PMID- 1979813
OWN - NLM
STAT- MEDLINE
DCOM- 19910207
LR  - 20220311
IS  - 0022-3565 (Print)
IS  - 0022-3565 (Linking)
VI  - 255
IP  - 3
DP  - 1990 Dec
TI  - (+)-N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine as a discriminative stimulus 
      in studies of 3,4-methylenedioxy-methamphetamine-like behavioral activity.
PG  - 1098-106
AB  - The stimulus properties of 3,4-methylenedioxymethamphetamine (MDMA)-like 
      compounds were studied in rats trained to discriminate saline from 
      (+)-N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine [(+)-MBDB] hydrochloride (7.18 
      mumol/kg; 1.75 mg/kg), the alpha-ethyl homolog of MDMA. In previous experiments 
      with (+)-MBDB as a test drug, complete substitution was observed for MDMA but not 
      for (+)-lysergic acid diethylamide or (+)-amphetamine. In the study reported 
      here, the (+)-MBDB cue generalized to MDMA and the parent drug, 
      3,4-methylenedioxyamphetamine. All three drugs exhibited a similar 
      stereoselectivity, the (+)-isomer having potency greater than the (-)-isomer. By 
      contrast, the hallucinogens, (+)-lysergic acid diethylamide, 
      2,5-dimethoxy-4-methylamphetamine and mescaline and the psychostimulants 
      (+)-amphetamine and (+)-methamphetamine did not substitute for (+)-MBDB. Cocaine 
      produced partial substitution. The results support the hypothesis that the 
      primary behavioral activity of MDMA-like compounds is unlike that of 
      hallucinogens and stimulants and may represent the effects of a novel drug class, 
      given the name entactogens. Although the mechanism of action for the 
      discriminative stimulus properties of MDMA-like compounds is not known, there is 
      evidence that presynaptic serotonergic, but not dopaminergic, mechanisms are 
      critical. Finally, 5,6-methylenedioxy-2-aminoindan a non-neurotoxic 
      3,4-methylenedioxyamphetamine rigid analog that was previously found to 
      substitute for MDMA but not for (+)-lysergic acid diethylamide was found in the 
      study described here to substitute completely for (+)-MBDB. The N-methyl 
      derivative 5,6-methylenedioxy-2-methylminoindan produced similar results. The 
      demonstration of entactogen-like discriminative stimulus properties, for drugs 
      devoid of neuronal degenerative toxicity potential, serves as evidence of the 
      independent mechanisms for these effects in rats.
FAU - Oberlender, R
AU  - Oberlender R
AD  - Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and 
      Pharmacal Sciences, Purdue University, West Lafayette, Indiana.
FAU - Nichols, D E
AU  - Nichols DE
LA  - eng
GR  - DA-04758/DA/NIDA NIH HHS/United States
PT  - Journal Article
PT  - Research Support, U.S. Gov't, P.H.S.
PL  - United States
TA  - J Pharmacol Exp Ther
JT  - The Journal of pharmacology and experimental therapeutics
JID - 0376362
RN  - 0 (Hallucinogens)
RN  - 0 (Indans)
RN  - 0DMJ6G3XBF (5,6-methylenedioxy-2-aminoindane)
RN  - 103818-46-8 (N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine)
RN  - 132741-82-3 (5,6-methylenedioxy-2-methylaminoindan)
RN  - 4764-17-4 (3,4-Methylenedioxyamphetamine)
RN  - KE1SEN21RM (N-Methyl-3,4-methylenedioxyamphetamine)
SB  - IM
MH  - 3,4-Methylenedioxyamphetamine/*analogs & derivatives/pharmacology
MH  - Animals
MH  - Behavior, Animal/*drug effects
MH  - Dose-Response Relationship, Drug
MH  - Hallucinogens/pharmacology
MH  - Indans/pharmacology
MH  - Learning/drug effects
MH  - Male
MH  - N-Methyl-3,4-methylenedioxyamphetamine
MH  - Rats
MH  - Rats, Inbred Strains
MH  - Stereoisomerism
EDAT- 1990/12/01 00:00
MHDA- 1990/12/01 00:01
CRDT- 1990/12/01 00:00
PHST- 1990/12/01 00:00 [pubmed]
PHST- 1990/12/01 00:01 [medline]
PHST- 1990/12/01 00:00 [entrez]
PST - ppublish
SO  - J Pharmacol Exp Ther. 1990 Dec;255(3):1098-106.