Recreational use, analysis and toxicity of tryptamines

Current Neuropharmacology

Volumn 13, Issue 1, 2015, Pages 26-46

  Tittarelli, Roberta ^a   Mannocchi, Giulio ^a   Pantano, Flaminia ^a   Romolo, Francesco Saverio ^a,b  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

Clinical effects; Emergency Departments; Fatalities; Forensic Toxicology; Intoxication; New Psychoactive Substances (NPS); Tryptamines

Indexed keywords

5 HYDROXYINDOLEACETIC ACID; 5 METHOXY N,N DIALLYLTRYPTAMINE; 5 METHOXY N,N DIMETHYLTRYPTAMINE; 5 METHOXY Α METHYLTRYPTAMINE; ALPHA 1 ADRENERGIC RECEPTOR; ALPHA 2 ADRENERGIC RECEPTOR; AMINE OXIDASE (FLAVIN CONTAINING); BUFOTENINE; CANNABINOID; CATHINONE; CHLORAMPHETAMINE; DIETHYL TRYPTAMINE; DIISOPROPYL TRYPTAMINE; DIPROPYL TRYPTAMINE; ERGOLINE DERIVATIVE; ETRYPTAMINE; KETAMINE; MELATONIN; N,N DIISOPROPYL 5 METHOXYTRYPTAMINE; N,N DIMETHYLTRYPTAMINE; NEUROTRANSMITTER TRANSPORTER; NORADRENALIN; PHENETHYLAMINE; PIPERAZINE; PSILOCIN; SEROTONIN; SEROTONIN RECEPTOR; TRYPTAMINE; TRYPTOPHAN; UNCLASSIFIED DRUG; UNINDEXED DRUG; DESIGNER DRUG; PSYCHOTROPIC AGENT; STREET DRUG; TRYPTAMINE DERIVATIVE;

ARTICLE; BIOSYNTHESIS; CHEMICAL STRUCTURE; DRUG METABOLISM; DRUG MISUSE; DRUG TOXICITY; EUPHORIA; HALLUCINATION; HEART ARRHYTHMIA; HUMAN; HYPERTHERMIA; INSOMNIA; MYDRIASIS; NONHUMAN; RESTLESSNESS; SEIZURE; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION; CHEMISTRY; CLASSIFICATION; INTOXICATION; MORTALITY; PATHOLOGY; SUBSTANCE-RELATED DISORDERS;

DESIGNER DRUGS; HUMANS; POISONING; PSYCHOTROPIC DRUGS; STREET DRUGS; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTANCE-RELATED DISORDERS; TRYPTAMINES;

EID: 84929316392     PISSN: 1570159X     EISSN: 18756190     Source Type: Journal    
DOI: 10.2174/1570159X13666141210222409     Document Type: Article

References (115)

