European Journal of Pharmacology
June 15, 1984
M Shannon, G Battaglia, R A Glennon et al.
The affinities of a series of 1-(2,5-dimethoxyphenyl)-2-aminopropane (2,5-DMA) derivatives, most of which are hallucinogenic in man, and several related agents were determined for rat cortical serotonin (5-HT) binding sites. Competition assays were performed in which these agents were competed for the 5-HT2 binding of [3H]ketanserin, or the 5-HT1 binding of [3H]LSD (in the presence of...
Pharmacology, Biochemistry, and Behavior
April 1984
Richard A Glennon, R Young
Rats trained to discriminate either (+)-amphetamine or (+/-)-MDA from saline in a two-lever drug discrimination task, were used to study the stimulus effects of MDA and its two optical isomers. Amphetamine-stimulus generalization occurred to S(+)-MDA, but not to its enantiomer R(-)-MDA. This, coupled with our earlier finding of DOM-stimulus generalization to R(-)-MDA but not to S(+)-MDA,...
Life Sciences
January 23, 1984
R A Glennon, R Young
Rats were trained to discriminate injections of either (+)-amphetamine (1.0 mg/kg) or racemic MDA (1.5 mg/kg) from saline in a two-lever drug discrimination task. After stable discrimination performances (greater than 85%) were attained in each group, stimulus generalization studies were conducted. The amphetamine-stimulus generalized to MDA, but not to the hallucinogenic agent DOM; the...
Journal of Medicinal Chemistry
January 1984
Richard A Glennon, John M. Jacyno, R Young et al.
A novel series of N,N-dimethylisotryptamine (isoDMT) derivatives, i.e., derivatives of 1-[2-(dimethylamino)ethyl]indole, was prepared and found to be isosteric with their corresponding N,N-dimethyltryptamine (DMT) counterparts with respect to serotonin receptor (rat fundus) affinity. Whereas the isoDMT derivatives possessed a greater affinity than did their corresponding DMT derivatives, they...
General pharmacology
1984
Richard A Glennon, R Young, W Soine
Rats trained to discriminate saline from either (+)-amphetamine, (+/-)-DOM, or (+/-)-3,4-MDA in a two-lever drug discrimination paradigm were administered doses of a novel positional isomer of 3,4-MDA, i.e. 2,3-MDA. The novel isomer produced neither amphetamine-appropriate nor DOM-appropriate responding: the 3,4-MDA stimulus did, however, generalize to 2,3-MDA.
Biochemical Pharmacology
April 1, 1983
Richard A Glennon, R Young, John M. Jacyno
Animals (rats), trained to discriminate the hallucinogenic agent 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) from saline in a two-lever operant procedure, were challenged with various doses of several indolealkylamine and phenalkylamine derivatives. In both series, the alpha-methyl analogs were found to be more active than either their N-methyl or alpha-demethyl counterparts....
European Journal of Pharmacology
January 21, 1983
Richard A Glennon, R Young, John M. Jacyno et al.
Stimulus generalization studies were conducted using rats trained to discriminate 1.0 mg/kg of the phenalkylamine hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) from saline in a two-lever operant procedure. The results suggest that certain indolealkylamine hallucinogens, including LSD and several alpha-methyltryptamine, N,N-dialkyltryptamine and beta-carboline derivatives,...
Psychopharmacology
1983
R Young, John A. Rosecrans, Richard A Glennon
25 citations
The discriminative effects of 5-methoxy-N,N-dimethyltryptamine (5-OMeDMT) were studied in rats trained to discriminate 1.5 mg/kg or 3.0 mg/kg 5-OMeDMT from saline. A series of antagonist and generalization tests revealed that (1) antagonism of the 5-OMeDMT stimulus response by the presumed serotonin antagonist BC-105 depended on the dose of 5-OMeDMT, (2) the 5-OMeDMT stimulus generalized to...
Journal of Medicinal Chemistry
October 1982
R A Glennon, R Young, F Benington et al.
The serotonin (5-HT) receptor affinities and behavioral (discriminative stimulus) properties of a series of 4-substituted derivatives of 1-(2,5-dimethoxyphenyl)-2-aminopropanes (2,5-DMA) were investigated. The substituents at the 4-position included H, OMe, OEt, Me, Et, F, Br, I, and NO2. Substituent lipophilicities (pi values) of these functionalities appear to have a minimal effect on either...
Pharmacology, Biochemistry, and Behavior
October 1982
Richard A Glennon, R Young
Prominent among the class of hallucinogenic phenylisopropylamines is the 2,5-dimethoxy substitution pattern; this pattern has long been recognized as being an important feature of the more potent agents within this class. The purpose of this present study was to explore the behavioral properties of a series of methoxylated phenylisopropylamines in order to determine the effect of other...
Life Sciences
June 14, 1982
R Young, John A. Rosecrans, Richard A Glennon
26 citations
Rats were trained to discriminate injections of either 5-OMe DMT (1.5 mg/kg) or LSD (0.096 mg/kg) from saline in a two-lever drug discrimination task. After stable discrimination performances were attained (greater than 85%) in each group, dose-response generalizations between the two groups of animals were examined. The results revealed that the 5-OMe DMT-stimulus response generalized to LSD...
Pharmacology, Biochemistry, and Behavior
April 1982
Richard A Glennon, R Young, John A. Rosecrans
Twenty-four rats, trained to discriminate 1.0 mg/kg of (+/-)-DOM, i.e. (+/-)-2,5-dimethoxy-4-methylphenylisopropylamine, from saline under a VI-15 schedule of reinforcement, were challenged with a series of DOM homologs. The agents examined included the 4-ethyl (DOET), -propyl (DOPR), -butyl (DOBU), -tertiary butyl (DOTB) and -amyl (DOAM) derivatives as well as the R(-)- and S(+)-isomers of...
