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3-Hydroxy agomelatine

Names

[ CAS No. ]:
166526-99-4

[ Name ]:
3-Hydroxy agomelatine

[Synonym ]:
N-[2-(3-Hydroxy-7-methoxy-1-naphthyl)ethyl]acetamide
Acetamide, N-[2-(3-hydroxy-7-methoxy-1-naphthalenyl)ethyl]-
N-(2-(3-hydroxy-7-methoxynaphthalen-1-yl)ethyl)acetamide

Biological Activity

[Description]:

3-Hydroxy agomelatine is a metabolite of Agomelatine. 3-Hydroxy agomelatine is a 5-HT2C receptor antagonist with an IC50 of 3.2 μM and a Ki of 1.8 μM[1].

[Related Catalog]:

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

[Target]

5-HT2C Receptor:3.2 μM (IC50)

5-HT2C Receptor:1.8 μM (Ki)


[In Vitro]

Agomelatine and S 21517 have moderately high affinities for 5-HT2C receptors (Ki = 0.21 μM and 0.13 μM, respectively). The metabolite 3-Hydroxy agomelatine (S 21540) has a 10-fold lower affinity (Ki = 1.8 μM). Agomelatine, S 21517 and 3-Hydroxy agomelatine (10-7-10-4 M) are antagonists at 5-HT2C receptors, with a rank order of efficacy as follows: S 21517>Agomelatine>3-Hydroxy agomelatine[1].

[In Vivo]

Increasing doses (from 1.25 to 40 mg/kg, intraperitoneal injection) of 3-Hydroxy agomelatine (S 21540) does not affect the penile erections induced by mCPP and Ro 60-0175 in Wistar rat[1].

[References]

[1]. Chagraoui A, et al. Agomelatine(S 20098) antagonizes the penile erections induced by the stimulation of 5-HT2C receptors in Wistar rats. Psychopharmacology (Berl). 2003 Oct;170(1):17-22.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
545.8±40.0 °C at 760 mmHg

[ Molecular Formula ]:
C15H17NO3

[ Molecular Weight ]:
259.300

[ Flash Point ]:
283.9±27.3 °C

[ Exact Mass ]:
259.120850

[ LogP ]:
1.53

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

[ Index of Refraction ]:
1.606

Related Compounds