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Chemical Compound Review

Cypentil     piperidine

Synonyms: Piperidin, azinane, PIPERIDINE, Azacyclohexane, Cyclopentimine, ...
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Disease relevance of piperidine

  • In the present study, the ability of the piperidine nitroxide TEMPOL to prevent the acute cardiac toxicity of Adriamycin (ADR), which depends on oxygen-derived free radical generation, was assessed in isolated rat hearts [1].
  • Post-alkylation treatments, including hot piperidine or digestion with the enzymes Escherichia coli 3-methyladenine-DNA glycosylase II, formamidopyrimidine-DNA glycosylase, Escherichia coli endonuclease III, or phage T4 UV endonuclease V did not increase the level of DNA breaks in NNKOAc-treated DNA [2].
  • (Alkylamino) piperidine bis(heteroaryl)piperizine analogs are potent, broad-spectrum nonnucleoside reverse transcriptase inhibitors of drug-resistant isolates of human immunodeficiency virus type 1 (HIV-1) and select for drug-resistant variants of HIV-1IIIB with reduced replication phenotypes [3].
  • They are the angles theta 1 and theta 3, defining the relative position of the protonated nitrogen and the polar function with each of the two aromatic rings, and the torsion angle eta 1, defining the orientation of the lone pair(s) on the polar proton-accepting function with respect to the lone pair on the piperidine nitrogen [4].
  • PPBP [4-phenyl-1-(4-phenylbutyl) piperidine] decreases brain injury after transient focal ischemia in rats [5].

Psychiatry related information on piperidine

  • Our present demonstration that these piperidine structures do, in fact, possess significant DAT activity, taken together with their reported lack of locomotor activity, provides a compelling argument for exploring this class of molecules further in animal behavioral experiments [6].
  • E2020 is a piperidine cholinesterase inhibitor (ChEI) which is structurally distinct from other compounds presently under study for treatment of Alzheimer's disease [7].
  • Longer reaction times afforded piperidine cis-2,6-HNC(5)H(8)(CH(2)CH(2)CH(2)R(f8))(2) (6, 98%) [8].
  • Uptake and metabolism of intraventricularly administered piperidine and its effects on sleep and wakefulness in the rat [9].

High impact information on piperidine

  • The transient molecular structure of a reaction intermediate produced by photoexcitation of NiTPP-L2 (NiTPP, nickeltetraphenylporphyrin; L, piperidine) in solution was determined by x-ray absorption fine structure (XAFS) data obtained on a 14-nanosecond time scale from a third-generation synchrotron source [10].
  • The distribution of sigma and phencyclindine binding sites in the gastrointestinal tract of the guinea pig was studied by autoradiography after in vitro incubation of tissue slices with (+)3H-SKF 10,047 and 3H-1-1-[(2-thienyl)cyclohexyl] piperidine to locate sigma and phencyclidine receptors, respectively [11].
  • Olefin cross metathesis followed by a hydrogenation/hydrogenolysis reaction stereoselectively formed the piperidine ring [12].
  • Although previous thrombin treatment of ABAE cells did not enhance prothrombin activation, addition of dansyl arginine-4-ethyl piperidine amide markedly inhibited activation of 125I-labeled prothrombin by factor Xa, indicating that thrombin formation is necessary for optimal prothrombin activation [13].
  • HQL-79 was stabilized by interaction of a phenyl ring of its diphenyl group with Trp104 and by its piperidine group with GSH and Arg14 through water molecules, which form a network with hydrogen bonding and salt bridges linked to Mg2+ [14].

Chemical compound and disease context of piperidine


Biological context of piperidine

  • Cleavage of the target DNAs was done by alkylation followed by treatment with piperidine, and the positions of the alkylated sites were estimated by identification of the cleaved products [20].
  • The results using DNAs of various base compositions indicated that damaged G, T and C (but not A) sites caused strand scissions after hot piperidine treatment and that the damage around the 8-oxo-G occurred at G sites in both single and double strands with high frequency [21].
  • Electronic-topological study of the structure-activity relationships in a series of piperidine morphinomimetics [22].
  • To determine the mechanism of this regulation, we examined the kinetics of the binding of the radiolabeled uncompetitive antagonist [3H]N-(1-[thienyl]cyclohexyl) piperidine (TCP) [23].
  • Assaying DNA damage in vitro, we demonstrate that piperidine nitroxides protect from both t-AP(*) and t-APOO(*) [24].

