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(S)-Amisulpride

Names

[ CAS No. ]:
71675-92-8

[ Name ]:
(S)-Amisulpride

[Synonym ]:
4-Amino-N-{[(2S)-1-ethyl-2-pyrrolidinyl]methyl}-5-(ethylsulfonyl)-2-methoxybenzamide
EINECS 275-831-7
(S)-AMISULPRIDE
Benzamide, 4-amino-N-[[(2S)-1-ethyl-2-pyrrolidinyl]methyl]-5-(ethylsulfonyl)-2-methoxy-
ES3TWM82E8

Biological Activity

[Description]:

(S)-Amisulpride (Esamisulpride) is a potent dopamine D2/D3 receptor antagonist. (S)-Amisulpride is an antagonist at the 5-HT7 receptor with a KI of 900 nM. (S)-Amisulpride has antipsychotic and antidepressant effects[1][2].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Dopamine Receptor
Signaling Pathways >> Neuronal Signaling >> Dopamine Receptor
Research Areas >> Neurological Disease
Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor
Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor

[Target]

D2 Receptor

D3 Receptor

5-HT7 Receptor:900 nM (Ki)


[In Vitro]

(S)-Amisulpride (Esamisulpride) displays high affinity binding at both D2 and D3 receptors and is approximately twice as potent as racamisulpride and 20–50 times more potent than (R)-amisulpride at these receptors[2]

[In Vivo]

The (S)-amisulpride (10mg/kg, s.c.) stimulus is rapidly acquired and was shown to be dose-related, time dependent (effective between 30 and 120min) and stereoselective male C57BL/6 mice[1].

[References]

[1]. Timothy J Donahue, et al. (S)-amisulpride as a discriminative stimulus in C57BL/6 mice and its comparison to the stimulus effects of typical and atypical antipsychotics. Eur J Pharmacol. 2014 Jul 5;734:15-22.

[2]. Vincent Grattan, et al. Antipsychotic Benzamides Amisulpride and LB-102 Display Polypharmacy as Racemates, S Enantiomers Engage Receptors D2 and D3, while R Enantiomers Engage 5-HT7. ACS Omega. 2019 Aug 15;4(9):14151-14154.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
558.9±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C17H27N3O4S

[ Molecular Weight ]:
369.48

[ Flash Point ]:
291.8±30.1 °C

[ Exact Mass ]:
369.172241

[ LogP ]:
1.60

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.546

Related Compounds