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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

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. Lipophilic derivatives of nipecotic acid are used as drugs for the treatment of epilepsy.

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.
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

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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Sigma-Aldrich

696439

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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
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
Phillip L W Colmers et al.
The Journal of physiology, 596(10), 1919-1929 (2018-02-09)
GABA transporter (GAT) blockade recruits extrasynaptic GABAA receptors (GABAA Rs) and amplifies constitutive presynaptic GABAB R activity. Extrasynaptic GABAA Rs contribute to a tonic current. Corticosteroids increase the tonic current mediated by extrasynaptic GABAA Rs. Corticotropin-releasing hormone (CRH) neurons in
Andrea Kragler et al.
European journal of medicinal chemistry, 43(11), 2404-2411 (2008-04-09)
A series of N-substituted aminomethylphenol derivatives was synthesized by reductive amination. To study the inhibitory potency of the target compounds at the murine GABA transporters (mGAT1-mGAT4), a [(3)H]GABA uptake test system in a 96-well format based on HEK cells stably
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
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