A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation

Bo Hong Chen, Ju Tsung Liu, Wen Xiong Chen, Hung Ming Chen, Cheng Huang Lin

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Certain characteristic fragmentations of tryptamines (indoleethylamine) and phenethylamines are described. Based on the GC-EI/MS, LC-ESI/MS and MALDI/TOFMS, the mass fragmentations of 13 standard compounds, including α-methyltryptamine (AMT), N,N-dimethyltryptamine (DMT), 5-methoxy-α-methyltryptamine (5-MeO-AMT), N,N-diethyltryptamine (DET), N,N-dipropyltryptamine (DPT), N,N-dibutyltryptamine (DBT), N,N-diisopropyltryptamine (DIPT), 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT), 5-methoxy-N,N-diisopropyltryptamine (5-MeO-DIPT), methamphetamine (MAMP), 3,4-methylenedioxyamphetamine (3,4-MDA), 3,4-methylenedioxymethamphetamine (3,4-MDMA) and 2-methylamino-1-(3,4-methylenedioxyphenyl)butane (MBDB), were compared. As a result, the parent ions of these analytes were hard to be obtained by GC/MS whereas the protonated molecular ions can be observed clearly by means of ESI/MS and MALDI/TOFMS. Furthermore, two major characteristic fragmentations, namely and α-cleavage ([M + H]+ → [3-vinylindole]+) and β-cleavage ([M + H]+ → [CH2N+RN1RN2]), are produced when the ESI and MALDI modes are used, respectively. In the case of ESI/MS, the fragment obtained from α-cleavage is the major process. In contrast to this, in the case of MALDI/TOFMS, the major fragment is produced via β-cleavage. The ionization efficiency and fragments formed from either α- or β-cleavages are closely related to the degree of alkylation of the side chain nitrogen in both cases.

Original languageEnglish
Pages (from-to)512-517
Number of pages6
JournalTalanta
Volume74
Issue number4
DOIs
Publication statusPublished - 2008 Jan 15

Keywords

  • ESI/MS
  • GC/MS
  • MALDI/TOFMS
  • Phenethylamine
  • Tryptamine

ASJC Scopus subject areas

  • Analytical Chemistry

Fingerprint Dive into the research topics of 'A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation'. Together they form a unique fingerprint.

Cite this