EMD-386088

EMD-386088
Clinical data
ATC code	none;
Identifiers
	IUPAC name 5-chloro-2-methyl-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole;
CAS Number	54635-62-0 ;
PubChem CID	10131112;
ChemSpider	8306627;
CompTox Dashboard (EPA)	DTXSID30436055 ;
Chemical and physical data
Formula	C14H14ClN2
Molar mass	245.73 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc2cc1c(cc2)[nH]c(C)c1C=3CCNCC=3;
	InChI InChI=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; Key:BPPGPYJBCVXILI-UHFFFAOYSA-N;
	(verify)

EMD-386088 is an indole derivative which is used in scientific research. It acts as a potent 5-HT₆ receptor partial agonist, with a K_i of 1 nM, a significantly higher affinity than older 5-HT₆ agonists such as EMDT, although it possesses moderate affinity for the 5-HT₃ receptor as well.^[1] 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.^[2]

EMD-386088 can be further reacted with a butyrophenone sidechain.^[3]

References

^ Mattsson C, Sonesson C, Sandahl A, Greiner HE, Gassen M, Plaschke J, et al. (October 2005). "2-Alkyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoles as novel 5-HT6 receptor agonists". Bioorganic & Medicinal Chemistry Letters. 15 (19): 4230–4234. doi:10.1016/j.bmcl.2005.06.067. PMID 16055331.
^ Jastrzębska-Więsek M, Siwek A, Partyka A, Antkiewicz-Michaluk L, Michaluk J, Romańska I, et al. (August 2016). "Study of a mechanism responsible for potential antidepressant activity of EMD 386088, a 5-HT6 partial agonist in rats". Naunyn-Schmiedeberg's Archives of Pharmacology. 389 (8): 839–849. doi:10.1007/s00210-016-1245-3. PMC 4939156. PMID 27106213.
^ Genus Possanza, Kurt Freter, & Sven Luttke, U.S. patent 3,980,658 (1976 to Boehringer Ingelheim GmbH).

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