Identification and characterization of N‐tert‐butoxycarbonyl‐MDMA: a new MDMA precursor
Michael P Collins, Christopher Donnelly, Shane Cameron, Mark Tahtouh, Helen Salouros
Drug Testing and Analysis August 30, 2016 DOI: 10.1002/dta.2059 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Case study Case report Peer reviewed |
|---|---|
| Duration | 305 minutes (conversion time monitored) |
| Topics | MDMA |
| Keywords | Mephedrone Safrole Designer drug Methamphetamine Pseudoephedrine High-performance liquid chromatography |
| Citations | 21 |
| Key findings | The seized liquid was identified as t-BOC-MDMA, a pro-drug that converts to MDMA under acidic conditions similar to stomach acid. |
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.
Comparable studies
Other case reports and case series on MDMA, most cited first.
| Study | Year | Design | Participants |
|---|---|---|---|
| 'Eve' and 'Ecstasy'. A report of five deaths associated with the use of MDEA and MDMA Individuals whose deaths were associated with MDMA or MDEA use | 1987 | Case series | n = 5 |
| Pathology of deaths associated with "ecstasy" and "eve" misuse. Young white men aged 20 to 25 who died after using ring-substituted amphetamines (MDMA... | 1996 | Case series | n = 7 |
| 'Eve' and 'Ecstasy' Individuals who died after using MDMA or MDEA | 1987 | Case series | n = 5 |
| A Method of Conducting Therapeutic Sessions with MDMA Clients with clear therapeutic purpose, excluding those with serious functional... | 1998 | Case study | n = 2 |
| Diversity of Psychopathology Associated with use of 3,4-Methylenedioxymethamphetamine (‘Ecstasy’) Psychiatric patients presenting between 1990 and 1992 whose symptoms developed in the... | 1994 | Case series | n = 13 |
Citations in the library
Cited by 3
- Prodrugs of New Psychoactive Substances (NPS): A New Challenge. Journal of Forensic Sciences May 1, 2020
- The use of prodrugs as drugs of abuse Wiley Interdisciplinary Reviews Forensic Science March 19, 2024
- N,N‐Diformylmescaline: A novel analogue of mescaline detected in Queensland Drug Testing and Analysis October 17, 2022