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{{Short description|Chemical compound}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 400123895 |
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| verifiedrevid = 424722665 |
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| IUPAC_name = 5-chloro-2-methyl-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1''H''-indole |
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| IUPAC_name = 5-chloro-2-methyl-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1''H''-indole |
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| image = EMD386088.png |
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| image = EMD-386088.svg |
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| CAS_number = 54635-62-0 |
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<!--Clinical data--> |
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| ATC_prefix = none |
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| tradename = |
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| pregnancy_category = |
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| PubChem = 10131112 |
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| legal_status = |
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| C = 14 | H = 14 | Cl = 1 | N = 2 |
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| routes_of_administration = |
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| molecular_weight = 245.727 g/mol |
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| smiles = Clc2cc1c(cc2)nc(C)c1C=3CCNCC=3 |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| bioavailability = |
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| metabolism = |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 54635-62-0 |
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| ATC_prefix = none |
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| ATC_suffix = |
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| PubChem = 10131112 |
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| ChemSpiderID = 8306627 |
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<!--Chemical data--> |
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| C=14 | H=14 | Cl=1 | N=2 |
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| smiles = Clc2cc1c(cc2)c(C)c1C=3CCNCC=3 |
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| 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 |
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| StdInChIKey = BPPGPYJBCVXILI-UHFFFAOYSA-N |
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'''EMD-386,088''' is an ] derivative which is used in ]. It acts as a ] and ] ] ], with a ] of 1 nM, a significantly higher ] than older 5-HT<sub>6</sub> agonists such as ], although it possesses moderate affinity for the ] as well.<ref>{{cite journal | last1 = Mattsson | first1 = C | last2 = Sonesson | first2 = C | last3 = Sandahl | first3 = A | last4 = Greiner | first4 = HE | last5 = Gassen | first5 = M | last6 = Plaschke | first6 = J | last7 = Leibrock | first7 = J | last8 = Böttcher | first8 = H | 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 = 4230–4 | year = 2005 | pmid = 16055331 | doi = 10.1016/j.bmcl.2005.06.067 }}</ref> |
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'''EMD-386088''' is an ] derivative which is used in ]. It acts as a ] ] ], with a ] of 1 nM, a significantly higher ] than older 5-HT<sub>6</sub> agonists such as ], although it possesses moderate affinity for the ] 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 ] and that this action is involved in the ]-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> |
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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> |
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== See also == |
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== See also == |
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* ] |
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* ] |
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== References == |
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== References == |
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{{Reflist}} |
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{{Reflist}} |
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{{Dopamine receptor modulators}} |
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{{Serotonergics}} |
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{{Serotonin receptor modulators}} |
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] |
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{{Nervous-system-drug-stub}} |