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Chemical Compound Review

Benzilate     2-diethylaminoethyl 2-(4-hexoxyphenyl)-2...

Synonyms: LS-32495, AC1L46MY, 6192-64-9, Topicaine hydrochloride
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Disease relevance of 2-diethylaminoethyl 2-(4-hexoxyphenyl)-2-hydroxy-2-phenyl-acetate

  • A significant decrease in [3H]quinuclidinyl benzilate binding to muscarinic receptors in the arcuate nucleus is now shown to occur in sudden infant death syndrome (SIDS) infants, compared to infants dying acutely of known causes [1].
  • Neither the affinity nor the maximal specific binding of [3H]quinuclidinyl benzilate in ventricular homogenates was changed by pertussis toxin treatment [2].
  • We compared the muscarinic cholinergic binding in lymphocytes of 44 patients with idiopathic Parkinson's disease with 23 age-matched normal volunteers, using [3H]quinuclidinyl benzilate [3].
  • In contrast, specific [3H]quinuclidinyl benzilate binding to the intact cells was unaffected by hypoxia [4].
  • The presence of muscarinic and nicotinic acetylcholine receptors (m- and nAChR, respectively) in small cell carcinomas (SCC) of the lung was assessed by measurement of specific binding of (-)[3H]quinuclidinyl benzilate ([3H]QNB) and 125I-alpha-bungarotoxin, respectively [5].

Psychiatry related information on 2-diethylaminoethyl 2-(4-hexoxyphenyl)-2-hydroxy-2-phenyl-acetate

  • A novel series of substituted (pyrroloamino)pyridines was synthesized, and the compounds were evaluated for cholinomimetic-like properties in vitro (inhibition of [3H]quinuclidinyl benzilate binding) and in vivo (reversal of scopolamine-induced dementia) as potential agents for the treatment of Alzheimer's disease [6].
  • Single electroconvulsive shock (ECS) induced no change in [3H]quinuclidinyl benzilate ([3H]QNB) binding to muscarinic cholinergic receptors in rat cortex and hippocampus [7].

High impact information on 2-diethylaminoethyl 2-(4-hexoxyphenyl)-2-hydroxy-2-phenyl-acetate

  • Ligand binding studies using [3H]quinuclidinyl benzilate and enriched left ventricular (LV) sarcolemma, demonstrated that muscarinic receptor density in heart failure declined 36% from a control of 5.6 +/- 0.6 pmol/mg, with no change in antagonist affinity [8].
  • However, the number of [3H]quinuclidynl benzilate binding sites (muscarinic cholinergic receptors) are 50--70% greater than (-) [3H]dihydroalprenolol binding sites (beta adrenergic receptors) in canine left ventricular tissue [9].
  • In contrast, in the same canine model 1 h of proximal left anterior descending coronary artery ligation did not result in a significant change in the number of [3H]quinuclidynl benzilate binding sites of their dissociation constants [9].
  • After hexamethonium administration in the normal rectum, the maximum specific binding (Bmax) of [3H]quinuclidinyl benzilate increased from 196.6 to 346.2 fmol/mg protein without affecting the dissociation constant [10].
  • Muscarinic receptors on rat isolated colonic epithelial cells. A correlation between inhibition of [3H]quinuclidinyl benzilate binding and alteration in ion transport [11].

Chemical compound and disease context of 2-diethylaminoethyl 2-(4-hexoxyphenyl)-2-hydroxy-2-phenyl-acetate

  • The binding of 3H-quinuclidinyl benzilate, a muscarinic cholinergic antagonist, of 3H-dihydroalprenolol, a beta adrenergic antagonist, and of 3H-flunitrazepam, a ligand which labels benzodiazepine receptors, was examined in several regions of control and Friedreich's ataxia (FA) brains [12].
  • Pilocarpine (100 and 150 mg/kg) was less effective in inducing catalepsy in the treated animals than in controls, although the treatment did not induce any alteration in saturation parameters of specific [3H]quinuclidinyl benzilate ([3H]QNB) binding to the homogenates of striatum, mesolimbic area and hippocampus [13].

