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Merck
CN

656364

(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
NACRES:
NA.22
PubChem Substance ID:
24884154
UNSPSC Code:
12352005
MDL number:
MFCD01630807
Assay:
97%
Form:
solid

Key Documents

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Product Name

(S)-(+)-3-Piperidinecarboxylic acid, 97%

InChI key

XJLSEXAGTJCILF-YFKPBYRVSA-N

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

assay

97%

form

solid

optical activity

[α]/D 3.0 to 6.5°, c = 1 in H2O

mp

254 °C (dec.)

functional group

carboxylic acid

Quality Level

100

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

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW7996
MKCW9049
MKCH4093
MKBT7024V
MKBG1467V

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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.
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
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
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