TCS-OX2-29

TCS-OX2-29
Identifiers
	IUPAC name (2S)-1-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-3,3-dimethyl-2-(pyridin-4-ylmethylamino)butan-1-one;
CAS Number	372523-75-6;
PubChem CID	10408514;
IUPHAR/BPS	4038;
Chemical and physical data
Formula	C23H31N3O3
Molar mass	397.509 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c3cnccc3CNC(C(C)(C)C)C(=O)N(Cc2cc1OC)CCc2cc1OC;
	(verify)

TCS-OX2-29 is an orexin antagonist. It was the first non-peptide antagonist developed that is selective for the orexin receptor subtype OX₂, with an IC₅₀ of 40nM and selectivity of around 250x for OX₂ over OX₁ receptors.^[1] Orexin antagonists are expected to be useful for the treatment of insomnia, with subtype-selective antagonists such as TCS-OX2-29 potentially offering more specificity of action compared to non-selective orexin antagonists like almorexant.^[2]

References

^ Hirose M, Egashira S, Goto Y, Hashihayata T, Ohtake N, Iwaasa H, Hata M, Fukami T, Kanatani A, Yamada K. N-acyl 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline: the first orexin-2 receptor selective non-peptidic antagonist. Bioorganic & Medicinal Chemistry Letters. 2003 Dec 15;13(24):4497-9. PMID 14643355
^ Roecker AJ, Coleman PJ. Orexin receptor antagonists: medicinal chemistry and therapeutic potential. Current Topics in Medicinal Chemistry. 2008;8(11):977-87. PMID 18673167

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[1] Hirose M, Egashira S, Goto Y, Hashihayata T, Ohtake N, Iwaasa H, Hata M, Fukami T, Kanatani A, Yamada K. N-acyl 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline: the first orexin-2 receptor selective non-peptidic antagonist. Bioorganic & Medicinal Chemistry Letters. 2003 Dec 15;13(24):4497-9. PMID 14643355

[2] Roecker AJ, Coleman PJ. Orexin receptor antagonists: medicinal chemistry and therapeutic potential. Current Topics in Medicinal Chemistry. 2008;8(11):977-87. PMID 18673167

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