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SML0139

Sigma-Aldrich

EMD386088

≥98% (HPLC)

Synonym(s):

5-Chloro-2-methyl-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-Indole hydrochloride, EMD-386088

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About This Item

Empirical Formula (Hill Notation):
C14H15ClN2 · HCl
CAS Number:
1171123-46-8
Molecular Weight:
283.20
MDL number:
MFCD09038557
UNSPSC Code:
12352202
PubChem Substance ID:
329825187
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

yellow

solubility

DMSO: ≥16 mg/mL

storage temp.

2-8°C

SMILES string

Cl.Cc1[nH]c2ccc(Cl)cc2c1C3=CCNCC3

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

InChI key

WWSNDUWIZDYGIQ-UHFFFAOYSA-N

Application

EMD386088 may be used to study 5-HT6-mediated cell signaling.

Biochem/physiol Actions

EMD-386088 is a potent serotonin 5-HT6-specific agonist. The IC50 for competition of LSD from 5-HT6 expressed in HEK cells is 7.4 nM, and the EC50 for stimulating cAMP production is 1 nM. EMD-386088 is inactive against other HT receptors except 5-HT3 (IC50 = 34 nM).
EMD386088 effectively reverses cholinergic and glutataminergic-induced deficits in cognitive functions. It may be a therapeutic option in improving associated learning in Alzheimer′s disease and schizophrenia. EMD386088 also exhibits anti-depressant and anxiolytic effects in rats.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P310

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Agnieszka Nikiforuk et al.
Psychopharmacology, 217(3), 411-418 (2011-04-19)
Preclinical data suggest a possible role for 5-HT6 receptors in depression and anxiety. However, the results of pharmacological studies are equivocal since both blockade and stimulation of 5-HT6 receptors may evoke antidepressant- and anxiolytic-like effects. In the present study, the
Magdalena Kotańska et al.
Frontiers in neuroscience, 11, 50-50 (2017-02-24)
Since 5-HT
S Woods et al.
British journal of pharmacology, 167(2), 436-449 (2012-05-10)
5-HT(6) receptors are abundant in the hippocampus, nucleus accumbens and striatum, supporting their role in learning and memory. Selective 5-HT(6) receptor antagonists produce pro-cognitive effects in several learning and memory paradigms while 5-HT(6) receptor agonists have been found to enhance
O Riccio et al.
Translational psychiatry, 1, e47-e47 (2011-01-01)
The serotonin transporter (SERT) is a key molecule involved in the homeostasis of extracellular levels of serotonin and is regulated developmentally. Genetic deletion of SERT in rodents increases extracellular levels of serotonin and affects cellular processes involved in neocortical circuit
Moritoshi Hirono et al.
Neuropharmacology, 118, 79-89 (2017-03-17)
Cerebellar Purkinje cells (PCs) project their axon collaterals to underneath of the PC layer and make GABAergic synaptic contacts with globular cells, a subgroup of Lugaro cells. GABAergic transmission derived from the PC axon collaterals is so powerful that it
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