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

Fingerprint

Methoxydimethyltryptamines
Tryptamines
Phenethylamines
Matrix-Assisted Laser Desorption-Ionization Mass Spectrometry
Screening
3,4-Methylenedioxyamphetamine
Ions
N-Methyl-3,4-methylenedioxyamphetamine
Methamphetamine
Alkylation
Ionization
N,N-Dimethyltryptamine
Nitrogen

Keywords

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

ASJC Scopus subject areas

  • Analytical Chemistry

Cite this

A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. / Chen, Bo Hong; Liu, Ju Tsung; Chen, Wen Xiong; Chen, Hung Ming; Lin, Cheng-Huang.

In: Talanta, Vol. 74, No. 4, 15.01.2008, p. 512-517.

Research output: Contribution to journalArticle

Chen, Bo Hong ; Liu, Ju Tsung ; Chen, Wen Xiong ; Chen, Hung Ming ; Lin, Cheng-Huang. / A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. In: Talanta. 2008 ; Vol. 74, No. 4. pp. 512-517.
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AU - Liu, Ju Tsung

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AU - Chen, Hung Ming

AU - Lin, Cheng-Huang

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N2 - 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.

AB - 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.

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