Analytical chemistry of synthetic routes to psychoactive tryptamines Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR

Analyst

Volumn 130, Issue 3, 2005, Pages 330-344

  Brandt, Simon D ^a   Freeman, Sally ^a   Fleet, Ian A ^a   McGagh, Peter ^a   Alder, John F ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; INDOLE 3 YL GLYOXALYLAMIDE; N,N DIISOPROPYL 5 METHOXYTRYPTAMINE; N,N DIMETHYLTRYPTAMINE; NITROGEN; PSILOCYBINE; PSYCHOTROPIC AGENT; TRYPTAMINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; GAS CHROMATOGRAPHY; ION TRAP MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; QUADRUPOLE MASS SPECTROMETRY; SYNTHESIS;

EID: 15244355527     PISSN: 00032654     EISSN: None     Source Type: Journal    
DOI: 10.1039/b413014f     Document Type: Article

References (58)

1. R. E. Schultes and A. Hofmann, The Botany and Chemistry of Hallucinogens, Charles C. Thomas, Springfield, Illinois, USA, 1980.
2. R. E. Schultes and A. Hofmann, Plants of the Gods: Their Sacred, Healing and Hallucinogenic Powers, Healing Arts Press, Rochester, VT, 1992.
3. R. J. Strassman and C. R. Qualls, Arch. Gen. Psychiatry, 1994, 51, 85.
4. R. J. Strassman, C. R. Qualls, E. H. Uhlenhuth and R. Kellner, Arch. Gen. Psychiatry, 1994, 51, 98.
5. R. J. Strassman, Behav. Brain Res., 1996, 73, 121.
6. D. J. McKenna, Pharmacol. Ther., 2004, 102, 111.
7. E. Gouzoulis-Mayfrank, K. Heekeren, B. Thelen, H. Lindenblatt, K. A. Kovar, H. Sass and M. A. Geyer, Behav. Pharmacol., 1998, 9, 561.
8. F. X. Vollenweider and M. A. Geyer, Brain Res. Bull., 2001, 56, 495.
9. F. Hasler, U. Grimberg, M. A. Benz, T. Huber and F. X. Vollenweider, Psychopharmacology, 2004, 172, 145.
10. D. E. Nichols, Pharmacol. Ther., 2004, 101, 131.
11. A. T. Shulgin and A. Shulgin, TIHKAL: The Continuation, Transform Press, Berkeley, 1997.
12. J. Ott, J. Psychoact. Drugs, 2001, 33, 273.
13. J. Ott, J. Psychoact. Drugs, 2001, 33, 403.
14. A. T. Shulgin, in Hallucinogens. A Forensic Drug Handbook, ed. R. R. Laing, Elsevier Science Ltd., London, 2003, p. 67.
15. J. F. Van Bocxlaer, K. M. Clauwaert, W. E. Lambert, D. L. Deforce, E. G. Van den Eeckhout and A. P. De Leenheer, Mass Spectrom. Rev., 2000, 19, 165.
16. M. J. Bogusz, J. Chromatogr. B: Biomed. Sci. Appl., 2000, 748, 3.
17. P. Marquet, Ther. Drug Monit., 2002, 24, 255.
18. K. Pihlainen, E. Sippola and R. Kostiainen, J. Chromatogr. A, 2003, 994, 93.
19. M. J. Bogusz, R. D. Maier, A. T. Schafer and M. Erkens, Int. J. Legal Med., 1998, 111, 147.
20. T. Kamata, M. Nishikawa, M. Katagi and H. Tsuchihashi, J. Chromatogr. B, 2003, 796, 421.
21. M. E. Speeter and W. C. Anthony, J. Am. Chem. Soc., 1954, 76, 6208.
22. S. Freeman and J. F. Alder, Eur. J. Med. Chem., 2002, 37, 527.
23. S. D. Brandt, S. Freeman, I. A. Fleet, P. McGagh and J. F. Alder, Analyst, 2004, 129, 1047.
24. J. C. Powers, J. Org. Chem., 1968, 33, 2044.
25. S. W. Bellman, J. W. Turczan and T. C. Kram, J. Forensic Sci., 1970, 15, 261.
