PMID- 25044512
OWN - NLM
STAT- MEDLINE
DCOM- 20160419
LR  - 20181212
IS  - 1942-7611 (Electronic)
IS  - 1942-7603 (Linking)
VI  - 7
IP  - 5
DP  - 2015 May
TI  - Preparation and characterization of the 'research chemical' diphenidine, its 
      pyrrolidine analogue, and their 2,2-diphenylethyl isomers.
PG  - 358-67
LID - 10.1002/dta.1689 [doi]
AB  - Substances with the diphenylethylamine nucleus represent a recent addition to the 
      product catalog of dissociative agents sold as 'research chemicals' on the 
      Internet. Diphenidine, i.e. 1-(1,2-diphenylethyl)piperidine (1,2-DEP), is such an 
      example but detailed analytical data are less abundant. The present study 
      describes the synthesis of diphenidine and its most obvious isomer, 
      1-(2,2-diphenylethyl)piperidine (2,2-DEP), in order to assess the ability to 
      differentiate between them. Preparation and characterization were also extended 
      to the two corresponding pyrrolidine analogues 1-(1,2-diphenylethyl)- and 
      1-(2,2-diphenylethyl)pyrrolidine, respectively. Analytical characterizations 
      included high-resolution electrospray mass spectrometry (HR-ESI-MS), liquid 
      chromatography ESI-MS/MS, gas chromatography ion trap electron and chemical 
      ionization MS, nuclear magnetic resonance spectroscopy (NMR) and infrared 
      spectroscopy. Differentiation between the two isomeric pairs was possible under 
      GC-(EI/CI)-MS conditions and included the formation of distinct iminium ions, 
      such as m/z 174 for 1,2-DEP and m/z 98 for 2,2-DEP, respectively. The pyrrolidine 
      counterparts demonstrated similar phenomena including the expected mass 
      difference of 14 Da due to the lack of one methylene unit in the ring. Two 
      samples obtained from an Internet vendor provided confirmation that diphenidine 
      was present in both samples, concurring with the product label. Finally, it was 
      confirmed that diphenidine (30 muM) reduced N-methyl-D-aspartate-mediated field 
      excitatory postsynaptic potentials (NMDA-fEPSPs) to a similar extent to that of 
      ketamine (30 muM) when using rat hippocampal slices. The appearance of 1,2- 
      diphenylethylamines appears to reflect the exploration of alternatives to 
      arylcyclohexylamine-type substances, such as methoxetamine, PCP and PCPy-based 
      analogues that also show NMDA receptor activity as demonstrated here for 
      diphenidine.
CI  - Copyright (c) 2014 John Wiley & Sons, Ltd.
FAU - Wallach, Jason
AU  - Wallach J
AD  - Department of Pharmaceutical Sciences, Philadelphia College of Pharmacy, 
      University of the Sciences, Philadelphia, PA, 19104, USA.
FAU - Kavanagh, Pierce V
AU  - Kavanagh PV
AD  - Department of Pharmacology and Therapeutics, School of Medicine, Trinity Centre 
      for Health Sciences, St. James Hospital, Dublin 8, Ireland.
FAU - McLaughlin, Gavin
AU  - McLaughlin G
AD  - Department of Pharmacology and Therapeutics, School of Medicine, Trinity Centre 
      for Health Sciences, St. James Hospital, Dublin 8, Ireland.
AD  - Department of Life and Physical Sciences, School of Science, Athlone Institute of 
      Technology, Dublin Road, Athlone, Co., Westmeath, Ireland.
FAU - Morris, Noreen
AU  - Morris N
AD  - Department of Life and Physical Sciences, School of Science, Athlone Institute of 
      Technology, Dublin Road, Athlone, Co., Westmeath, Ireland.
FAU - Power, John D
AU  - Power JD
AD  - Department of Pharmacology and Therapeutics, School of Medicine, Trinity Centre 
      for Health Sciences, St. James Hospital, Dublin 8, Ireland.
FAU - Elliott, Simon P
AU  - Elliott SP
AD  - ROAR Forensics, Malvern Hills Science Park, Geraldine Road, WR14 3SZ, UK.
FAU - Mercier, Marion S
AU  - Mercier MS
AD  - Department of Physiology and Pharmacology, University of Bristol, Dorothy Hodgkin 
      Building, Whitson Street, Bristol, BS1 3NY, UK.
FAU - Lodge, David
AU  - Lodge D
AD  - Department of Physiology and Pharmacology, University of Bristol, Dorothy Hodgkin 
      Building, Whitson Street, Bristol, BS1 3NY, UK.
FAU - Morris, Hamilton
AU  - Morris H
AD  - Department of Anthropology, The New School for Social Research, 66 West 12th 
      Street, NY, 10011, New York, USA.
FAU - Dempster, Nicola M
AU  - Dempster NM
AD  - School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, 
      Byrom Street, Liverpool, L3 3AF, UK.
FAU - Brandt, Simon D
AU  - Brandt SD
AD  - School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, 
      Byrom Street, Liverpool, L3 3AF, UK.
LA  - eng
PT  - Journal Article
DEP - 20140715
PL  - England
TA  - Drug Test Anal
JT  - Drug testing and analysis
JID - 101483449
RN  - 0 (Piperidines)
RN  - 0 (Pyrrolidines)
RN  - 690G0D6V8H (Ketamine)
RN  - H8Q4VPL82Y (diphenidine)
SB  - IM
MH  - Animals
MH  - Chemistry Techniques, Analytical/*methods
MH  - Excitatory Postsynaptic Potentials/*drug effects/physiology
MH  - Female
MH  - Hippocampus/drug effects/physiology
MH  - Isomerism
MH  - Ketamine/pharmacology
MH  - Male
MH  - Piperidines/*chemical synthesis/*pharmacology
MH  - Pyrrolidines/*chemistry
MH  - Rats
OTO - NOTNLM
OT  - Internet
OT  - NMDA receptor
OT  - PCP
OT  - arylcyclohexylamines
OT  - diarylethylamines
OT  - diphenidine
OT  - isomers
OT  - psychoactive
OT  - 'research chemicals'
EDAT- 2014/07/22 06:00
MHDA- 2016/04/20 06:00
CRDT- 2014/07/22 06:00
PHST- 2014/05/10 00:00 [received]
PHST- 2014/06/07 00:00 [revised]
PHST- 2014/06/08 00:00 [accepted]
PHST- 2014/07/22 06:00 [entrez]
PHST- 2014/07/22 06:00 [pubmed]
PHST- 2016/04/20 06:00 [medline]
AID - 10.1002/dta.1689 [doi]
PST - ppublish
SO  - Drug Test Anal. 2015 May;7(5):358-67. doi: 10.1002/dta.1689. Epub 2014 Jul 15.