The identification of a chlorinated MDMA

The abuse of the designer amphetamines such as 3,4-methylenedioxymethamphetamine (MDMA) is increasing throughout the world. They have become popular drugs at all night techno dance parties, and their detection is an important issue. The objective of the presented study was to identify an unknown compound detected by thin-layer chromatography (TLC) in the urine of an illicit drug abuser. The compound was isolated by TLC and analyzed by gas chromatography-mass spectrometry (GC-MS) in electron ionization (EI) and positive ion chemical ionization (PICI) mode to elucidate its chemical structure. Based on EI-MS and PICI-MS mass spectral data, the unknown compound was indicated to be a structure similar to MDMA, substituted by a single chlorine atom-a chlorinated MDMA (Cl-MDMA). To confirm the Cl-MDMA structure, the unknown compound was silylated, trifluoroacetylated, acetylated, heptafluorobutyrylated, and analyzed by GC-MS. The position of the chlorine atom cannot be assigned exactly from the mass spectral data presented here; however, we believe that the unknown compound could be 6-Cl-MDMA.