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Volumn 60, Issue 1, 2010, Pages 30-35

Synthesis and determination of acute and chronic pain activities of 1-[1-(3-methylphenyl)(tetralyl)]piperidine as a new derivative of phencyclidine via tail immersion and formalin tests

Author keywords

1 Tetralone derivatives, analgesic effects, formalin test, tail immersion test; CAS 1867 66 9; CAS 956 90 1; Ketamine; Phencyclidine

Indexed keywords

1 [1 (3 METHYLPHENYL)(TETRALYL)]PIPERIDINE; CAS 1867 66 9; CAS 956 90 1; KETAMINE; PHENCYCLIDINE DERIVATIVE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 74949120181     PISSN: 00044172     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0031-1296245     Document Type: Article
Times cited : (10)

References (35)
  • 3
    • 0002627270 scopus 로고
    • The analgesic and anesthetic effects of 1-(1-phenylcyclohexyl) piperidine.HCl on the monkey
    • Chen G, Weston JK. The analgesic and anesthetic effects of 1-(1-phenylcyclohexyl) piperidine.HCl on the monkey. Anesth Analg. 1960;39:132-7.
    • (1960) Anesth Analg , vol.39 , pp. 132-137
    • Chen, G.1    Weston, J.K.2
  • 4
    • 0023219059 scopus 로고
    • Non-competitive antagonists of excitatory amino acid receptors
    • Kemp JA, Foster AC, Wong EHF. Non-competitive antagonists of excitatory amino acid receptors. Trends Neurosci. 1987;10:294-8.
    • (1987) Trends Neurosci , vol.10 , pp. 294-298
    • Kemp, J.A.1    Foster, A.C.2    Wong, E.H.F.3
  • 6
    • 0036384325 scopus 로고    scopus 로고
    • NMDA receptor antagonists ketamine and PCP have direct effects on the dopamine D (2) and serotonin 5-HT (2) receptors-implications for models of schizophrenia
    • Kapur S, Seeman P. NMDA receptor antagonists ketamine and PCP have direct effects on the dopamine D (2) and serotonin 5-HT (2) receptors-implications for models of schizophrenia. Mol Psychiatry. 2002;7(8):837-44.
    • (2002) Mol Psychiatry , vol.7 , Issue.8 , pp. 837-844
    • Kapur, S.1    Seeman, P.2
  • 7
    • 77952810889 scopus 로고
    • Pharmacologic effects of Ci-581, a new dissociative anesthetic, in man
    • Domino EF, Chodoff P, Corssen G. Pharmacologic effects of Ci-581, a new dissociative anesthetic, in man. Clin Pharmacol Ther. 1965;6:279-91.
    • (1965) Clin Pharmacol Ther , vol.6 , pp. 279-291
    • Domino, E.F.1    Chodoff, P.2    Corssen, G.3
  • 8
    • 0030975604 scopus 로고    scopus 로고
    • Effects of chronic administration of NMDA antagonists on synaptic development
    • Brooks WJ, Petit TL, LeBoutillier JC. Effects of chronic administration of NMDA antagonists on synaptic development. Synapse. 1997;26:104-13.
    • (1997) Synapse , vol.26 , pp. 104-113
    • Brooks, W.J.1    Petit, T.L.2    LeBoutillier, J.C.3
  • 9
    • 33646576836 scopus 로고    scopus 로고
    • Survival signaling pathways activated by NMDA receptors
    • Hetman M, Kharebava G. Survival signaling pathways activated by NMDA receptors. Curr Top Med Chem. 2006;6:787-99.
    • (2006) Curr Top Med Chem , vol.6 , pp. 787-799
    • Hetman, M.1    Kharebava, G.2
  • 10
    • 34249093924 scopus 로고    scopus 로고
    • Pathologically activated therapeutics for neuroprotection: Mechanism of NMDA receptor block by memantine and S-nitrosylation
    • Lipton SA. Pathologically activated therapeutics for neuroprotection: mechanism of NMDA receptor block by memantine and S-nitrosylation. Curr Drug Targets. 2007;8:621-32.
    • (2007) Curr Drug Targets , vol.8 , pp. 621-632
    • Lipton, S.A.1
  • 11
    • 33646593147 scopus 로고    scopus 로고
    • NMDA receptors are not alone: Dynamic regulation of NMDA receptor structure and function by neuregulins and transient cholesterol-rich membrane domains leads to disease-specific nuances of glutamate-signaling
