A GAT inhibitor
Related Products
Isomer(s)
36313L-Pipecolic Acid
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Nipecotic Acid

Item No. 36126

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-piperidinecarboxylic acid
CAS Number
498-95-3
Synonyms
  • (±)-Nipecotic Acid
  • (R,S)-Nipecotic Acid
  • 3-Piperidine Carboxylic Acid
  • DL-Piperidine 3-Carboxylic Acid
Molecular Formula
C6H11NO2
Formula Weight
129.2
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: Slightly solubleDMSO: Slightly solubleEthanol: Slightly solublePBS (pH 7.2): 10 mg/ml
SMILES
O=C(C1CCCNC1)O
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

    $32

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    250 mg

    $74

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    500 mg

    $141

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    Product Description

    Nipecotic acid is an inhibitor of GABA transporters (GAT; IC50s = 2.6, 310, 29, and 16 µM for mouse GAT-1, GAT-2, GAT-3, and GAT-4, respectively).1 It does not bind GABAA or GABAB receptors (IC50s = >100 µM for both) but does bind the adenosine A3 receptor (IC50 = 0.01 µM).2,3 Nipecotic acid inhibits GABA uptake in isolated rabbit choroid plexus (IC50 = 244 µM).4 It inhibits lactate dehydrogenase (LDH) release (EC50 = ~5 µM) and aggregation of a mutant form of huntingtin, htt-N63-148Q, in PC12 cells.5 Intraventricular administration of nipecotic acid (300 µg/animal) decreases tail flick reaction time in a rat model of morphine-induced analgesia.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kragler, A., Höfner, G., and Wanner, K.T. Novel parent structures for inhibitors of the murine GABA transporters mGAT3 and mGAT4. Eur. J. Pharmacol. 519(1-2), 43-47 (2005).

    2. Bowery, N.G., Hill, D.R., and Hudson, A.L. Characteristics of GABAB receptor binding sites on rat whole brain synaptic membranes. Br. J. Pharmacol. 78(1), 191-206 (1983).

    3. Minetti, P., Tinti, M.O., Carminati, P., et al. 2-n-Butyl-9-methyl-8-[1,2,3]triazol-2-yl-9H-purin-6-ylamine and analogues as A2A adenosine receptor antagonists. Design, synthesis, and pharmacological characterization. J. Med. Chem. 48(22), 6887-6896 (2005).

    4. Ramanathan, V.K., Brett, C.M., and Giacomini, K.M. Na+-dependent γ-aminobutyric acid (GABA) transport in the choroid plexus of rabbit. Biochim. Biophys. Acta 1330(1), 94-102 (1997).

    5. Wang, W., Duan, W., Igarashi, S., et al. Compounds blocking mutant huntingtin toxicity identified using a Huntington’s disease neuronal cell model. Neurobiol. Dis. 20(2), 500-508 (2005).

    6. Mantegazza, P., Tammiso, R., Vicentini, L., et al. Nipecotic acid and guvacine antagonism on morphine analgesia in rats. Pharmacol. Res. Commun. 11(8), 657-662 (1979).