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Identification of 2-Chloro-4,5-methylenedioxymethylamphetamine in an Illicit Drug Seizure

NCJ Number
185062
Journal
Journal of Forensic Sciences Volume: 45 Issue: 5 Dated: September 2000 Pages: 1119-1125
Author(s)
Robert J. Lewis Ph.D.; David Reed Ph.D.; Adrian G. Service B.S.; Alan M. Langford Ph.D.
Editor(s)
R. E. Gaensslen Ph.D.
Date Published
September 2000
Length
7 pages
Annotation
This work outlines the unequivocal identification of the "ecstasy" analog, 2-chloro-4,5-methylenedioximethylamphetamine (MDMA), using combined gas chromatography-mass spectroscopy (GC/MS) and proton magnetic resonance spectroscopy (H-NMR).
Abstract
A routine analysis of an ecstasy tablet by GC/MS using electronic ionization after derivatization with heptafluorobutyric anhydride identified the major component as MDMA. A second peak of approximately two-thirds the intensity of the MDMA peak was also evident from the total ion current chromatogram. Closer scrutiny of mass spectral data for this peak indicated a structure similar to MDMA to which was substituted a single chlorine atom. This substance was isolated by thin layer chromatography (TLC) and subsequently identified as 2-chloro-4,5-methylenedioxy methylamphetamine using data obtained from proton magnetic resonance spectroscopy and GC/MS using electron impact and positive ion chemical ionization methods. Each TLC plate was viewed under ultraviolet light which visualized two clearly defined and resolved bands. The calculated relative front value for the MDMA standard corresponded to one of the separated bands of the extracted sample. The relative front value for the remaining band was calculated using GC/MS and H-NMR techniques. It was determined the analysis of designer drugs such as ecstasy by chromatographic methods was duplicated by the unavailability of reference materials. However, by using a systematic approach involving such techniques as GC/MS and H-NMR, it was relatively simple to achieve an unambiguous identification of these drug types. A chlorinated analog of MDMA was identified by mass spectrometry and its isomeric form was confirmed as 2-chloro-4,5-methylenedioxymethylamphetamine by H-NMR. 9 references, 1 table, and 8 figures

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