An analytical perspective on favoured synthetic routes to the psychoactive tryptamines

Journal of Pharmaceutical and Biomedical Analysis

Volumn 36, Issue 4, 2004, Pages 675-691

  Brandt, Simon D ^a   Freeman, Sally ^a   McGagh, Peter ^a   Abdul Halim, Norliza ^a   Alder, John F ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

Analytical chemistry; Forensic studies; Neurobiological procedures; Tryptamines

Indexed keywords

ACID; INDOLE DERIVATIVE; PSYCHOTROPIC AGENT; TRYPTAMINE;

ANALYTIC METHOD; CHIRALITY; DECARBOXYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; FORENSIC MEDICINE; NEUROBIOLOGY; OXIDATION; PRIORITY JOURNAL; REVIEW;

CHEMISTRY, ANALYTICAL; PSYCHOTROPIC DRUGS; TRYPTAMINES;

EID: 7944239256     PISSN: 07317085     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jpba.2004.08.022     Document Type: Review

References (91)

1. J.R. Cooper F.E. Bloom R.H. Roth The Biochemical Basis of Neuropharmacology seventh ed. 1996 Oxford University Press Oxford, UK
2. D.E. Nichols Pharmacol. Ther. 101 2004 131 181
3. A.T. Shulgin, and A. Shulgin TIHKAL: The Continuation 1997 Transform Press Berkeley
4. R.R. Laing Hallucinogens: A Forensic Drug Handbook 2003 Elsevier Science Ltd. London, UK
5. S. Freeman, and J.F. Alder Eur. J. Med. Chem. 37 2002 527 539
6. J. Ott J. Psychoactive Drugs 31 1999 171 177
7. J. Ott J. Psychoactive Drugs 33 2001 273 281
8. J. Ott J. Psychoactive Drugs 33 2001 403 407
9. R.J. Sundberg Indoles, Best Synthetic Methods Series 1996 Academic Press Ltd London, UK
10. M.E. Speeter, and W.C. Anthony J. Am. Chem. Soc. 76 1954 6208 6210
11. H.C. Brown, and S. Krishnamurthy Tetrahedron 35 1979 567 607
12. F. Troxler, F. Seemann, and A. Hofmann Helv. Chim. Acta 42 1959 2073 2103
13. R.V. Heinzelman, and J. Szmuszkovicz Prog. Drug Res. 6 1963 75 150
14. R.G. Taborsky, P. Delvigs, D. Palaic, and F.M. Bumpus J. Med. Chem. 10 1967 403 407
15. V. Plavsic, S. Iskric, S. Kveder, M. Tucan-Foretic, D. Wolf, V. Gjuris, and Z. Supek J. Pharm. Pharmacol. 28 1976 424 428
16. D.L. Crookes, K.P. Parry, and G.F. Smith Pol. J. Chem. 53 1979 73 78
17. W. Gielsdorf, K. Schubert, and K. Allin Arch. Kriminol. 166 1980 21 32
18. J.S. Cowie, A.L. Holtham, and L.V. Jones J. Forensic Sci. 27 1982 527 540
19. S.D. Brandt, S. Freeman, I.A. Fleet, P. McGagh, J.F. Alder, Analyst (2004), accepted DOI:10.1039/B407239C.
20. I. Egle, N. MacLean, L. Demchyshyn, L. Edwards, A. Slassi, and A. Tehim Bioorg. Med. Chem. Lett. 14 2004 727 729
21. V.M. Micovic, and M.L. Mihailovic J. Org. Chem. 18 1953 1190 1200
22. F.V. Brutcher Jr., and W.D. Vanderwerff J. Org. Chem. 23 1958 146 147
23. R. Littell, and G.R. Allen Jr. J. Org. Chem. 38 1973 1504 1510
24. A. Alemany, E.F. Alvarez, O.N. Lopez, and M.E.R. Herraez Bull. Soc. Chim. France 12 1974 2883 2888
25. W.B. Wright Jr. J. Org. Chem. 25 1960 1033 1036
26. W.B. Wright Jr. J. Org. Chem. 27 1962 1042 1045
27. J.M. Khanna, V.M. Dixit, and N. Anand Synthesis 9 1975 607 608
