PMID- 27162021
OWN - NLM
STAT- MEDLINE
DCOM- 20160815
LR  - 20191210
IS  - 1355-0306 (Print)
IS  - 1355-0306 (Linking)
VI  - 56
IP  - 3
DP  - 2016 May
TI  - The synthesis and characterisation of MDMA derived from a catalytic oxidation of 
      material isolated from black pepper reveals potential route specific impurities.
PG  - 223-230
LID - S1355-0306(16)00005-8 [pii]
LID - 10.1016/j.scijus.2016.01.003 [doi]
AB  - This work examines the chemical synthesis of 
      3,4-methylenedioxy-N-methylamphetamine (MDMA) from piperonal prepared via a 
      catalytic ruthenium tetroxide oxidation of piperine extracted from black pepper. 
      A variety of oxidation conditions were experimented with including different 
      solvent systems and co-oxidants. A sample of prepared piperonal was successfully 
      converted into MDMA via 3,4-methylenedioxyphenyl-2-nitropropene (MDP2NP) and 
      3,4-methylenedioxyphenyl-2-propanone (MDP2P) and the impurities within each 
      product characterised by GC-MS to give a contaminant profile of the synthetic 
      pathway. Interestingly, it was discovered that a chlorinated analogue of 
      piperonal (6-chloropiperonal) was created during the oxidation process by an as 
      yet unknown mechanism. This impurity reacted alongside piperonal to give 
      chlorinated analogues of each precursor, ultimately yielding 
      2-chloro-4,5-methylenedioxymethamphetamine (6-Cl-MDMA) as an impurity within the 
      MDMA sample. The methodology developed is a simple way to synthesise a 
      substantial amount of precursor material with easy to obtain reagents. The 
      results also show that chlorinated MDMA analogues, previously thought to be 
      deliberately included adulterants, may in fact be route specific impurities with 
      potential application in determining the origin and synthesis method of seized 
      illicit drugs.
CI  - Copyright (c) 2016 The Chartered Society of Forensic Sciences. Published by 
      Elsevier Ireland Ltd. All rights reserved.
FAU - Plummer, Christopher M
AU  - Plummer CM
AD  - Australian Centre for Research on Separation Science (ACROSS), School of Science, 
      RMIT University, GPO Box 2476, Melbourne, Victoria 3001, Australia.
FAU - Breadon, Thomas W
AU  - Breadon TW
AD  - Australian Centre for Research on Separation Science (ACROSS), School of Science, 
      RMIT University, GPO Box 2476, Melbourne, Victoria 3001, Australia.
FAU - Pearson, James R
AU  - Pearson JR
AD  - Victoria Police Forensic Services Centre, Macleod, Victoria 3085, Australia.
FAU - Jones, Oliver A H
AU  - Jones OAH
AD  - Australian Centre for Research on Separation Science (ACROSS), School of Science, 
      RMIT University, GPO Box 2476, Melbourne, Victoria 3001, Australia. Electronic 
      address: oliver.jones@rmit.edu.au.
LA  - eng
PT  - Journal Article
DEP - 20160206
PL  - England
TA  - Sci Justice
JT  - Science & justice : journal of the Forensic Science Society
JID - 9508563
RN  - 0 (Benzaldehydes)
RN  - 0 (Benzodioxoles)
RN  - 0 (Hallucinogens)
RN  - 0 (Illicit Drugs)
RN  - KE109YAK00 (piperonal)
RN  - KE1SEN21RM (N-Methyl-3,4-methylenedioxyamphetamine)
SB  - IM
MH  - Benzaldehydes/chemistry
MH  - Benzodioxoles/chemistry
MH  - Drug Contamination
MH  - Hallucinogens/*chemical synthesis
MH  - Humans
MH  - Illicit Drugs/*chemistry
MH  - N-Methyl-3,4-methylenedioxyamphetamine/*chemical synthesis
MH  - Oxidation-Reduction
MH  - Piper nigrum/*chemistry
OTO - NOTNLM
OT  - Clandestine synthesis
OT  - MDMA
OT  - Pepper
OT  - Route specific impurities
OT  - Ruthenium tetroxide
EDAT- 2016/05/11 06:00
MHDA- 2016/08/16 06:00
CRDT- 2016/05/11 06:00
PHST- 2015/10/22 00:00 [received]
PHST- 2016/01/27 00:00 [revised]
PHST- 2016/01/29 00:00 [accepted]
PHST- 2016/05/11 06:00 [entrez]
PHST- 2016/05/11 06:00 [pubmed]
PHST- 2016/08/16 06:00 [medline]
AID - S1355-0306(16)00005-8 [pii]
AID - 10.1016/j.scijus.2016.01.003 [doi]
PST - ppublish
SO  - Sci Justice. 2016 May;56(3):223-230. doi: 10.1016/j.scijus.2016.01.003. Epub 2016 
      Feb 6.