Chemistry:Isonipecotic acid

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Isonipecotic acid
Clinical data
Other namesPiperidine-4-carboxylic acid; P4C; 4-Piperidinecarboxylic acid; Hexahydroisonicotinic acid; 4-Carboxypiperidine
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC6H11NO2
Molar mass129.159 g·mol−1
3D model (JSmol)
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Isonipecotic acid, also known as piperidine-4-carboxylic acid (P4C), is a conformationally constrained derivative of γ-aminobutyric acid (GABA) and a moderately potent GABAA receptor partial agonist.[1][2][3] It consists of a piperidine ring with a carboxylic acid moiety in the iso position.[1] The drug showed moderate-efficacy partial agonism of α1, α2, α3, and α5 subunit-containing GABAA receptors (Emax = 46–57%), but showed full or near-full agonism of α4 and α6 subunit-containing GABAA receptors (Emax = 83–104%).[2] Isonipecotic acid is unable to cross the blood–brain barrier.[4] It was first described in the scientific literature by at least 1944[5] and was identified as a GABAA receptor agonist by 1978.[6]

See also

References

  1. ↑ 1.0 1.1 "GABA agonists and antagonists". Medicinal Research Reviews 12 (6): 593–636. November 1992. doi:10.1002/med.2610120604. PMID 1331633. 
  2. ↑ 2.0 2.1 "GABA(A) receptor ligands and their therapeutic potentials". Current Topics in Medicinal Chemistry 2 (8): 817–832. August 2002. doi:10.2174/1568026023393525. PMID 12171573. 
  3. ↑ "Activation of single heteromeric GABA(A) receptor ion channels by full and partial agonists". The Journal of Physiology 557 (Pt 2): 389–413. June 2004. doi:10.1113/jphysiol.2003.054734. PMID 14990676. 
  4. ↑ "Esters of nipecotic and isonipecotic acids as potential anticonvulsants". Journal of Pharmaceutical Sciences 71 (11): 1214–1219. November 1982. doi:10.1002/jps.2600711108. PMID 7175711. Bibcode: 1982JPhmS..71.1214M. "Isonipecotic acid (Ib) was shown to be a potent and specific y-aminobutyric acid agonist in the [3H]y-aminobutyric acid-binding assay procedure (13,14). As in the case of nipecotic acid, isonipecotic acid was also too polar to penetrate the blood-brain barrier.". 
  5. ↑ "The preparation of pyridine-4-carboxylic acid and of piperidine-4-carboxylic acid by catalytic reduction of 2,6-dichloropyridine-4-carboxylic acid". Recueil des Travaux Chimiques des Pays-Bas 63 (7): 141–146. 1944. doi:10.1002/recl.19440630704. ISSN 0165-0513. https://onlinelibrary.wiley.com/doi/10.1002/recl.19440630704. Retrieved 6 October 2025. 
  6. ↑ "Isoguvacine, isonipecotic acid, muscimol and N-methyl isoguvacine on the GABA receptor in rat sympathetic ganglia". Experientia 34 (9): 1193–1195. September 1978. doi:10.1007/BF01922953. PMID 214333. 

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See also
Receptor/signaling modulators
GABAA receptor positive modulators
GABA metabolism/transport modulators

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