Identification of five pyrrolidinyl substituted cathinones and the collision-induced dissociation of electrospray-generated pyrrolidinyl substituted cathinones

Drug Test Anal. 2017 May;9(5):778-787. doi: 10.1002/dta.2035. Epub 2016 Jul 29.

Abstract

This article reports on the analytical properties of five pyrrolidinyl substituted cathinones: α-pyrrolidinononaphenone (α-PNP, 1), 4-chloro-α-pyrrolidinopropiophenone (4-Cl-α-PPP, 2), 4-chloro-α-pyrrolidinovalerophenone (4-Cl-α-PVP, 3), 5-dihydrobenzofuranpyrovalerone (5-DBFPV, 4), and 2-(pyrrolidin-1-yl)-1-(5,6,7,8-tetrahydronaphthalen-2-yl)hexan-1-one (β-THNPH, 5). These identifications were based on liquid chromatography-quadrupole time-of-flight-mass spectrometry (LC-QTOF-MS), gas chromatography-mass spectrometry (GC-MS) and nuclear magnetic resonance spectroscopy (NMR). To our knowledge, no analytical data about α-PNP, 4-Cl-α-PPP, 4-Cl-α-PVP, and β-THNPH have appeared until now, making this the first report on these compounds. Moreover, in order to study the collision-induced dissociation (CID) characteristic fragmentation routes of pyrrolidinyl substituted cathinones, a total number of 13 pyrrolidinyl substituted cathinones were selected and discussed. The major fragmentation pathways under CID mode are produced, leading to the formation of characteristic ions. Product ions of [M-C4 H9 N]+ and Cn H2n N+ indicate the presence of pyrrolidinyl substitution. Characteristic fragments are also produced via the cleavages of the CH-N(CH2 )4 bond and the CO-CHN bond. Copyright © 2016 John Wiley & Sons, Ltd.

Keywords: 4-Cl-α-PPP; 4-Cl-α-PVP; Pyrrolidinyl substituted cathinones; α-PNP; β-THNPH.

MeSH terms

  • Alkaloids / analysis*
  • Chromatography, Liquid
  • Gas Chromatography-Mass Spectrometry
  • Halogenation
  • Illicit Drugs / analysis*
  • Magnetic Resonance Spectroscopy
  • Propiophenones / analysis*
  • Psychotropic Drugs / analysis*
  • Pyrrolidines / analysis*
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Alkaloids
  • Illicit Drugs
  • Propiophenones
  • Psychotropic Drugs
  • Pyrrolidines
  • alpha-pyrrolidinovalerophenone
  • alpha-pyrrolidinopropiophenone
  • cathinone