ArticleNeuropsychopharmacology : official publication of the American College of Neuropsychopharmacology2017
N-Alkylated Analogs of 4-Methylamphetamine (4-MA) Differentially Affect Monoamine Transporters and Abuse Liability.
Article in Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed, 30 citations in OpenAlex.
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- Rapid, open-source, and automated quantification of the head twitch response in C57BL/6J mice using DeepLabCut and Simple Behavioral Analysis.bioRxiv : the preprint server for biology · 2025Article
- Locomotor and discriminative stimulus effects of fluorinated analogs of amphetamine and methamphetamine in mice and rats.The Journal of pharmacology and experimental therapeutics · 2025Article
- Structure-activity relationships for locomotor stimulant effects and monoamine transporter interactions of substituted amphetamines and cathinones.Neuropharmacology · 2024Article
- Structural and functional perspectives on interactions between synthetic cathinones and monoamine transporters.Advances in pharmacology (San Diego, Calif.) · 2024Article
- Structure-Activity Relationships for a Recently Controlled Synthetic Cathinone Dopamine Transporter Reuptake Inhibitor: α-Pyrrolidinohexiophenone (α-PHP).ACS chemical neuroscience · 2023Article
- Neurochemical and Cardiovascular Effects of 4-Chloro Ring-Substituted Synthetic Cathinones in Rats.The Journal of pharmacology and experimental therapeutics · 2023Article
- Effects of the Phenethylamine 2-Cl-4,5-MDMA and the Synthetic Cathinone 3,4-MDPHP in Adolescent Rats: Focus on Sex Differences.Biomedicines · 2022Article
- Non-conserved residues dictate dopamine transporter selectivity for the potent synthetic cathinone and psychostimulant MDPV.Neuropharmacology · 2021Article
- Comparative Neuropharmacology and Pharmacokinetics of Methamphetamine and Its Thiophene Analog Methiopropamine in Rodents.International journal of molecular sciences · 2021Article
- Behavioral effects of four novel synthetic cathinone analogs in rodents.Addiction biology · 2021Article
- Functional characterization of N-octyl 4-methylamphetamine variants and related bivalent compounds at the dopamine and serotonin transporters using CaToxicology and applied pharmacology · 2021Article
- Eutylone and Its Structural Isomers Interact with Monoamine Transporters and Induce Locomotor Stimulation.ACS chemical neuroscience · 2021Article
- Amphetamine-like Neurochemical and Cardiovascular Effects ofThe Journal of pharmacology and experimental therapeutics · 2021Article
- Methylenedioxymethamphetamine-like discriminative stimulus effects of pyrrolidinyl cathinones in rats.Journal of psychopharmacology (Oxford, England) · 2020Article
- Investigation of the Optical Isomers of Methcathinone, and Two Achiral Analogs, at Monoamine Transporters and in Intracranial Self-Stimulation Studies in Rats.ACS chemical neuroscience · 2020Article
- Multi-modal antidepressant-like action of 6- and 7-chloro-2-aminodihydroquinazolines in the mouse tail suspension test.Psychopharmacology · 2019Article
- The Supplement AdulterantThe Journal of pharmacology and experimental therapeutics · 2019Article
- 2-Aminoindan and its ring-substituted derivatives interact with plasma membrane monoamine transporters and αPsychopharmacology · 2019Article
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Authors and funding
10 authors at 2 institutions in 1 country.
Funding
Abstract
Clandestine chemists synthesize novel stimulant drugs by exploiting structural templates known to target monoamine transporters for dopamine, norepinephrine, and serotonin (DAT, NET, and SERT, respectively). 4-Methylamphetamine (4-MA) is an emerging drug of abuse that interacts with transporters, but limited structure-activity data are available for its analogs. Here we employed uptake and release assays in rat brain synaptosomes, voltage-clamp current measurements in cells expressing transporters, and calcium flux assays in cells coexpressing transporters and calcium channels to study the effects of increasing N-alkyl chain length of 4-MA on interactions at DAT, NET, and SERT. In addition, we performed intracranial self-stimulation in rats to understand how the chemical modifications affect abuse liability. All 4-MA analogs inhibited uptake at DAT, NET, and SERT, but lengthening the amine substituent from methyl to ethyl, propyl, and butyl produced a stepwise decrease in potency. N-methyl 4-MA was an efficacious substrate-type releaser at DAT that evoked an inward depolarizing current and calcium influx, whereas other analogs did not exhibit these effects. N-methyl and N-ethyl 4-MA were substrates at NET, whereas N-propyl and N-butyl 4-MA were not. All analogs acted as SERT substrates, though N-butyl 4-MA had very weak effects. Intracranial self-stimulation in rats showed that elongating the N-alkyl chain decreased abuse-related effects in vivo that appeared to parallel reductions in DAT activity. Overall, converging lines of evidence show that lengthening the N-alkyl substituent of 4-MA reduces potency to inhibit transporters, eliminates substrate activity at DAT and NET, and decreases abuse liability of the compounds.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.