Anatomical context of piperidine

  • Antiproliferative effect of the piperidine nitroxide TEMPOL on neoplastic and nonneoplastic mammalian cell lines [25].
  • Rat liver microsome studies on a selected number of compounds show these olefinic piperidine compounds (6) to be considerably more stable than SNC-80 [26].
  • This study demonstrates that piperidine treatment prevented the invasion of Salmonella typhimurium into model intestinal epithelium by nearly 95% [18].
  • The introduction of two methyl groups on the piperidine ring brought about a dramatic change in the pharmacological profile of 2-[(cis- and trans-3,5-dimethylpiperidinyl)ethyl]-4-amino-5-chloro-2- methoxybenzoate, 7g,h. 7g (Ki = 0.26 +/- 0.06 nM) inhibited the relaxant action of 5-HT in the rat esophagus muscle with a pA2 value of 8 [27].
  • The results of the evaluation of the new analogues as CCK receptor ligands, in rat pancreas and cerebral cortex preparations, showed that, whereas replacement of oxygen with sulfur is allowed, reduction of the 1- or 3-oxo groups or the contraction of the fused piperidine ring lead to the complete loss of binding affinity at CCK(1) receptors [28].

Associations of piperidine with other chemical compounds

  • The effects of pH on the inhibition constants for pepstatin A and the substituted piperidine also suggest that the inhibitors bind to distinct conformational forms of the enzyme [29].
  • Pre-equilibrium binding studies indicate that the substituted piperidine can displace a fluorescently labeled statine inhibitor from the enzyme active site [29].
  • Reaction of DNA with K2PdCl4 at pH 2.0 followed by a piperidine workup produces specific cleavage at adenine (A) residues [30].
  • In order to understand, at the molecular level, the mechanism of action and the structure-activity relationships of this series of DNA intercalators, new dimers with additional methylene groups between the two piperidine rings have been synthesized [31].
  • A comparison was made between the effects of two different anesthetics, alpha-D-gluco-chloralose and 1-1-phenylcyclohexyl piperidine hydrochloride (Sernylan), on cerebral blood flow (CBF), brain metabolism and cerebrovascular CO2 responsiveness in primates [32].

Gene context of piperidine

  • In the present series, (-)-methyl 1-methyl-4beta-(2-naphthyl)piperidine-3beta-carboxylate (6) was found to be the most potent piperidine-based ligand, exhibiting K(i)'s of 21 nM and 7.6 nM at the DAT and 5-HTT, respectively [33].
  • Derivatization of 1a by quaternarizing the piperidine nitrogen with various alkyl groups and by installing substituents into the xanthene moiety dramatically improved the inhibitory activity against both human and murine CCR1 receptors [34].
  • Donepezil HCI is a piperidine-based reversible acetylcholinesterase (AChE) inhibitor, chemically distinct from other cholinesterase (ChE) inhibitors and rationally designed to treat the symptoms of Alzheimer's disease (AD) [35].
  • Our medicinal chemistry efforts in this area have resulted in the identification of N-alkyl piperidine sulfones as CCR5 antagonists [36].
  • A second major polar metabolite of irinotecan, aminopentanecarboxylic acid (APC), is the product of CYP3A4-mediated oxidation of the terminal piperidine ring [37].