Biological context of 2-diethylaminoethyl 2-(4-hexoxyphenyl)-2-hydroxy-2-phenyl-acetate

  • We have determined the various kinetic parameters of two muscarinic antagonists (N-methyl-4-[3H]piperidyl benzilate and (-)-N-[3H]methylscopolamine) by following directly their binding kinetics [14].
  • Agonist-induced down-regulation of up to 60-70% of hm2 receptors was demonstrated by determining the loss of [3H]quinuclidinyl benzilate binding sites in the cells [15].
  • Conversely, the rate of alkylation by N-ethylmaleimide, as monitored by the binding of [(3)H]quinuclidinyl benzilate, was decreased by antagonists while agonists were without effect [16].
  • After transfection, A9 L cells expressed muscarinic receptor mRNA and saturable, high affinity binding sites for the muscarinic antagonists 3H-quinuclidinyl benzilate and 3H-pirenzepine [17].
  • Hill coefficients and IC50 values derived from the inhibition of specific [3H]L-quinuclidinyl benzilate receptor binding suggest the presence of two muscarinic binding sites, differing both in affinity for pirenzepine and in tissue distribution [18].

Anatomical context of 2-diethylaminoethyl 2-(4-hexoxyphenyl)-2-hydroxy-2-phenyl-acetate

  • We found that crude membranes prepared from rat isolated colonic epithelial cells had a specific, saturable, high affinity receptor for L-[benzilic-4,4-3H]quinuclidinyl benzilate, a potent muscarinic antagonist with an apparent dissociation coefficient of 0.56 +/- 0.11 nM and a maximum number of binding sites of 42.5 +/- 5.7 fmol/mg protein [11].
  • Characterization of muscarinic cholinergic receptors in the lower esophageal sphincter of the cat: binding of [3H]quinuclidinyl benzilate [19].
  • In this study, these receptors were characterized and quantitated in homogenates of salt gland from domestic ducks adapted to conditions of low (freshwater, FW) and high (saltwater, SW) salt stress using the cholinergic antagonist [3H]-quinuclidinyl benzilate (QNB) [20].
  • Using [3H]quinuclidinyl benzilate as a specific cholinergic muscarinic ligand, it has been demonstrated that lymphocytes have muscarinic binding sites [21].
  • The effects of various substrates on the binding of agonists to muscarinic receptors were studied in the rat hypothalamus and adenohypophysis by competition experiments using the highly specific tritiated muscarinic antagonist N-methyl-4-piperidyl benzilate [22].

Associations of 2-diethylaminoethyl 2-(4-hexoxyphenyl)-2-hydroxy-2-phenyl-acetate with other chemical compounds


Gene context of 2-diethylaminoethyl 2-(4-hexoxyphenyl)-2-hydroxy-2-phenyl-acetate

  • The autoradiographic studies of total, M1, and M2 muscarinic receptors were conducted using [(3)H]quinuclidinyl benzilate, [(3)H]pirenzepine, and [(3)H]AF-DX384 as ligands, respectively [28].
  • The density and distribution of muscarinic receptors in the brain were determined by quantitative [3H]quinuclidinyl benzilate autoradiography and did not differ between the eNOS mutants and wild-type mice [29].
  • Binding studies using the nonselective muscarinic antagonist [3H]quinuclidinyl benzilate, the M1-selective antagonist pirenzepine, and the M2-selective antagonist AFDX-116 indicate that the receptors have the pharmacological properties of the cardiac (M2) receptor subtype [30].
  • The activities of the enzymes, acetylcholinesterase and choline acetyltransferase, as well as the binding of [3H]-3-quinuclidinyl benzilate in seven brain regions, were assessed [31].
  • Muscarinic receptor density, assessed by binding of the muscarinic receptor antagonist L-[benzilic-4,4'-(3)HCN]quinuclidinyl benzilate ([(3)H]QNB), was decreased by 20% after EGF treatment [32].

Analytical, diagnostic and therapeutic context of 2-diethylaminoethyl 2-(4-hexoxyphenyl)-2-hydroxy-2-phenyl-acetate


