New morpholine analogues of phencyclidine: Chemical synthesis and pain perception in rats

Pharmacology Biochemistry and Behavior

Volumn 98, Issue 2, 2011, Pages 227-233

  Ahmadi, Abbas ^a   Khalili, Mohsen ^b   Hajikhani, Ramin ^a   Naserbakht, Moslem ^a  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b SHAHED UNIVERSITY   (Iran)

Author keywords

Formalin test; Hydroxyl methyl derivative; Methoxy morpholine derivative; Pain activities; Phencyclidine; Tail immersion test

Indexed keywords

1 (1 PHENYLCYCOHEXYL)MORPHOLINE; 2 PROPANOL; ANALGESIC AGENT; ETHER; FORMALDEHYDE; HYDROXYMETHYL 1 (1 PHENYLCYCOHEXYL)MORPHOLINE; METHOXY 1 (1 PHENYLCYCOHEXYL)MORPHOLINE; METHYL 1 (1 PHENYLCYCOHEXYL)MORPHOLINE; MORPHOLINE DERIVATIVE; PHENCYCLIDINE; PHENCYCLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CHRONIC PAIN; COMPARATIVE STUDY; CONTROLLED STUDY; DOSE TIME EFFECT RELATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; IMMERSION; NOCICEPTION; NONHUMAN; PAIN; PRIORITY JOURNAL; RAT;

ANALGESICS; ANIMALS; FEMALE; MODELS, ANIMAL; PAIN MEASUREMENT; PAIN PERCEPTION; PHENCYCLIDINE; RATS; STRUCTURE-ACTIVITY RELATIONSHIP;

RATTUS;

EID: 79251533925     PISSN: 00913057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.pbb.2010.12.019     Document Type: Article

References (36)

