Synthesis and determination of acute and chronic pain activities of 1-[1-(4-methylphenyl)(cyclohexyl)] morpholine as a new phencyclidine derivative in rats

Arzneimittel-Forschung/Drug Research

Volumn 61, Issue 2, 2011, Pages 92-97

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

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b SHAHED UNIVERSITY   (Iran)

Author keywords

Acute and chronic pain; CAS 2201 40 3; CAS 77 10 1; Methyl morpholine derivative of phencyclidine; Tail immersion and formalin tests

Indexed keywords

1 (1 PHENYLCYCLOHEXYL)MORPHOLINE; 1 [1 (4 METHYLPHENYL)(CYCLOHEXYL)]MORPHOLINE; PHENCYCLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ARTICLE; CHRONIC PAIN; DRUG SYNTHESIS; FEMALE; NONHUMAN; PAIN; RAT;

EID: 79952311109     PISSN: 00044172     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0031-1296173     Document Type: Article

References (31)

1. Ahmadi A, Mahmoudi A. Synthesis with improved yield and study on analgesic effect of 2-methoxyphencyclidine. Arzneimittelforschung. 2006;56(5):346-50. (Pubitemid 43875443)
2. Al-deeb OAA. Synthesis and analgesic activity of new phencyclidine derivatives. Arzneimittelforschung. 1994;44(10):1141-4.
3. Mori A, Noda Y, Mamiya T, Miyamoto Y, Nakajima A, Furukawa H, et al. 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. 2001;119:33-40. (Pubitemid 32063352)
4. 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. (Pubitemid 41367752)
5. Al-deeb OAA. New analgesics derived from the phencyclidine analogue thiencyclidine. Arzneimittelforschung. 1996;46(5):505-8.
6. Ogunbadeniyi AM, Adejare A, Syntheses of fluorinated phencyclidine analogs. J Fluorine Chem. 2002;114:39-42.
7. Ahmadi A, Shafiezadeh M, Fathollahi Y, Darvich MR, Mahmoudi A, Bahmani M, et al. Synthesis with improved yield and study on analgesic effect of 2-hydroxyphencyclidine. Arzneimittelforschung. 2005;55(3):172-6. (Pubitemid 40460020)
8. Kamenka JM, Ung MSN, Herrmann P. Determination conformationnelle de derives de la phencyclidine en vue d'une correlation acture-active. Eur J Med Chem Ther. 1979;14(IV):301-8. (Pubitemid 10238282)
9. 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;25:431-5. (Pubitemid 12078648)
10. Itzhak Y, Kalir A, Weissman BA, Cohen S. Newanalgesic drugs derived from phencyclidine. J Med Chem. 1981;24: 496-9.
11. 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.
12. Ahmadi A, Khalili M, Mihandoust F, Barghi L. 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. 2010;60(1):30-5.
13. Ahmadi A, Solati J, Hajikhani R, Onagh M, Javadi M. Synthesis and analgesic effects of 1-[1-(2-methylphenyl)(cyclohexyl)]-3-piperidinol as a new derivative of phencyclidine in mice. Arzneimittelforschung. 2010;60(8):492-6.
14. Johnson PY, Pan R, Quan Wen J, Halfman CJ. Synthesis of amine derivatives of phencyclidine. J Org Chem. 1981;46:2049-54.
15. Chen DM, Chen K, Wang H. Antithrombotic effects of morpholine and piperazine ring derivatives and their molecular mechanism. Yao Xue Xue Bao. 2003;38(9):641-5.
16. Regnier G, Guillonneau C, Lepagnol J, Lestage P. Assignee: Adir et compagnie, Courbevoie, France; Morpholine compounds, compositions and use. United States Patent. 1991;5026701.
17. Kaneyoshi K, Takayuki D, Mitsuo Y. Assignee: Takeda Chemical Industries LTD., Japan; Tetracyclic morpholine derivatives and their use as analgesics. European Patent. 1994;0610793.
18. Rekka E, Retsas S, Demopoulos VJ, Kourounakis PN. Lipophilicity of some substituted morpholine derivatives synthesized as potential antinociceptive agents. Arch Pharm (Weinheim). 1990;323(1):53-6. (Pubitemid 20098719)
19. Soine WH, Clandestine drug synthesis. Med Res Rev. 1986;6(1):41-74. (Pubitemid 16147392)
20. Budd RD, Phencyclidine (PCP)-structure versus reactivity. Clin Toxicol. 1981;18(9):1033-41.
21. Geneste P, Kamenka JM, Dessapt P. Method for stereo-selective production of substituted cyclohexylcyanhydrines. Bull Soc Chim Fr. 1980;II:187-91.
22. Abdol-Rahman MO, Aboul-Eneim MN, Tammom GH. Action of Grignard reagents aryl lithium on 1,1-disubstituted cyclohexane derivatives. Egypt J Chem. 1975;18(3):581-6.
23. Maddox VH, Godefroi EF, Parcell RF. The synthesis of phencyclidine and other 1-arylcyclohexylamines. J Med Chem. 1965;8:230-5.
24. Ramabadran K, Bansinath M, Turndorf H, Puig MM. Tail immersion test for the evaluation of a nociceptive reaction in mice: methodological considerations. J Pharmacol Methods. 1989;21(1):21-31. (Pubitemid 19064683)
25. Molina N, Bedran-de-Castro MT, Bedran-de-Castro JC. Sex-related differences in the analgesic response to the rat tail immersion test. Braz J Med Biol Res. 1994;27(7):1669-72. (Pubitemid 24250186)
26. 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.
27. 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.
28. Mozayani A. Phencyclidine-effects on human performance and behavior. Forensic Sci Rev. 2003;15(1):62-74.
29. Dougherty PM, Staats PS. Intrathecal drug therapy for chronic pain from basic science to clinical practice. Anesthesiology. 1999;91:1891-918.
30. Proksch JW, Gentry WB, Owens SM. 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. 2000; 28(7):742-7. (Pubitemid 30470822)
31. Deleuze-Masquefa C, Michaud M, Vignon J, Kamenka JM. 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. 1997;40(25):4019-25.