Structure–Activity Relationship of Novel Second-Generation Synthetic Cathinones: Mechanism of Action, Locomotion, Reward, and Immediate-Early Genes Article Swipe
Núria Nadal‐Gratacós
,
Ana Sofia Alberto‐Silva
,
Míriam Rodríguez-Soler
,
Edurne Urquizu
,
María Espinosa‐Velasco
,
Kathrin Jäntsch
,
Marion Holy
,
Xavier Batllori
,
Xavier Berzosa
,
David Pubill
,
Jordi Camarasa
,
Harald H. Sitte
,
Elena Escubedo
,
Raúl López‐Arnau
·
YOU?
·
· 2021
· Open Access
·
· DOI: https://doi.org/10.3389/fphar.2021.749429
YOU?
·
· 2021
· Open Access
·
· DOI: https://doi.org/10.3389/fphar.2021.749429
Several new synthetic cathinones, which mimic the effect of classical psychostimulants such as cocaine or MDMA, have appeared in the global illicit drug market in the last decades. In fact, the illicit drug market is continually evolving by constantly adding small modifications to the common chemical structure of synthetic cathinones. Thus, the aim of this study was to investigate the in vitro and in vivo structure–activity relationship (SAR) of six novel synthetic cathinones currently popular as recreational drugs, pentedrone, pentylone, N-ethyl-pentedrone (NEPD), N-ethyl-pentylone (NEP), 4-methyl-pentedrone (4-MPD), and 4-methyl-ethylaminopentedrone (4-MeAP), which structurally differ in the absence or presence of different aromatic substituents and in their amino terminal group. Human embryonic kidney (HEK293) cells expressing the human isoforms of SERT and DAT were used for the uptake inhibition and release assays. Moreover, Swiss CD-1 mice were used to investigate the psychostimulant effect, rewarding properties (3, 10, and 30 mg/kg, i.p.), and the induction of immediate-early genes (IEGs), such as Arc and c-fos in the dorsal striatum (DS) and ventral striatum (VS) as well as bdnf in the medial prefrontal cortex (mPFC), of the test compounds. Our results demonstrated that all tested synthetic cathinones are potent dopamine (DA) uptake inhibitors, especially the N-ethyl analogs, while the ring-substituted cathinones tested showed higher potency as SERT inhibitors than their no ring-substituted analogs. Moreover, unlike NEP, the remaining test compounds showed clear “hybrid” properties, acting as DAT blockers but SERT substrates. Regarding the locomotion, NEP and NEPD were more efficacious (10 mg/kg) than their N-methyl analogs, which correlates with their higher potency inhibiting the DAT and an overexpression of Arc levels in the DS and VS. Furthermore, all compounds tested induced an increase in c-fos expression in the DS, except for 4-MPD, the least effective compound in inducing hyperlocomotion. Moreover, NEP induced an up-regulation of bdnf in the mPFC that correlates with its 5-HTergic properties. Finally, the present study demonstrated for the first time that NEP, 4-MPD, and 4-MeAP induce reward in mice. Altogether, this study provides valuable information about the mechanism of action and psychostimulant and rewarding properties as well as changes in the expression of IEGs related to addiction induced by novel second-generation synthetic cathinones.
