Forensic Science International
Volume 195, Issue 1 , Pages 78-85, 25 February 2010

Differentiation of methylenedioxybenzylpiperazines (MDBP) by GC–IRD and GC–MS

  • Karim M. Abdel-Hay

      Affiliations

    • Department of Pharmacal Sciences, Harrison School of Pharmacy, Auburn University, Auburn, AL 36849, USA
    • ,
  • Tamer Awad

      Affiliations

    • Department of Pharmacal Sciences, Harrison School of Pharmacy, Auburn University, Auburn, AL 36849, USA
    • Department of Pharmaceutical Analytical Chemistry, Faculty of Pharmacy, Suez Canal University, Ismaillia 41552, Egypt
    • ,
  • Jack DeRuiter

      Affiliations

    • Department of Pharmacal Sciences, Harrison School of Pharmacy, Auburn University, Auburn, AL 36849, USA
    • ,
  • C. Randall Clark

      Affiliations

    • Department of Pharmacal Sciences, Harrison School of Pharmacy, Auburn University, Auburn, AL 36849, USA
    • Corresponding Author InformationCorresponding author. Tel.: +1 334 844 8326; fax: +1 334 844 8331.

Received 20 August 2009; received in revised form 4 November 2009; accepted 17 November 2009. published online 21 December 2009.

Abstract 

The substituted benzylpiperazine, 3,4-methylenedioxybenzylpiperazine (3,4-MDBP) and its regioisomer 2,3-methylenedioxybenzylpiperazine (2,3-MDBP) have almost identical mass spectra. Perfluoroacylation of the secondary amine nitrogen of these regioisomeric piperazines gave mass spectra with differences in relative abundance of some fragment ions. However the spectra did not yield any unique fragments for specific identification of one regioisomer to the exclusion of the other compound.

Gas chromatographic separation coupled with infrared detection (GC–IRD) provides direct confirmatory data for structural differentiation between the two regioisomers. The mass spectrum in combination with the vapor-phase infrared spectrum provides for specific confirmation of each of the regioisomeric piperazines. The underivatized and perfluoroacyl derivative forms of the ring substituted benzylpiperazines were resolved on a 30-m capillary column containing an Rxi-50 stationary phase.

Keywords: Methylenedioxybenzylpiperazine, MDBP, GC–IRD, Regioisomers, GC–MS, Perfluoroacylation

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PII: S0379-0738(09)00473-3

doi:10.1016/j.forsciint.2009.11.016

Forensic Science International
Volume 195, Issue 1 , Pages 78-85, 25 February 2010

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