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Chemical Compound Review

piperidinium     3,4,5,6-tetrahydro-2H-pyridine

Synonyms: AC1LCVCZ, CHEBI:589779, ZINC01529277, A802265, piperidin-1-ium, ...
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High impact information on piperidine

  • A monoclonal antibody, 14D9, which has been elicited against a cationic hapten, N-alkyl-N-methyl-3-glutarylamidomethyl piperidinium, in which alkyl = [4-(2-hydroxyethylamido)carbonyl]phenylmethyl, is capable of inverting the intrinsic order of reactivity in a series of structurally related enol ethers and ketals towards hydrolysis [1].
  • Since the piperidinium compound stimulates ganglia, it is concluded the either planarity of the aryl--O--C system is not essential for this type of activity or receptor interaction can involve appreciable bond distortion [2].
  • Conformational analysis. Part 16. Conformational free energies in substituted piperidines and piperidinium salts [3].
  • The tertiary amines disappeared rapidly from the blood cells in vitro and in vivo and the piperidinium derivative (RAD 179) formed from the haloalkylamines disappeared almost as rapidly as the tertiary amines from the plasma in vivo [4].
  • Fourier transform infrared spectroscopy (FTIR) of the 2-methylpiperidine indicated that at reaction conditions a piperidinium ion intermediate was formed on both the sulfide and the phosphide [5].

Anatomical context of piperidine

  • The measurements showed that pyrrolidinium bromides were slightly more effective in a protection of erythrocytes than the corresponding piperidinium ones [6].
  • Piperidinium bromides, differing in the alkyl chain length (8, 10, 12, 14 and 16 carbon atoms in the chain) were synthesised to protect biological and/or model membranes against peroxidation and following negative consequences [7].

Associations of piperidine with other chemical compounds

  • A comparison of the results obtained for piperidinium bromides with those obtained for the widely used antioxidant 3,5-di-t-butyl-4-hydroxytoluene-(BHT) revealed that only two shortest alkyl chain salts were less efficient than BHT in protecting erythrocyte membranes [7].
  • Two chemically synthesized piperidinium derivatives i.e l-methyl-1-(3,4) dihydroxy phenacyl-4-hydroxy piperidinium chloride and 1-methyl-(4-p) methoxy phenacyl 4-hydroxy piperidinium bromide have been evaluated for their analgesic activity in intact albino mice by tail immersion method because of their structural similarity with opioids [8].

Gene context of piperidine

  • A similar comparison with antioxidant efficiency of flavonoids extracted from Rosa rugosa showed that they protected the membranes studied more weakly than the least effective eight-carbon alkyl chain piperidinium bromide [7].

Analytical, diagnostic and therapeutic context of piperidine


  1. Antibody-catalyzed reversal of chemoselectivity. Sinha, S.C., Keinan, E., Reymond, J.L. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  2. Conformations and "nictinic" activites of cyclic analogues of choline aryl ether. Clark, E.R., Hughes, I.E., Smith, C.F. J. Med. Chem. (1976) [Pubmed]
  3. Conformational analysis. Part 16. Conformational free energies in substituted piperidines and piperidinium salts. Abraham, R.J., Medforth, C.J., Smith, P.E. J. Comput. Aided Mol. Des. (1991) [Pubmed]
  4. Pharmacokinetics of haloalkylamines: cyclization and distribution in blood in vitro and in vivo. Ross, S.B. J. Pharm. Pharmacol. (1975) [Pubmed]
  5. Mechanism of hydrodenitrogenation on phosphides and sulfides. Oyama, S.T., Lee, Y.K. The journal of physical chemistry. B, Condensed matter, materials, surfaces, interfaces & biophysical. (2005) [Pubmed]
  6. Antioxidative properties of pyrrolidinium and piperidinium salts. Kleszczyńska, H., Oświecimska, M., Bonarska, D., Sarapuk, J. Z. Naturforsch., C, J. Biosci. (2002) [Pubmed]
  7. Protective effect of quaternary piperidinium salts on lipid oxidation in the erythrocyte membrane. Kleszczyńska, H., Oświecimska, M., Sarapuk, J., Witek, S., Przestalski, S. Z. Naturforsch., C, J. Biosci. (1999) [Pubmed]
  8. Pharmacological evaluation of newly synthesized piperidinium derivatives for their analgesic activity. Khan, R.A., Rasheed, H., Saify, Z.S., Rehman, A.B., Arif, M. Pakistan journal of pharmaceutical sciences. (1997) [Pubmed]
  9. Preparation and evaluation of radioiodinated (iodophenyl)cholines and their morpholinium and piperidinium analogues as myocardial perfusion imaging agents. Zabel, P.L., Zea-Ponce, Y., Brown, G.W., Morrissey, G., Hunter, D.H., Driedger, A.A., Chamberlain, M.J. J. Med. Chem. (1986) [Pubmed]
  10. Novel piperidinium and pyridinium agents as water-soluble acetylcholinesterase inhibitors for the reversal of neuromuscular blockade. Palin, R., Clark, J.K., Cowley, P., Muir, A.W., Pow, E., Prosser, A.B., Taylor, R., Zhang, M.Q. Bioorg. Med. Chem. Lett. (2002) [Pubmed]
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