PMID- 27574107
OWN - NLM
STAT- MEDLINE
DCOM- 20170718
LR  - 20220318
IS  - 1942-7611 (Electronic)
IS  - 1942-7603 (Linking)
VI  - 9
IP  - 3
DP  - 2017 Mar
TI  - Identification and characterization of N-tert-butoxycarbonyl-MDMA: a new MDMA 
      precursor.
PG  - 399-404
LID - 10.1002/dta.2059 [doi]
AB  - 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  degrees 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  degrees 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. (c) 
      2016 Commonwealth of Australia. Drug Testing and Analysis (c) 2016 John Wiley & 
      Sons, Ltd.
CI  - (c) 2016 Commonwealth of Australia. Drug Testing and Analysis (c) 2016 John Wiley & 
      Sons, Ltd.
FAU - Collins, Michael
AU  - Collins M
AD  - Australian Forensic Drug Laboratory, National Measurement Institute, Riverside 
      Corporate Park, North Ryde, Sydney, Australia.
FAU - Donnelly, Christopher
AU  - Donnelly C
AD  - Australian Forensic Drug Laboratory, National Measurement Institute, Riverside 
      Corporate Park, North Ryde, Sydney, Australia.
FAU - Cameron, Shane
AU  - Cameron S
AD  - Australian Federal Police, Sydney, Australia.
FAU - Tahtouh, Mark
AU  - Tahtouh M
AD  - Australian Federal Police, Sydney, Australia.
FAU - Salouros, Helen
AU  - Salouros H
AD  - Australian Forensic Drug Laboratory, National Measurement Institute, Riverside 
      Corporate Park, North Ryde, Sydney, Australia.
LA  - eng
PT  - Journal Article
DEP - 20160929
PL  - England
TA  - Drug Test Anal
JT  - Drug testing and analysis
JID - 101483449
RN  - 0 (Hallucinogens)
RN  - 0 (Illicit Drugs)
RN  - 0 (Prodrugs)
RN  - 44RAL3456C (Methamphetamine)
RN  - 8BA8T27317 (mephedrone)
RN  - KE1SEN21RM (N-Methyl-3,4-methylenedioxyamphetamine)
SB  - IM
MH  - Australia
MH  - Gas Chromatography-Mass Spectrometry
MH  - Hallucinogens/*chemistry
MH  - Illicit Drugs/*chemistry
MH  - Magnetic Resonance Spectroscopy
MH  - Methamphetamine/analogs & derivatives/chemistry
MH  - N-Methyl-3,4-methylenedioxyamphetamine/*analogs & derivatives
MH  - Prodrugs/*chemistry
OTO - NOTNLM
OT  - Ecstasy
OT  - MDMA
OT  - NMR
OT  - precursor chemicals
OT  - t-BOC-MDMA
EDAT- 2016/08/31 06:00
MHDA- 2017/07/19 06:00
CRDT- 2016/08/31 06:00
PHST- 2016/06/17 00:00 [received]
PHST- 2016/08/24 00:00 [revised]
PHST- 2016/08/24 00:00 [accepted]
PHST- 2016/08/31 06:00 [pubmed]
PHST- 2017/07/19 06:00 [medline]
PHST- 2016/08/31 06:00 [entrez]
AID - 10.1002/dta.2059 [doi]
PST - ppublish
SO  - Drug Test Anal. 2017 Mar;9(3):399-404. doi: 10.1002/dta.2059. Epub 2016 Sep 29.