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N-Methyl-1-(4-methoxyphenyl)-2-aminopropane (PMMA) and N-Methyl-1-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) produce non-identical discriminative stimuli in rats.
Pharmacol Biochem Behav. 2007 Mar; 86(3):477-84.PB

Abstract

N-Methyl-1-(3,4-methylenedioxyphenyl)-2-aminopropane (methylenedioxymethamphetamine, MDMA, Ecstasy) and its structurally abbreviated congener N-methyl-1-(4-methoxyphenyl)-2-aminopropane (para-methoxymethamphetamine, PMMA) are chemically related designer drugs, and PMMA is sometimes sold on the clandestine market as a substitute for MDMA. Prior drug discrimination studies have found that MDMA and PMMA substitute for one another suggesting that they produce similar discriminative stimulus effects in rats. However, there also are some indications that the two agents produce distinct stimulus effects. In this study, further comparisons were made between the stimulus effects of these two agents. Sprague-Dawley rats were trained to discriminate either 1.25 mg/kg of PMMA or 1.5 mg/kg of MDMA from saline vehicle in a two-lever operant paradigm. A structure-activity comparison revealed that MDMA and PMMA behave similarly upon homologation of their terminal amine substituents. In contrast, the PMMA stimulus, unlike an MDMA stimulus, failed to generalize completely to the psychostimulant cocaine, 8-hydroxy-2-(N,N-di-n-propylamino)tetralin (8-OH DPAT), and R(-)-1-(3-methoxyphenyl)-2-aminopropane [R(-)MMA]. In an additional group of animals, a (+)amphetamine stimulus partially generalized to R(-)MMA. Taken together, the results argue and re-emphasize the conclusion that the stimulus effects produced by MDMA and PMMA are similar, but non-identical, and that PMMA is the less "stimulant-like" of the two.

Authors+Show Affiliations

Department of Medicinal, Chemistry School of Pharmacy Medical College of Virginia, Virginia Commonwealth University Richmond, VA 23298-0540, USA. glennon@vcu.eduNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Comparative Study
Journal Article
Research Support, N.I.H., Extramural

Language

eng

PubMed ID

17307247

Citation

Glennon, Richard A., et al. "N-Methyl-1-(4-methoxyphenyl)-2-aminopropane (PMMA) and N-Methyl-1-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) Produce Non-identical Discriminative Stimuli in Rats." Pharmacology, Biochemistry, and Behavior, vol. 86, no. 3, 2007, pp. 477-84.
Glennon RA, Young R, Dukat M, et al. N-Methyl-1-(4-methoxyphenyl)-2-aminopropane (PMMA) and N-Methyl-1-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) produce non-identical discriminative stimuli in rats. Pharmacol Biochem Behav. 2007;86(3):477-84.
Glennon, R. A., Young, R., Dukat, M., Chang-Fong, J., & El-Zahabi, M. (2007). N-Methyl-1-(4-methoxyphenyl)-2-aminopropane (PMMA) and N-Methyl-1-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) produce non-identical discriminative stimuli in rats. Pharmacology, Biochemistry, and Behavior, 86(3), 477-84.
Glennon RA, et al. N-Methyl-1-(4-methoxyphenyl)-2-aminopropane (PMMA) and N-Methyl-1-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) Produce Non-identical Discriminative Stimuli in Rats. Pharmacol Biochem Behav. 2007;86(3):477-84. PubMed PMID: 17307247.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - N-Methyl-1-(4-methoxyphenyl)-2-aminopropane (PMMA) and N-Methyl-1-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) produce non-identical discriminative stimuli in rats. AU - Glennon,Richard A, AU - Young,Richard, AU - Dukat,Małgorzata, AU - Chang-Fong,Jean, AU - El-Zahabi,Mohamed, Y1 - 2007/01/18/ PY - 2006/10/06/received PY - 2007/01/03/revised PY - 2007/01/10/accepted PY - 2007/2/20/pubmed PY - 2007/5/23/medline PY - 2007/2/20/entrez SP - 477 EP - 84 JF - Pharmacology, biochemistry, and behavior JO - Pharmacol Biochem Behav VL - 86 IS - 3 N2 - N-Methyl-1-(3,4-methylenedioxyphenyl)-2-aminopropane (methylenedioxymethamphetamine, MDMA, Ecstasy) and its structurally abbreviated congener N-methyl-1-(4-methoxyphenyl)-2-aminopropane (para-methoxymethamphetamine, PMMA) are chemically related designer drugs, and PMMA is sometimes sold on the clandestine market as a substitute for MDMA. Prior drug discrimination studies have found that MDMA and PMMA substitute for one another suggesting that they produce similar discriminative stimulus effects in rats. However, there also are some indications that the two agents produce distinct stimulus effects. In this study, further comparisons were made between the stimulus effects of these two agents. Sprague-Dawley rats were trained to discriminate either 1.25 mg/kg of PMMA or 1.5 mg/kg of MDMA from saline vehicle in a two-lever operant paradigm. A structure-activity comparison revealed that MDMA and PMMA behave similarly upon homologation of their terminal amine substituents. In contrast, the PMMA stimulus, unlike an MDMA stimulus, failed to generalize completely to the psychostimulant cocaine, 8-hydroxy-2-(N,N-di-n-propylamino)tetralin (8-OH DPAT), and R(-)-1-(3-methoxyphenyl)-2-aminopropane [R(-)MMA]. In an additional group of animals, a (+)amphetamine stimulus partially generalized to R(-)MMA. Taken together, the results argue and re-emphasize the conclusion that the stimulus effects produced by MDMA and PMMA are similar, but non-identical, and that PMMA is the less "stimulant-like" of the two. SN - 0091-3057 UR - https://www.unboundmedicine.com/medline/citation/17307247/N_Methyl_1__4_methoxyphenyl__2_aminopropane__PMMA__and_N_Methyl_1__34_methylenedioxyphenyl__2_aminopropane__MDMA__produce_non_identical_discriminative_stimuli_in_rats_ DB - PRIME DP - Unbound Medicine ER -