3-Hydroxy agomelatine

• CAT Number: R027519
• CAS Number: 166526-99-4
• Molecular Formula: C15H17NO3
• Molecular Weight: 259.30
• Purity: ≥95%
• Synonyms: N-[2-(3-hydroxy-7-methoxynaphthalen-1-yl)ethyl]acetamide
• InChI: InChI=1S/C15H17NO3/c1-10(17)16-6-5-12-8-13(18)7-11-3-4-14(19-2)9-15(11)12/h3-4,7-9,18H,5-6H2,1-2H3,(H,16,17)
• InChIKey: VUBBOOVHTBZRTJ-UHFFFAOYSA-N
• SMILES: CC(=O)NCCC1=C2C=C(C=CC2=CC(=C1)O)OC

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].
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].
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].

Reference

[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.
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