28. R. Stauffer Helv. Chim. Acta 49 1966 1199 1203
29. E.H.P. Young J. Chem. Soc. 3 1958 3493 3496
30. A.S.F. Ash, and W.R. Wragg J. Chem. Soc. 1958 2892 3887
31. F. Troxler, in: W.J. Houlihan (Ed.), Indoles, vol. 25 (2), Wiley-Interscience, Chichester, UK, 1972, pp. 179-537.
32. E. Leete J. Am. Chem. Soc. 81 1959 6023 6026
33. E. Leete, and L. Marion Can. J. Chem. 31 1953 775 784
34. K.R. Grose, and L.F. Bjeldanes Chem. Res. Toxicol. 5 1992 188 193
35. H.L. Bradlow, D.W. Sepkovic, N.T. Telang, and M.P. Osborne Ann. N. Y. Acad. Sci. 889 1999 204 213
36. M.J. Anderton, R. Jukes, J.H. Lamb, M.M. Manson, A. Gescher, W.P. Steward, and M.L. Williams J. Chromatogr. B 787 2003 281 291
37. K.A. Regal, G.M. Laws, C. Yuan, G.S. Yost, and G.L. Skiles Chem. Res. Toxicol. 14 2001 1014 1024
38. M. Chakrabarty, R. Basak, and N. Ghosh Tetrahedron Lett. 42 2001 3913 3915
39. M. Chakrabarty, R. Basak, N. Ghosh, and Y. Harigaya Tetrahedron 60 2004 1941 1949
40. M. Chakrabarty, R. Basak, and Y. Harigaya Heterocycles 55 2001 2431 2447
41. H.R. Snyder, and L. Katz J. Am. Chem. Soc. 69 1947 3140 3142
42. D.W. Henry, and E. Leete J. Am. Chem. Soc. 79 1957 5254 5256
43. B. Heath-Brown, and P.G. Philpott J. Chem. Soc. 1965 7165 7178
44. G.D.H. Dijkstra, M.T.M. Tulp, P.H.H. Hermkens, J.H. Vanmaarseveen, H.W. Scheeren, and C.G. Kruse Recl. Trav. Chim. Pays-Bas 112 1993 131 136
45. D.E. Nichols, R. Oberlender, and D.J. McKenna Biochem. Physiol. Subst. Abuse 3 1991 1 39
46. S.S. Hong, R. Young, and R.A. Glennon Pharmacol. Biochem. Behav. 70 2001 311 316
47. V.M. Potapov, A.P. Terent'ev, M.N. Preobrazhenskaya, and N.N. Suvorov Zh. Obshch. Khim. 33 1963 2702 2705
48. J.B. Hester, M.E. Greig, W.C. Anthony, R.V. Heinzelman, and J. Szmuszkovicz J. Med. Chem. 7 1964 274 279
49. A. Fujii, Y. Fujima, H. Harada, M. Ikunaka, T. Inoue, S. Kato, and K. Matsuyama Tetrahedron-Asymmetry 12 2001 3235 3240
50. H. Kitaguchi, P.A. Fitzpatrick, J.E. Huber, and A.M. Klibanov J. Am. Chem. Soc. 111 1989 3094 3095
51. D.B. Repke, and W.J. Ferguson J. Heterocyclic. Chem. 13 1976 775 778
52. D.E. Nichols, D.H. Lloyd, M.P. Johnson, and A.J. Hoffman J. Med. Chem. 31 1988 1406 1412
53. D.E. Nichols, C.F. Barfknecht, D.B. Rusterholz, F. Benington, and R.D. Morin J. Med. Chem. 16 1973 480 483
54. J. Ezquerra, C. Pedregal, C. Lamas, A. Pastor, P. Alvarez, and J.J. Vaquero Tetrahedron 53 1997 8237 8248
55. A. Frey, H. Ott, H. Bruderer, and P. Stadler Chimia 14 1960 423
56. US Patent Application, 20030096379 (2003).
57. G.F. Smith Adv. Heterocyclic Chem. 2 1963 287 309
58. J. Bergman, E. Koch, and B. Pelcman Tetrahedron Lett. 36 1995 3945 3948
59. C.Y. Chen, D.R. Lieberman, L.J. Street, A.R. Guiblin, R.D. Larsen, and T.R. Verhoeven Synth. Commun. 26 1996 1977 1984
60. X.H. Xu, M.G. Bartlett, and J.T. Stewart J. Pharm. Biomed. Anal. 26 2001 367 377
61. B. Robinson The Fischer Indole Synthesis 1982 John Wiley & Sons Ltd Chichester
