GC-MS, GC-MS/MS and GC-IR differentiation of desoxy cathinone derivatives: Cyclic tertiary amines related to MDPV

•This study compares the analytical properties of a series of cyclic tertiary aminoketones and the corresponding desoxy phenethylamines.•The molecules represent a combination of alkyl side-chain and cyclic amines to yield identical elemental composition and major fragment ions.•GC retention is related to the cyclic tertiary amine portion of the molecule with the azetidine isomer eluting first and the azapane isomer last.•The EI mass spectra for all the compounds in this study yield a base peak iminium cation of identical elemental composition (C8H16N)+.•The vapor phase IR spectra show a unique doublet absorption for the 3,4-methylenedioxy aromatic ring substitution pattern.

The desoxy phenethylamine analogues in this study represent a combination of alkyl side-chain and cyclic amines (azetidine, pyrrolidine, piperidine and azepane) to yield a set of molecules of identical elemental composition as well as major mass spectral fragment ions (base peaks) of identical elemental composition. These desoxy phenethylamine analogues of the aminoketone designer drug, 3,4-methylenedioxy-pyrrovalerone (MDPV) related to the natural product cathinone were prepared from piperonal (3,4-methylenedioxybenzaldehyde) via the intermediate precursor ketones. The aminoketones and the desoxy phenethylamine regioisomers were each separated in capillary gas chromatography experiments using an Rxi®-17Sil MS stationary phase with the aminoketones showing greater retention than the corresponding desoxyamines.

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