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MDMA-like stimulus effects of alpha-ethyltryptamine and the alpha-ethyl homolog of DOM.
Pharmacol Biochem Behav. 1993 Oct; 46(2):459-62.PB

Abstract

One-carbon homologation of phenylalkylamine or indolylalkylamine hallucinogens containing an alpha-methyl substituent typically results in a reduction of hallucinogenic potency; however, this same structural change has little to no effect on agents that produce MDMA-like effects. In the present investigation, rats trained to discriminate 1.5 mg/kg of MDMA (3,4-methylenedioxymethamphetamine) from saline vehicle were employed to determine if the alpha-ethyl homologs of the hallucinogens 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) and alpha-methyltryptamine (alpha-MeT)--that is, alpha-EH DOM (BL-3912) and alpha-EtT, respectively--would produce stimulus effects similar to those of MDMA. Although the MDMA stimulus failed to generalize to DOM (previously published) and alpha-MeT (this study), MDMA stimulus generalization occurred both to alpha-EH DOM (ED50 = 1.3 mg/kg) and alpha-EtT (ED50 = 3.5 mg/kg). A (+)amphetamine stimulus (training dose = 1.0 mg/kg) only partially generalized to these two agents, suggesting that the MDMA stimulus generalization involves more than a simple amphetamine-like action. As such, this is the first demonstration that classical hallucinogens can produce MDMA-like effects upon homologation and that MDMA-like stimulus effects can be associated with an indolylalkylamine. Furthermore, these results continue to support the concept that an intact methylenedioxy ring system, such as that found in MDMA and other MDMA-related agents, is not a structural requirement for drugs to produce MDMA-like effects.

Authors+Show Affiliations

Department of Medicinal Chemistry, School of Pharmacy, Medical College of Virginia, Virginia Commonwealth University, Richmond 23298-0540.

Pub Type(s)

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

Language

eng

PubMed ID

7903460

Citation

Glennon, R A.. "MDMA-like Stimulus Effects of Alpha-ethyltryptamine and the Alpha-ethyl Homolog of DOM." Pharmacology, Biochemistry, and Behavior, vol. 46, no. 2, 1993, pp. 459-62.
Glennon RA. MDMA-like stimulus effects of alpha-ethyltryptamine and the alpha-ethyl homolog of DOM. Pharmacol Biochem Behav. 1993;46(2):459-62.
Glennon, R. A. (1993). MDMA-like stimulus effects of alpha-ethyltryptamine and the alpha-ethyl homolog of DOM. Pharmacology, Biochemistry, and Behavior, 46(2), 459-62.
Glennon RA. MDMA-like Stimulus Effects of Alpha-ethyltryptamine and the Alpha-ethyl Homolog of DOM. Pharmacol Biochem Behav. 1993;46(2):459-62. PubMed PMID: 7903460.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - MDMA-like stimulus effects of alpha-ethyltryptamine and the alpha-ethyl homolog of DOM. A1 - Glennon,R A, PY - 1993/10/1/pubmed PY - 1993/10/1/medline PY - 1993/10/1/entrez SP - 459 EP - 62 JF - Pharmacology, biochemistry, and behavior JO - Pharmacol Biochem Behav VL - 46 IS - 2 N2 - One-carbon homologation of phenylalkylamine or indolylalkylamine hallucinogens containing an alpha-methyl substituent typically results in a reduction of hallucinogenic potency; however, this same structural change has little to no effect on agents that produce MDMA-like effects. In the present investigation, rats trained to discriminate 1.5 mg/kg of MDMA (3,4-methylenedioxymethamphetamine) from saline vehicle were employed to determine if the alpha-ethyl homologs of the hallucinogens 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) and alpha-methyltryptamine (alpha-MeT)--that is, alpha-EH DOM (BL-3912) and alpha-EtT, respectively--would produce stimulus effects similar to those of MDMA. Although the MDMA stimulus failed to generalize to DOM (previously published) and alpha-MeT (this study), MDMA stimulus generalization occurred both to alpha-EH DOM (ED50 = 1.3 mg/kg) and alpha-EtT (ED50 = 3.5 mg/kg). A (+)amphetamine stimulus (training dose = 1.0 mg/kg) only partially generalized to these two agents, suggesting that the MDMA stimulus generalization involves more than a simple amphetamine-like action. As such, this is the first demonstration that classical hallucinogens can produce MDMA-like effects upon homologation and that MDMA-like stimulus effects can be associated with an indolylalkylamine. Furthermore, these results continue to support the concept that an intact methylenedioxy ring system, such as that found in MDMA and other MDMA-related agents, is not a structural requirement for drugs to produce MDMA-like effects. SN - 0091-3057 UR - https://www.unboundmedicine.com/medline/citation/7903460/MDMA_like_stimulus_effects_of_alpha_ethyltryptamine_and_the_alpha_ethyl_homolog_of_DOM_ L2 - https://linkinghub.elsevier.com/retrieve/pii/0091-3057(93)90379-8 DB - PRIME DP - Unbound Medicine ER -