| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
GABA Receptor[1]
Nipecotic acid targets GABA transporters, particularly mGAT1. It inhibits the uptake of GABA into neurons and glial cells. The compound acts as a competitive inhibitor at the GABA transporter. It has an IC50 of 1 mM for mouse GAT2. |
|---|---|
| ln Vitro |
Applying nipecotic acid (1 mM) to outside-out patches of paraventricular neurones induced inward unitary currents[1].
In cell-free systems, Nipecotic acid potently inhibits GABA uptake. It is taken up by rat brain slices via a sodium-dependent, high-affinity system with a Km of 11 μM. The compound's inhibitory effect on GABA uptake is competitive. GABA and other GABA uptake inhibitors also inhibit the uptake of nipecotic acid. Cellular uptake assays demonstrate that Nipecotic acid inhibits [³H]GABA uptake in cells expressing GABA transporters. The compound is taken up by neuronal cells via the GABA transporter. It can be released from brain slices by increased potassium ion concentration in a calcium-dependent manner. |
| ln Vivo |
The blood-brain barrier (BBB) is not easily crossed by nipecotic acid[2].
In vivo, Nipecotic acid has been studied for its effects on GABAergic neurotransmission. Derivatives of nipecotic acid, such as tiagabine, are used clinically as anti-epileptic drugs. The compound itself serves as a pharmacological tool for studying GABA uptake mechanisms. |
| Enzyme Assay |
GABA uptake inhibition assays for Nipecotic acid are performed using synaptosomal preparations or cells expressing GABA transporters. [³H]GABA is used as the substrate, and uptake is measured in the presence of varying concentrations of nipecotic acid. IC50 values are determined from inhibition curves. The compound's competitive mechanism is confirmed by Lineweaver-Burk analysis.
|
| Cell Assay |
Cellular assays for Nipecotic acid are conducted using cultured neurons, glial cells, or cells expressing recombinant GABA transporters. Cells are pre-incubated with nipecotic acid at various concentrations, then [³H]GABA is added. Uptake is terminated after a defined period, and accumulated radioactivity is measured. IC50 values are calculated from concentration-response data.
|
| ADME/Pharmacokinetics |
Pharmacokinetic properties of Nipecotic acid have been characterized in rodent models. The compound is taken up by brain tissue via a sodium-dependent high-affinity system. Lipophilic derivatives of nipecotic acid, such as tiagabine, have improved oral bioavailability and CNS penetration. The parent compound has limited blood-brain barrier penetration.
|
| Toxicity/Toxicokinetics |
Preclinical toxicity data for Nipecotic acid are limited. As a GABA uptake inhibitor, it may have proconvulsant or anticonvulsant effects depending on the context. The compound is used as a research tool at concentrations that inhibit GABA uptake without significant toxicity.
|
| References | |
| Additional Infomation |
Nipecotic acid is a piperidine monocarboxylic acid with the structure piperidine, where a hydrogen atom at the 3-position is replaced by a carboxylic acid group. It is both a piperidine monocarboxylic acid and a β-amino acid.
Nipecotic acid is a key pharmacological tool for studying GABA transporters. Its derivatives, particularly tiagabine, are clinically approved for epilepsy treatment. The compound's ability to inhibit GABA uptake makes it valuable for understanding GABAergic neurotransmission and developing new therapeutic agents. |
| Molecular Formula |
C6H11NO2
|
|---|---|
| Molecular Weight |
129.16
|
| Exact Mass |
129.078
|
| CAS # |
498-95-3
|
| PubChem CID |
4498
|
| Appearance |
White to off-white solid powder
|
| Density |
1.1±0.1 g/cm3
|
| Boiling Point |
265.8±33.0 °C at 760 mmHg
|
| Melting Point |
261ºC (dec.)
|
| Flash Point |
114.5±25.4 °C
|
| Vapour Pressure |
0.0±1.1 mmHg at 25°C
|
| Index of Refraction |
1.479
|
| LogP |
-0.04
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
9
|
| Complexity |
114
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
C1CC(CNC1)C(=O)O
|
| InChi Key |
XJLSEXAGTJCILF-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C6H11NO2/c8-6(9)5-2-1-3-7-4-5/h5,7H,1-4H2,(H,8,9)
|
| Chemical Name |
piperidine-3-carboxylic acid
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
H2O: 50 mg/mL (387.12 mM)
DMSO: < 1 mg/mL |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 50 mg/mL (387.12 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.
(Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 7.7423 mL | 38.7117 mL | 77.4234 mL | |
| 5 mM | 1.5485 mL | 7.7423 mL | 15.4847 mL | |
| 10 mM | 0.7742 mL | 3.8712 mL | 7.7423 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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