    • Schrattenholz A, Soskic V. NMDA receptors are not alone: dynamic regulation of NMDA receptor structure and function by neuregulins and transient cholesterol-rich membrane domains leads to disease-specific nuances of glutamate-signaling. Curr Top Med Chem. 2006;6:663-86.
    • (2006) Curr Top Med Chem , vol.6 , pp. 663-686
    • Schrattenholz, A.1    Soskic, V.2
  • 12
    • 0020629581 scopus 로고
    • The dissociative anaesthetics, ketamine and phencyclidine, selectively reduce excitation of central mammalian neurones by N-methyl-aspartate
    • Anis NA, Berry SC, Burton NR, Lodge D. The dissociative anaesthetics, ketamine and phencyclidine, selectively reduce excitation of central mammalian neurones by N-methyl-aspartate. Br J Pharmacol. 1983;79:565-75.
    • (1983) Br J Pharmacol , vol.79 , pp. 565-575
    • Anis, N.A.1    Berry, S.C.2    Burton, N.R.3    Lodge, D.4
  • 13
    • 0025970493 scopus 로고
    • Actions of ketamine, phencyclidine and MK-801 on NMDA receptor currents in cultured mouse hippocampal neurones
    • MacDonald JF, Bartlett MC, Mody I, Pahapill P, Reynolds JN, Salter MW, et al. Actions of ketamine, phencyclidine and MK-801 on NMDA receptor currents in cultured mouse hippocampal neurones. J Physiol. 1991;432:483-508.
    • (1991) J Physiol , vol.432 , pp. 483-508
    • MacDonald, J.F.1    Bartlett, M.C.2    Mody, I.3    Pahapill, P.4    Reynolds, J.N.5    Salter, M.W.6
  • 14
    • 0024596865 scopus 로고
    • The excitatory amino acid receptors: Their classes, pharmacology, and distinct properties in the function of the central nervous system
    • Monaghan DT, Bridges RJ, Cotman CW. The excitatory amino acid receptors: their classes, pharmacology, and distinct properties in the function of the central nervous system. Annu Rev Pharmacol Toxicol. 1989;29:365-402.
    • (1989) Annu Rev Pharmacol Toxicol , vol.29 , pp. 365-402
    • Monaghan, D.T.1    Bridges, R.J.2    Cotman, C.W.3
  • 15
    • 0030907708 scopus 로고    scopus 로고
    • Multiple mechanisms of ketamine blockade of N-methyl-D-aspartate receptors
    • Orser BA, Pennefather PS, MacDonald JF. Multiple mechanisms of ketamine blockade of N-methyl-D-aspartate receptors. Anesthesiology. 1997;86:903-17.
    • (1997) Anesthesiology , vol.86 , pp. 903-917
    • Orser, B.A.1    Pennefather, P.S.2    MacDonald, J.F.3
  • 16
    • 0019968939 scopus 로고
    • Chemical synthesis and molecular pharmacology of hydroxylated 1-(1-phenylcyclohexyl) piperidine derivatives
    • Kamenka JM, Chiche B, Goudal R, Geneste P, Vignon J, Vincent JP, et al. Chemical synthesis and molecular pharmacology of hydroxylated 1-(1-phenylcyclohexyl) piperidine derivatives. J Med Chem. 1982;25:431-435.
    • (1982) J Med Chem , vol.25 , pp. 431-435
    • Kamenka, J.M.1    Chiche, B.2    Goudal, R.3    Geneste, P.4    Vignon, J.5    Vincent, J.P.6
  • 17
    • 0028675805 scopus 로고
    • Synthesis and analgesic activity of new phencyclidine derivatives
    • Al-Deeb OA. Synthesis and analgesic activity of new phencyclidine derivatives. Arzneimittelforschung. 1994;44(10):1141-4.
    • (1994) Arzneimittelforschung , vol.44 , Issue.10 , pp. 1141-1144
    • Al-Deeb, O.A.1
  • 18
    • 25444488532 scopus 로고    scopus 로고
    • Synthesis and biological properties of 2-hydroxy-1-(1-phenyltetralin)piperidine and some of its intermediates as derivatives of phencyclidine
    • Ahmadi A, Mahmoudi A. Synthesis and biological properties of 2-hydroxy-1-(1-phenyltetralin)piperidine and some of its intermediates as derivatives of phencyclidine Arzneimittelforschung. 2005;55(9):528-32.
    • (2005) Arzneimittelforschung , vol.55 , Issue.9 , pp. 528-532
    • Ahmadi, A.1    Mahmoudi, A.2
  • 19
    • 0030066552 scopus 로고    scopus 로고