Analytical, diagnostic and therapeutic context of piperidine


  1. Protective effect of the nitroxide tempol against the cardiotoxicity of adriamycin. Monti, E., Cova, D., Guido, E., Morelli, R., Oliva, C. Free Radic. Biol. Med. (1996) [Pubmed]
  2. Characterization and mapping of DNA damage induced by reactive metabolites of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) at nucleotide resolution in human genomic DNA. Cloutier, J.F., Drouin, R., Weinfeld, M., O'Connor, T.R., Castonguay, A. J. Mol. Biol. (2001) [Pubmed]
  3. (Alkylamino) piperidine bis(heteroaryl)piperizine analogs are potent, broad-spectrum nonnucleoside reverse transcriptase inhibitors of drug-resistant isolates of human immunodeficiency virus type 1 (HIV-1) and select for drug-resistant variants of HIV-1IIIB with reduced replication phenotypes. Olmsted, R.A., Slade, D.E., Kopta, L.A., Poppe, S.M., Poel, T.J., Newport, S.W., Rank, K.B., Biles, C., Morge, R.A., Dueweke, T.J., Yagi, Y., Romero, D.L., Thomas, R.C., Sharma, S.K., Tarpley, W.G. J. Virol. (1996) [Pubmed]
  4. Molecular determinants of mu receptor recognition for the fentanyl class of compounds. Cometta-Morini, C., Maguire, P.A., Loew, G.H. Mol. Pharmacol. (1992) [Pubmed]
  5. PPBP [4-phenyl-1-(4-phenylbutyl) piperidine] decreases brain injury after transient focal ischemia in rats. Takahashi, H., Kirsch, J.R., Hashimoto, K., London, E.D., Koehler, R.C., Traystman, R.J. Stroke (1996) [Pubmed]
  6. Chemistry and pharmacology of the piperidine-based analogues of cocaine. Identification of potent DAT inhibitors lacking the tropane skeleton. Kozikowski, A.P., Araldi, G.L., Boja, J., Meil, W.M., Johnson, K.M., Flippen-Anderson, J.L., George, C., Saiah, E. J. Med. Chem. (1998) [Pubmed]
  7. The effect of the selective reversible acetylcholinesterase inhibitor E2020 on extracellular acetylcholine and biogenic amine levels in rat cortex. Giacobini, E., Zhu X, D., Williams, E., Sherman, K.A. Neuropharmacology (1996) [Pubmed]
  8. Syntheses and reactivities of disubstituted and trisubstituted fluorous pyridines with high fluorous phase affinities: solid state, liquid crystal, and ionic liquid-phase properties. Rocaboy, C., Hampel, F., Gladysz, J.A. J. Org. Chem. (2002) [Pubmed]
  9. Uptake and metabolism of intraventricularly administered piperidine and its effects on sleep and wakefulness in the rat. Nixon, R.A., Karnovsky, M.L. Brain Res. (1977) [Pubmed]
  10. Capturing a photoexcited molecular structure through time-domain x-ray absorption fine structure. Chen, L.X., Jäger, W.J., Jennings, G., Gosztola, D.J., Munkholm, A., Hessler, J.P. Science (2001) [Pubmed]
  11. Autoradiographic localization of sigma opioid receptors in the gastrointestinal tract of the guinea pig. Roman, F., Pascaud, X., Chomette, G., Bueno, L., Junien, J.L. Gastroenterology (1989) [Pubmed]
  12. Total synthesis of (+/-)-halichlorine, (+/-)-pinnaic acid, and (+/-)-tauropinnaic acid. Christie, H.S., Heathcock, C.H. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  13. Prothrombin is activated on vascular endothelial cells by factor Xa and calcium. Rodgers, G.M., Shuman, M.A. Proc. Natl. Acad. Sci. U.S.A. (1983) [Pubmed]
  14. Structural and functional characterization of HQL-79, an orally selective inhibitor of human hematopoietic prostaglandin D synthase. Aritake, K., Kado, Y., Inoue, T., Miyano, M., Urade, Y. J. Biol. Chem. (2006) [Pubmed]
