title: GC-MS studies on the regioisomeric methoxy-methyl-phenethylamines related to MDEA, MDMMA, and MBDB.
abstract: Three regioisomeric 3,4-methylenedioxyphenethylamines having the same molecular weight and major mass spectral fragments of equal mass have been reported as drugs of abuse in forensic studies in recent years. These compounds are 3,4-methylenedioxy-N-ethylamphetamine (MDEA), 3,4-methylenedioxy-N-N-dimethylamphetamine (MDMMA), and N-methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine (MBDB). The mass spectra of the regioisomers (4-methoxy-3-methyl and 4-methoxy-2-methyl-phenethylamines) are essentially equivalent to the three compounds reported as drugs of abuse. This project focused on the synthesis, mass spectral characterization, and chromatographic analysis of these six regioisomeric methoxy methyl phenethylamines. Additionally, the mass spectral and chromatographic properties of these compounds will be compared to the isobaric 2,3- and 3,4-methylenedioxyphenethyl-amines of the same side chain. The six regioisomeric methoxy-methyl-phenethylamines were synthesized from commercially available starting materials. Side chain differentiation by mass spectrometry was possible after the formation of the perfluoroacyl derivatives, pentafluoropropionylamides (PFPA) and heptafluorobutrylamides (HFBA). Gas chromatographic separation on Rtx-1 was successful at resolving the perfluoroacyl derivatives of the 4-methoxy-3-methyl phenethylamines from those of the 4-methoxy-2-methyl phenethylamines. The 4-methoxy-3-methyl-phenethylamine derivatives eluted before the 4-methoxy-2-methyl-phenethylamine derivatives as both the PFPA and HFBA derivatives.
authors.affiliation: Department of Pharmacal Sciences, School of Pharmacy, Auburn University, Auburn, AL 36849, USA.
authors.forename: Ashley
authors.initials: A
authors.lastname: Thigpen
authors.forename: Tamer
authors.initials: T
authors.lastname: Awad
authors.forename: Jack
authors.initials: J
authors.lastname: Deruiter
authors.forename: C Randall
authors.initials: CR
authors.lastname: Clark
mesh_terms: D015104:3,4-Methylenedioxyamphetamine / Q000031:analogs & derivatives* / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods*; D015394:Molecular Structure; D010627:Phenethylamines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D010627:Phenethylamines; C051570:N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine; D015104:3,4-Methylenedioxyamphetamine; C051800:3,4-methylenedioxyethamphetamine