    • New analgesics derived from the phencyclidine analogue thiencyclidine
    • Al-Deeb OA. New analgesics derived from the phencyclidine analogue thiencyclidine. Arzneimittelforschung. 1996;46(5):505-8.
    • (1996) Arzneimittelforschung , vol.46 , Issue.5 , pp. 505-508
    • Al-Deeb, O.A.1
  • 21
    • 0018689942 scopus 로고
    • Determination conformationnelle de derives de la phencyclidine en vue d'une corrélation structure-active.
    • Geneste P, Kamenka JM, Ung SN, Herrmann P, Goudal R, Trouiller G. Determination conformationnelle de derives de la phencyclidine en vue d'une corrélation structure-active. Eur J Med Chem. 1979;14:301-8.
    • (1979) Eur J Med Chem , vol.14 , pp. 301-308
    • Geneste, P.1    Kamenka, J.M.2    Ung, S.N.3    Herrmann, P.4    Goudal, R.5    Trouiller, G.6
  • 22
    • 66149174597 scopus 로고    scopus 로고
    • Synthesis and study on analgesic effects of 1-[1-(4-methylphenyl)(cyclohexyl)]4- piperidinol and 1-[1-(4-methoxyphenyl)(cyclohexyl)]4-piperidinol as two new phencyclidine derivatives
    • Ahmadi A, Khalili M, Abbassi S, Javadi M, Mahmoudi A, Hajikhani R. Synthesis and study on analgesic effects of 1-[1-(4-methylphenyl)(cyclohexyl)]4- piperidinol and 1-[1-(4-methoxyphenyl)(cyclohexyl)]4-piperidinol as two new phencyclidine derivatives. Arzneimittelforschung. 2009;59(4):202-6.
    • (2009) Arzneimittelforschung , vol.59 , Issue.4 , pp. 202-206
    • Ahmadi, A.1    Khalili, M.2    Abbassi, S.3    Javadi, M.4    Mahmoudi, A.5    Hajikhani, R.6
  • 23
    • 74949098711 scopus 로고    scopus 로고
    • Kaorv H. O-H stretching absorption and conformation of the β-methyl derivatives of 1-tetralol, 4-chromanol, 4-thiochromanol, and 4-thiochromanol 1,1-dioxide. Bull Chem Soc Japan. 1974;47(10):2607-8.
    • Kaorv H. O-H stretching absorption and conformation of the β-methyl derivatives of 1-tetralol, 4-chromanol, 4-thiochromanol, and 4-thiochromanol 1,1-dioxide. Bull Chem Soc Japan. 1974;47(10):2607-8.
  • 24
    • 66149164416 scopus 로고
    • Method for stereoselective production of substituted cyclohexylcyanhydrines
    • Geneste P, Kamenka JM, Dessapt P. Method for stereoselective production of substituted cyclohexylcyanhydrines. Bull Soc Chim Fr. 1980;II:187-91.
    • (1980) Bull Soc Chim Fr , vol.2 , pp. 187-191
    • Geneste, P.1    Kamenka, J.M.2    Dessapt, P.3
  • 25
    • 0033822145 scopus 로고    scopus 로고
    • Antinociceptive effect of the combination of pentazocine with morphine in the tail-immersion and scald-pain tests in rats
    • Hamura H, Yoshida M, Shimizu K, Matsukura T, Suzuki H, Narita M, et al. Antinociceptive effect of the combination of pentazocine with morphine in the tail-immersion and scald-pain tests in rats. Jpn J Pharmacol. 2000;83(4):286-92.
    • (2000) Jpn J Pharmacol , vol.83 , Issue.4 , pp. 286-292
    • Hamura, H.1    Yoshida, M.2    Shimizu, K.3    Matsukura, T.4    Suzuki, H.5    Narita, M.6
  • 26
    • 56949085589 scopus 로고    scopus 로고
    • Minocycline prevents the development of neuropathic pain, but not acute pain: Possible anti-inflammatory and antioxidant mechanisms
    • Padi SSV, Kulkarni S. K. Minocycline prevents the development of neuropathic pain, but not acute pain: Possible anti-inflammatory and antioxidant mechanisms. Eur J Pharmacol. 2008;601:79-87.
    • (2008) Eur J Pharmacol , vol.601 , pp. 79-87
    • Padi, S.S.V.1    Kulkarni, S.K.2
  • 28
    • 0017643233 scopus 로고
    • The formalin test: A quantitative study of the analgesic effects of morphine, meperidine, and brain stem stimulation in rats and cats
    • Dubuisson D, Dennis SG. The formalin test: a quantitative study of the analgesic effects of morphine, meperidine, and brain stem stimulation in rats and cats. Pain. 1977;4(2):161-74.
