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I18008

Sigma-Aldrich

Isonipecotic acid

97%

Synonym(s):

4-Piperidinecarboxylic acid, Hexahydroisonicotinic acid

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About This Item

Empirical Formula (Hill Notation):
C6H11NO2
CAS Number:
498-94-2
Molecular Weight:
129.16
Beilstein/REAXYS Number:
112553
EC Number:
207-872-3
MDL number:
MFCD00006004
UNSPSC Code:
12352100
PubChem Substance ID:
24278166
NACRES:
NA.22

assay

97%

mp

>300 °C (lit.)

SMILES string

OC(=O)C1CCNCC1

InChI

1S/C6H11NO2/c8-6(9)5-1-3-7-4-2-5/h5,7H,1-4H2,(H,8,9)

InChI key

SRJOCJYGOFTFLH-UHFFFAOYSA-N

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Application

Reactant for synthesis of:
  • Antibiotic nitroxoline derivatives for cathepsin B inhibition
  • Sphingosine-1-phosphate receptor agonists
  • RhoA inhibitors for cardiovascular disease therapy
  • Alkyl piperidine and piperazine hydroxamic acids as HDAC inhibitors
  • CHK1 inhibitors
  • IKK2 inhibitors for investigations into rheumatoid arthritis treatment

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Alicja Nowaczyk et al.
Journal of molecular graphics & modelling, 85, 171-181 (2018-09-17)
Inhibition of 4-aminobutanoic acid (GABA) uptake is a strategy for enhancing GABA transmission. The utility of this approach is demonstrated by the successful development of such agents for the treatment of epilepsy and pain. Existing reports on acute brain slice
Jenna Elizabeth Hunt et al.
American journal of physiology. Gastrointestinal and liver physiology, 318(5), G980-G987 (2020-04-21)
Glucagon-like peptide (GLP)-1 and -2-secreting L cells have been shown to express the bile acid receptor Takeda G protein-receptor-5 (TGR5) and increase secretion upon receptor activation. Previous studies have explored GLP-1 secretion following acute TGR5 activation, but chronic activation and
Iris Thondorf et al.
Bioorganic & medicinal chemistry, 19(21), 6409-6418 (2011-10-01)
The proton-coupled amino acid transporter hPAT1 has recently gained much interest due to its ability to transport small drugs thereby allowing their oral administration. A three-dimensional quantitative structure-activity relationship (3D QSAR) study has been performed on its natural and synthetic
Michela Semeraro et al.
Clinica chimica acta; international journal of clinical chemistry, 440, 108-112 (2014-12-03)
Pipecolic acid (PA) is an important biochemical marker for the diagnosis of peroxisomal disorders. PA is also a factor responsible for hepatic encephalopathy and a possible biomarker for pyridoxine-dependent seizures. We developed an easy and rapid PA quantification method, by
Jing Yuan et al.
Nature chemical biology, 5(10), 765-771 (2009-09-08)
Studies of gene function and molecular mechanisms in Plasmodium falciparum are hampered by difficulties in characterizing and measuring phenotypic differences between individual parasites. We screened seven parasite lines for differences in responses to 1,279 bioactive chemicals. Hundreds of compounds were
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