title: Identification and characterization of N-tert-butoxycarbonyl-MDMA: a new MDMA precursor.
abstract: In September 2015, 80 litres of a viscous, light-red liquid, described as hair product, was seized by the Australian Border Force (ABF). Initial testing by ABF indicated that the liquid was the 3,4-methylenedioxymethamphetamine (MDMA) precursor chemical safrole and custody of the material was transferred to the Australian Federal Police (AFP) who coordinated all subsequent investigations. Initial gas chromatography-mass spectrometry (GC-MS) analysis by the AFP indicated that the material was not safrole and samples of the liquid were transferred to the National Measurement Institute Australia (NMIA) for identification. Using a combination of nuclear magnetic resonance spectroscopy (NMR), GC-MS, infrared spectroscopy, and synthesis, the unknown substance was identified as N-tert.-butoxycarbonyl-MDMA (t-BOC-MDMA). The substance was also converted in high yield to MDMA (aqueous HCl, 80 °C, 30 min). The possibility that the t-BOC-MDMA may act as a pro-drug following ingestion was explored by exposure to simulated gastric juice (pH 1.5) and monitored by NMR (37 °C) at various intervals. The majority of t-BOC-MDMA was converted to MDMA after 305 min, which suggested that this derivatized form might serve as a pro-drug in vivo. An investigation into the chemistry of potential pro-drugs showed that t-BOC derivatives of methamphetamine, pseudoephedrine and 4-methylmethcahtinone (mephedrone) could also be prepared using di-tert.-butyl dicarbonate. The appearance of t-BOC-derivatives on the drug market requires further monitoring. © 2016 Commonwealth of Australia. Drug Testing and Analysis © 2016 John Wiley & Sons, Ltd.
authors: Australian Forensic Drug Laboratory, National Measurement Institute, Riverside Corporate Park, North Ryde, Sydney, Australia.
authors: Michael
authors: M
authors: Collins
authors: Australian Forensic Drug Laboratory, National Measurement Institute, Riverside Corporate Park, North Ryde, Sydney, Australia.
authors: Christopher
authors: C
authors: Donnelly
authors: Australian Federal Police, Sydney, Australia.
authors: Shane
authors: S
authors: Cameron
authors: Australian Federal Police, Sydney, Australia.
authors: Mark
authors: M
authors: Tahtouh
authors: Australian Forensic Drug Laboratory, National Measurement Institute, Riverside Corporate Park, North Ryde, Sydney, Australia.
authors: Helen
authors: H
authors: Salouros
mesh_terms: D001315:Australia; D008401:Gas Chromatography-Mass Spectrometry; D006213:Hallucinogens / Q000737:chemistry*; D013287:Illicit Drugs / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008694:Methamphetamine / Q000031:analogs & derivatives / Q000737:chemistry; D018817:N-Methyl-3,4-methylenedioxyamphetamine / Q000031:analogs & derivatives*; D011355:Prodrugs / Q000737:chemistry*
chemical_list: D006213:Hallucinogens; D013287:Illicit Drugs; D011355:Prodrugs; D008694:Methamphetamine; C548233:mephedrone; D018817:N-Methyl-3,4-methylenedioxyamphetamine
keywords: Ecstasy; MDMA; NMR; precursor chemicals; t-BOC-MDMA