PMID- 20466553
OWN - NLM
STAT- MEDLINE
DCOM- 20100827
LR  - 20171116
IS  - 1464-3391 (Electronic)
IS  - 0968-0896 (Linking)
VI  - 18
IP  - 11
DP  - 2010 Jun 1
TI  - Synthesis and in vitro toxicity of 4-MTA, its characteristic clandestine 
      synthesis byproducts and related sulfur substituted alpha-alkylthioamphetamines.
PG  - 4009-31
LID - 10.1016/j.bmc.2010.04.022 [doi]
AB  - 4-Methylthioamphetamine (4-MTA) is recognised as a 
      3,4-methylenedioxymethamphetamine (MDMA)-like drug of abuse. Such 
      amphetamine-type drugs often contain byproducts of uncontrolled, illegal 
      clandestine synthetic processes. We report the isolation and structural 
      identification of a number of novel pyridines, dihydropyridone and 
      N,N-di(1-aryl-2-propyl) amines as route-specific byproducts associated with 
      clandestine synthesis of 4-MTA and related amphetamines. We report the in vitro 
      cytotoxicity of 4-MTA, its synthesis byproducts together with some structurally 
      related sulfur substituted alpha-alkyl phenethylamines in cell lines 
      overexpressing human monoamine transporters as well as in a primary neuronal cell 
      line model and a dopaminergic neuroblastoma cell line. 4-MTA along with a number 
      of other structurally related amphetamine derivatives and synthetic impurities 
      were found to be cytotoxic to these cells within pharmacologically defined 
      concentrations implying that 4-MTA is a cytotoxic agent in vitro and therefore 
      might have the potential to be a neurotoxic agent in vivo.
FAU - Cloonan, Suzanne M
AU  - Cloonan SM
AD  - School of Biochemistry and Immunology, Trinity College Dublin, Ireland.
FAU - Keating, John J
AU  - Keating JJ
FAU - Corrigan, Desmond
AU  - Corrigan D
FAU - O'Brien, John E
AU  - O'Brien JE
FAU - Kavanagh, Pierce V
AU  - Kavanagh PV
FAU - Williams, D Clive
AU  - Williams DC
FAU - Meegan, Mary J
AU  - Meegan MJ
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20100413
PL  - England
TA  - Bioorg Med Chem
JT  - Bioorganic & medicinal chemistry
JID - 9413298
RN  - 0 (Amphetamines)
RN  - 0 (Phenethylamines)
RN  - 44RAL3456C (Methamphetamine)
RN  - 6JP2T8KXTR (4-methylthioamphetamine)
RN  - 70FD1KFU70 (Sulfur)
SB  - IM
MH  - Amphetamines/*chemical synthesis/pharmacology/*toxicity
MH  - Cell Line
MH  - Cell Line, Tumor
MH  - Cells, Cultured
MH  - Humans
MH  - Methamphetamine
MH  - Neurons/cytology/*drug effects
MH  - Phenethylamines
MH  - Sulfur
EDAT- 2010/05/15 06:00
MHDA- 2010/08/28 06:00
CRDT- 2010/05/15 06:00
PHST- 2009/11/27 00:00 [received]
PHST- 2010/04/05 00:00 [revised]
PHST- 2010/04/07 00:00 [accepted]
PHST- 2010/05/15 06:00 [entrez]
PHST- 2010/05/15 06:00 [pubmed]
PHST- 2010/08/28 06:00 [medline]
AID - S0968-0896(10)00326-3 [pii]
AID - 10.1016/j.bmc.2010.04.022 [doi]
PST - ppublish
SO  - Bioorg Med Chem. 2010 Jun 1;18(11):4009-31. doi: 10.1016/j.bmc.2010.04.022. Epub 
      2010 Apr 13.