ST1936

Names

[ Name ]:
ST1936

[Synonym ]:
2-(5-Chloro-2-methyl-1H-indol-3-yl)-N,N-dimethylethanamine
ST-1936
1H-Indole-3-ethanamine, 5-chloro-N,N,2-trimethyl-

Biological Activity

[Description]:

ST1936 is a selective, nanomolar affinity 5-HT6 receptor agonist with Ki values of 13 nM, 168 nM and 245 nM for human 5-HT6, 5-HT7 and 5-HT2B receptors, respectively. ST1936 also shows moderate affinity (Ki of 300 nM) for human and rat α2 adrenergic receptor[1].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor

Research Areas >> Neurological Disease

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor

Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor

[Target]

5-HT6 Receptor:13 nM (Ki)

5-HT7 Receptor:168 nM (Ki)

5-HT2B Receptor:245 nM (Ki)

α1-adrenergic receptor:390 nM (Ki, rat)

α2-adrenergic receptor:300 nM (Ki, rat)

α2-adrenergic receptor:300 nM (Ki, human)

[In Vitro]

ST1936 appears to be relatively selective for 5-HT6 receptors, although it has shown affinity also for 5-HT2B, 5-HT1A, 5-HT7 receptor and α-adrenergic receptors when tested in a broad crossreactivity panel that comprised G-protein-coupled receptors, ion channel binding sites, enzymes, and transporters[1]. ST1936 behaves as a full 5-HT6 agonist on cloned cells and is able to increase Ca2+ concentration, phosphorylation of Fyn kinase, and regulate the activation of ERK1/2 that is a downstream target of Fyn kinase[2]. ST1936 reduces the frequency of spontaneous excitatory postsynaptic currents, with an IC50 of 1.3 μM[3].

[In Vivo]

ST1936 (5, 10, 20 mg/kg; i.p.) increases in a dose dependent manner extracellular dopamine (DA) and NA levels in the prefrontal cortex (PFCX)[4]. ST1936 (5, 10, 20 mg/kg; i.p.) increases extracellular DA and NA levels in the nucleus accumbens (NAc) core. Doses of 10 mg/kg increases dialysate DA (peak: 179%) while higher dose increases both DA and NA dialysates (201% and 231%, respectively). Doses of 5 mg/kg does not produce any effect[4].

[References]

[1]. Borsini F, et al. Effects of ST1936, a selective serotonin-6 agonist, on electrical activity of putative mesencephalic dopaminergic neurons in the rat brain. J Psychopharmacol. 2015 Jul;29(7):802-11.

[2]. Riccioni T, et al. ST1936 stimulates cAMP, Ca2+, ERK1/2 and Fyn kinase through a full activation of cloned human 5-HT6 receptors. Eur J Pharmacol. 2011;661(1-3):8-14.

[3]. Tassone A, et al. Activation of 5-HT6 receptors inhibits corticostriatal glutamatergic transmission. Neuropharmacology. 2011;61(4):632-637.

[4]. Valentini V, et al. A microdialysis study of ST1936, a novel 5-HT6 receptor agonist. Neuropharmacology. 2011;60(4):602-608.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
377.0±42.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₃H₁₇ClN₂

[ Molecular Weight ]:
236.740

[ Flash Point ]:
181.8±27.9 °C

[ Exact Mass ]:
236.108032

[ LogP ]:
3.31

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.614

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ RIDADR ]:
NONH for all modes of transport

Related Compounds

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