Related Topics
Concepts
Dopamine
Pharmacology
Chemistry
Behavioural despair test
Striatum
In vivo
Neuroscience
Biology
Hippocampus
Antidepressant
Biotechnology
Metadata
- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.3389/fphar.2021.749429
- OA Status
- gold
- Cited By
- 31
- References
- 75
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W3210645845
All OpenAlex metadata
Raw OpenAlex JSON
- OpenAlex ID
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https://openalex.org/W3210645845Canonical identifier for this work in OpenAlex
- DOI
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https://doi.org/10.3389/fphar.2021.749429Digital Object Identifier
- Title
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Structure–Activity Relationship of Novel Second-Generation Synthetic Cathinones: Mechanism of Action, Locomotion, Reward, and Immediate-Early GenesWork title
- Type
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articleOpenAlex work type
- Language
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enPrimary language
- Publication year
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2021Year of publication
- Publication date
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2021-10-26Full publication date if available
- Authors
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Núria Nadal‐Gratacós, Ana Sofia Alberto‐Silva, Míriam Rodríguez-Soler, Edurne Urquizu, María Espinosa‐Velasco, Kathrin Jäntsch, Marion Holy, Xavier Batllori, Xavier Berzosa, David Pubill, Jordi Camarasa, Harald H. Sitte, Elena Escubedo, Raúl López‐ArnauList of authors in order
- Landing page
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https://doi.org/10.3389/fphar.2021.749429Publisher landing page
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YesWhether a free full text is available
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goldOpen access status per OpenAlex
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https://doi.org/10.3389/fphar.2021.749429Direct OA link when available
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Dopamine, Pharmacology, Chemistry, Behavioural despair test, Striatum, In vivo, Neuroscience, Biology, Hippocampus, Antidepressant, BiotechnologyTop concepts (fields/topics) attached by OpenAlex
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31Total citation count in OpenAlex
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2025: 7, 2024: 11, 2023: 7, 2022: 5, 2021: 1Per-year citation counts (last 5 years)
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75Number of works referenced by this work
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-
10Other works algorithmically related by OpenAlex
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| abstract_inverted_index.(mPFC), | 178 |
| abstract_inverted_index.N-ethyl | 199 |
| abstract_inverted_index.Several | 0 |
| abstract_inverted_index.absence | 94 |
| abstract_inverted_index.assays. | 128 |
| abstract_inverted_index.changes | 346 |
| abstract_inverted_index.cocaine | 13 |
| abstract_inverted_index.effect, | 139 |
| abstract_inverted_index.illicit | 21, 31 |
| abstract_inverted_index.induced | 274, 295, 355 |
| abstract_inverted_index.popular | 74 |
| abstract_inverted_index.potency | 208, 255 |
| abstract_inverted_index.present | 311 |
| abstract_inverted_index.related | 352 |
| abstract_inverted_index.release | 127 |
| abstract_inverted_index.results | 184 |
| abstract_inverted_index.ventral | 166 |
| abstract_inverted_index.(4-MPD), | 85 |
| abstract_inverted_index.(HEK293) | 110 |
| abstract_inverted_index.Finally, | 309 |
| abstract_inverted_index.N-methyl | 248 |
| abstract_inverted_index.analogs, | 200, 249 |
| abstract_inverted_index.analogs. | 216 |
| abstract_inverted_index.appeared | 17 |
| abstract_inverted_index.aromatic | 99 |
| abstract_inverted_index.blockers | 231 |
| abstract_inverted_index.chemical | 45 |
| abstract_inverted_index.compound | 289 |
| abstract_inverted_index.decades. | 27 |
| abstract_inverted_index.dopamine | 193 |
| abstract_inverted_index.evolving | 36 |
