title: Organic impurity profiling of 3,4-methylenedioxymethamphetamine (MDMA) synthesised from catechol.
abstract: This work examines the organic impurity profile of 3,4-methylenedioxymethamphetamine (MDMA) that has been synthesised from catechol (1,2-dihydroxybenzene), a common chemical reagent available in industrial quantities. The synthesis of MDMA from catechol proceeded via the common MDMA precursor safrole. Methylenation of catechol yielded 1,3-benzodioxole, which was brominated and then reacted with magnesium allyl bromide to form safrole. Eight organic impurities were identified in the synthetic safrole. Safrole was then converted to 3,4-methylenedioxyphenyl-2-propanone (MDP2P) using two synthetic methods: Wacker oxidation (Route 1) and an isomerisation/peracid oxidation/acid dehydration method (Route 2). MDMA was then synthesised by reductive amination of MDP2P. Thirteen organic impurities were identified in MDMA synthesised via Route 1 and eleven organic impurities were identified in MDMA synthesised via Route 2. Overall, organic impurities in MDMA prepared from catechol indicated that synthetic safrole was used in the synthesis. The impurities also indicated which of the two synthetic routes was utilised.
authors.affiliation: Centre for Forensic Science, University of Technology Sydney, Sydney, NSW 2007, Australia.
authors.forename: Erin
authors.initials: E
authors.lastname: Heather
authors.affiliation: Centre for Forensic Science, University of Technology Sydney, Sydney, NSW 2007, Australia.
authors.forename: Ronald
authors.initials: R
authors.lastname: Shimmon
authors.affiliation: Centre for Forensic Science, University of Technology Sydney, Sydney, NSW 2007, Australia. Electronic address: andrew.mcdonagh@uts.edu.au.
authors.forename: Andrew M
authors.initials: AM
authors.lastname: McDonagh
mesh_terms: D002396:Catechols / Q000737:chemistry; D002849:Chromatography, Gas; D004340:Drug Contamination; D053593:Forensic Toxicology; D013287:Illicit Drugs / Q000138:chemical synthesis*; D018817:N-Methyl-3,4-methylenedioxyamphetamine / Q000138:chemical synthesis*; D012451:Safrole / Q000737:chemistry
chemical_list: D002396:Catechols; D013287:Illicit Drugs; D018817:N-Methyl-3,4-methylenedioxyamphetamine; C034221:catechol; D012451:Safrole
keywords: 3,4-Methylendioxymethamphetamine; Chemical profiling; Chemical synthesis; Illicit drugs; MDMA; Safrole