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656356

Sigma-Aldrich

(R)-(–)-3-Piperidinecarboxylic acid

97%

Synonym(s):

(R)-(–)-Nipecotic acid

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10 G
$374.00

About This Item

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

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Quality Level

assay

97%

form

solid

optical activity

[α]22/D −5°, c = 1 in H2O

mp

251-255 °C

application(s)

peptide synthesis

functional group

carboxylic acid

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-/m1/s1

InChI key

XJLSEXAGTJCILF-RXMQYKEDSA-N

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General description

(R)-(-)-3-Piperidinecarboxylic acid is an inhibitor of GABA (γ-aminobutyric acid) uptake.[1]

pictograms

Exclamation mark

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

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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.
Søren Skovstrup et al.
ChemMedChem, 5(7), 986-1000 (2010-05-22)
A homology model of the human GABA transporter (GAT-1) based on the recently reported crystal structures of the bacterial leucine transporter from Aquifex aeolicus (LeuT) was developed. The stability of the resulting model embedded in a membrane environment was analyzed
Saori Ikeda et al.
American journal of physiology. Gastrointestinal and liver physiology, 303(3), G291-G297 (2012-06-09)
Taurine is essential for the hepatic synthesis of bile salts and, although taurine is synthesized mainly in pericentral hepatocytes, taurine and taurine-conjugated bile acids are abundant in periportal hepatocytes. One possible explanation for this discrepancy is that the active supply
Ryo Shintani et al.
Organic letters, 11(2), 457-459 (2008-12-17)
A new synthetic method of multisubstituted nipecotic acid (piperidine-3-carboxylic acid) derivatives has been developed by way of palladium-catalyzed decarboxylative cyclization of gamma-methylidene-delta-valerolactones with imines. By employing the diethoxyphosphinoyl group as the N-protecting group for imines, the reaction proceeds smoothly with
Søren Skovstrup et al.
PloS one, 7(6), e39360-e39360 (2012-06-28)
The entire substrate translocation pathway in the human GABA transporter (GAT-1) was explored for the endogenous substrate GABA and the anti-convulsive drug tiagabine. Following a steered molecular dynamics (SMD) approach, in which a harmonic restraining potential is applied to the

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