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211672

Sigma-Aldrich

Nipecotic acid

98%

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C6H11NO2
Numero CAS:
498-95-3
Peso molecolare:
129.16
Numero CE:
207-873-9
Numero MDL:
MFCD00005992
Codice UNSPSC:
12352100
ID PubChem:
24278161
NACRES:
NA.22

Saggio

98%

Stato

solid

Punto di fusione

261 °C (dec.) (lit.)

Solubilità

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

Gruppo funzionale

carboxylic acid

Stringa SMILE

OC(=O)C1CCCNC1

InChI

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

Informazioni sul gene

human ... SLC23A2(9962)

Descrizione generale

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].

Applicazioni

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

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H315,H319,H335

Classi di pericolo

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

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Certificati d'analisi (COA)

Lot/Batch Number
S29602
14620JS
08010MQ
07508CN
05920JF

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Slide 1 of 2

1 of 2

(±)-Vigabatrin

Sigma-Aldrich

V8261

(±)-Vigabatrin

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

Sigma-Aldrich

696439

(S)-Ethyl piperidine-3-carboxylate

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
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
O Kakinohana et al.
Neuroscience, 141(3), 1569-1583 (2006-06-27)
Transient spinal cord ischemia may lead to a progressive degeneration of spinal interneurons and subsequently to increased hind limb motor tone. In the present work we sought to characterize the rigidity and spasticity components of this altered motor function by:
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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