62. P. Remuzon, C. Dussy, J.P. Jacquet, M. Soumeillant, and D. Bouzard Tetrahedron Lett. 36 1995 6227 6230
63. P.R. Brodfuehrer, B.C. Chen, T.R. Sattelberg, P.R. Smith, J.P. Reddy, D.R. Stark, S.L. Quinlan, and J.G. Reid J. Org. Chem. 62 1997 9192 9202
64. B. Pete, I. Bitter, C. Szantay, I. Schon, and L. Toke Heterocycles 48 1998 1139 1149
65. A. Skwierawska, and E. Paluszkiewicz Pol. J. Chem. 77 2003 329 332
66. E. Späth, and E. Lederer Ber. 63B 1930 120 125
67. J. Bosch, T. Roca, M. Armengol, and D. Fernandez-Forner Tetrahedron 57 2001 1041 1048
68. J.L. Castro, R. Baker, A.R. Guiblin, S.C. Hobbs, M.R. Jenkins, M.G. Russell, M.S. Beer, J.A. Stanton, K. Scholey, R.J. Hargreaves, M.I. Graham, and V.G. Matassa J. Med. Chem. 37 1994 3023 3032
69. C.Y. Chen, C.H. Senanayake, T.J. Bill, R.D. Larsen, T.R. Verhoeven, and P.J. Reider J. Org. Chem. 59 1994 3738 3741
70. E.D. Cox, and J.M. Cook Chem. Rev. 95 1995 1797 1842
71. B.E. Love Org. Prep. Proced. Int. 28 1996 1 64
72. R.H. Hill Jr., S.P. Caudill, R.M. Philen, S.L. Bailey, W.D. Flanders, W.J. Driskell, M.L. Kamb, L.L. Needham, and E.J. Sampson Arch. Environ. Contam. Toxicol. 25 1993 134 142
73. B. Müller, C. Pacholski, T. Simat, and H. Steinhart Adv. Exp. Med. Biol. 467 1999 481 486
74. B.L. Williamson, L.M. Benson, A.J. Tomlinson, A.N. Mayeno, G.J. Gleich, and S. Naylor Toxicol. Lett. 92 1997 139 148
75. A.N. Mayeno, F. Lin, C.S. Foote, D.A. Loegering, M.M. Ames, C.W. Hedberg, and G.J. Gleich Science 250 1990 1707 1708
76. M.J. Smith, E.P. Mazzola, T.J. Farrell, J.A. Sphon, S.W. Page, D. Ashley, S.R. Sirimanne, R.H. Hill Jr., and L.L. Needham Tetrahedron Lett. 32 1991 991 994
77. T.J. Simat, K.K. Kleeberg, B. Muller, and A. Sierts Adv. Exp. Med. Biol. 467 1999 469 480
78. B.L. Williamson, A.J. Tomlinson, P.K. Mishra, G.J. Gleich, and S. Naylor Chem. Res. Toxicol. 11 1998 234 240
79. M. Hashimoto, Y. Eda, Y. Osanai, T. Iwai, and S. Aoki Chem. Lett. 1986 893 896
80. T. Kametani, S. Takano, S. Hibino, and M. Takeshita Synthesis 9 1972 475
81. T. Kametani, T. Suzuki, K. Takahashi, and K. Fukumoto Synthesis 2 1974 131 132
82. S. Takano, T. Nishimura, and K. Ogasawara Heterocycles 6 1977 1167 1171
83. http://www.rhodium.ws/chemistry/tryptophan.html.
84. W.A. Remers W.J. Houlihan Indoles, vol. 25 (1) 1972 Wiley-Interscience Chichester, UK 1 226
85. M. Nakagawa, S. Kato, S. Kataoka, and T. Hino J. Am. Chem. Soc. 101 1979 3136 3137
86. T. Tabatabaie, and G. Dryhurst J. Med. Chem. 35 1992 2261 2274
87. M.Z. Wrona, Z.L. Yang, M. McAdams, S. O'Connor-Coates, and G. Dryhurst J. Neurochem. 64 1995 1390 1400
88. M.Z. Wrona, X.R. Jiang, Y. Kotake, and G. Dryhurst Chem. Res. Toxicol. 16 2003 493 501
89. A. Numan, and N.D. Danielson Anal. Chim. Acta 460 2002 49 60
90. K. Klarskov, K.L. Johnson, L.M. Benson, J.D. Cragun, G.J. Gleich, M. Wrona, X.R. Jiang, G. Dryhurst, and S. Naylor J. Rheumatol. 30 2003 89 95
91. M. Somei Adv. Heterocyclic Chem. 82 2002 101 155