone (mebroqualone) derivatives through reductive asymmet
The enantiomers of methaqualone and their unequal anticonvulsive activity
Mannschreck,Koller,Stuhler,et al.
, p. 381 - 383 (2007/10/02)
It is shown that methaqualone (1) is a chiral molecule. Its enantiomers were enriched by liquid chromatography on triacetylcellulose up to optical purities of 0.75 and 0.68, respectively. The interconversion of (M)- and (P)-1 is slow enough (ΔG? = 131.6 kJ/mol at 135°C) to prevent any thermal racemization at room temperature. Both enantiomers possess anticonvulsive activity, (-)-1 being significantly (p 0.05) more potent than (+)-1.
