Nipecotic acid, S(+)- | CAS#59045-82-8 | GABA uptake inhibitor

MedKoo Cat#: 596421 | Name: Nipecotic acid, S(+)-

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Nipecotic acid, S(+)- is a GABA uptake inhibitor.

Chemical Structure

Nipecotic acid, S(+)-

CAS#59045-82-8

Theoretical Analysis

MedKoo Cat#: 596421

Name: Nipecotic acid, S(+)-

CAS#: 59045-82-8

Chemical Formula: C6H11NO2

Exact Mass: 129.0790

Molecular Weight: 129.16

Elemental Analysis: C, 55.80; H, 8.58; N, 10.84; O, 24.77

Price and Availability

Size	Price	Availability	Quantity
1g	USD 210.00
10g	USD 590.00

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Synonym

Nipecotic acid, S(+)-; J423.228C; L-beta-Homoproline; S(+)-nipecotic acid; (S)-Nipecotic acid;

IUPAC/Chemical Name

(S)-piperidine-3-carboxylic acid

InChi Key

XJLSEXAGTJCILF-YFKPBYRVSA-N

InChi Code

InChI=1S/C6H11NO2/c8-6(9)5-2-1-3-7-4-5/h5,7H,1-4H2,(H,8,9)/t5-/m0/s1

SMILES Code

O=C([C@@H]1CNCCC1)O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Nipecotic acid, S(+)- is a GABA uptake inhibitor.

In vitro activity:

The GABA-related compound nipecotic acid is commonly used to inhibit GABA uptake. This report shows that nipecotic acid can also directly activate GABA(A)-like chloride channels. When applied to outside-out patches of paraventricular neurones, nipecotic acid (1 mM) activated inward unitary currents (approximately 3 pA at a holding potential of -60 mV, E(Cl)+44 mV). The EC(50) for ion channel activation was approximately 300 microM, 3 fold greater than that found for GABA itself in this preparation. The nipecotic acid activated channels had similar conductance and kinetic properties to those of GABA activated channels in the same patches, reversed near E(Cl) and were inhibited by bicuculline (3 microM). Reference: Br J Pharmacol. 2001 Jul;133(5):673-8. https://pubmed.ncbi.nlm.nih.gov/11429391/

In vivo activity:

The effect of nipecotic acid on the extracellular levels of the putative hippocampal inhibitory transmitters, gamma-aminobutyric acid (GABA) and taurine, and also excitability in the dentate gyrus, were studied in anaesthetised rats using the dialytrode technique. Nipecotic acid drastically elevated the levels of extracellular GABA and taurine and the amplitude of population spikes in the dentate was concomitantly decreased. Reference: Neuropharmacology. 1984 May;23(5):595-8. https://pubmed.ncbi.nlm.nih.gov/6738829/

Preparing Stock Solutions

The following data is based on the product molecular weight 129.16 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Barrett-Jolley R. Nipecotic acid directly activates GABA(A)-like ion channels. Br J Pharmacol. 2001 Jul;133(5):673-8. doi: 10.1038/sj.bjp.0704128. PMID: 11429391; PMCID: PMC1572836. 3. Zhou C, Guo L, Morriello G, Pasternak A, Pan Y, Rohrer SP, Birzin ET, Huskey SE, Jacks T, Schleim KD, Cheng K, Schaeffer JM, Patchett AA, Yang L. Nipecotic and iso-nipecotic amides as potent and selective somatostatin subtype-2 receptor agonists. Bioorg Med Chem Lett. 2001 Feb 12;11(3):415-7. doi: 10.1016/s0960-894x(00)00687-9. PMID: 11212124. 1. Madtes P Jr, Redburn D. Metabolism of [3H]nipecotic acid in the rabbit retina. J Neurochem. 1985 May;44(5):1520-3. doi: 10.1111/j.1471-4159.1985.tb08790.x. PMID: 3989547. 4. Lerma J, Herreras O, Herranz AS, Munoz D, del Rio RM. In vivo effects of nipecotic acid on levels of extracellular GABA and taurine, and hippocampal excitability. Neuropharmacology. 1984 May;23(5):595-8. doi: 10.1016/0028-3908(84)90036-4. PMID: 6738829.

In vitro protocol:

In vivo protocol:

1. Madtes P Jr, Redburn D. Metabolism of [3H]nipecotic acid in the rabbit retina. J Neurochem. 1985 May;44(5):1520-3. doi: 10.1111/j.1471-4159.1985.tb08790.x. PMID: 3989547. 2. Lerma J, Herreras O, Herranz AS, Munoz D, del Rio RM. In vivo effects of nipecotic acid on levels of extracellular GABA and taurine, and hippocampal excitability. Neuropharmacology. 1984 May;23(5):595-8. doi: 10.1016/0028-3908(84)90036-4. PMID: 6738829.

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