The Synthesis and Chemical Profiling of 3,4-Methylene-Dioxymethamphetamine (MDMA) and Analogues

This work examines the organic impurity profiles of 3,4-methylenedioxymethamphetamine (MDMA) and its analogue methylone that were synthesised from uncontrolled ‘pre-precursors’. Methylone was synthesised from catechol by one synthetic route. Safrole was synthesised from catechol by two synthetic routes (Routes 1 and 2) and from eugenol by one synthetic route (Route 3). MDMA was synthesised from catechol- and eugenol-derived safrole via two routes (Routes A and B), which resulted in the synthesis of MDMA from catechol via four routes (Routes 1A, 1B, 2A and 2B) and from eugenol via two routes (Routes 3A and 3B). Five organic impurities were identified in methylone, and fourteen organic impurities were identified in the three intermediate compounds. Neither the catechol precursor nor the 1,3-benzodioxole intermediate could be identified based on the impurities detected in methylone using standard techniques, which demonstrated limitations in the determination of the precursor chemical and synthetic pathways used. Eight organic impurities were identified in safrole synthesised from catechol via Routes 1 and 2, and seven organic impurities in safrole synthesised from eugenol via Route 3. Importantly, nine impurities had not previously been reported in literature. Seven, four and seven route specific impurities were identified in safrole from Routes 1, 2 and 3, respectively. The route specific impurities indicated both the use of the ‘pre-precursors’ catechol and eugenol, and the route used to synthesise safrole from the respective ‘pre-precursor’. Thirteen organic impurities were identified in MDMA synthesised by Route 1A, ten organic impurities in MDMA from Route 1B, twelve organic impurities in MDMA from Routes 2A and 2B, and eleven organic impurities in MDMA from Routes 3A and 3B. Importantly, thirteen impurities had not previously been reported in literature. Six impurities in MDMA from Route 1A, four impurities in MDMA from Routes 1B, 2A, and 2B, and three impurities in MDMA from Routes 3A and 3B were considered specific to the use of catechol- or eugenol-derived safrole. The route specific impurities identified in MDMA indicated that the ‘pre-precursors’ catechol and eugenol were used in the respective synthetic pathways. The route specific impurities identified in MDMA also indicated the route used to synthesise safrole from the respective ‘pre-precursor’, and the route used to synthesise MDMA from the safrole intermediate. Thus, the use of the ‘pre-precursors’ catechol and eugenol, and the synthetic routes that were used in its preparation, could be ascertained by the organic impurity profiling of MDMA under the conditions used here.

Author dc:creator

• Heather, Erin Nicole

Statement dc:rights

• au.edu.uts.lib/ppc
• The author owns the copyright in this thesis including all reproduction and reuse rights for the work. The work may not be altered without the permission of the copyright owner. Attribution is essential when quoting or paraphrasing from this thesis.
• info:eu-repo/semantics/openAccess

Language dc:language.iso

en_US

Handle dc:identifier.uri

http://hdl.handle.net/10453/144077

OAI identifier oai:identifier

oai:opus.lib.uts.edu.au:10453/144077