View source for EMD-386088

{{Short description|Chemical compound}}
{{Drugbox
| verifiedrevid = 424722665
| IUPAC_name = 5-chloro-2-methyl-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1''H''-indole
| image = EMD-386088.svg
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| tradename =
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| routes_of_administration =
<!--Pharmacokinetic data-->
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<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 54635-62-0
| ATC_prefix = none
| ATC_suffix =
| PubChem = 10131112
| ChemSpiderID      = 8306627
<!--Chemical data-->
| C=14 | H=14 | Cl=1 | N=2
| smiles = Clc2cc1c(cc2)[nH]c(C)c1C=3CCNCC=3
| StdInChI          = 1S/C14H15ClN2/c1-9-14(10-4-6-16-7-5-10)12-8-11(15)2-3-13(12)17-9/h2-4,8,16-17H,5-7H2,1H3
| StdInChIKey       = BPPGPYJBCVXILI-UHFFFAOYSA-N
}}
'''EMD-386088''' is an [[indole]] derivative which is used in [[scientific research]]. It acts as a [[potency (pharmacology)|potent]] [[5-HT6 receptor|5-HT<sub>6</sub> receptor]] [[partial agonist]], with a [[Dissociation constant|K<sub>i</sub>]] of 1 nM, a significantly higher [[affinity (pharmacology)|affinity]] than older 5-HT<sub>6</sub> agonists such as [[EMDT]], although it possesses moderate affinity for the [[5-HT3 receptor|5-HT<sub>3</sub> receptor]] as well.<ref>{{cite journal | vauthors = Mattsson C, Sonesson C, Sandahl A, Greiner HE, Gassen M, Plaschke J, Leibrock J, Böttcher H | display-authors = 6 | title = 2-Alkyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoles as novel 5-HT6 receptor agonists | journal = Bioorganic & Medicinal Chemistry Letters | volume = 15 | issue = 19 | pages = 4230–4234 | date = October 2005 | pmid = 16055331 | doi = 10.1016/j.bmcl.2005.06.067 }}</ref> Subsequent research has determined that EMD-386088 is also a [[dopamine reuptake inhibitor]] and that this action is involved in the [[antidepressant]]-like effects of the drug in rodents.<ref name="pmid27106213">{{cite journal | vauthors = Jastrzębska-Więsek M, Siwek A, Partyka A, Antkiewicz-Michaluk L, Michaluk J, Romańska I, Kołaczkowski M, Wesołowska A | display-authors = 6 | title = Study of a mechanism responsible for potential antidepressant activity of EMD 386088, a 5-HT6 partial agonist in rats | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 389 | issue = 8 | pages = 839–849 | date = August 2016 | pmid = 27106213 | pmc = 4939156 | doi = 10.1007/s00210-016-1245-3 }}</ref>
EMD-386088 can be further reacted with a butyrophenone sidechain.<ref>Genus Possanza, Kurt Freter, & Sven Luttke, {{US patent|3980658}} (1976 to Boehringer Ingelheim GmbH).</ref>
== See also ==
* [[EMDT]]
* [[ST-1936]]
== References ==
{{Reflist}}
{{Dopamine receptor modulators}}
{{Serotonin receptor modulators}}
[[Category:5-HT6 agonists]]
[[Category:Dopamine reuptake inhibitors]]
[[Category:Indoles]]
[[Category:Tetrahydropyridines]]
[[Category:Chloroarenes]]
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