    • (1977) Pain , vol.4 , Issue.2 , pp. 161-174
    • Dubuisson, D.1    Dennis, S.G.2
  • 29
    • 0019407168 scopus 로고
    • Isolation, identification and synthesis of compounds cosynthesized in the preparation of phencyclidine
    • Jones LA, Beaver RW, Schmoeger TL, Ort JF, Leander JD. Isolation, identification and synthesis of compounds cosynthesized in the preparation of phencyclidine. J Org Chem. 1981;46:3330-3.
    • (1981) J Org Chem , vol.46 , pp. 3330-3333
    • Jones, L.A.1    Beaver, R.W.2    Schmoeger, T.L.3    Ort, J.F.4    Leander, J.D.5
  • 30
    • 33344475261 scopus 로고    scopus 로고
    • Selective pathways for the metabolism of phencyclidine by cytochrome P450 2B enzymes: Identification of electrophilic methabolites, glutathione and N-acetyl cysteine adducts
    • Shebley M, Jushchyshyn MI, Hollenberg F. Selective pathways for the metabolism of phencyclidine by cytochrome P450 2B enzymes: identification of electrophilic methabolites, glutathione and N-acetyl cysteine adducts. Drug Metab Dispos. 2006;34(3):375-83.
    • (2006) Drug Metab Dispos , vol.34 , Issue.3 , pp. 375-383
    • Shebley, M.1    Jushchyshyn, M.I.2    Hollenberg, F.3
  • 31
    • 74949124932 scopus 로고    scopus 로고
    • Societe de conseils de recherché et d
    • applications scientfiques S.C.R.A.S, FR, assignee. Phencyclidine derivatives, preparation method and pharmaceutical compositions containing same. United States patent US 6,342,511B1. 2002
    • Kamenka JM, Hamon J, Vignon J, inventors; Societe de conseils de recherché et d'applications scientfiques (S.C.R.A.S.) (FR), assignee. Phencyclidine derivatives, preparation method and pharmaceutical compositions containing same. United States patent US 6,342,511B1. 2002.
    • Kamenka, J.M.1    Hamon, J.2    Vignon, J.3    inventors4
  • 32
    • 0029937786 scopus 로고    scopus 로고
    • Systemic ketamine attenuates nociceptive behaviors in a rat model of peripheral neuropathy
    • Qian J, Brown SD, Carlton SM. Systemic ketamine attenuates nociceptive behaviors in a rat model of peripheral neuropathy. Brain Res. 1996;715:51-62.
    • (1996) Brain Res , vol.715 , pp. 51-62
    • Qian, J.1    Brown, S.D.2    Carlton, S.M.3
  • 33
    • 0032947439 scopus 로고    scopus 로고
    • Oral ketamine is antinociceptive in the rat formalin test: Role of the metabolite, nor ketamine
    • Shimoyama M, Shimoyama N, Gorman AL. Oral ketamine is antinociceptive in the rat formalin test: role of the metabolite, nor ketamine. Pain. 1999;81:85-93.
    • (1999) Pain , vol.81 , pp. 85-93
    • Shimoyama, M.1    Shimoyama, N.2    Gorman, A.L.3
  • 34
    • 0032902566 scopus 로고    scopus 로고
    • Prolonged analgesic effect of ketamine, an N-methyl-D-asparate receptor inhibitor, in patients with chronic pain
    • Rabben T, Skjelbred P, Oye I. Prolonged analgesic effect of ketamine, an N-methyl-D-asparate receptor inhibitor, in patients with chronic pain. J Pharmacol Exp Ther. 1999;289:1060.
    • (1999) J Pharmacol Exp Ther , vol.289 , pp. 1060
    • Rabben, T.1    Skjelbred, P.2    Oye, I.3
  • 35
    • 0141543797 scopus 로고    scopus 로고
    • Orally administered paracetamol does not act locally in the rat formalin test: Evidence for a supraspinal, serotonin-dependent antinociceptive mechanism
    • Bonnefont J, Alloui A, Chapuy E, Clottes E, Eschalier A. Orally administered paracetamol does not act locally in the rat formalin test: evidence for a supraspinal, serotonin-dependent antinociceptive mechanism. Anesthesiology. 2003;99(4):976-81.
    • (2003) Anesthesiology , vol.99 , Issue.4 , pp. 976-981
    • Bonnefont, J.1    Alloui, A.2    Chapuy, E.3    Clottes, E.4    Eschalier, A.5


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