Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2018; 50(21): 4201-4215
DOI: 10.1055/s-0037-1609935
DOI: 10.1055/s-0037-1609935
short review
Syntheses of Ketamine and Related Analogues: A Mini Review
The authors thank the Auckland Cancer Society Research Centre for their generous financial support.Further Information
Publication History
Received: 18 June 2018
Accepted after revision: 27 July 2018
Publication Date:
20 August 2018 (online)
Abstract
Ketamine [2-(2-chlorophenyl)-2-(methylamino)cyclohexanone] is a dissociative anaesthetic, first developed in 1963 by Parke-Davis. It finds widespread application in the treatment of battlefield injuries, and in emergency departments for use in children. In recent times the clinical interest in ketamine has increased due to the positive impact it has in treating depression and the rapid onset of its antidepressant effect. This review covers the synthetic effort towards ketamine and related analogues over the past 60 years to give readers an overview of past, current, and future research outlook pertaining to ketamine-like molecules.
1 Introduction
2 Early Work
3 Synthesis
3.1 Ketamine
3.2 Norketamine
3.3 Ketamine Analogues
4 Future Outlook and Conclusion
-
References
- 1 Tyler MW. Yourish HB. Ionescu DF. Haggarty SJ. ACS Chem. Neurosci. 2017; 8: 1122
- 2 Wiik AV. Patel P. Bovis J. Cowper A. Pastides PS. Hulme A. Evans S. Stewart C. World J. Orthop. 2018; 9: 50
- 3 Stevic M. Ristic N. Budic I. Ladjevic N. Trifunovic B. Rakic I. Majstorovic M. Burazor I. Simic D. Lasers Med. Sci. 2017; 32: 1525
- 4 Bey T. Patel A. Calif. J. Emerg. Med. 2007; 8: 9
- 5 Stirling J. McCoy L. Subst. Use Misuse 2010; 45: 2428
- 6 Trivedi S. Kumar R. Tripathi AK. Mehta RK. J. Clin. Diagn. Res. 2016; 10: 1
- 7 Smith KM. Larive LL. Romanelli F. Am. J. Health-Syst. Pharm. 2002; 59: 1067
- 8 Zarate CA. Brutsche NE. Ibrahim L. Franco-Chaves J. Diazgranados N. Cravchik A. Selter J. Marquardt CA. Liberty V. Luckenbaugh DA. Biol. Psychiatry 2012; 71: 939
- 9 Salvadore G. Singh JB. CNS Neurosci. Ther. 2013; 19: 428
- 10 Zhang C. Wang Y. Laufer R. WO 2017180589, 2017
- 11 Coppola M. Mondola R. Med. Hypotheses 2012; 79: 504
- 12 Zanos P. Gould TD. Mol. Psychiatry 2018; 23: 801
- 13 Kavalali ET. Monteggia LM. Curr. Opin. Pharmacol. 2015; 20: 35
- 14 Dale E. Bang-Andersen B. Sanchez C. Biochem Pharmacol. 2015; 95: 81
- 15 Sleigh J. Harvey M. Voss L. Denny B. Trends Anaesthesia Crit. Care 2014; 4: 76
- 16 Mion G. Villevieille T. CNS Neurosci. Ther. 2013; 19: 370
- 17 Karakas E. Furukawa H. Science (Washington, D. C.) 2014; 344: 992
- 18 Pan J. Chen Q. Willenbring D. Mowrey D. Kong X. Cohen A. Divito CB. Xu Y. Tang P. Structure 2012; 20: 1463
- 19 Stevens CL. Chang CH. J. Org. Chem. 1962; 27: 4392
- 20 Stevens CL. Elliott RD. Winch BL. J. Am. Chem. Soc. 1963; 85: 1464
- 21 Stevens CL. Thuillier A. Daniher FA. J. Org. Chem. 1965; 30: 2962
- 22 Stevens CL. Klundt IL. Munk ME. Pillai MD. J. Org. Chem. 1965; 30: 2967
- 23 Stevens CL. Treat TA. Pillai PM. Schmonsees W. Glick MD. J. Am. Chem. Soc. 1973; 95: 1978
- 24 Stevens CL. Ash AB. Thuillier A. Amin JH. Balys A. Dennis WE. Dickerson JP. Glinski RP. Hanson HT. Pillai MD. Stoddard JW. J. Org. Chem. 1966; 31: 2593
- 25 Stevens CL. Hanson HT. Taylor KG. J. Am. Chem. Soc. 1966; 88: 2769
