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;
CompTox Dashboard (EPA)	DTXSID801028419 ;
Chemical and physical data
Formula	C23H31N3O3
Molar mass	397.519 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, et al. (December 2003). "N-acyl 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline: the first orexin-2 receptor selective non-peptidic antagonist". Bioorganic & Medicinal Chemistry Letters. 13 (24): 4497–9. doi:10.1016/j.bmcl.2003.08.038. PMID 14643355.
^ Roecker AJ, Coleman PJ (2008). "Orexin receptor antagonists: medicinal chemistry and therapeutic potential". Current Topics in Medicinal Chemistry. 8 (11): 977–87. doi:10.2174/156802608784936746. PMID 18673167.

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[1] Hirose M, Egashira S, Goto Y, Hashihayata T, Ohtake N, Iwaasa H, et al. (December 2003). "N-acyl 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline: the first orexin-2 receptor selective non-peptidic antagonist". Bioorganic & Medicinal Chemistry Letters. 13 (24): 4497–9. doi:10.1016/j.bmcl.2003.08.038. PMID 14643355.

[2] Roecker AJ, Coleman PJ (2008). "Orexin receptor antagonists: medicinal chemistry and therapeutic potential". Current Topics in Medicinal Chemistry. 8 (11): 977–87. doi:10.2174/156802608784936746. PMID 18673167.

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[2]

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
CompTox Dashboard (EPA)	DTXSID801028419
Chemical and physical data
Formula	C₂₃H₃₁N₃O₃
Molar mass	397.519 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES c3cnccc3CNC(C(C)(C)C)C(=O)N(Cc2cc1OC)CCc2cc1OC
(verify)