title: Identification of metabolites of 3,4-methylenedioxymethamphetamine in rats.
abstract: Liquid chromatography with electrochemical detection (LC/ECD) and gas chromatography/mass spectrometry (GC/MS) were used to identify metabolites of N-methyl-3,4-methylenedioxyamphetamine (MDMA) in samples of rat plasma and urine. Several potential metabolites, based on what is known about the metabolism of the desmethyl analog (i.e., MDA), were synthesized as standards to aid in the identification of the MDMA metabolites. MDA and N-methyl-1-(4-hydroxy-3-methoxy-phenyl)-2-aminopropane (3b) were identified in urine by HPLC and confirmed by GC/MS. 1-(4-Hydroxy-3-methyoxyphenyl)2-aminopropane, (3a), N-methyl-1-(3-hydroxy-4-methoxyphenyl)-2-aminopropane (2b) and 1-(3,4-dihydroxyphenyl)-2-aminopropane (4a) were tentatively identified by LC/ECD but insufficient sample size precluded confirmation by mass spectrometry. MDA was also identified in brain and plasma extracts. Because MDA is a metabolite of MDMA in humans, and because it has been speculated that the neurotoxic effects of MDA and MDMA may be due to a metabolite, the results of the present study may ultimately aid our understanding of the neurotoxic mechanism of these drugs of abuse.
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, Medical College of Virginia/Virginia Commonwealth University, Richmond 23298.
authors.forename: M Y
authors.initials: MY
authors.lastname: Yousif
authors.forename: R L
authors.initials: RL
authors.lastname: Fitzgerald
authors.forename: N
authors.initials: N
authors.lastname: Narasimhachari
authors.forename: J A
authors.initials: JA
authors.lastname: Rosecrans
authors.forename: R V
authors.initials: RV
authors.lastname: Blanke
authors.forename: R A
authors.initials: RA
authors.lastname: Glennon
mesh_terms: D015104:3,4-Methylenedioxyamphetamine / Q000031:analogs & derivatives* / Q000493:pharmacokinetics; D000818:Animals; D002851:Chromatography, High Pressure Liquid; D015198:Designer Drugs; D008401:Gas Chromatography-Mass Spectrometry; D008658:Inactivation, Metabolic / Q000502:physiology; D007279:Injections, Subcutaneous; D008297:Male; D018817:N-Methyl-3,4-methylenedioxyamphetamine; D051381:Rats; D011919:Rats, Inbred Strains
chemical_list: D015198:Designer Drugs; D015104:3,4-Methylenedioxyamphetamine; D018817:N-Methyl-3,4-methylenedioxyamphetamine; C051800:3,4-methylenedioxyethamphetamine