Analytical characterisation of the routes by thermolytic decarboxylation from tryptophan to tryptamine using ketone catalysts, resulting in tetrahydro-β-carboline formation

Journal of Pharmaceutical and Biomedical Analysis

Volumn 41, Issue 3, 2006, Pages 872-882

  Brandt, Simon D ^a   Mansell, David ^b   Freeman, Sally ^b   Fleet, Ian A ^c   Alder, John F ^c  

^a LIVERPOOL JOHN MOORES UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF MANCHESTER   (United Kingdom)

^c UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

Analytical chemistry; Biological activities; Decarboxylation; Fingerprint; Forensic; Hallucinogens; Synthesis; Tetrahydro carbolines; Tryptamines

Indexed keywords

KETONE; REAGENT; SOLVENT; TRYPTAMINE; TRYPTOLINE; TRYPTOPHAN;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CYCLIZATION; DECARBOXYLATION; DRUG DEGRADATION; DRUG IMPURITY; DRUG STRUCTURE; GAS CHROMATOGRAPHY; ION TRAP MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PICTET SPENGLER REACTION; PRIORITY JOURNAL; SUBSTITUTION REACTION; TANDEM MASS SPECTROMETRY;

CARBOLINES; CARBOXYLIC ACIDS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; KETONES; MAGNETIC RESONANCE SPECTROSCOPY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TRYPTAMINES; TRYPTOPHAN;

EID: 33646428920     PISSN: 07317085     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jpba.2006.02.007     Document Type: Article

References (52)

