Isonipecotic acid

Isonipecotic acid
Clinical data
Other namesPiperidine-4-carboxylic acid; P4C; 4-Piperidinecarboxylic acid; Hexahydroisonicotinic acid; 4-Carboxypiperidine
Identifiers
IUPAC name
  • piperidine-4-carboxylic acid
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.007.158
Chemical and physical data
FormulaC6H11NO2
Molar mass129.159 g·mol−1
3D model (JSmol)
SMILES
  • C1CNCCC1C(=O)O
InChI
  • InChI=1S/C6H11NO2/c8-6(9)5-1-3-7-4-2-5/h5,7H,1-4H2,(H,8,9) ☒N
  • Key:SRJOCJYGOFTFLH-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

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 (EmaxTooltip maximal efficacy = 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 2 Kerr DI, Ong J (November 1992). "GABA agonists and antagonists". Medicinal Research Reviews. 12 (6): 593–636. doi:10.1002/med.2610120604. PMID 1331633.
  2. 1 2 Frølund B, Ebert B, Kristiansen U, Liljefors T, Krogsgaard-Larsen P (August 2002). "GABA(A) receptor ligands and their therapeutic potentials". Current Topics in Medicinal Chemistry. 2 (8): 817–832. doi:10.2174/1568026023393525. PMID 12171573.
  3. ↑ Mortensen M, Kristiansen U, Ebert B, Frølund B, Krogsgaard-Larsen P, Smart TG (June 2004). "Activation of single heteromeric GABA(A) receptor ion channels by full and partial agonists". The Journal of Physiology. 557 (Pt 2): 389–413. doi:10.1113/jphysiol.2003.054734. PMC 1665090. PMID 14990676.
  4. ↑ Crider AM, Tita TT, Wood JD, Hinko CN (November 1982). "Esters of nipecotic and isonipecotic acids as potential anticonvulsants". Journal of Pharmaceutical Sciences. 71 (11): 1214–1219. Bibcode:1982JPhmS..71.1214M. doi:10.1002/jps.2600711108. PMID 7175711. 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. ↑ Wibaut JP (1944). "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. doi:10.1002/recl.19440630704. ISSN 0165-0513. Retrieved 6 October 2025.
  6. ↑ Bowery NG, Collins JF, Hudson AL, Neal MJ (September 1978). "Isoguvacine, isonipecotic acid, muscimol and N-methyl isoguvacine on the GABA receptor in rat sympathetic ganglia". Experientia. 34 (9): 1193–1195. doi:10.1007/BF01922953. PMID 214333.
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