  15. The effects of SB 206284A, a novel neuronal calcium-channel antagonist, in models of cerebral ischemia. Wood, N.I., Barone, F.C., Benham, C.D., Brown, T.H., Campbell, C.A., Cooper, D.G., Evans, M.L., Feuerstein, G.Z., Hamilton, T.C., Harries, M.H., King, P.D., Meakin, J.E., Murkitt, K.L., Patel, S.R., Price, W.J., Roberts, J.C., Rothaul, A.L., Samson, N.A., Smith, S.J., Hunter, A.J. J. Cereb. Blood Flow Metab. (1997) [Pubmed]
  16. Antagonism by piperidine of levodopa effects in Parkinson disease. Tolosa, E.S., Cotzias, G.C., Papavasiliou, P.S., Lazarus, C.B. Neurology (1977) [Pubmed]
  17. Generation of predictive pharmacophore models for CCR5 antagonists: study with piperidine- and piperazine-based compounds as a new class of HIV-1 entry inhibitors. Debnath, A.K. J. Med. Chem. (2003) [Pubmed]
  18. Inhibition of Salmonella typhimurium enteropathogenicity by piperidine, a metabolite of the polyamine cadaverine. Köhler, H., Rodrigues, S.P., Maurelli, A.T., McCormick, B.A. J. Infect. Dis. (2002) [Pubmed]
  19. Cloning and characterization of the genes encoding a cytochrome P450 (PipA) involved in piperidine and pyrrolidine utilization and its regulatory protein (PipR) in Mycobacterium smegmatis mc2155. Poupin, P., Ducrocq, V., Hallier-Soulier, S., Truffaut, N. J. Bacteriol. (1999) [Pubmed]
  20. Sequence-dependent cleavage of DNA by alkylation with antisense oligodeoxyribonucleotides containing a 2-(N-iodoacetylaminoethyl)thio-adenine. Kido, K., Inoue, H., Ohtsuka, E. Nucleic Acids Res. (1992) [Pubmed]
  21. Neighboring base damage induced by permanganate oxidation of 8-oxoguanine in DNA. Koizume, S., Inoue, H., Kamiya, H., Ohtsuka, E. Nucleic Acids Res. (1998) [Pubmed]
  22. Electronic-topological study of the structure-activity relationships in a series of piperidine morphinomimetics. Sim, E., Dimoglo, A., Shvets, N., Ahsen, V. Current medicinal chemistry. (2002) [Pubmed]
  23. N-methyl-D-aspartate receptor regulation of uncompetitive antagonist binding in rat brain membranes: kinetic analysis. Bonhaus, D.W., McNamara, J.O. Mol. Pharmacol. (1988) [Pubmed]
  24. Nitroxides inhibit peroxyl radical-mediated DNA scission and enzyme inactivation. Offer, T., Samuni, A. Free Radic. Biol. Med. (2002) [Pubmed]
  25. Antiproliferative effect of the piperidine nitroxide TEMPOL on neoplastic and nonneoplastic mammalian cell lines. Gariboldi, M.B., Lucchi, S., Caserini, C., Supino, R., Oliva, C., Monti, E. Free Radic. Biol. Med. (1998) [Pubmed]
  26. N,N-Diethyl-4-(phenylpiperidin-4-ylidenemethyl)benzamide: a novel, exceptionally selective, potent delta opioid receptor agonist with oral bioavailability and its analogues. Wei, Z.Y., Brown, W., Takasaki, B., Plobeck, N., Delorme, D., Zhou, F., Yang, H., Jones, P., Gawell, L., Gagnon, H., Schmidt, R., Yue, S.Y., Walpole, C., Payza, K., St-Onge, S., Labarre, M., Godbout, C., Jakob, A., Butterworth, J., Kamassah, A., Morin, P.E., Projean, D., Ducharme, J., Roberts, E. J. Med. Chem. (2000) [Pubmed]
  27. New esters of 4-amino-5-chloro-2-methoxybenzoic acid as potent agonists and antagonists for 5-HT4 receptors. Yang, D., Soulier, J.L., Sicsic, S., Mathé-Allainmat, M., Brémont, B., Croci, T., Cardamone, R., Aureggi, G., Langlois, M. J. Med. Chem. (1997) [Pubmed]
  28. 5-(Tryptophyl)amino-1,3-dioxoperhydropyrido[1,2-c]pyrimidine-based potent and selective CCK(1) receptor antagonists: structure-activity relationship studies on the central 1,3-dioxoperhydropyrido[1,2-c]pyrimidine scaffold. Bartolomé-Nebreda, J.M., García-López, M.T., González-Muñiz, R., Cenarruzabeitia, E., Latorre, M., Del Río, J., Herranz, R. J. Med. Chem. (2001) [Pubmed]
