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Discriminative stimulus properties of alpha-ethyltryptamine optical isomers.
Pharmacol Biochem Behav. 2001 Oct-Nov; 70(2-3):311-6.PB

Abstract

alpha-Ethyltryptamine (alpha-ET) possesses central stimulant and hallucinogenic activity. Also, in tests of stimulus generalization using rats trained to discriminate the controlled substance analog (i.e., designer drug) N-methyl-1-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) from vehicle, alpha-ET substituted for MDMA. These previous studies employed racemic alpha-ET. Because psychoactive phenylalkylamines with abuse potential can produce one or more of three distinct stimulus effects (i.e., amphetamine-, DOM- and/or PMMA-like effects) in animals trained to discriminate either the stimulant (+)amphetamine, the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM), or N-methyl-1-(4-methoxyphenyl)-2-aminopropane (PMMA) from vehicle, and because these effects can be stereoselective, the individual optical isomers of alpha-ET were examined in groups of animals trained to discriminate (+)amphetamine, DOM, PMMA and MDMA from saline vehicle. (-)alpha-ET (ED(50)=7.8 mg/kg), but not (+)alpha-ET (maximum of 53% drug-appropriate responding), substituted for (+)amphetamine, whereas (+)alpha-ET (ED(50)=2.7 mg/kg), but not (-)alpha-ET (maximum of 33% drug-appropriate responding), substituted for DOM. Both optical isomers of alpha-ET substituted for PMMA and MDMA with ED(50) values of 1.6 and 1.4 mg/kg (PMMA-trained animals) and 1.3 and 2.0 mg/kg (MDMA-trained animals) for (-)alpha-ET and (+)alpha-ET, respectively. The results of this investigation suggest that both optical isomers of alpha-ET are capable of producing an MDMA/PMMA-like effect at nearly comparable doses, and that the stimulant or amphetamine-like nature of alpha-ET resides primarily with its (-)isomer whereas hallucinogenic or DOM-like character resides primarily with the (+)enantiomer.

Authors+Show Affiliations

Department of Medicinal Chemistry, School of Pharmacy, Virginia Commonwealth University, 410 N. 12th Street, Box 980540 VCU, 554A Smith Building, Richmond, VA 23298, USA.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

11701202

Citation

Hong, S S., et al. "Discriminative Stimulus Properties of Alpha-ethyltryptamine Optical Isomers." Pharmacology, Biochemistry, and Behavior, vol. 70, no. 2-3, 2001, pp. 311-6.
Hong SS, Young R, Glennon RA. Discriminative stimulus properties of alpha-ethyltryptamine optical isomers. Pharmacol Biochem Behav. 2001;70(2-3):311-6.
Hong, S. S., Young, R., & Glennon, R. A. (2001). Discriminative stimulus properties of alpha-ethyltryptamine optical isomers. Pharmacology, Biochemistry, and Behavior, 70(2-3), 311-6.
Hong SS, Young R, Glennon RA. Discriminative Stimulus Properties of Alpha-ethyltryptamine Optical Isomers. Pharmacol Biochem Behav. 2001 Oct-Nov;70(2-3):311-6. PubMed PMID: 11701202.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Discriminative stimulus properties of alpha-ethyltryptamine optical isomers. AU - Hong,S S, AU - Young,R, AU - Glennon,R A, PY - 2001/11/10/pubmed PY - 2002/2/6/medline PY - 2001/11/10/entrez SP - 311 EP - 6 JF - Pharmacology, biochemistry, and behavior JO - Pharmacol Biochem Behav VL - 70 IS - 2-3 N2 - alpha-Ethyltryptamine (alpha-ET) possesses central stimulant and hallucinogenic activity. Also, in tests of stimulus generalization using rats trained to discriminate the controlled substance analog (i.e., designer drug) N-methyl-1-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) from vehicle, alpha-ET substituted for MDMA. These previous studies employed racemic alpha-ET. Because psychoactive phenylalkylamines with abuse potential can produce one or more of three distinct stimulus effects (i.e., amphetamine-, DOM- and/or PMMA-like effects) in animals trained to discriminate either the stimulant (+)amphetamine, the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM), or N-methyl-1-(4-methoxyphenyl)-2-aminopropane (PMMA) from vehicle, and because these effects can be stereoselective, the individual optical isomers of alpha-ET were examined in groups of animals trained to discriminate (+)amphetamine, DOM, PMMA and MDMA from saline vehicle. (-)alpha-ET (ED(50)=7.8 mg/kg), but not (+)alpha-ET (maximum of 53% drug-appropriate responding), substituted for (+)amphetamine, whereas (+)alpha-ET (ED(50)=2.7 mg/kg), but not (-)alpha-ET (maximum of 33% drug-appropriate responding), substituted for DOM. Both optical isomers of alpha-ET substituted for PMMA and MDMA with ED(50) values of 1.6 and 1.4 mg/kg (PMMA-trained animals) and 1.3 and 2.0 mg/kg (MDMA-trained animals) for (-)alpha-ET and (+)alpha-ET, respectively. The results of this investigation suggest that both optical isomers of alpha-ET are capable of producing an MDMA/PMMA-like effect at nearly comparable doses, and that the stimulant or amphetamine-like nature of alpha-ET resides primarily with its (-)isomer whereas hallucinogenic or DOM-like character resides primarily with the (+)enantiomer. SN - 0091-3057 UR - https://www.unboundmedicine.com/medline/citation/11701202/Discriminative_stimulus_properties_of_alpha_ethyltryptamine_optical_isomers_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0091-3057(01)00605-0 DB - PRIME DP - Unbound Medicine ER -