Literature DB >> 32875347

The psychoactive aminoalkylbenzofuran derivatives, 5-APB and 6-APB, mimic the effects of 3,4-methylenedioxyamphetamine (MDA) on monoamine transmission in male rats.

Simon D Brandt1, Hailey M Walters2, John S Partilla2, Bruce E Blough3, Pierce V Kavanagh4, Michael H Baumann5.   

Abstract

RATIONALE: The nonmedical use of new psychoactive substances (NPS) is a worldwide public health concern. The so-called "benzofury" compounds, 5-(2-aminopropyl)benzofuran (5-APB) and 6-(2-aminopropyl)benzofuran (6-APB), are NPS with stimulant-like properties in human users. These substances are known to interact with monoamine transporters and 5-HT receptors in transfected cells, but less is known about their effects in animal models.
METHODS: Here, we used in vitro monoamine transporter assays in rat brain synaptosomes to characterize the effects of 5-APB and 6-APB, together with their N-methyl derivatives 5-MAPB and 6-MAPB, in comparison with 3,4-methylenedioxyamphetamine (MDA) and 3,4-methylenedioxymethamphetamine (MDMA). In vivo neurochemical and behavioral effects of 5-APB (0.3 and 1.0 mg/kg, i.v.) and 6-APB (0.3 and 1.0 mg/kg, i.v.) were assessed in comparison with MDA (1.0 and 3.0 mg/kg, i.v.) using microdialysis sampling in the nucleus accumbens of conscious male rats.
RESULTS: All four benzofuran derivatives were substrate-type releasers at dopamine transporters (DAT), norepinephrine transporters (NET), and serotonin transporters (SERT) with nanomolar potencies, similar to the profile of effects produced by MDA and MDMA. However, the benzofurans were at least threefold more potent than MDA and MDMA at evoking transporter-mediated release. Like MDA, both benzofurans induced dose-related elevations in extracellular dopamine and serotonin in the brain, but benzofurans were more potent than MDA. The benzofuran derivatives also induced profound behavioral activation characterized by forward locomotion which lasted for at least 2 h post-injection.
CONCLUSIONS: Overall, benzofurans are more potent than MDA in vitro and in vivo, producing sustained stimulant-like effects in rats. These data suggest that benzofuran-type compounds may have abuse liability and could pose risks for adverse effects, especially if used in conjunction with abused drugs or medications which enhance monoamine transmission in the brain.

Entities:  

Keywords:  Benzofury; Designer drugs; Locomotor activity; MDMA, MDA; Microdialysis; Monoamine transporter; Release; Synthetic stimulants

Mesh:

Substances:

Year:  2020        PMID: 32875347      PMCID: PMC7686291          DOI: 10.1007/s00213-020-05648-z

Source DB:  PubMed          Journal:  Psychopharmacology (Berl)        ISSN: 0033-3158            Impact factor:   4.530


  56 in total

1.  Abuse of New Psychoactive Substances: Threats and Solutions.

Authors:  Michael H Baumann; Nora D Volkow
Journal:  Neuropsychopharmacology       Date:  2015-08-25       Impact factor: 7.853

2.  Structure-activity relationships of bath salt components: substituted cathinones and benzofurans at biogenic amine transporters.

Authors:  Amy J Eshleman; Shanthi Nagarajan; Katherine M Wolfrum; John F Reed; Tracy L Swanson; Aaron Nilsen; Aaron Janowsky
Journal:  Psychopharmacology (Berl)       Date:  2018-11-05       Impact factor: 4.530

3.  Preventive effects of fructose and N-acetyl-L-cysteine against cytotoxicity induced by the psychoactive compounds N-methyl-5-(2-aminopropyl)benzofuran and 3,4-methylenedioxy-N-methamphetamine in isolated rat hepatocytes.

Authors:  Yoshio Nakagawa; Toshinari Suzuki; Akiko Inomata
Journal:  J Appl Toxicol       Date:  2017-09-26       Impact factor: 3.446

Review 4.  The dopamine-containing neuron: maestro or simple musician in the orchestra of addiction?

