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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

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

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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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
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
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.
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
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