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656364

Sigma-Aldrich

(S)-(+)-3-Piperidinecarboxylic acid

97%

Synonym(s):

(S)-(+)-Nipecotic acid

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About This Item

Empirical Formula (Hill Notation):
C6H11NO2
CAS Number:
59045-82-8
Molecular Weight:
129.16
MDL number:
MFCD01630807
UNSPSC Code:
12352005
PubChem Substance ID:
24884154
NACRES:
NA.22

Assay

97%

form

solid

optical activity

[α]/D 3.0 to 6.5°, c = 1 in H2O

mp

254 °C (dec.)

SMILES string

OC(=O)[C@H]1CCCNC1

InChI

1S/C6H11NO2/c8-6(9)5-2-1-3-7-4-5/h5,7H,1-4H2,(H,8,9)/t5-/m0/s1

InChI key

XJLSEXAGTJCILF-YFKPBYRVSA-N

Gene Information

rat ... Slc6a1(79212)

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General description

(S)-(-)-3-Piperidinecarboxylic acid is an inhibitor of GABA (γ-aminobutyric acid) uptake.

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

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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Anna-Lucia Koerling et al.
Neuropharmacology, 148, 394-405 (2018-11-26)
In addition to reducing seizures, anti-epileptic treatments should preserve physiological network activity. Here, we used a thalamocortical slice preparation displaying physiological slow oscillations to investigate the effects of anticonvulsant drugs on physiological activity and epileptiform activity in two pharmacological epilepsy
Michael P DeNinno et al.
Bioorganic & medicinal chemistry letters, 21(10), 3095-3098 (2011-04-05)
The first highly potent and selective PDE8 inhibitors are disclosed. The initial tetrahydroisoquinoline hit was transformed into a nipecotic amide series in order to address a reactive metabolite issue. Reduction of lipophilicity to address metabolic liabilities uncovered an interesting diastereomer-dependent
Hong Gao et al.
Neuropharmacology, 58(8), 1220-1227 (2010-03-17)
Zolpidem is a widely prescribed sleep aid with relative selectivity for GABA(A) receptors containing alpha1-3 subunits. We examined the effects of zolpidem on the inhibitory currents mediated by GABA(A) receptors using whole-cell patch-clamp recordings from DMV neurons in transverse brainstem
Inhibition of the uptake of GABA and related amino acids in rat brain slices by the optical isomers of nipecotic acid.
G A Johnston et al.
Journal of neurochemistry, 26(5), 1029-1032 (1976-05-01)
Carmela Napolitano et al.
Molecules (Basel, Switzerland), 14(9), 3268-3274 (2009-09-29)
As a novel example of improved entry of poorly delivered drugs into the brain by means of nutrient conjugates, L-carnitine was conjugated to nipecotic acid and the capacity to antagonize PTZ-induced convulsions of this novel entity was evaluated.
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