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265128

Sigma-Aldrich

5-Fluoroindole-2-carboxylic acid

99%

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About This Item

Empirical Formula (Hill Notation):
C9H6FNO2
CAS Number:
399-76-8
Molecular Weight:
179.15
EC Number:
206-919-5
MDL number:
MFCD00005612
UNSPSC Code:
12352100
PubChem Substance ID:
24277978
NACRES:
NA.22

Assay

99%

form

solid

mp

259 °C (dec.) (lit.)

SMILES string

OC(=O)c1cc2cc(F)ccc2[nH]1

InChI

1S/C9H6FNO2/c10-6-1-2-7-5(3-6)4-8(11-7)9(12)13/h1-4,11H,(H,12,13)

InChI key

WTXBRZCVLDTWLP-UHFFFAOYSA-N

Related Categories

General description

5-Fluoroindole-2-carboxylic acid is an antagonist of the glycine site within the NMDA (N-methyl-D-aspartate) receptor complex.

Application

Reactant for the synthesis of:
  • Fungicidal agents
  • Antitumor agents
  • 2,3-dioxygenase (IDO) inhibitors
  • Factor Xa inhibitors
  • Enantioselective D3 receptor antagonists
  • Ligands for hFPRL1 (or ALXR) receptor in inflammation
  • Antibacterial agents
  • Inhibitors of hepatitis C virus NS3·4A protease

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

265128-5G:
265128-1G:
265128-VAR:
265128-100G:
265128-BULK:

Certificates of Analysis (COA)

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R Bakshi et al.
Neuroscience letters, 110(1-2), 113-117 (1990-03-02)
Intrathecal (i.t.) administration of the opioid dynorphin causes neurological dysfunction and tissue damage. It has been suggested that these effects of dynorphin may be mediated, in part, by N-methyl-D-aspartate (NMDA) receptors. In the present studies, recently developed compounds that block
R Kapoor et al.
Clinical and experimental pharmacology & physiology, 25(3-4), 216-219 (1998-05-20)
1. The effects of the specific N-methyl-D-aspartate (NMDA)-glycine site antagonist 5-fluoro indole-2-carboxylic acid (FICA) and NMDA, microinjected into the vasodepressor caudal ventrolateral medulla, were compared in spontaneously hypertensive rats (SHR) and in Wistar-Kyoto (WKY) rats. 2. 5-Fluoro indole-2-carboxylic acid elicited
Chung-Yi Wu et al.
Chemistry & biology, 13(3), 261-268 (2006-04-28)
Severe acute respiratory syndrome (SARS) is caused by a newly emerged coronavirus that infected more than 8000 individuals and resulted in more than 800 fatalities in 2003. Currently, there is no effective treatment for this epidemic. SARS-3CL(pro) has been shown
T J Grudt et al.
Molecular pharmacology, 37(4), 477-481 (1990-04-01)
Whole-cell and single-channel patch-clamp recordings from hippocampal neurons in culture have been used to study the receptor channel selectivity of the glutamate analog quisqualate. The dose-response relationship of quisqualate acting at the N-methyl-D-aspartate (NMDA) receptor was measured as that portion
R Kamiński et al.
Journal of neural transmission (Vienna, Austria : 1996), 105(2-3), 133-146 (1998-07-11)
5-Fluoroindole-2-carboxylic acid, an antagonist of the glycine site within the NMDA receptor complex, administered intraperitoneally in doses of 150 and 200 mg/kg, 120 min before electroconvulsions, significantly raised the convulsive threshold from 6.8 to 7.9 and 8.3 mA, respectively. At
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