Main Article Content
Abstract
In the present study, a variety of novel tramadol esters (2-6) were synthesized via the reaction of (±)-cis-2-[(dimethylamino)methyl]- 1-(3-methoxy-phenyl)cyclohexanol (tramadol) (1) with acid chlorides and triethylamine. Treatment of compound 1 with epichlorohydrin afforded corresponding ether derivative 7. The reaction of compound 1 with isothiocyanates gave the novel carbamothioate derivatives 8- 12. Tramadol derivatives were found more sensitive for detection with (HPLC-DAD) than tramadol itself.
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References
- Tramadol Hydrochloride, United States Pharmacopeia, 35 National Formulary 30, The United States Pharmacopeial Convention, Rockville, MD, pp. 4904-4905 (2011).
- Tramadol Hydrochloride, USP Dictionary Online of USAN and Inter-national, Drug Names, The United States Pharmacopeial Convention; http://www. uspusan. com/usan/pub/toc/go_usan 09552_1.xml (2012).
- R. Smyj, X.P. Wang and F. Han, Profiles Drug Subst. Excip. Relat. Methodol., 38, 463 (2013); https://doi.org/10.1016/B978-0-12-407691-4.00011-3.
- R.J. Kupper and A. Stumpf, Synthesis of (±)-2-((Dimethylamino)methyl)-1-(aryl)cyclohexanols, U.S. Patent 6,649,783 B2 (2003).
- H. Schickaneder and A. Nikolopoulos, Tramadol, Salts Thereof and Process for their Preparation, U.S. Patent 6,469,213 B1 (2002).
- Chemie Grunenthal GmbH, British Patent, 997,399 (1965).
- W. Lintz, S. Erlacin, E. Frankus and U. Uragg, Arzneimittelforschung, 31, 1932 (1981).
- K. Flick and E. Frankus, 1-(m-Substituted phenyl)-2-aminomethyl Cyclo-hexanols, U.S. Patent, 3,652,589 (1972).
- R.B. Raffa, E. Friderichs, W. Reimann, R.P. Shank, E.E. Codd and J.L. Vaught, J. Pharmacol. Exp. Ther., 260, 275 (1992).
- M. Bogusz and M. Wu, J. Anal. Toxicol., 15, 188 (1991); https://doi.org/10.1093/jat/15.4.188.
- A. Tracqui, P. Kintz and P. Mangin, J. Forensic Sci., 40, 254 (1995).
- S.P. Elliott and A.K. Hale, J. Anal. Toxicol., 22, 279 (1998); https://doi.org/10.1093/jat/22.4.279.
- S.H. Gan and R. Ismail, J. Chromatogr. B Biomed. Sci. Appl., 759, 325 (2001); https://doi.org/10.1016/S0378-4347(01)00237-7.
- A. Kucuk and Y. Kadioglu, FABAD J. Pharm. Sci., 30, 196 (2005).
- H. Schiitz, J. Clin. Chem. Clin. Biochem., 17, 85 (1979).
- Clarke’s Analysis of Drugs and Poisons, Tramadol, Pharmaceutical Press (2004).
- R. Herraez-Hernandez, P. Campins-Falco and A. Sevillano-Cabeza, J. Chromatogr. Sci., 35, 169 (1997); https://doi.org/10.1093/chromsci/35.4.169.
- S. Nojiri, N. Taguchi, M. Oishi and S. Suzuki, J. Chromatogr. A, 893, 195 (2000); https://doi.org/10.1016/S0021-9673(00)00694-4.
- A. Khodairy, A.M. El-Sayed, H. Salah and H. Abdel-Ghany, Synth. Commun., 37, 3245 (2007); https://doi.org/10.1080/00397910601055214.
- H.A. Ghany, A.M. El-Sayed, A. Khodairy and H. Salah, Synth. Commun., 31, 2523 (2001); https://doi.org/10.1081/SCC-100105132.
- A. Khodairy, H.A. Ghany, A.M. El-Sayed and H. Salah, J. Chil. Chem. Soc., 50, 1195 (2003); https://doi.org/10.1002/jccs.200300170.
- A. Khodairy and A. Phosphorus, Sulfur, Silicon, 180, 1893 (2005); https://doi.org/10.1080/104265090889611.
- A.M. El-Sayed, A. Khodairy, H. Salah and H. Abdel-Ghany, Phosphorus Sulfur Silicon Relat. Elem., 182, 711 (2007); https://doi.org/10.1080/10426500601087301.
- A. Khodairy, Synth. Commun., 41, 612 (2011); https://doi.org/10.1080/00397911003629507.
- H. Salah, E.A. Ahmed and M.M. Hassan, Arab. J. Chem. (2015); https://doi.org/10.1016/j.arabjc.2015.03.008.
- A. Khodairy, E.A. Ahmed and H.A. Ghany, J. Heterocycl. Chem., 54, 242 (2017); https://doi.org/10.1002/jhet.2573.
- A.-A. Y. El-Sayed, K.M. Mohamed, M.A. Hilal, S.A. Mohamed, K.E. Aboul-Hagag and A.Y. Nasser, Chromatogr. Sep. Techniq., 2, 114 (2011); https://doi.org/10.4172/2157-7064.1000114.