  1. Decreased muscarinic receptor binding in the arcuate nucleus in sudden infant death syndrome. Kinney, H.C., Filiano, J.J., Sleeper, L.A., Mandell, F., Valdes-Dapena, M., White, W.F. Science (1995) [Pubmed]
  2. Pertussis toxin treatment blocks hyperpolarization by muscarinic agonists in chick atrium. Sorota, S., Tsuji, Y., Tajima, T., Pappano, A.J. Circ. Res. (1985) [Pubmed]
  3. Changes of muscarinic cholinergic binding by lymphocytes in Parkinson's disease with and without dementia. Rabey, J.M., Grynberg, E., Graff, E. Ann. Neurol. (1991) [Pubmed]
  4. Differential effects of hypoxia on ligand binding properties of nicotinic and muscarinic acetylcholine receptors on cultured bovine adrenal chromaffin cells. Lee, K., Ito, A., Koshimura, K., Ohue, T., Takagi, Y., Miwa, S. J. Neurochem. (1995) [Pubmed]
  5. Acetylcholine receptors in small cell carcinomas. Cunningham, J.M., Lennon, V.A., Lambert, E.H., Scheithauer, B. J. Neurochem. (1985) [Pubmed]
  6. Substituted (pyrroloamino)pyridines: potential agents for the treatment of Alzheimer's disease. Davis, L., Olsen, G.E., Klein, J.T., Kapples, K.J., Huger, F.P., Smith, C.P., Petko, W.W., Cornfeldt, M., Effland, R.C. J. Med. Chem. (1996) [Pubmed]
  7. Effect of electroconvulsive shock on muscarinic cholinergic receptors in rat cerebral cortex and hippocampus. Lerer, B., Stanley, M., Demetriou, S., Gershon, S. J. Neurochem. (1983) [Pubmed]
  8. Impaired cardiac muscarinic receptor function in dogs with heart failure. Vatner, D.E., Lee, D.L., Schwarz, K.R., Longabaugh, J.P., Fujii, A.M., Vatner, S.F., Homcy, C.J. J. Clin. Invest. (1988) [Pubmed]
  9. Beta adrenergic and muscarinic cholinergic receptors in canine myocardium. Effects of ischemia. Mukherjee, A., Wong, T.M., Buja, L.M., Lefkowitz, R.J., Willerson, J.T. J. Clin. Invest. (1979) [Pubmed]
  10. Qualitative and quantitative analysis of muscarinic acetylcholine receptors in the piebald lethal mouse model of Hirschsprung's disease. Ueki, S., Okamoto, E., Kuwata, K., Toyosaka, A., Nagai, K. Gastroenterology (1985) [Pubmed]
  11. Muscarinic receptors on rat isolated colonic epithelial cells. A correlation between inhibition of [3H]quinuclidinyl benzilate binding and alteration in ion transport. Zimmerman, T.W., Binder, H.J. Gastroenterology (1982) [Pubmed]
  12. Brain neurotransmitter receptors in Friedreich's ataxia. Reisine, T.D., Azari, J., Johnson, P.C., Barbeau, A., Huxtable, R., Yamamura, H.I. The Canadian journal of neurological sciences. Le journal canadien des sciences neurologiques. (1979) [Pubmed]
  13. Alteration in dopaminergic and muscarinic cholinergic receptors after subchronic treatment with haloperidol in the developing rat brain. Kajiyama, H., Nomura, Y. J. Pharmacobio-dyn. (1981) [Pubmed]
  14. Analysis of ligand binding to receptors by competition kinetics. Application to muscarinic antagonists in rat brain cortex. Schreiber, G., Henis, Y.I., Sokolovsky, M. J. Biol. Chem. (1985) [Pubmed]
  15. Internalization and down-regulation of human muscarinic acetylcholine receptor m2 subtypes. Role of third intracellular m2 loop and G protein-coupled receptor kinase 2. Tsuga, H., Kameyama, K., Haga, T., Honma, T., Lameh, J., Sadée, W. J. Biol. Chem. (1998) [Pubmed]
  16. Effects of N-ethylmaleimide on conformational equilibria in purified cardiac muscarinic receptors. Sum, C.S., Park, P.S., Wells, J.W. J. Biol. Chem. (2002) [Pubmed]
  17. Expression of a cloned muscarinic receptor in A9 L cells. Brann, M.R., Buckley, N.J., Jones, S.V., Bonner, T.I. Mol. Pharmacol. (1987) [Pubmed]
  18. Evidence for multiple muscarinic receptor subtypes in human brain. Garvey, J.M., Rossor, M., Iversen, L.L. J. Neurochem. (1984) [Pubmed]
