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M14951

Sigma-Aldrich

5-Methoxyindole-2-carboxylic acid

97%

Synonym(s):

NSC 30927

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About This Item

Empirical Formula (Hill Notation):
C10H9NO3
CAS Number:
4382-54-1
Molecular Weight:
191.18
Beilstein:
157478
EC Number:
224-487-6
MDL number:
MFCD00005614
UNSPSC Code:
12352100
PubChem Substance ID:
24896653
NACRES:
NA.22

Assay

97%

mp

199-201 °C (lit.)

SMILES string

COc1ccc2[nH]c(cc2c1)C(O)=O

InChI

1S/C10H9NO3/c1-14-7-2-3-8-6(4-7)5-9(11-8)10(12)13/h2-5,11H,1H3,(H,12,13)

InChI key

YEBJVSLNUMZXRJ-UHFFFAOYSA-N

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Application

Reactant for preparation of:
  • Anticancer agents
  • A fluorescent small molecule probe for in vivo lipid imaging
  • Indoleamine 2,3-dioxygenase (IDO) inhibitors
  • Selective Dopamine D3 receptor ligands
  • 5-HT4 receptor ligands
  • Inhibitors of Mycobacterium tuberculosis pantothenate synthetase
  • Hypoxia selective cytotoxins
  • Potent antitumor bifunctional DNA alkylating agents

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jinzi Wu et al.
Biochemical and biophysical research communications, 497(1), 444-450 (2018-02-16)
We previously reported that 5-methoxyindole-2-carboxylic acid (MICA) could induce preconditioning effect in the ischemic brain of rat. In the present study, we addressed the question of whether MICA could also trigger a postconditioning effect in ischemic stroke. To this end
Nathalie Sumien et al.
Behavioural brain research, 378, 112278-112278 (2019-10-21)
Stroke leads to devastating outcomes including impairments of sensorimotor and cognitive function that may be long lasting. New intervention strategies are needed to overcome the long-lasting effects of ischemic injury. Previous studies determined that treatment with 5-methoxyindole-2-carboxylic acid (MICA) conferred
Jinzi Wu et al.
Free radical biology & medicine, 113, 244-254 (2017-10-12)
The objective of this study was to investigate a possible role of mitochondrial dihydrolipoamide dehydrogenase (DLDH) as a chemical preconditioning target for neuroprotection against ischemic injury. We used 5-methoxyindole-2-carboxylic acid (MICA), a reportedly reversible DLDH inhibitor, as the preconditioning agent
Luna Yamamori et al.
Zoological science, 34(3), 173-178 (2017-06-08)
Scyphozoa, Cubozoa and Hydrozoa are classes in the phylum Cnidaria that undergo metagenesis involving a dramatic morphological transition. In Scyphozoa and Cubozoa, when exposed to species- or strain-specific transition-inducing stimuli, asexually reproducing benthic polyps transform into sexually reproducing planktonic medusae.

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