Pharmacology, Biochemistry, and Behavior
April 1982
Richard A Glennon, R Young, John A. Rosecrans
Rats trained to discriminate racemic 2,5-dimethoxy-4-methylphenylisopropylamine, (+/-)-DOM (1.0 mg/kg), from saline in a two-lever drug discrimination task were challenged with the optimal isomers of DOM as well as with several related agents which represent minor molecular modifications of the DOM structure. Generalization of the (+/-)-DOM stimulus was found to occur to R(-)-DOM, S(+)-DOM,...
Life Sciences
February 1, 1982
Richard A Glennon, R Young, F Benington et al.
8 citations
Rats, trained to discriminate 1.5 mg/kg of the hallucinogenic agent 5-methoxy-N,N-dimethyltryptamine (5-OMe DMT) from saline in a two-lever drug discrimination task, were challenged with various doses of the 4-methoxy, 4-methylthio and 5-methylthio derivatives of DMT. The 5-OMe DMT cue was found to generalize to all three of these agents; the order of potency is 5-OMe greater than 5-SMe greater...
European Journal of Pharmacology
December 17, 1981
Richard A Glennon, John A. Rosecrans, R Young
21 citations
Rats were trained to discriminate injections of 5-methoxy-N,N-dimethyltryptamine (5-OMe DMT, 3.0 mg/kg) a hallucinogenic agent for which a serotonergic mechanism has been implicated, from saline in a two-lever drug discrimination task. After reliable levels of accuracy (greater than or equal to 85%) were attained, the ability of the 5-OMe DMT cue to generalize to 36 substituted...
Pharmacology, Biochemistry, and Behavior
March 1981
Richard A Glennon, D L Doot, R Young
Using an isolated rat fundus preparation, the 4-methyl (DOM), ethyl (DOET), propyl (DOPR) butyl (DOBU), tertiary butyl (DOTB) and amyl (DOAM) derivatives of 2,5-dimethoxy-phenylisopropylamine (2,5-DMA) were found to possess quite similar serotonin receptor affinities (pA2 - 7.02-7.22). The fundus preparation could not be used to determine pD2 values because all of the compounds were found to...
Journal of Medicinal Chemistry
November 1, 1980
Richard A Glennon, E. Schubert, John M. Jacyno et al.
33 citations
Several 7-substituted derivatives of N,N-dimethyltryptamine (DMT) were prepared and evaluated in the rat fundus serotonin receptor assay and in a behavioral (discriminative stimulus) assay in rats. Both 7-Me- and 5-OMe-7-Me-DMT possess a higher pA2, and 5,7-(OMe)2-DMT a lower pA2, than that of DMT itself. Like DMT, all three of these compounds produce behavioral effects in rats which are...
Journal of Medicinal Chemistry
September 1980
Richard A Glennon, Stephen M. Liebowitz, D Leming-Doot et al.
Mono-O-demethylation of several 2,5-dimethoxyphenalkylamines increases their affinity for the serotonin receptors of the isolated rat fundus preparation. In several instances, demethylation of methoxyphenalkylamines results in compounds which produce an antagonism which is not of a competitive nature. With respect to 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM), demethylation of the...
Psychopharmacology
1980
Richard A Glennon, R Young, John A. Rosecrans et al.
46 citations
A choice between two levers in an operant chamber was used to train 24 rats, under a variable-interval 15 s schedule of sweetened milk reinforcement, to discriminate a hallucinogenic (psychotomimetic) agent, 5-methoxy-N,N-dimethyltryptamine (5-OMe DMT), from saline administration. The 5-OMe DMT stimulus generalized in a dose-related manner to each of 14 tryptamine related analogs. With the...
Journal of Medicinal Chemistry
November 1, 1979
Richard A Glennon, Peter K. Gessner, Damodar D. Godse et al.
17 citations
Bufotenine (5-hydroxy-N,N-dimethyltryptamine) has been reported to be behaviorally inactive or only very weakly active in man and animals; this may be a consequence of its low partition coefficient and resultant inability to penetrate the blood--brain barrier. The acetyl, propionyl, butyryl, isobutyryl, and pivalyl esters of bufotenine were prepared for future pharmacological evaluation....
Journal of Pharmaceutical Sciences
July 1, 1979
Richard A Glennon, Lemont B. Kier, Alexander T. Shulgin
29 citations
The hallucinogenic (psychotomimetic) potency of 10 mescaline analogs was examined by molecular connectivity analysis. Potencies could be described by a two-term relating equation, which explained 94% of the variance in activity, on the basis of structural variation, 2,5-Dimethoxy substitution as well as the nature of the 4-position substituent played an important role in determining...
Chemischer Informationsdienst
December 26, 1978
Richard A Glennon, Stephen M. Liebowitz, Elizabeth C. Mack
AbstractDie Phenalkylamine (I) und bzw. Tryptamine (II) werden auf pharmakologische Wirkung untersucht.
Journal of Medicinal Chemistry
1978
Richard A Glennon, Stephen M. Liebowitz, Elizabeth C. Mack
35 citations
Hallucinogenic phenylalkylamine and N,N-dimethyltryptamine analogues are known to affect serotonergic systems both in vivo and in vitro. Using a rat stomach fundus model, the 5-HT receptor binding affinities of several of these analogues were determined and compared. The most behaviorally potent analogues examined, DOB, DOM, and 5-methoxy-N,N-dimethyltryptamine, were found to possess rather...