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656356

Sigma-Aldrich

(R)-(–)-3-Piperidinecarboxylic acid

97%

Synonym(s):

(R)-(–)-Nipecotic acid

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About This Item

Empirical Formula (Hill Notation):
C6H11NO2
CAS Number:
25137-00-2
Molecular Weight:
129.16
MDL number:
MFCD01630787
UNSPSC Code:
12352005
PubChem Substance ID:
24884153
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

optical activity

[α]22/D −5°, c = 1 in H2O

mp

251-255 °C

application(s)

peptide synthesis

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

Gene Information

human ... SLC6A1(6529) , SLC6A11(6538) , SLC6A12(6539)
mouse ... Slc6a1(232333)
rat ... Slc6a1(79212) , Slc6a12(50676)

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General description

(R)-(-)-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

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
MKCG0324
MKCF7919
MKCC0250
MKBT4834V
MKBS9524V

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Khashayar Nassery et al.
Archives of oral biology, 52(7), 607-613 (2007-02-06)
The purpose of this study was to determine whether (a) an uptake system for gamma-aminobutyric acid (GABA) exists in human dental pulp, (b) GABA can be released from nerves in this tissue, and (c) GABA(B) autoreceptors modulate release of this
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
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