PMID- 2886126
OWN - NLM
STAT- MEDLINE
DCOM- 19870819
LR  - 20231213
IS  - 0006-2952 (Print)
IS  - 0006-2952 (Linking)
VI  - 36
IP  - 14
DP  - 1987 Jul 15
TI  - Stereochemical effects of 3,4-methylenedioxymethamphetamine (MDMA) and related 
      amphetamine derivatives on inhibition of uptake of [3H]monoamines into 
      synaptosomes from different regions of rat brain.
PG  - 2297-303
AB  - 3,4-Methylenedioxymethamphetamine (MDMA) is a recently popularized recreational 
      drug, although some have advocated its psychotherapeutic potential. Since the 
      pharmacology of MDMA is largely uncharacterized, the stereochemical profiles of 
      MDMA and some of its homologs were derived on inhibition of synaptosomal uptake 
      of [3H]monoamines and compared to those of amphetamine and the hallucinogenic 
      phenylisopropylamine 2,5-dimethoxy-4-methylamphetamine (DOM). In contrast to the 
      5-fold stereoselectivity observed with amphetamine, only the S-(+) enantiomer of 
      MDMA and 3,4-methylenedioxyamphetamine (MDA) inhibited [3H]dopamine uptake into 
      striatal synaptosomes. Neither stereoisomer of the alpha-ethyl homolog of MDMA, 
      N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine (MBDB), inhibited [3H]dopamine 
      uptake. The two stereoisomers of amphetamine and the MDMA-related compounds were 
      equipotent in inhibiting [3H]norepinephrine uptake into hypothalamic 
      synaptosomes. Both stereoisomers of MDMA, MDA and MBDB were potent inhibitors of 
      [3H]serotonin uptake into hippocampal synaptosomes, but only S-(+)-amphetamine 
      produced an appreciable inhibition of [3H]serotonin uptake. Neither stereoisomer 
      of DOM inhibited synaptosomal uptake of any [3H]monoamine. These results suggest 
      that MDMA and its homologs may be more closely related to amphetamine rather than 
      to DOM in their biochemical mode of action. The pronounced effects of the 
      methylenedioxy-substituted compounds on [3H]serotonin and [3H]norepinephrine 
      uptake implicate these neurotransmitters in the pharmacological effects of these 
      drugs.
FAU - Steele, T D
AU  - Steele TD
FAU - Nichols, D E
AU  - Nichols DE
FAU - Yim, G K
AU  - Yim GK
LA  - eng
GR  - BRSG 5586/RS/DRS NIH HHS/United States
GR  - DA-02189/DA/NIDA NIH HHS/United States
PT  - Comparative Study
PT  - Journal Article
PT  - Research Support, U.S. Gov't, P.H.S.
PL  - England
TA  - Biochem Pharmacol
JT  - Biochemical pharmacology
JID - 0101032
RN  - 0 (Amphetamines)
RN  - 103818-46-8 (N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine)
RN  - 15588-95-1 (DOM 2,5-Dimethoxy-4-Methylamphetamine)
RN  - 333DO1RDJY (Serotonin)
RN  - 4764-17-4 (3,4-Methylenedioxyamphetamine)
RN  - CK833KGX7E (Amphetamine)
RN  - KE1SEN21RM (N-Methyl-3,4-methylenedioxyamphetamine)
RN  - VTD58H1Z2X (Dopamine)
RN  - X4W3ENH1CV (Norepinephrine)
SB  - IM
MH  - DOM 2,5-Dimethoxy-4-Methylamphetamine/pharmacology
MH  - 3,4-Methylenedioxyamphetamine/analogs & derivatives/*pharmacology
MH  - Amphetamine/pharmacology
MH  - Amphetamines/*pharmacology
MH  - Animals
MH  - Biological Transport/drug effects
MH  - Corpus Striatum/*drug effects/metabolism
MH  - Depression, Chemical
MH  - Dopamine/*metabolism
MH  - Hippocampus/*drug effects/metabolism
MH  - Hypothalamus/*drug effects/metabolism
MH  - Male
MH  - N-Methyl-3,4-methylenedioxyamphetamine
MH  - Norepinephrine/*metabolism
MH  - Rats
MH  - Rats, Inbred Strains
MH  - Serotonin/*metabolism
MH  - Stereoisomerism
MH  - Synaptosomes/*drug effects/metabolism
EDAT- 1987/07/15 00:00
MHDA- 1987/07/15 00:01
CRDT- 1987/07/15 00:00
PHST- 1987/07/15 00:00 [pubmed]
PHST- 1987/07/15 00:01 [medline]
PHST- 1987/07/15 00:00 [entrez]
AID - 0006-2952(87)90594-6 [pii]
AID - 10.1016/0006-2952(87)90594-6 [doi]
PST - ppublish
SO  - Biochem Pharmacol. 1987 Jul 15;36(14):2297-303. doi: 
      10.1016/0006-2952(87)90594-6.