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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

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Certificates of Analysis (COA)

Lot/Batch Number
S23987V
06822TW
01920CS
12721MR
02818BR

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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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