- M.A. Hilal and K.M. Mohamed, J. Chromatogr. Sci., 52, 1186 (2014); https://doi.org/10.1093/chromsci/bmt174.
- A.-A.Y. El-Sayed, K.M. Mohamed, A.Y. Nasser, J. Button and D.W. Holt, J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 926, 9 (2013); https://doi.org/10.1016/j.jchromb.2013.02.019.
References
Tramadol Hydrochloride, United States Pharmacopeia, 35 National Formulary 30, The United States Pharmacopeial Convention, Rockville, MD, pp. 4904-4905 (2011).
Tramadol Hydrochloride, USP Dictionary Online of USAN and Inter-national, Drug Names, The United States Pharmacopeial Convention; http://www. uspusan. com/usan/pub/toc/go_usan 09552_1.xml (2012).
R. Smyj, X.P. Wang and F. Han, Profiles Drug Subst. Excip. Relat. Methodol., 38, 463 (2013); https://doi.org/10.1016/B978-0-12-407691-4.00011-3.
R.J. Kupper and A. Stumpf, Synthesis of (±)-2-((Dimethylamino)methyl)-1-(aryl)cyclohexanols, U.S. Patent 6,649,783 B2 (2003).
H. Schickaneder and A. Nikolopoulos, Tramadol, Salts Thereof and Process for their Preparation, U.S. Patent 6,469,213 B1 (2002).
Chemie Grunenthal GmbH, British Patent, 997,399 (1965).
W. Lintz, S. Erlacin, E. Frankus and U. Uragg, Arzneimittelforschung, 31, 1932 (1981).
K. Flick and E. Frankus, 1-(m-Substituted phenyl)-2-aminomethyl Cyclo-hexanols, U.S. Patent, 3,652,589 (1972).
R.B. Raffa, E. Friderichs, W. Reimann, R.P. Shank, E.E. Codd and J.L. Vaught, J. Pharmacol. Exp. Ther., 260, 275 (1992).
M. Bogusz and M. Wu, J. Anal. Toxicol., 15, 188 (1991); https://doi.org/10.1093/jat/15.4.188.
A. Tracqui, P. Kintz and P. Mangin, J. Forensic Sci., 40, 254 (1995).
S.P. Elliott and A.K. Hale, J. Anal. Toxicol., 22, 279 (1998); https://doi.org/10.1093/jat/22.4.279.
S.H. Gan and R. Ismail, J. Chromatogr. B Biomed. Sci. Appl., 759, 325 (2001); https://doi.org/10.1016/S0378-4347(01)00237-7.
A. Kucuk and Y. Kadioglu, FABAD J. Pharm. Sci., 30, 196 (2005).
H. Schiitz, J. Clin. Chem. Clin. Biochem., 17, 85 (1979).
Clarke’s Analysis of Drugs and Poisons, Tramadol, Pharmaceutical Press (2004).
R. Herraez-Hernandez, P. Campins-Falco and A. Sevillano-Cabeza, J. Chromatogr. Sci., 35, 169 (1997); https://doi.org/10.1093/chromsci/35.4.169.
S. Nojiri, N. Taguchi, M. Oishi and S. Suzuki, J. Chromatogr. A, 893, 195 (2000); https://doi.org/10.1016/S0021-9673(00)00694-4.
A. Khodairy, A.M. El-Sayed, H. Salah and H. Abdel-Ghany, Synth. Commun., 37, 3245 (2007); https://doi.org/10.1080/00397910601055214.
H.A. Ghany, A.M. El-Sayed, A. Khodairy and H. Salah, Synth. Commun., 31, 2523 (2001); https://doi.org/10.1081/SCC-100105132.
A. Khodairy, H.A. Ghany, A.M. El-Sayed and H. Salah, J. Chil. Chem. Soc., 50, 1195 (2003); https://doi.org/10.1002/jccs.200300170.
A. Khodairy and A. Phosphorus, Sulfur, Silicon, 180, 1893 (2005); https://doi.org/10.1080/104265090889611.
A.M. El-Sayed, A. Khodairy, H. Salah and H. Abdel-Ghany, Phosphorus Sulfur Silicon Relat. Elem., 182, 711 (2007); https://doi.org/10.1080/10426500601087301.
A. Khodairy, Synth. Commun., 41, 612 (2011); https://doi.org/10.1080/00397911003629507.
H. Salah, E.A. Ahmed and M.M. Hassan, Arab. J. Chem. (2015); https://doi.org/10.1016/j.arabjc.2015.03.008.
A. Khodairy, E.A. Ahmed and H.A. Ghany, J. Heterocycl. Chem., 54, 242 (2017); https://doi.org/10.1002/jhet.2573.
A.-A. Y. El-Sayed, K.M. Mohamed, M.A. Hilal, S.A. Mohamed, K.E. Aboul-Hagag and A.Y. Nasser, Chromatogr. Sep. Techniq., 2, 114 (2011); https://doi.org/10.4172/2157-7064.1000114.
M.A. Hilal and K.M. Mohamed, J. Chromatogr. Sci., 52, 1186 (2014); https://doi.org/10.1093/chromsci/bmt174.
A.-A.Y. El-Sayed, K.M. Mohamed, A.Y. Nasser, J. Button and D.W. Holt, J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 926, 9 (2013); https://doi.org/10.1016/j.jchromb.2013.02.019.