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Synthesis and antinociception properties of phencyclidine derivatives with modified aromatic or cycloalkyl rings and amino group

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Abstract

Phencyclidine is an arylcyclohexylamine compound which has received a lot of investigative attention due to the complex spectrum of behaviours and its complicated interactions with the central nervous system. Phencyclidine administration may act as stimulant, depressant, hallucinogen, and analgesic depending on dose and tested species. In this study, new phenyl and thienyl analogues with specific affinity for the phencyclidine sites in NMDA receptors, dopamine uptake blocking, or both of them were synthesized. The acute and chronic pain properties of these compounds were studied using the tail immersion and formalin tests on mice and the results were compared with control and phencyclidine groups at a dose of 10 mg/kg. The outcomes indicated that all synthesized compounds showed better activities to decrease acute thermal and chemical, but not chronic pains. Also, these effects were more significant for phenyl (group 1) compared to thiophene (group 2) analogues, which is probably due to the higher affinity of group 1 for inhibition of dopamine reuptake compared to binding to the phencyclidine sites in NMDA receptors in this family.

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References

  1. Carlson KM, Wagner GC (2005) Life Sci 77:372

    Article  CAS  Google Scholar 

  2. Johnson KM, Jones SM (1990) Annu Rev Pharmacol Toxicol 39:707

    Article  Google Scholar 

  3. Pechnick RN, Bresee CJ, Poland RE (2006) Life Sci 78:2006

    Article  CAS  Google Scholar 

  4. Albuquerque EX, Aguayo LG, Warnick JE, Ickowicz RK, Blaustein MP (1983) Fed Proc 42:2584

    CAS  Google Scholar 

  5. Johnson KM, Snell LD, Morter RS (1987) Pharmacol Biochem Behav 28:128

    Google Scholar 

  6. Sircar R, Zukin S (1986) In Clouet DH (ed) Phencyclidine: an update. NIDA Research Monograph, vol 64. National Institute on Drug Abuse, Rockville, p 14

  7. Al-deeb OAA (1996) Arzneimittelforsch 46:505

    CAS  Google Scholar 

  8. Kamenka JM, Hamon J, Vignon J (2002) Phencyclidine derivatives, preparation method and pharmaceutical compositions containing same. US Patent 6,342,511

  9. Ahmadi A, Khalili M, Abbassi S, Javadi M, Mahmoudi A, Hajikhani R (2009) Arzneimittelforsch 59:202

    CAS  Google Scholar 

  10. Ahmadi A, Khalili M, Hajikhani R, Naserbakht M (2011) Pharmacol Biochem Behav 98:227

    Article  CAS  Google Scholar 

  11. Ahmadi A, Kermani M, Naderi N, Hajikhani R, Rezaee NM, Javadi M, Nahri-Niknafs B (2012) Curr Med Chem 19:763

    Article  CAS  Google Scholar 

  12. Ahmadi A, Khalili M, Marami S, Ghadiri A, Nahri-Niknafs B (2014) Mini Rev Med Chem 14:64

    Article  CAS  Google Scholar 

  13. Ferle-Vidovic A, Kastelan M, Petrovic D, Suman L, Kaselj M, Skare D, Mlinari-Majerski K (1993) Eur J Med Chem 28:243

    Article  CAS  Google Scholar 

  14. Chaudieu I, Vignon J, Chicheportiche M, Kamenka JM, Trouiller G, Chicheportiche R (1989) Pharmacol Biochem Behav 32:699

