Skip to main content
main-content

13.06.2016 | Original Article | Ausgabe 2/2016 Open Access

Forensic Toxicology 2/2016

Chiral enantioresolution of cathinone derivatives present in “legal highs”, and enantioselectivity evaluation on cytotoxicity of 3,4-methylenedioxypyrovalerone (MDPV)

Zeitschrift:
Forensic Toxicology > Ausgabe 2/2016
Autoren:
Bárbara Silva, Carla Fernandes, Maria Elizabeth Tiritan, Madalena M.M. Pinto, Maria João Valente, Márcia Carvalho, Paula Guedes de Pinho, Fernando Remião

Abstract

Recently, great interest has been focused on synthetic cathinones since their consumption has increased exponentially. All synthetic cathinones exist as chiral molecules; the biological and/or toxicological properties of cathinones generally differ according to the enantiomers in human body. In this study, a chiral liquid chromatography method was developed to separate and determine the enantiomeric ratio of synthetic cathinones present in “legal highs” acquired in old smart shops or over the Internet. All the synthetic cathinones were efficiently enantio-separated with α and Rs ranging from 1.24 to 3.62 and from 1.24 to 10.52, respectively, using polysaccharide-based chiral stationary phases. All synthetic cathinones, with the exception of 4-methylethcathinone (4-MEC), were present in the commercialized “legal highs” in an enantiomeric proportion of 50:50. One of the studied chiral compounds was 3,4-methylenedioxypyrovalerone (MDPV), one of the most consumed cathinone derivative worldwide. Our research group has recently reported its hepatotoxicity in the racemic form. Thus, the analytical enantioresolution of the MDPV was scaled up to multi-milligram using a semi-preparative amylose tris-3,5-dimethylphenylcarbamate column (20 cm × 7.0 mm ID, 7 µm particle size). Both enantiomers were isolated with high enantiomeric purity (enantiomeric excess > 99 %). The toxicity of S-(−)-MDPV and R-(+)-MDPV was evaluated, for the first time, using primary cultures of rat hepatocytes. It was also possible to verify that MDPV enantiomers showed hepatotoxicity in a concentration-dependent manner, but displayed no enantioselective toxicity in this cell culture model.

Bitte loggen Sie sich ein, um Zugang zu diesem Inhalt zu erhalten

★ PREMIUM-INHALT
e.Med Interdisziplinär

Mit e.Med Interdisziplinär erhalten Sie Zugang zu allen CME-Fortbildungen und Fachzeitschriften auf SpringerMedizin.de. Zusätzlich können Sie eine Zeitschrift Ihrer Wahl in gedruckter Form beziehen – ohne Aufpreis.

Bis zum 22.10. bestellen und 100 € sparen!

Literatur
Über diesen Artikel

Weitere Artikel der Ausgabe 2/2016

Forensic Toxicology 2/2016Zur Ausgabe

Neu im Fachgebiet Rechtsmedizin

29.08.2018 | Schwerpunkt: Ektopes Gewebe | Ausgabe 5/2018

Ektopien des Thymus und ektope Thymustumoren

28.08.2018 | Schwerpunkt: Ektopes Gewebe | Ausgabe 5/2018

Ektopes Gewebe des weiblichen Genitaltraktes

22.08.2018 | Schwerpunkt: Ektopes Gewebe | Ausgabe 5/2018 Open Access

Ektopien der Niere, Harnwege und männlichen Geschlechtsorgane

22.08.2018 | Schwerpunkt: Ektopes Gewebe | Ausgabe 5/2018

Histopathologie und Klinik der Extrauteringravidität

 

 

 
 

Bildnachweise