Authors:  Antonello Bonci; Giorgio Bernardi; Pernilla Grillner; Nicola B Mercuri
Journal:  Trends Pharmacol Sci       Date:  2003-04       Impact factor: 14.819

Review 5.  Bath salts, mephedrone, and methylenedioxypyrovalerone as emerging illicit drugs that will need targeted therapeutic intervention.

Authors:  Richard A Glennon
Journal:  Adv Pharmacol       Date:  2014

6.  5-(2-Aminopropyl)benzofuran and phenazepam demonstrate the possibility of dependence by increasing dopamine levels in the brain.

Authors:  Hye Jin Cha; Kwang-Wook Lee; Jang-Hyeon Eom; Young-Hoon Kim; Jisoon Shin; Jaesuk Yun; Kyoungmoon Han; Hyung Soo Kim
Journal:  Pharmacol Biochem Behav       Date:  2016-08-06       Impact factor: 3.533

7.  In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1.

Authors:  Linda D Simmler; Danièle Buchy; Sylvie Chaboz; Marius C Hoener; Matthias E Liechti
Journal:  J Pharmacol Exp Ther       Date:  2016-01-20       Impact factor: 4.030

8.  Acute psychosis associated with recreational use of benzofuran 6-(2-aminopropyl)benzofuran (6-APB) and cannabis.

Authors:  Wui Ling Chan; David M Wood; Simon Hudson; Paul I Dargan
Journal:  J Med Toxicol       Date:  2013-09

9.  Evidence for the involvement of dopamine transporters in behavioral stimulant effects of modafinil.

Authors:  Dorota Zolkowska; Raka Jain; Richard B Rothman; John S Partilla; Bryan L Roth; Vincent Setola; Thomas E Prisinzano; Michael H Baumann
Journal:  J Pharmacol Exp Ther       Date:  2009-02-05       Impact factor: 4.030

Review 10.  Amphetamines, new psychoactive drugs and the monoamine transporter cycle.

Authors:  Harald H Sitte; Michael Freissmuth
Journal:  Trends Pharmacol Sci       Date:  2014-12-23       Impact factor: 14.819

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  3 in total

1.  Pharmacotherapy of Patients Taking New Psychoactive Substances: A Systematic Review and Analysis of Case Reports.

Authors:  Michal Ordak; Aleksandra Zmysłowska; Miłosz Bielski; Daniel Rybak; Maja Tomaszewska; Katarzyna Wyszomierska; Aleksandra Kmiec; Natalia Garlicka; Maria Zalewska; Michal Zalewski; Tadeusz Nasierowski; Elzbieta Muszynska; Magdalena Bujalska-Zadrozny
Journal:  Front Psychiatry       Date:  2021-04-23       Impact factor: 4.157

2.  (2-Aminopropyl)benzo[β]thiophenes (APBTs) are novel monoamine transporter ligands that lack stimulant effects but display psychedelic-like activity in mice.

Authors:  Deborah Rudin; John D McCorvy; Grant C Glatfelter; Dino Luethi; Dániel Szöllősi; Tea Ljubišić; Pierce V Kavanagh; Geraldine Dowling; Marion Holy; Kathrin Jaentsch; Donna Walther; Simon D Brandt; Thomas Stockner; Michael H Baumann; Adam L Halberstadt; Harald H Sitte
Journal:  Neuropsychopharmacology       Date:  2021-11-08       Impact factor: 8.294

3.  Domino C-C/C-O bond formation: palladium-catalyzed regioselective synthesis of 7-iodobenzo[b]furans using 1,2,3-triiodobenzenes and benzylketones.

Authors:  Raed M Al-Zoubi; Walid K Al-Jammal; Michael J Ferguson; Graham K Murphy
Journal:  RSC Adv       Date:  2021-09-08       Impact factor: 4.036

  3 in total

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