Synonym
EMD-386088 HCl; EMD 386088 HCl; EMD386088 HCl; EMD-386088 hydrochloride
IUPAC/Chemical Name
5-Chloro-2-methyl-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole hydrochloride
InChi Key
WWSNDUWIZDYGIQ-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H15ClN2.ClH/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;1H
SMILES Code
CC(N1)=C(C2=CCNCC2)C3=C1C=CC(Cl)=C3.[H]Cl
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Potent 5-HT6 agonist.
In vitro activity:
When examined the effects of EMD386088, a 5-HT6R agonist, on cell viability, this study found that EMD386088 potentiated cell death in cultured neuronal, native HEK293, and HEK/HA-5-HT6R cells. The results demonstrated that EMD386088 induces its cytotoxic effects, regardless of the presence of 5-HT6Rs, by the downregulation of ERK1/2 activities.
Reference: Toxicol In Vitro. 2011 Dec;25(8):2035-40. https://pubmed.ncbi.nlm.nih.gov/21864673/
In vivo activity:
The acute treatment with EMD386088 caused significant increases in CREB and BDNF protein levels in PFC, and an increase in BDNF in Hp of OB rats, while AMI injection decreased CREB and did not change BDNF levels. After the chronic administration of EMD386088, the increasing levels of BDNF and CREB were still observed in PFC and Hp.
Reference: Pharmacol Rep. 2018 Dec;70(6):1047-1056. https://pubmed.ncbi.nlm.nih.gov/30292720/
|
Solvent |
mg/mL |
mM |
| Solubility |
| Water |
7.1 |
25.00 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
283.19
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Jastrzębska-Więsek M, Siwek A, Kazek G, Nawieśniak B, Partyka A, Marcinkowska M, Kołaczkowski M, Wesołowska A. Partial agonist efficacy of EMD386088, a 5-HT6 receptor ligand, in functional in vitro assays. Pharmacol Rep. 2013;65(4):998-1005. doi: 10.1016/s1734-1140(13)71081-8. PMID: 24145094.
2. Yun HM, Rhim H. 5-HT6 receptor ligands, EMD386088 and SB258585, differentially regulate 5-HT6 receptor-independent events. Toxicol In Vitro. 2011 Dec;25(8):2035-40. doi: 10.1016/j.tiv.2011.08.004. Epub 2011 Aug 16. PMID: 21864673.
3. Jastrzębska-Więsek M, Gdula-Argasińska J, Siwek A, Partyka A, Szewczyk B, Kołaczkowski M, Wesołowska A. Chronic antidepressant-like effect of EMD386088, a partial 5-HT6 receptor agonist, in olfactory bulbectomy model may be connected with BDNF and/or CREB signalling pathway. Pharmacol Rep. 2018 Dec;70(6):1047-1056. doi: 10.1016/j.pharep.2018.05.009. Epub 2018 May 24. PMID: 30292720.
4. Amodeo DA, Peterson S, Pahua A, Posadas R, Hernandez A, Hefner E, Qi D, Vega J. 5-HT6 receptor agonist EMD386088 impairs behavioral flexibility and working memory. Behav Brain Res. 2018 Sep 3;349:8-15. doi: 10.1016/j.bbr.2018.04.032. Epub 2018 Apr 30. PMID: 29715539.
In vitro protocol:
1. Jastrzębska-Więsek M, Siwek A, Kazek G, Nawieśniak B, Partyka A, Marcinkowska M, Kołaczkowski M, Wesołowska A. Partial agonist efficacy of EMD386088, a 5-HT6 receptor ligand, in functional in vitro assays. Pharmacol Rep. 2013;65(4):998-1005. doi: 10.1016/s1734-1140(13)71081-8. PMID: 24145094.
2. Yun HM, Rhim H. 5-HT6 receptor ligands, EMD386088 and SB258585, differentially regulate 5-HT6 receptor-independent events. Toxicol In Vitro. 2011 Dec;25(8):2035-40. doi: 10.1016/j.tiv.2011.08.004. Epub 2011 Aug 16. PMID: 21864673.
In vivo protocol:
1. Jastrzębska-Więsek M, Gdula-Argasińska J, Siwek A, Partyka A, Szewczyk B, Kołaczkowski M, Wesołowska A. Chronic antidepressant-like effect of EMD386088, a partial 5-HT6 receptor agonist, in olfactory bulbectomy model may be connected with BDNF and/or CREB signalling pathway. Pharmacol Rep. 2018 Dec;70(6):1047-1056. doi: 10.1016/j.pharep.2018.05.009. Epub 2018 May 24. PMID: 30292720.
2. Amodeo DA, Peterson S, Pahua A, Posadas R, Hernandez A, Hefner E, Qi D, Vega J. 5-HT6 receptor agonist EMD386088 impairs behavioral flexibility and working memory. Behav Brain Res. 2018 Sep 3;349:8-15. doi: 10.1016/j.bbr.2018.04.032. Epub 2018 Apr 30. PMID: 29715539.
1: Jastrzębska-Więsek M, Siwek A, Partyka A, Antkiewicz-Michaluk L, Michaluk J, Romańska I, Kołaczkowski M, Wesołowska A. Study of a mechanism responsible for potential antidepressant activity of EMD 386088, a 5-HT6 partial agonist in rats. Naunyn Schmiedebergs Arch Pharmacol. 2016 Aug;389(8):839-49. doi: 10.1007/s00210-016-1245-3. PubMed PMID: 27106213; PubMed Central PMCID: PMC4939156.
2: Jastrzębska-Więsek M, Siwek A, Partyka A, Szewczyk B, Sowa-Kućma M, Wasik A, Kołaczkowski M, Wesołowska A. Antidepressant-like activity of EMD 386088, a 5-HT6 receptor partial agonist, following systemic acute and chronic administration to rats. Naunyn Schmiedebergs Arch Pharmacol. 2015 Oct;388(10):1079-88. doi: 10.1007/s00210-015-1141-2. PubMed PMID: 26077660.
3: Jastrzębska-Więsek M, Siwek A, Partyka A, Kubacka M, Mogilski S, Wasik A, Kołaczkowski M, Wesołowska A. Pharmacological evaluation of the anxiolytic-like effects of EMD 386088, a partial 5-HT6 receptor agonist, in the rat elevated plus-maze and Vogel conflict tests. Neuropharmacology. 2014 Oct;85:253-62. doi: 10.1016/j.neuropharm.2014.05.036. PubMed PMID: 24905144.
4: Nikiforuk A, Fijał K, Potasiewicz A, Popik P, Kos T. The 5-hydroxytryptamine (serotonin) receptor 6 agonist EMD 386088 ameliorates ketamine-induced deficits in attentional set shifting and novel object recognition, but not in the prepulse inhibition in rats. J Psychopharmacol. 2013 May;27(5):469-76. doi: 10.1177/0269881113480991. PubMed PMID: 23479455.
5: Nikiforuk A, Kos T, Wesołowska A. The 5-HT6 receptor agonist EMD 386088 produces antidepressant and anxiolytic effects in rats after intrahippocampal administration. Psychopharmacology (Berl). 2011 Oct;217(3):411-8. doi: 10.1007/s00213-011-2297-1. PubMed PMID: 21499701.
