Journal of Medicinal Chemistry
September 1, 1995
Robert Oberlender, P. V. Ramachandran, Michael P. Johnson et al.
8 citations
The potency of hallucinogenic amphetamine derivatives of the 1-(2,5-dimethoxy-4-alkylphenyl)-2-aminopropane type drops dramatically when the length of the 4-alkyl substituent exceeds propyl or when the substituent is branched. This investigation was directed toward evaluating changes in behavioral and biochemical pharmacology resulting from introducing chirality into the 4-alkyl group of such...
Journal of Medicinal Chemistry
1992
Robert Oberlender, Robert C. Pfaff, Michael P. Johnson et al.
17 citations
The (R)- and (S)-2-butylamides of d-lysergic acid were prepared and evaluated in behavioral and biochemical assays of 5-HT2 agonist activity. In rats trained to discriminate 0.08 mg/kg LSD tartrate from saline, both isomers completely substituted for the training stimulus. Similarly, both isomers were found to possess very high affinity in displacing [125I]-(R)-DOI...
Journal of Medicinal Chemistry
May 1, 1991
Michael P. Johnson, Stewart Frescas, Robert Oberlender et al.
53 citations
The racemate and the enantiomers of 1-(3-methoxy-4-methyphenyl)-2- aminopropane (6) and racemic 5-methoxy-6-methyl-2-aminoindan (11) were tested for stimulus generalization in the two-lever drug-discrimination paradigm. Both 6 and 11 were found to substitute with high potency in 3,4-(methylenedioxy)methamphetamine (1) and (S)-1-(1,3-benzodioxol-5-yl)-2-(methylamino)butane (2) trained rats. In...
Journal of Medicinal Chemistry
1991
David E. Nichols, Scott E. Snyder, Robert Oberlender et al.
45 citations
Two 2,3-dihydrobenzofuran analogues of hallucinogenic amphetamines were prepared and evaluated for activity in the two-lever drug-discrimination paradigm in rats trained to discriminate saline from LSD tartrate (0.08 mg/kg) and for the ability to displace [125I]-(R)-DOI [( 125I]-(R)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane) from rat cortical homogenate 5-HT2 receptors. The compounds,...
Journal of Medicinal Chemistry
February 1, 1990
David E. Nichols, William K. Brewster, Michael P. Johnson et al.
83 citations
Four cyclic analogues of the psychoactive phenethylamine derivative 3,4-(methylenedioxy)amphetamine were studied. These congeners, 5,6- and 4,5-(methylenedioxy)-2-aminoindan (3a and 4a, respectively), and 6,7- and 5,6-(methylenedioxy)-2-aminotetralin (3b and 4b, respectively) were tested for stimulus generalization in the two-lever drug-discrimination paradigm. Two groups of rats were trained...
Ecstasy: The Clinical, Pharmacological and Neurotoxicological Effects of the Drug MDMA
1990
David F. Nichols, Robert Oberlender
6 citations
It has been hypothesized that MDMA and substances that possess a psychopharmacological effect similar to MDMA are members of a novel pharmacological class named entactogens [1–3]. In this chapter evidence will be presented to support this, through a discussion of the data acquired in efforts directed toward testing this hypothesis. Although these studies are far from complete, the results...
Pharmacology, biochemistry, and behavior
November 1989
D E Nichols, R Oberlender, K Burris et al.
The 3,4-ethylidenedioxy and 3,4-isopropylidenedioxy analogues, EDA and IDA, respectively, of 3, 4-methylenedioxyamphetamine (MDA) were compared to MDA in drug-stimulated [3H]-serotonin overflow from prelabelled rat hippocampal slices, [3H]-dopamine overflow from prelabelled rat caudate slices, in their ability to displace the 5-HT2 agonist R-[125I]-DOI from rat brain cortical binding sites....
Psychopharmacology
1988
R Oberlender, D E Nichols
The term entactogen has recently been introduced to describe a new pharmacological class of compounds best represented by 3,4-methylenedioxymethamphetamine, MDMA, and its alpha-ethyl homologue MBDB. The present study was designed to test the similarities of the discriminative stimulus properties produced by MDMA and MBDB, as well as to elaborate further the distinction between entactogens,...
Journal of Medicinal Chemistry
October 1, 1986
David E. Nichols, Andrew J. Hoffman, Robert Oberlender et al.
189 citations
The alpha-ethyl phenethylamine derivative 1-(1,3-benzodioxol-5-yl)-2-butanamine was prepared. An asymmetric synthesis was used to prepare the enantiomers of this compound and the related alpha-methyl homologue (MDA). The racemates and enantiomers of both compounds were evaluated in the two-lever drug discrimination assay in rats trained to discriminate saline from 0.08 mg/kg of LSD tartrate....
Chemischer Informationsdienst
June 10, 1986
D. E. Nichols, Andrew J. Hoffman, Robert Oberlender et al.
AbstractDie aus den Dihydrobenzofuranen (I) zugänglichen Aldehyde (II) werden durch Kondensation mit Nitroethan und anschließende Reduktion in die Aminopropyl‐Derivate (V) übergeführt, die auf LSD‐analoge Wirkung bei Ratten geprüft werden.
Journal of Medicinal Chemistry
February 1, 1986
David E. Nichols, Andrew J. Hoffman, Robert Oberlender et al.
34 citations
Two analogues, 6-(2-aminopropyl)-5-methoxy-2,3-dihydrobenzofuran and 6-(2-aminopropyl)-5-methoxy-2-methyl-2,3-dihydrobenzofuran, of the hallucinogenic agent 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) were synthesized and tested in the two-lever drug discrimination paradigm. In rats trained to discriminate saline from LSD tartrate (0.08 mg/kg), stimulus generalization occurred to both...
Journal of Medicinal Chemistry
September 1, 1984
David E. Nichols, K. P. Jadhav, Robert Oberlender et al.
12 citations
cis- and trans-2-(2,4,5-trimethoxyphenyl)cyclobutylamine and trans-2-(2,5-dimethoxy-4-methylphenyl)cyclobutylamine were synthesized as conformationally restricted analogues of hallucinogenic phenylisopropylamines. In rats trained to discriminate saline from LSD (0.08 mg/kg, ip) in a two-lever drug discrimination paradigm, no generalization of the LSD stimulus to the cis trimethoxy compound...