  29. Novel inhibition of porcine pepsin by a substituted piperidine. Preference for one of the enzyme conformers. Marcinkeviciene, J., Kopcho, L.M., Yang, T., Copeland, R.A., Glass, B.M., Combs, A.P., Falahatpisheh, N., Thompson, L. J. Biol. Chem. (2002) [Pubmed]
  30. Adenine specific DNA chemical sequencing reaction. Iverson, B.L., Dervan, P.B. Nucleic Acids Res. (1987) [Pubmed]
  31. 1H and 31P nuclear magnetic resonance studies of the differences in DNA deformation induced by anti-tumoral 7H-pyrido[4,3-c]carbazole dimers. Delepierre, M., Maroun, R., Garbay-Jaureguiberry, C., Igolen, J., Roques, B.P. J. Mol. Biol. (1989) [Pubmed]
  32. Comparative effects of chloralose anesthesia and Sernylan analgesia on cerebral blood flow, CO2 responsiveness, and brain metabolism in the baboon. Sándor, P., Nyáry, I., Reivich, M., Kovách, A.G. Stroke (1977) [Pubmed]
  33. Further SAR studies of piperidine-based analogues of cocaine. 2. Potent dopamine and serotonin reuptake inhibitors. Tamiz, A.P., Zhang, J., Flippen-Anderson, J.L., Zhang, M., Johnson, K.M., Deschaux, O., Tella, S., Kozikowski, A.P. J. Med. Chem. (2000) [Pubmed]
  34. Design, synthesis, and discovery of a novel CCR1 antagonist. Naya, A., Sagara, Y., Ohwaki, K., Saeki, T., Ichikawa, D., Iwasawa, Y., Noguchi, K., Ohtake, N. J. Med. Chem. (2001) [Pubmed]
  35. Perspectives in the management of Alzheimer's disease: clinical profile of donepezil. Rogers, S.L. Dementia and geriatric cognitive disorders. (1998) [Pubmed]
  36. Syntheses and biological evaluation of 5-(piperidin-1-yl)-3-phenyl-pentylsulfones as CCR5 antagonists. Shankaran, K., Donnelly, K.L., Shah, S.K., Caldwell, C.G., Chen, P., Finke, P.E., Oates, B., MacCoss, M., Mills, S.G., DeMartino, J.A., Gould, S.L., Malkowitz, L., Siciliano, S.J., Springer, M.S., Kwei, G., Carella, A., Carver, G., Danzeisen, R., Hazuda, D., Holmes, K., Kessler, J., Lineberger, J., Miller, M.D., Emini, E.A., Schleif, W.A. Bioorg. Med. Chem. Lett. (2004) [Pubmed]
  37. Pharmacology of irinotecan. Kuhn, J.G. Oncology (Williston Park, N.Y.) (1998) [Pubmed]
  38. Function of adenovirus terminal protein in the initiation of DNA replication. Tamanoi, F., Stillman, B.W. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  39. Solid-phase methods for sequencing of nucleic acids I. Simultaneous sequencing of different oligodeoxyribonucleotides using a new, mechanically stable anion-exchange paper. Rosenthal, A., Schwertner, S., Hahn, V., Hunger, H.D. Nucleic Acids Res. (1985) [Pubmed]
  40. Dehydromonocrotaline generates sequence-selective N-7 guanine alkylation and heat and alkali stable multiple fragment DNA crosslinks. Pereira, T.N., Webb, R.I., Reilly, P.E., Seawright, A.A., Prakash, A.S. Nucleic Acids Res. (1998) [Pubmed]
  41. ADL 8-2698, a trans-3,4-dimethyl-4-(3-hydroxyphenyl) piperidine, prevents gastrointestinal effects of intravenous morphine without affecting analgesia. Liu, S.S., Hodgson, P.S., Carpenter, R.L., Fricke, J.R. Clin. Pharmacol. Ther. (2001) [Pubmed]
  42. Piperidine in chronic schizophrenic patients: a controlled double-blind study. Luchins, D.J., Gillin, J.C., Wagner, R.L., DeLisi, L.E., Morihisa, J.M., Weinberger, D.R., Bigelow, L.B., Klein, S.T., Wyatt, R.J. Biol. Psychiatry (1981) [Pubmed]
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