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TCS-1205

From Wikipedia, the free encyclopedia

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 mass337.335 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

TCS 1205 is aGABAA receptorpositive allosteric modulator of thetryptamine family. It is abenzodiazepine siteagonist selective for certainsubunits.

Pharmacology

[edit]

TCS 1205 acts at thebenzodiazepine binding site, it is selective for theα1 andα2 subunits of theGABAA receptor.[1]In vivo, it hasanxiolytic effects but no sedative effects.[2][3]

Chemistry

[edit]

Despite acting at thebenzodiazepine receptor, it does not contain thebenzodiazepine structure, it could therefore be classed as anonbenzodiazepine. The drug is asubstituted tryptaminederivative.

References

[edit]
  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.
Alcohols
Barbiturates
Benzodiazepines
Carbamates
Flavonoids
Imidazoles
Kava constituents
Monoureides
Neuroactive steroids
Nonbenzodiazepines
Phenols
Piperidinediones
Pyrazolopyridines
Quinazolinones
Volatiles/gases
Others/unsorted
Tryptamines
4-Hydroxytryptamines
andesters/ethers
5-Hydroxy- and
5-methoxytryptamines
N-Acetyltryptamines
α-Alkyltryptamines
Cyclized tryptamines
Isotryptamines
Related compounds
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