1. Vollenweider F.X., and Geyer M.A. Brain Res. Bull. 56 (2001) 495-507
2. Carter O.L., Pettigrew J.D., Hasler F., Wallis G.M., Liu G.B., Hell D., and Vollenweider F.X. Neuropsychopharmacology 30 (2005) 1154-1162
3. Carter O.L., Pettigrew J.D., Burr D.C., Alais D., Hasler F., and Vollenweider F.X. Neuroreport 15 (2004) 1947-1951
4. Hasler F., Grimberg U., Benz M.A., Huber T., and Vollenweider F.X. Psychopharmacology 172 (2004) 145-156
5. Nichols D.E. Pharmacol. Ther. 101 (2004) 131-181
6. Strassman R.J. Behav. Brain Res. 73 (1996) 121-124
7. Freeman S., and Alder J.F. Eur. J. Med. Chem. 37 (2002) 527-539
8. Meatherall R., and Sharma P. J. Anal. Toxicol. 27 (2003) 313-317
9. Wilson J.M., McGeorge F., Smolinske S., and Meatherall R. For. Sci. Int. 148 (2005) 31-36
10. (October 2005). http://www.dea.gov/programs/forensicsci/microgram/bulletins_index.html
11. Brandt S.D., Freeman S., Fleet I.A., McGagh P., and Alder J.F. Analyst 129 (2004) 1047-1057
12. Vorce S.P., and Sklerov J.H. J. Anal. Toxicol. 28 (2004) 407-410
13. Huhn C., Pütz M., Martin N., Dahlenburg R., and Pyell U. Electrophoresis 26 (2005) 2391-2401
14. Kikura-Hanajiri R., Hayashi M., Saisho K., and Goda Y. J. Chromatogr. B 825 (2005) 29-37
15. Brandt S.D., Freeman S., McGagh P., Abdul-Halim N., and Alder J.F. J. Pharm. Biomed. Anal. 36 (2004) 675-691
16. Hashimoto M., Eda Y., Osanai Y., Iwai T., and Aoki S. Chem. Lett. (1986) 893-896
17. Kametani T., Takano S., Hibino S., and Takeshita M. Synthesis (1972) 475
18. Barton D.H.R., Kirby G.W., Prager R.H., and Wilson E.M. J. Chem. Soc. 25 (1965) 3990-3994
19. Kametani T., Suzuki T., Takahashi K., and Fukumoto K. Synthesis (1974) 131-132
20. Takano S., Nishimura T., and Ogasawara K. Heterocycles 6 (1977) 1167-1171
21. Eckstein M., Misztal S., Terczynska A., Sienkiewicz B., Roszkowski A., and Adamus M. Pol. J. Pharmacol. Pharm. 39 (1987) 725-727
22. Chatelus G. Bull. Soc. Chim. France 10 (1964) 2523-2532
23. Al-Sayyab A.F., and Lawson A. J. Chem. Soc. (1968) 406-410
24. Al-Sayyab A.F., Lawson A., and Stevens J.O. J. Chem. Soc. (1968) 411-415
25. (June 2005). http://designer-drugs.com/pte/12.162.180.114/dcd/chemistry/tryptophan.html
26. Anon., Drone 342, published on the now defunct Hive website, 27 September 1998.
27. E. Xenou, Synthesis of dimethyltryptamine from tryptophan, M.Sc. Dissertation, University of Manchester UMIST, 2000.
28. Kuo F.M., Tseng M.C., Yen Y.H., and Chu Y.H. Tetrahedron 60 (2004) 12075-12084
29. Jones G.B., and Chapman B.J. J. Org. Chem. 58 (1993) 5558-5559
30. Couch M.W., and Williams C.M. Anal. Biochem. 50 (1972) 612-622
31. Gynther J. Acta Chem. Scand. B B42 (1988) 433-441
32. Rodríguez J.G., and Gil-Lopetegui P. J. Heterocycl. Chem. 30 (1993) 373-378
33. Coutts R.T., Locock R.A., and Slywka G.W.A. Org. Mass Spectrom. 3 (1970) 879-889
34. Herraiz T. Rapid Commun. Mass Spectrom. 11 (1997) 762-768
35. Brandt S.D., Freeman S., Fleet I.A., McGagh P., and Alder J.F. Analyst 130 (2005) 330-344
36. Harrison A.G. Chemical Ionization Mass Spectrometry (1992), CRC Press, Inc., Boca Raton, Florida
37. Bouchonnet S., Libong D., and Sablier M. Eur. J. Mass Spectrom. 10 (2004) 509-521
38. Cox E.D., and Cook J.M. Chem. Rev. 95 (1995) 1797-1842
39. Horiguchi Y., Nakamura M., Kida A., Kodama H., Saitoh T., and Sano T. Heterocycles 59 (2003) 691-705
40. Singh H., Sarin R., and Singh K. Indian J. Chem. 27B (1988) 132-134
41. McKenna D.J. Pharmacol. Ther. 102 (2004) 111-129
42. Callaway J.C. Phytochemistry and neuropharmacology of Ayahuasca. In: Metzner R. (Ed). Ayahuasca. Hallucinogens, Consciousness, and the Spirit of Nature (1999), Thunder's Press, New York 250-275
43. Husbands S.M., Glennon R.A., Gorgerat S., Gough R., Tyacke R., Crosby J., Nutt D.J., Lewis J.W., and Hudson A.L. Drug Alcohol Depend. 64 (2001) 203-208
44. Glennon R.A., Grella B., Tyacke R.J., Lau A., Westaway J., and Hudson A.L. Bioorg. Med. Chem. Lett. 14 (2004) 999-1002
45. Audia J.E., Evrard D.A., Murdoch G.R., Droste J.J., Nissen J.S., Schenck K.W., Fludzinski P., Lucaites V.L., Nelson D.L., and Cohen M.L. J. Med. Chem. 39 (1996) 2773-2780
46. Grella B., Teitler M., Smith C., Herrick-Davis K., and Glennon R.A. Bioorg. Med. Chem. Lett. 13 (2003) 4421-4425
47. Airaksinen M.M., and Kari I. Med. Biol. 59 (1981) 190-211
48. In: Cordell G.A. (Ed). The Alkaloids: Chemistry and Pharmacology vol. 43 (1993), Academic Press, San Diego
49. Gutsche B., and Herderich M. J. Agric. Food Chem. 45 (1997) 2458-2462
50. Herraiz T., and Papavergou E. J. Agric. Food Chem. 52 (2004) 2652-2658
51. Tulyaganov T.S., Nazarov O.M., Levkovich M.G., and Abdullaev N.D. Chem. Nat. Compd. 37 (2001) 61-64
52. Üstünes L., Özer A., Laekeman G.M., Corthout J., Pieters L.A.C., Baeten W., Herman A.G., Claeys M., and Vlietinck A.J. J. Nat. Prod. 54 (1991) 959-966