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MDMA-like stimulus effects of alpha-ethyltryptamine and the alpha-ethyl homolog of DOM.

Richard A Glennon

Pharmacology, Biochemistry, and Behavior October 1993 DOI: 10.1016/0091-3057(93)90379-8 (opens in new tab)

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Study at a glance

AI-extracted from the abstract
Characteristics Drug discrimination study in rats Peer reviewed
Population Rats trained to discriminate MDMA from saline
Interventions MDMA DOM alpha-methyltryptamine alpha-EH DOM (BL-3912) alpha-EtT (+)amphetamine
Dose MDMA training dose 1.5 mg/kg; (+)amphetamine training dose 1.0 mg/kg
Topics MDMA
Key points Alpha-ethyl homologation of the hallucinogens DOM and alpha-methyltryptamine produced compounds (alpha-EH DOM and alpha-EtT) that fully substituted for an MDMA discriminative stimulus in rats, whereas the parent hallucinogens did not. The authors argue this is the first evidence that classical hallucinogens can produce MDMA-like effects upon homologation and that an indolylalkylamine can do so, and that an intact methylenedioxy ring is not required for MDMA-like effects.

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.

Comparable studies

Other preclinical and animal studies on MDMA, most cited first.

Study Year Design Participants
Neurotoxicity of the psychedelic amphetamine, methylenedioxymethamphetamine. Rats (implied by typical neurochemical study context) 1987 Experimental study
3,4-Methylenedioxymethamphetamine and 3,4-methylenedioxyamphetamine destroy serotonin terminals in rat brain: quantification of neurodegeneration by measurement of [3H]paroxetine-labeled serotonin uptake sites. Rat brain 1987 Animal experiment
Comparison of the monoamine transporters from human and mouse in their sensitivities to psychostimulant drugs Human and mouse dopamine, norepinephrine, and serotonin transporters expressed in cells 2006 In vitro laboratory study
Small Changes in Ambient Temperature Cause Large Changes in 3,4-Methylenedioxymethamphetamine (MDMA)-Induced Serotonin Neurotoxicity and Core Body Temperature in the Rat Rats 1998 Experimental study
Altered Serotonin Innervation Patterns in the Forebrain of Monkeys Treated with (±)3,4-Methylenedioxymethamphetamine Seven Years Previously: Factors Influencing Abnormal Recovery Squirrel monkeys treated with MDMA 1999 Observational cohort

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