26. M. W. Couch and C. M. Williams, Anal. Biochem., 1972, 50, 612.
27. S. E. Hattox and R. C. Murphy, Biomed. Mass Spectrom., 1975, 2, 272.
28. G. J. Shaw, G. J. Wright and G. W. Milne, Biomed. Mass. Spectrom., 1977, 4, 348.
29. B. Holmstedt and J. E. Lindgren, in Ethnopharmacologic Search for Psychoactive Drugs, ed. D. H. Efron, B. Holmstedt and N. S. Kline, (Reprint), Raven Press, New York, 1979, p. 339.
30. J. H. Beynon R. A. Saunders and A. E. Williams, The Mass Spectra of Organic Molecules, Elsevier, Amsterdam, Netherlands, 1968.
31. G. Diamantini, G. Tarzia, G. Spadoni, M. D'Alpaos and P. Traldi, Rapid Commun. Mass Spectrom., 1998, 12, 1538.
32. T. R. Bosin, T. L. Harrison and S. D. Jr., Res. Commun. Chem. Pathol. Pharmacol., 1974, 7, 519.
33. D. G. I. Kingston, J. T. Bursey and M. M. Bursey, Chem. Rev., 1974, 74, 215.
34. J. Gynther, Acta Chem. Scand. B, 1988, B42, 433.
35. R. D. Bowen, Mass Spectrom. Rev., 1991, 10, 225.
36. H. J. Veith and J. H. Gross, Org. Mass Spectrom., 1991, 26, 1097.
37. R. D. Bowen, J. Chem. Soc., Perkin Trans. 2, 1993, 12, 2363.
38. R. D. Bowen, J. Chem. Soc., Perkin Trans. 2, 1993, 3, 285.
39. T. I. Solling and S. Hammerum, J. Chem. Soc., Perkin Trans. 2, 2001, 2324.
40. R. D. Bowen, J. Chem. Soc., Perkin Trans. 2, 1982, 4, 409.
41. S. J. Mandeville, R. D. Bowen, M. A. Trikoupis and J. K. Terlouw, Int. J. Mass Spectrom., 2000, 199, 189.
42. S. McClean, R. C. Robinson, C. Shaw and W. F. Smyth, Rapid Commun. Mass Spectrom., 2002, 16, 346.
43. H. Budzikiewicz, C. Djerassi and D. H. Williams, Mass Spectrometry of Organic Compounds, Holden-Day, San Francisco, 1967.
44. P. Rösner and T. Junge, J. Mass Spectrom., 1996, 31, 1047.
45. L. M. Jackman, in Dynamic Nucluear Magnetic Resonance Spectroscopy, ed. L. M. Jackman and F. A. Cotton, Academic Press, New York, 1975, p. 203.
46. W. E. Stewart and T. H. Siddall, III, Chem. Rev., 1970, 70, 517.
47. D. B. Repke, W. J. Ferguson and D. K. Bates, J. Heterocycl. Chem., 1977, 14, 71.
48. D. B. Repke, W. J. Ferguson and D. K. Bates, J. Heterocycl. Chem., 1981, 18, 175.
49. D. B. Grotjahn, J. Heterocycl. Chem., 1983, 20, 1031.
50. M. Spaeth, P. Plischka, F. M. Bohnen, R. Herbst-Irmer and H. Laatsch, J. Prakt. Chem., 1997, 339, 243.
51. M. S. Morales-Ríos, R. E. del Rio and P. Joseph-Nathan, Magn. Reson. Chem., 1989, 27, 1039.
52. A. A. Tymiak, K. L. Rinehart and G. J. Bakus, Tetrahedron, 1985, 41, 1039.
53. P. Joseph-Nathan, R. E. del Rio and M. S. Morales-Ríos, Heterocycles, 1988, 27, 377.
54. M. S. Morales-Rios and P. Joseph-Nathan, J. Heterocycl. Chem., 1986, 23, 1617.
55. M. S. Morales-Ríos, J. Espineira and P. Joseph-Nathan, Magn. Reson. Chem., 1987, 25, 377.
56. S. A. Barker, J. A. Monti and S. T. Christian, Int. Rev. Neurobiol., 1981, 22, 83.
57. S. A. Barker, M. A. Littlefield-Chabaud and C. David, J. Chromatogr. B: Biomed. Sci. Appl., 2001, 751, 37.
58. T. Forsström, J. Tuominen and J. Karkkainen, Scand. J. Clin. Lab. Invest., 2001, 61, 547.