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211672

Sigma-Aldrich

Nipecotic acid

98%

Synonym(s):

(±)-β-Homoproline, 3-Carboxypiperidine, 3-Piperidinecarboxylic acid, Hexahydronicotinic acid

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About This Item

Empirical Formula (Hill Notation):
C6H11NO2
CAS Number:
498-95-3
Molecular Weight:
129.16
EC Number:
207-873-9
MDL number:
MFCD00005992
UNSPSC Code:
12352100
PubChem Substance ID:
24278161
NACRES:
NA.22

assay

98%

form

solid

mp

261 °C (dec.) (lit.)

solubility

water: soluble 50 mg/mL, clear, colorless to faintly yellow

functional group

carboxylic acid

SMILES string

OC(=O)C1CCCNC1

InChI

1S/C6H11NO2/c8-6(9)5-2-1-3-7-4-5/h5,7H,1-4H2,(H,8,9)

InChI key

XJLSEXAGTJCILF-UHFFFAOYSA-N

Gene Information

human ... SLC23A2(9962)

General description

R(−)-Nipecotic acid is a potential inhibitor of uptake of γ-aminobutyric acid (GABA) in rat brain slices[1]. Lipophilic derivatives of nipecotic acid are used as drugs for the treatment of epilepsy[2].

application

Nipecotic acid was used in determination of the antiepileptic drug vigabatrin and the amino acid neurotransmitters in rat brain extracellular fluid by capillary electrophoresis with laser-induced fluorescence detection[3].
Reactant for concurrent esterification and N-acteylation of amino acids with orthoesters

Reactant for synthesis of:
Anticonvulsants
HCV NS5B polymerase inhibitors
Cathepsin S inhibitors
Orally bioavailable P2Y12 antagonists for inhibition of platelet aggregation
Positive allosteric modulator of metabotropic glutamate receptor 4

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_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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Certificates of Analysis (COA)

Lot/Batch Number
S29602
08622MR
07729LU
05602PX
04208MU

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(±)-Vigabatrin

Sigma-Aldrich

V8261

(±)-Vigabatrin

(S)-Ethyl piperidine-3-carboxylate 97%

Sigma-Aldrich

696439

(S)-Ethyl piperidine-3-carboxylate

Nadia Benturquia et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 806(2), 237-244 (2004-06-03)
Capillary electrophoresis with laser-induced fluorescence detection (CE-LIFD) coupled to in vivo microdialysis sampling was used in order to monitor simultaneously a drug and several neurotransmitters in the brain extracellular fluid. Determination of the antiepileptic drug vigabatrin and the amino acid
Hui-Ling Diao et al.
Frontiers in physiology, 8, 897-897 (2017-11-23)
The globus pallidus is a central nucleus in the basal ganglia motor control circuit. Morphological studies have revealed the expression of adenosine A2A receptors in the globus pallidus. To determine the modulation of adenosine A2A receptors on the activity of
Gabriele Quandt et al.
Bioorganic & medicinal chemistry, 21(11), 3363-3378 (2013-04-20)
γ-Amino butyric acid (GABA) is the major inhibitory neurotransmitter in the mammalian central nervous system (CNS). A malfunction of the GABAergic neurotransmission is connected to several neuronal disorders like epilepsy, Alzheimer's disease, neuropathic pain, and depression. One possibility to enhance
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)
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.
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