Nipecotic acid

Nipecotic acid
Identifiers
	IUPAC name Piperidine-3-carboxylic acid;
CAS Number	498-95-3;
PubChem CID	4498;
IUPHAR/BPS	4564;
ChemSpider	4342;
UNII	1U1QTN40SY;
ChEMBL	ChEMBL277498;
CompTox Dashboard (EPA)	DTXSID00870568 ;
ECHA InfoCard	100.007.159
Chemical and physical data
Formula	C6H11NO2
Molar mass	129.159 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CC(CNC1)C(=O)O;

Nipecotic acid is a GABA reuptake inhibitor used in scientific research.^[1]^[2]^[3] It has very little to no blood–brain barrier penetration itself, but structural modifications have been made to improve this.^[4]^[5]

References

^ Macdonald RL (2012). Eadie MJ, Vajda FJ (eds.). Antiepileptic drugs: pharmacology and therapeutics (First ed.). [S.l.]: Springer. p. 130. ISBN 978-3-642-64244-9. In contrast, prolonged (1 h) exposure to gabapentin enhanced the shunting effect on CAl region excitatory postsynaptic potentials induced by the GABA uptake inhibitor, nipecotic acid, which promotes GABA release.
^ Takahashi K, Miyoshi S, Kaneko A, Copenhagen DR (1995). "Actions of nipecotic acid and SKF89976A on GABA transporter in cone-driven horizontal cells dissociated from the catfish retina". The Japanese Journal of Physiology. 45 (3): 457–473. doi:10.2170/jjphysiol.45.457. PMID 7474528.
^ Wahab A, Heinemann U, Albus K (October 2009). "Effects of gamma-aminobutyric acid (GABA) agonists and a GABA uptake inhibitor on pharmacoresistant seizure like events in organotypic hippocampal slice cultures". Epilepsy Research. 86 (2–3): 113–123. doi:10.1016/j.eplepsyres.2009.05.008. PMID 19535226. S2CID 32999271.
^ Shek E (1994). "Chemical delivery systems and prodrugs of anticonvulsive drugs". Advanced Drug Delivery Reviews. 14 (2–3): 227–241. doi:10.1016/0169-409X(94)90041-8. Nipecotic acid is a potent in vitro inhibitor of neuronal and glial GABA uptake. However, because nipecotic acid does not penetrate the blood-brain barrier (BBB) it lacks any in vivo activity [23,24].
^ Dhanawat M, Gupta S, Mehta DK, Das R (February 2021). "Design, Synthesis and Enhanced BBB Penetration Studies of L-serine-Tethered Nipecotic Acid-Prodrug". Drug Research. 71 (2): 94–103. doi:10.1055/a-1290-0119. PMID 33241549.

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[1] Macdonald RL (2012). Eadie MJ, Vajda FJ (eds.). Antiepileptic drugs: pharmacology and therapeutics (First ed.). [S.l.]: Springer. p. 130. ISBN 978-3-642-64244-9. In contrast, prolonged (1 h) exposure to gabapentin enhanced the shunting effect on CAl region excitatory postsynaptic potentials induced by the GABA uptake inhibitor, nipecotic acid, which promotes GABA release.

[pmid7474528-2] Takahashi K, Miyoshi S, Kaneko A, Copenhagen DR (1995). "Actions of nipecotic acid and SKF89976A on GABA transporter in cone-driven horizontal cells dissociated from the catfish retina". The Japanese Journal of Physiology. 45 (3): 457–473. doi:10.2170/jjphysiol.45.457. PMID 7474528.

[pmid19535226-3] Wahab A, Heinemann U, Albus K (October 2009). "Effects of gamma-aminobutyric acid (GABA) agonists and a GABA uptake inhibitor on pharmacoresistant seizure like events in organotypic hippocampal slice cultures". Epilepsy Research. 86 (2–3): 113–123. doi:10.1016/j.eplepsyres.2009.05.008. PMID 19535226. S2CID 32999271.

[Shek1994-4] Shek E (1994). "Chemical delivery systems and prodrugs of anticonvulsive drugs". Advanced Drug Delivery Reviews. 14 (2–3): 227–241. doi:10.1016/0169-409X(94)90041-8. Nipecotic acid is a potent in vitro inhibitor of neuronal and glial GABA uptake. However, because nipecotic acid does not penetrate the blood-brain barrier (BBB) it lacks any in vivo activity [23,24].

[5] Dhanawat M, Gupta S, Mehta DK, Das R (February 2021). "Design, Synthesis and Enhanced BBB Penetration Studies of L-serine-Tethered Nipecotic Acid-Prodrug". Drug Research. 71 (2): 94–103. doi:10.1055/a-1290-0119. PMID 33241549.

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See also

References