  19. Characterization of muscarinic cholinergic receptors in the lower esophageal sphincter of the cat: binding of [3H]quinuclidinyl benzilate. Rimele, T.J., Rogers, W.A., Gaginella, T.S. Gastroenterology (1979) [Pubmed]
  20. Characterization of muscarinic acetylcholine receptors in the avian salt gland. Hootman, S.R., Ernst, S.A. J. Cell Biol. (1981) [Pubmed]
  21. Muscarinic cholinergic receptors in murine lymphocytes: demonstration by direct binding. Gordon, M.A., Cohen, J.J., Wilson, I.B. Proc. Natl. Acad. Sci. U.S.A. (1978) [Pubmed]
  22. Molecular regulation of receptors: interaction of beta-estradiol and progesterone with the muscarinic system. Sokolovsky, M., Egozi, Y., Avissar, S. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  23. Muscarinic acetylcholine receptors of the developing retina. Sugiyama, H., Daniels, M.P., Nirenberg, M. Proc. Natl. Acad. Sci. U.S.A. (1977) [Pubmed]
  24. Purification of the muscarinic acetylcholine receptor from porcine atria. Peterson, G.L., Herron, G.S., Yamaki, M., Fullerton, D.S., Schimerlik, M.I. Proc. Natl. Acad. Sci. U.S.A. (1984) [Pubmed]
  25. Affinity labeling of muscarinic receptors in rat cerebral cortex with a photolabile antagonist. Amitai, G., Avissar, S., Balderman, D., Sokolovsky, M. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  26. Loss of muscarinic receptors and of stimulated phospholipid labeling in ibotenate-treated hippocampus. Fisher, S.K., Frey, K.A., Agranoff, B.W. J. Neurosci. (1981) [Pubmed]
  27. Guanine nucleotide regulation of a mammalian myocardial muscarinic receptor system. Evidence for homo- and heterotropic cooperativity in ligand binding analyzed by computer-assisted curve fitting. Mattera, R., Pitts, B.J., Entman, M.L., Birnbaumer, L. J. Biol. Chem. (1985) [Pubmed]
  28. Increased diisopropylfluorophosphate-induced toxicity in mu-opioid receptor knockout mice. Tien, L.T., Fan, L.W., Ma, T., Loh, H.H., Ho, I.K. J. Neurosci. Res. (2004) [Pubmed]
  29. Neuronal NOS-cGMP-dependent ACh-induced relaxation in pial arterioles of endothelial NOS knockout mice. Meng, W., Ayata, C., Waeber, C., Huang, P.L., Moskowitz, M.A. Am. J. Physiol. (1998) [Pubmed]
  30. Characterization of muscarinic acetylcholine receptors expressed by an atrial cell line derived from a transgenic mouse tumor. Morton, M.E., Brumwell, C., Gartside, C.L., Hauschka, S.D., Nathanson, N.M. Circ. Res. (1994) [Pubmed]
  31. Cholinergic adaptations to chronic oxotremorine infusion. Marks, M.J., Artman, L.D., Patinkin, D.M., Collins, A.C. J. Pharmacol. Exp. Ther. (1981) [Pubmed]
  32. EGF inhibits muscarinic receptor-mediated calcium signaling in a human salivary cell line. Zhang, B.X., Yeh, C.K., Hymer, T.K., Lifschitz, M.D., Katz, M.S. Am. J. Physiol., Cell Physiol. (2000) [Pubmed]
  33. Dynamic targeting of the agonist-stimulated m2 muscarinic acetylcholine receptor to caveolae in cardiac myocytes. Feron, O., Smith, T.W., Michel, T., Kelly, R.A. J. Biol. Chem. (1997) [Pubmed]
  34. Muscarinic cholinergic receptors in rat heart. Effects of thyroidectomy. Sharma, V.K., Banerjee, S.P. J. Biol. Chem. (1977) [Pubmed]
  35. In vivo determination of muscarinic acetylcholine receptor availability in schizophrenia. Raedler, T.J., Knable, M.B., Jones, D.W., Urbina, R.A., Gorey, J.G., Lee, K.S., Egan, M.F., Coppola, R., Weinberger, D.R. The American journal of psychiatry. (2003) [Pubmed]
  36. In vivo quantification of cerebral muscarinic receptors in normal human aging using positron emission tomography and [11C]tropanyl benzilate. Lee, K.S., Frey, K.A., Koeppe, R.A., Buck, A., Mulholland, G.K., Kuhl, D.E. J. Cereb. Blood Flow Metab. (1996) [Pubmed]
  37. Endogenous inhibitor of ligand binding to the muscarinic acetylcholine receptor. Diaz-Arrastia, R., Ashizawa, T., Appel, S.H. J. Neurochem. (1985) [Pubmed]
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