1. M.O. Abdol-Rahman, M.N. Aboul-Eneim, and G.H. Tammom Action of Grignard reagents aryllithium on 1, 1-disubstituted cyclohexane derivatives Egypt J Chem 18 3 1975 581 586
2. A. Ahmadi, and A. Mahmoudi Synthesis and biological properties of 2- hydroxy-1- (1- phenyltetralin) piperidine and some of its intermediates as derivatives of phencyclidine Arzneimittelforschung 55 9 2005 528 532 (Pubitemid 41367752)
3. A. Ahmadi, and A. Mahmoudi Synthesis with improved yield and study on analgesic effect of 2-methoxyphencyclidine Arzneimittelforschung 56 5 2006 346 350 (Pubitemid 43875443)
4. A. Ahmadi, M. Khalili, S. Abbassi, M. Javadi, A. Mahmoudi, and R. Hajikhani 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 59 4 2009 202 206
5. A. Ahmadi, M. Khalili, F. Mihandoust, and L. Barghi Synthesis and determination of acute and chronic pain activities of 1-[1-[3-methyphenyl] [tetralyl]] piperidine as a new derivative of phencyclidine via tail immersion and formalin tests Arzneimittelforschung 60 1 2010 30 35
6. A. Ahmadi, M. Khalili, R. Hajikhani, and M. Naserbakht Synthesis and determination of acute and chronic pain activities of 1-[1-[4-methylphenyl] [cyclohexyl] morpholine as a new phencyclidine derivative in Rats Arzneimittelforschung 61 2011 1 11
7. O.A.A. Al-deeb Synthesis and analgesic activity of new phencyclidine derivatives Arzneimittelforschung 44 II 1994 1141 1144
8. O.A.A. Al-deeb New analgesic derived from the phencyclidine analogue hiencyclidine Arzneimittelforschung 46 I 1996 505 508
9. A.H. Beckett, and P. Kourounakis The relationship between chemical structure and basicity in some morpholine compounds Arzneimittelforschung 26 1976 1810 1811
10. R.D. Budd Phencyclidine (PCP)-structure versus reactivity Clin Toxicol 18 9 1981 1033 1041
11. D.M. Chen, K. Chen, and H. Wang Antithrombotic effects of morpholine and piperazine ring derivatives and their molecular mechanism Yao Xue Xue Bao 38 9 2003 641 645
12. BA. Chizh, PM. Headley, and TM. Tzschentke NMDA receptor antagonists as analgesics: focus on the NR2B subtype Trends Pharmacol Sci 22 2001 636 642 (Pubitemid 33135525)
13. C. Deleuze-Masquefa, M. Michaud, J. Vignon, and J.M. Kamenka 1-[1-2-Benzo [b] thiopheneyl)cyclohexyl]piperidine hydrochloride (BTCP) yields two active primary metabolites in vitro: synthesis, identification from rat liver microsome extracts, and affinity for the neuronal dopamine transporter J Med Chem 40 25 1997 4019 4025 (Pubitemid 28008397)
14. P.M. Dougherty, and P.S. Staats Intrathecal drug therapy for chronic pain from basic science to clinical practice Anesthesiology 91 1999 1891 1918
15. D. Dubuisson, and S.G. Dennis The formalin test: a quantitative study of the analgesic effects of morphine, meperidine, and brain stem stimulation in rats and cats Pain 4 2 1977 161 174 (Pubitemid 8234766)
16. R. Erard, R. Luisada, and R. Peele The PCP psychosis prolonged intoxication or drug-precipitated functional illness? J Psychoact Drugs 12 1980 235
17. P. Geneste, J.M. Kamenka, and P. Dessapt Method for stereoselective production of substituted cyclohexylcyanhydrines Bull Soc Chim Fr 2 1980 187 191
18. H. Hamura, M. Yoshida, K. Shimizu, T. Matsukura, H. Suzuki, and M. Narita Antinociceptive effect of the combination of pentazocine with morphine in the tail-immersion and scald-pain tests in rats Jpn J Pharmacol 83 4 2000 286 292
19. C.R. Honey, Z. Miljkovic, and J.F. Macdonald Ketamine and phencyclidine cause a voltage-dependent block of responses to L aspartic acid Neurosci Lett 61 1985 135 139 (Pubitemid 16201138)
20. S. Hunskaar, and K. Hole The formalin test in mice: dissociation between inflammatory and non-inflammatory pain Pain 30 1987 103 114 (Pubitemid 17094194)
21. Y. Itzhak, A. Kalir, B.A. Weissman, and S. Cohen New analgesic drugs derived from phencyclidine J Med Chem 24 1981 496 499 (Pubitemid 11021881)
22. Y. Jacquet The NMDA receptor: central role in pain inhibition in rat periaqueductal gray Eur J Pharmacol 154 1988 271 276
23. P.Y. Johnson, R. Pan, J. Quan Wen, and C.J. Halfman Synthesis of amine derivatives of phencyclidine J Org Chem 46 1981 2049 2054
24. S. Kapur, and P. Seeman NMDA receptor antagonists ketamine and PCP have direct effects on the dopamine D2 and serotonin 5-HT2 receptors-implications for models of schizophrenia Mol Psychiatry 7 2002 837 844
25. V.H. Maddox, E.F. Godefroi, and R.F. Parcell The synthesis of phencyclidine and other 1-arylcyclohexylamines J Med Chem 8 1965 230 235
26. N. Molina, M.T. Bedran-de-Castro, and J.C. Bedran-de-Castro Sex-related differences in the analgesic response to the rat tail immersion test Braz J Med Biol Res 27 7 1994 1669 1672 (Pubitemid 24250186)
27. A. Mori, Y. Noda, T. Mamiya, Y. Miyamoto, A. Nakajima, and H. Furukawa Phencyclidine-induced discriminative stimulus is mediated via phencyclidine binding sites on the N-methyl-D-aspartate receptor-ion channel complex, not via sigma receptors Behav Brain Res 119 2001 33 40 (Pubitemid 32063352)
28. A. Mozayani Phencyclidine-effects on human performance and behavior Forensic Sci Rev 15 1 2003 62 74
29. A.M. Ogunbadeniyi, and A. Adejare Syntheses of fluorinated phencyclidine analogs J Fluorine Chem 114 2002 39 42
30. J.W. Olney, J. Labruyere, G. Wang, D.F. Wozniak, M.T. Price, and M.A. Sesma NMDA antagonist neurotoxicity: mechanism and prevention Science 254 1991 1515 1518 (Pubitemid 21917493)
31. J.W. Proksch, W.B. Gentry, and S.M. Owens The effect of rate of drug administration on the extent and time course of phencyclidine distribution in rat brain, testis, and serum Drug Metab Dispos 28 7 2000 742 747 (Pubitemid 30470822)
32. K. Ramabadran, M. Bansinath, H. Turndorf, and M.M. Puig Tail immersion test for the evaluation of a nociceptive reaction in mice. Methodological considerations J Pharmacol Methods 21 1 1989 21 31 (Pubitemid 19064683)
33. E. Rekka, S. Retsas, V.J. Demopoulos, and P.N. Kourounakis Lipophilicity of some substituted morpholine derivatives synthesized as potential antinociceptive agents Arch Pharm (Weinheim) 323 1 1990 53 56 (Pubitemid 20098719)
34. M. Shebley, M.I. Jushchyshyn, and F. Hollenberg 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 34 3 2006 375 383 (Pubitemid 43290895)
35. M. Shibata, T. Ohkubo, H. Takahashi, and R. Inoki Modified formalin test: characteristic biphasic pain response Pain 38 1989 347 352 (Pubitemid 19251258)
36. W.H. Soine Clandestine drug synthesis Med Res Rev 6 1 1986 41 74 (Pubitemid 16147392)