| abstract_inverted_index.increase | 276 |
| abstract_inverted_index.inducing | 291 |
| abstract_inverted_index.isoforms | 115 |
| abstract_inverted_index.presence | 96 |
| abstract_inverted_index.provides | 330 |
| abstract_inverted_index.striatum | 163, 167 |
| abstract_inverted_index.terminal | 105 |
| abstract_inverted_index.valuable | 331 |
| abstract_inverted_index.(4-MeAP), | 88 |
| abstract_inverted_index.5-HTergic | 307 |
| abstract_inverted_index.Moreover, | 129, 217, 293 |
| abstract_inverted_index.Regarding | 235 |
| abstract_inverted_index.addiction | 354 |
| abstract_inverted_index.classical | 9 |
| abstract_inverted_index.compounds | 223, 272 |
| abstract_inverted_index.currently | 73 |
| abstract_inverted_index.different | 98 |
| abstract_inverted_index.effective | 288 |
| abstract_inverted_index.embryonic | 108 |
| abstract_inverted_index.induction | 150 |
| abstract_inverted_index.mechanism | 335 |
| abstract_inverted_index.remaining | 221 |
| abstract_inverted_index.rewarding | 140, 341 |
| abstract_inverted_index.structure | 46 |
| abstract_inverted_index.synthetic | 2, 48, 71, 189, 359 |
| abstract_inverted_index.cathinones | 72, 190, 204 |
| abstract_inverted_index.compounds. | 182 |
| abstract_inverted_index.constantly | 38 |
| abstract_inverted_index.correlates | 251, 304 |
| abstract_inverted_index.especially | 197 |
| abstract_inverted_index.expressing | 112 |
| abstract_inverted_index.expression | 279, 349 |
| abstract_inverted_index.inhibiting | 256 |
| abstract_inverted_index.inhibition | 125 |
| abstract_inverted_index.inhibitors | 211 |
| abstract_inverted_index.pentylone, | 79 |
| abstract_inverted_index.prefrontal | 176 |
| abstract_inverted_index.properties | 141, 342 |
| abstract_inverted_index.Altogether, | 327 |
| abstract_inverted_index.cathinones, | 3 |
| abstract_inverted_index.cathinones. | 49, 360 |
| abstract_inverted_index.continually | 35 |
| abstract_inverted_index.efficacious | 243 |
| abstract_inverted_index.information | 332 |
| abstract_inverted_index.inhibitors, | 196 |
| abstract_inverted_index.investigate | 58, 136 |
| abstract_inverted_index.locomotion, | 237 |
| abstract_inverted_index.pentedrone, | 78 |
| abstract_inverted_index.properties, | 227 |
| abstract_inverted_index.properties. | 308 |
| abstract_inverted_index.substrates. | 234 |
| abstract_inverted_index.Furthermore, | 270 |
| abstract_inverted_index.demonstrated | 185, 313 |
| abstract_inverted_index.recreational | 76 |
| abstract_inverted_index.relationship | 66 |
| abstract_inverted_index.structurally | 90 |
| abstract_inverted_index.substituents | 100 |
| abstract_inverted_index.“hybrid” | 226 |
| abstract_inverted_index.modifications | 41 |
| abstract_inverted_index.up-regulation | 297 |
| abstract_inverted_index.overexpression | 261 |
| abstract_inverted_index.immediate-early | 152 |
| abstract_inverted_index.psychostimulant | 138, 339 |
| abstract_inverted_index.hyperlocomotion. | 292 |
| abstract_inverted_index.psychostimulants | 10 |
| abstract_inverted_index.ring-substituted | 203, 215 |
| abstract_inverted_index.N-ethyl-pentylone | 82 |
| abstract_inverted_index.second-generation | 358 |
| abstract_inverted_index.N-ethyl-pentedrone | 80 |
| abstract_inverted_index.4-methyl-pentedrone | 84 |
| abstract_inverted_index.structure–activity | 65 |
| abstract_inverted_index.4-methyl-ethylaminopentedrone | 87 |
| cited_by_percentile_year.max | 99 |
| cited_by_percentile_year.min | 89 |
| corresponding_author_ids | https://openalex.org/A5019145772, https://openalex.org/A5009158490 |
| countries_distinct_count | 2 |
| institutions_distinct_count | 14 |
| corresponding_institution_ids | https://openalex.org/I71999127 |
| sustainable_development_goals[0].id | https://metadata.un.org/sdg/3 |
| sustainable_development_goals[0].score | 0.8199999928474426 |
| sustainable_development_goals[0].display_name | Good health and well-being |
| citation_normalized_percentile.value | 0.94135429 |
| citation_normalized_percentile.is_in_top_1_percent | False |
| citation_normalized_percentile.is_in_top_10_percent | True |