- 26 Stevens CL. Thuillier A. Taylor KG. Daniher FA. Dickerson JP. Hanson HT. Nielsen NA. Tikotkar NA. Weier RM. J. Org. Chem. 1966; 31: 2601
- 27 Li L. Vlisides PE. Front. Hum. Neurosci. 2016; 10: 1
- 28 Stevens CL. DE 1793315 B1, 1972
- 29 Stevens CL. BE 634208, 1962
- 30 Stevens CL. US 3254124 A, 1966
- 31 Zhang ZQ. Chen T. Zhang FM. Org. Lett. 2017; 19: 1124
- 32 Gant TG. Sarshar S. US 20080268071 A1, 2008
- 33 Zanos P. Moaddel R. Morris PJ. Georgiou P. Fischell J. Elmer GI. Alkondon M. Yuan P. Pribut HJ. Singh NS. Dossou KS. S. Fang Y. Huang X.-P. Mayo CL. Wainer IW. Albuquerque EX. Thompson SM. Thomas CJ. Zarate CA. Jr. Gould TD. Nature (London) 2016; 533: 481
- 34 Sulake RS. Chen C. Lin HR. Lua AC. Bioorg. Med. Chem. Lett. 2011; 21: 5719
- 35 Yokoyama T. Yokoyama R. Nomura S. Matsumoto S. Fujiyama R. Kiyooka S.-I. Bull. Chem. Soc. Jpn. 2009; 82: 1528
- 36 Yokoyama R. Matsumoto S. Nomura S. Higaki T. Yokoyama T. Kiyooka S.-I. Tetrahedron 2009; 65: 5181
- 37 Yang X. Toste FD. J. Am. Chem. Soc. 2015; 137: 3205
- 38 Brunner H. Kagan HB. Kreutzer G. Tetrahedron: Asymmetry 2003; 14: 2177
- 39 Parcell RF. Sanchez JP. J. Org. Chem. 1981; 46: 5055
- 40 Hong SC. Davisson JN. J. Pharm. Sci. 1981; 71: 912
- 41 Han Y. Mahender Reddy K. Corey EJ. Org. Lett. 2017; 19: 5224
- 42 Biermann M. Zheng G. Hojahmat M. Moskalev NV. Crooks PA. Tetrahedron Lett. 2015; 56: 2608
- 43 Leung LY. Baillie TA. J. Med. Chem. 1986; 29: 2396
- 44 Morris PJ. Moaddel R. Zanos P. Moore CE. Gould T. Zarate CA. Jr. Thomas CJ. Org. Lett. 2017; 19: 4572
- 45 Chen CY. Floegel O. Justus M. Maurer A. Reuter K. Strittmatter T. Wedel T. US 20160332962 A1, 2016
- 46 Wang S. Li C. Beijing Daxue Xuebao, Ziran Kexueban 1987; 2: 116
- 47 Moghimi A. Rahmani S. Zare R. Sadeghzadeh M. Synth. Commun. 2014; 44: 2021
- 48 Zarantonello P. Bettini E. Paio A. Simoncelli C. Terreni S. Cardullo F. Bioorg. Med. Chem. Lett. 2011; 21: 2059
- 49 Emnett C. Li H. Jiang X. Benz A. Boggiano J. Conyers S. Wozniak DF. Zorumski CF. Reichert DE. Mennerick S. Sci. Rep. 2016; 6: 38808
- 50 Ahmadi A. Khalili M. Hajikhani R. Hosseini H. Afshin N. Nahri-Niknafs B. Med. Chem. (Sharjah, United Arab Emirates) 2012; 8: 246
- 51 Elhawi H. Eini H. Douvdevani A. Byk G. Molecules 2012; 17: 6784
- 52 Burak K. Lipnicka U. Orszanska H. Rykowski Z. Witkiewicz K. Wrzesien J. Bogdal M. Krzywosinski L. Borkowska B. Farmaco, Ed. Sci. 1985; 40: 285
- 53 Yang DJ. Davisson JN. J. Med. Chem. 1985; 28: 1361
- 54 Sato S. Takeda N. Ueda M. Miyata O. Synthesis 2016; 48: 882
- 55 Holtman JR. Crooks PA. Chakraborty U. US 8710070 B2, 2014
- 56 Jose J. Gamage SA. Harvey MG. Voss LJ. Sleigh JW. Denny WA. Bioorg. Med. Chem. 2013; 21: 5098
- 57 Harvey M. Sleigh J. Voss L. Pruijn F. Jose J. Gamage S. Denny W. Pharmacology 2015; 96: 226
- 58 Harvey M. Sleigh J. Voss L. Jose J. Gamage S. Pruijn F. Liyanage S. Denny W. Anesth. Analg. (Philadelphia, PA, U. S.) 2015; 121: 925
- 59 Sleigh J. Denny WA. Jose J. Gamage SA. Harvey MG. Voss LJ. AU 2013328280 B2, 2017
- 60 Schwartz J. Murrough JW. Iosifescu DV. Evidence-Based Mental Health 2016; 19: 35
- 61 Gao M. Rejaei D. Liu H. Acta Pharmacol. Sin. 2016; 37: 865
- 62 Fan JC. Song JJ. Wang Y. Chen Y. Hong DX. Asian Pac. J. Trop. Med. 2017; 10: 1007
- 63 Malsy M. Gebhardt K. Gruber M. Wiese C. Graf B. Bundscherer A. BMC Anesthesiol. 2015; 15: 1