PMID- 17891159
OWN - NLM
STAT- MEDLINE
DCOM- 20080205
LR  - 20181113
IS  - 0007-1188 (Print)
IS  - 1476-5381 (Electronic)
IS  - 0007-1188 (Linking)
VI  - 152
IP  - 7
DP  - 2007 Dec
TI  - Comparative potencies of 3,4-methylenedioxymethamphetamine (MDMA) analogues as 
      inhibitors of [3H]noradrenaline and [3H]5-HT transport in mammalian cell lines.
PG  - 1121-30
AB  - BACKGROUND AND PURPOSE: Illegal 'ecstasy' tablets frequently contain 
      3,4-methylenedioxymethamphetamine (MDMA)-like compounds of unknown 
      pharmacological activity. Since monoamine transporters are one of the primary 
      targets of MDMA action in the brain, a number of MDMA analogues have been tested 
      for their ability to inhibit [3H]noradrenaline uptake into rat PC12 cells 
      expressing the noradrenaline transporter (NET) and [3H]5-HT uptake into HEK293 
      cells stably transfected with the 5-HT transporter (SERT). EXPERIMENTAL APPROACH: 
      Concentration-response curves for the following compounds at both NET and SERT 
      were determined under saturating substrate conditions: 
      4-hydroxy-3-methoxyamphetamine (HMA), 4-hydroxy-3-methoxymethamphetamine (HMMA), 
      3,4-methylenedioxy-N-hydroxyamphetamine (MDOH), 
      2,5-dimethoxy-4-bromophenylethylamine (2CB), 3,4-dimethoxymethamphetamine (DMMA), 
      3,4-methylenedioxyphenyl-2-butanamine (BDB), 
      3,4-methylenedioxyphenyl-N-methyl-2-butanamine (MBDB) and 
      2,3-methylenedioxymethamphetamine (2,3-MDMA). KEY RESULTS: 2,3-MDMA was 
      significantly less potent than MDMA at SERT, but equipotent with MDMA at NET. 2CB 
      and BDB were both significantly less potent than MDMA at NET, but equipotent with 
      MDMA at SERT. MBDB, DMMA, MDOH and the MDMA metabolites HMA and HMMA, were all 
      significantly less potent than MDMA at both NET and SERT. CONCLUSIONS AND 
      IMPLICATIONS: This study provides an important insight into the structural 
      requirements of MDMA analogue affinity at both NET and SERT. It is anticipated 
      that these results will facilitate understanding of the likely pharmacological 
      actions of structural analogues of MDMA.
FAU - Montgomery, T
AU  - Montgomery T
AD  - 1School of Biomolecular and Biomedical Science, Conway Institute of Biomolecular 
      and Biomedical Research, University College Dublin, Dublin, Ireland.
FAU - Buon, C
AU  - Buon C
FAU - Eibauer, S
AU  - Eibauer S
FAU - Guiry, P J
AU  - Guiry PJ
FAU - Keenan, A K
AU  - Keenan AK
FAU - McBean, G J
AU  - McBean GJ
LA  - eng
PT  - Comparative Study
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20070924
PL  - England
TA  - Br J Pharmacol
JT  - British journal of pharmacology
JID - 7502536
RN  - 0 (Serotonin Plasma Membrane Transport Proteins)
RN  - KE1SEN21RM (N-Methyl-3,4-methylenedioxyamphetamine)
RN  - X4W3ENH1CV (Norepinephrine)
SB  - IM
MH  - Animals
MH  - Biological Transport/drug effects
MH  - Cell Line
MH  - Dose-Response Relationship, Drug
MH  - Humans
MH  - Molecular Structure
MH  - N-Methyl-3,4-methylenedioxyamphetamine/*analogs & 
      derivatives/chemistry/*pharmacology
MH  - Norepinephrine/*antagonists & inhibitors/metabolism
MH  - PC12 Cells
MH  - Rats
MH  - Serotonin Plasma Membrane Transport Proteins/*drug effects/metabolism
MH  - Stereoisomerism
MH  - Structure-Activity Relationship
PMC - PMC2095113
EDAT- 2007/09/25 09:00
MHDA- 2008/02/06 09:00
PMCR- 2008/12/01
CRDT- 2007/09/25 09:00
PHST- 2007/09/25 09:00 [pubmed]
PHST- 2008/02/06 09:00 [medline]
PHST- 2007/09/25 09:00 [entrez]
PHST- 2008/12/01 00:00 [pmc-release]
AID - 0707473 [pii]
AID - 10.1038/sj.bjp.0707473 [doi]
PST - ppublish
SO  - Br J Pharmacol. 2007 Dec;152(7):1121-30. doi: 10.1038/sj.bjp.0707473. Epub 2007 
      Sep 24.