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TCS-1205

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TCS-1205
Names
IUPAC name
2-(5-Nitro-1H-indol-3-yl)-2-oxo-N-[(1R)-1-phenylethyl]acetamide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • Key: VCKKJKQZHHPPDR-LLVKDONJSA-N
  • InChI=1S/C18H15N3O4/c1-11(12-5-3-2-4-6-12)20-18(23)17(22)15-10-19-16-8-7-13(21(24)25)9-14(15)16/h2-11,19H,1H3,(H,20,23)/t11-/m1/s1
  • CC(C1=CC=CC=C1)NC(=O)C(=O)C2=CNC3=C2C=C(C=C3)[N+](=O)[O-]
Properties
C18H15N3O4
Molar mass 337.335 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

TCS 1205 is a GABAA receptor positive allosteric modulator of the tryptamine family. It is a benzodiazepine site agonist selective for certain subunits.

Pharmacology

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TCS 1205 acts at the benzodiazepine binding site, it is selective for the α1 and α2 subunits of the GABAA receptor.[1] In vivo, it has anxiolytic effects but no sedative effects.[2][3]

Chemistry

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Despite acting at the benzodiazepine receptor, it does not contain the benzodiazepine structure, it could therefore be classed as a nonbenzodiazepine. The drug is a substituted tryptamine derivative.

References

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  1. ↑ "TCS 1205" (PDF). Certificate of Analysis. Tocris Bioscience.
  2. ↑ "TCS 1205". AbMole BioScience.
  3. ↑ Taliani S, Cosimelli B, Da Settimo F, Marini AM, La Motta C, Simorini F, et al. (June 2009). "Identification of anxiolytic/nonsedative agents among indol-3-ylglyoxylamides acting as functionally selective agonists at the gamma-aminobutyric acid-A (GABAA) alpha2 benzodiazepine receptor". Journal of Medicinal Chemistry. 52 (12): 3723–3734. doi:10.1021/jm9001154. PMID 19469479.
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