    Article  CAS  Google Scholar 

  15. Cacabelos R, Takeda M, Winblad B (1999) Int J Geriatr Psychiatry 14:3

    Article  CAS  Google Scholar 

  16. Seeman P, Caruso C, Lasaga M (2008) Synapse 62:149

    Article  CAS  Google Scholar 

  17. Chen YW, Chu CC, Chen YC, Wang JJ, Hung CH (2011) Anesth Analg 113:191

    Article  CAS  Google Scholar 

  18. Mount C, Downton C (2006) Nat Med 12:780

    Article  CAS  Google Scholar 

  19. Miyata T, Kasé Y, Kamikawa Y, Kataoka M, Kikuchi K, Touchi T (1969) Life Sci 8:843

    Article  CAS  Google Scholar 

  20. Schachtel BP, Voelker M, Sanner KM, Gagney D, Bey M, Schachtel EJ, Becka M (2010) J Clin Pharmacol 50:1429

    Article  CAS  Google Scholar 

  21. Bruylants P (1926) Bull Soc Chim Belg 35:139

    Google Scholar 

  22. Kalir A, Edery H, Pelah Z, Balderman D, Porath G (1969) J Med Chem 12:473

    Article  CAS  Google Scholar 

  23. Patterson SL, Jones DC, Shanks EJ, Frearson JA, Gilbert IH, Wyatt PG, Fairlamb AH (2009) ChemMedChem 4:1341

    Article  CAS  Google Scholar 

  24. March J (1977) Advanced organic chemistry: reactions mechanisms and structure, 2nd edn. McGraw Hill, St. Louis, p 816

    Google Scholar 

  25. Carey FA, Sundberg RJ (1977) Advanced Organic Chemistry, Part B: Reactions and Synthesis. Plenum Press, New York, p 172

    Google Scholar 

  26. Yoshimura J, Ohgo Y, Sato T (1964) J Am Chem Soc 86:3858

    Article  CAS  Google Scholar 

  27. Vignon J, Pinet V, Cerruti C, Kamenka JM, Chicheportiche R (1988) Eur J Pharmacol 148:427

    Article  CAS  Google Scholar 

  28. Vignon J, Lazdunski M (1984) Biochem Pharmacol 33:700

    Article  CAS  Google Scholar 

  29. Michaud M, Warren H, Drian MJ, Rambaud J, Cerruti P, Nicolas JP, Vignon J, Privat A, Kamenka JM (1994) Eur J Med Chem 29:869

    Article  CAS  Google Scholar 

  30. Godefroi EF, Maddox VH, Parcell RF (1963) Process for producing a depressant-like effect on the central nervous system. US Patent 3,097,136

  31. Dubuisson D, Dennis SG (1977) Pain 4:161

    Article  CAS  Google Scholar 

  32. Ahmadi A, Solati J, Hajikhani R, Onagh M, Javadi M (2010) Arzneimittelforsch 60:492

    CAS  Google Scholar 

  33. Ramabadran K, Bansinath M, Turndorf H, Puig MM (1989) J Pharmacol Methods 21:21

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was a research project at Islamic Azad University and the authors would like to express their gratitude to them. They thank Fariba Ansari for her assistance with the pharmacological tests. They appreciate Mojtaba Chaichi, EFL educator at Safir English Language Academy, for proofreading the initial draft of this article.

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Authors and Affiliations

  1. Department of Medicinal Chemistry, Pharmaceutical Sciences Branch, Islamic Azad University, Tehran, Iran

    Abbas Ahmadi, Mahnaz Barzin, Fatemeh Bakhtiari, Maede Barjeste & Babak Nahri-Niknafs

  2. Department of Chemistry, Faculty of Science, Karaj Branch, Islamic Azad University, Karaj, Iran

    Mohsen Pooladi

  3. Neurophysiology Research Center, Shahed University, Tehran, Iran

    Mohsen Khalili

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  1. Abbas Ahmadi
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  2. Mohsen Khalili
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  3. Mahnaz Barzin
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  7. Babak Nahri-Niknafs
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Correspondence to Abbas Ahmadi.

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Ahmadi, A., Khalili, M., Barzin, M. et al. Synthesis and antinociception properties of phencyclidine derivatives with modified aromatic or cycloalkyl rings and amino group. Monatsh Chem 147, 457–464 (2016). https://doi.org/10.1007/s00706-015-1472-1

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  • DOI: https://doi.org/10.1007/s00706-015-1472-1

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