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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

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

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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Robert A Darnall et al.
American journal of physiology. Regulatory, integrative and comparative physiology, 302(5), R551-R560 (2011-12-14)
Arousal is an important defense against hypoxia during sleep. Rat pups exhibit progressive arousal impairment (habituation) with multiple hypoxia exposures. The mechanisms are unknown. The medullary raphe (MR) is involved in autonomic functions, including sleep, and receives abundant GABAergic inputs.
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.
Moslem Mohammadi et al.
Toxicology, 244(1), 42-48 (2007-12-07)
A synaptosomal model was used to evaluate in vivo effects of paraoxon on the uptake of [(3)H]GABA in rat cerebral cortex and hippocampus. Male Wistar rats were given a single intraperitoneal injection of one of three doses of paraoxon (0.1
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
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