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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

Quality Level

100

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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
Joanna R Dodd et al.
The Journal of biological chemistry, 282(21), 15528-15533 (2007-04-03)
The creatine transporter (CRT) is a member of a large family of sodium-dependent neurotransmitter and amino acid transporters. The CRT is closely related to the gamma-aminobutyric acid (GABA) transporter, GAT-1, yet GABA is not an effective substrate for the CRT.
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
Philip M Duy et al.
Experimental physiology, 95(7), 774-787 (2010-04-27)
Hyperthermic prolongation of the laryngeal chemoreflex (LCR) in decerebrate piglets is prevented or reversed by GABA(A) receptor antagonists and adenosine A(2A) (Ad-A(2A)) receptor antagonists administered in the nucleus of the solitary tract (NTS). Therefore, we tested the hypothesis that enhanced
Sabrina S Jedlicka et al.
International journal of neural systems, 19(3), 197-212 (2009-07-04)
In this work we quantified the in vitro calibration relationships between high frequency electrical stimulation and GABA and glutamate release in both mature retinoic acid differentiated P19 neurons and immortalized embryonic cortical cells engineered to express glutamic acid decarboxylase, GAD65.
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