1. Available from: http://www.unodc.org/documents/scientific/NPS_ 2013_SMART.pdf [Last access on 24th August, 2014]
2. Zuba, D. Identification of cathinones and other active components of "legal highs" by mass spectrometric methods. TrAC, 2012, 32, 15-30. http://dx.doi.org/10.1016/j.trac.2011.09.009
3. Musselman, M.E.; Hampton, J.P. "Not for Human Consumption": A Review of Emerging Designer Drugs. Pharmacotherapy, 2014, 34(7), 745-757. http://dx.doi.org/10.1002/phar.1424
4. Davies, S.; Wood, D.M.; Smith, G.; Button, J.; Ramsey, J.; Archer, R.; Wolt, D.W.; Dargan, P.I. Purchasing 'legal highs' on the Internet- is there consistency in what you get? QJM, 2010, 103(7), 489-493. http://dx.doi.org/10.1093/qjmed/hcq056
5. Arnold, C. The new danger of synthetic drugs. Lancet, 2013, 382(9886), 15-16. http://dx.doi.org/10.1016/s0140-6736(13)61512-3
6. Available from: https://www.gov.uk/government/uploads/system/ uploads/attachment_data/file/119139/acmdnps2011.pdf [Last access on 24th July, 2014].
7. Brandt, S.D.; Freeman, S.; McGagh, P.; Abdul-Halim, N.; Alder, J.F. An analytical perspective on favoured synthetic routes to the psychoactive tryptamines. J. Pharm. Biomed. Anal., 2004, 36(4), 675-691. http://dx.doi.org/10.1016/j.jpba.2004.08.022
8. Martins, P.B.C.; Freeman, S.; Alder, J.F.; Passie, T.; Brandt, S.D. Profiling psychoactive tryptamine-drug synthesis by focusing on detection using mass spectrometry. TrAC, 2010, 29(4), 285-296. http://dx.doi.org/10.1016/j.trac.2010.01.009
9. Jones, R.S. Tryptamine: a neuromodulator or neurotransmitter in mammalian brain? Prog. Neurobiol., 1982, 19(1-2), 117-139. http://dx.doi.org/10.1016/0301-0082(82)90023-5
10. Corkery, J.M.; Durkin, E.; Elliott, S.; Schifano, F.; Ghodse, H.A. The recreational tryptamine 5-MeO-DALT (N,N-diallyl-5- methoxytryptamine): A brief review. Prog. Neuropsychopharm. Biol. Psychiatry, 2012, 39(2), 259-262. http://dx.doi.org/10.1016/ j.pnpbp.2012.05.022
11. Gibbons, S. 'Legal Highs' - Novel and emerging psychoactive drugs: a chemical overview for the toxicologist. Clin. Toxicol., 2012, 50(1), 15-24. http://dx.doi.org/10.3109/15563650.2011. 645952
12. Chilton, W.S.; Bigwood, J.; Jensen, R.E. Psilocin, bufotenine and serotonin: historical and biosynthetic observations. J. Psychedelic Drugs, 1979,11(1-2), 61-69. http://dx.doi.org/10.1080/02791072. 1979.10472093
13. Lyttle, T.; Goldstein, D.; Gartz, J. Bufo toads and bufotenine: fact and fiction surrounding an alleged psychedelic. J. Psychoactive Drugs, 1996, 28(3): 267-290. http://dx.doi.org/10.1080/02791072. 1996.10472488
14. Hill, S.L.; Thomas, S.H. Clinical Toxicology of newer recreational drugs. Clin. Toxicol., 2011, 49(8), 705-719. http://dx.doi.org/10. 3109/15563650.2011.615318
15. Fantegrossi, W.E.; Murnane, A.C.; Reissig, C.J. The behavioral pharmacology of hallucinogens. Biochem. Pharmacol., 2008, 75(1), 17-33. http://dx.doi.org/10.1016/j.bcp.2007.07.018
16. Nagai, F.; Nonaka, R.; Satoh, K.; Kaminura, H. The effects of nonmedically used psychoactive drugs on monoamine neurotransmission in rat brain. Eur. J. Pharmacol., 2007, 559(2-3), 132-137. http://dx.doi.org/10.1016/j.ejphar.2006.11.075
17. Ray, T.S. Psychedelics and the human receptorome. PLoS One, [Online] 2010, 5(2), e9019. doi:10.1371/journal.pone.0009019 [Last access on 24th August, 2014]. doi:10.1371/journal.pone. 0009019
18. Lessin, A.W.; Long, R.F.; Parkes, M.W. Central stimulant actions of α -alkyl substituted tryptamine in mice. Br. J. Pharmacol. Chemoter., 1965, 24, 49-67. http://dx.doi.org/10.1111/j.1476-5381. 1965.tb02079.x
19. Shulgin, A.T., Shulgin A. TIHKAL: the continuation Tryptamines I have known and loved; Transform Press: Berkley, 1997. http://dx. doi.org/10.3109/15563650.2014.885983
20. Kamour, A.; James, D.; Spears, R.; Cooper, G.; Lupton, D.J.; Eddleston, M.; Thompson, J.P.; Vale, A.J.; Thanacoody, H.K.R.; Hill, S.L.; Thomas, S.H.L. Patterns of presentation and clinical toxicity after reported use of alpha methyltryptamine in the United Kingdom. A report from the UK National Poisons Information Service. Clin. Toxicol., 2014, 52(3), 192-197.
21. Available from: http://www.deadiversion.usdoj.gov/drug_chem_ info/amt.pdf [Last access on 1th August, 2014]
22. Available from: https://legal-high-inhaltsstoffe.de/sites/default/files/ uploads/amt.pdf [Last access on 1th August August, 2014]
23. Wilcox, J. Psychoactive properties of alpha-methyltryptamine: analysis from self reports of users. J. Psychoactive Drugs, 2012, 44(3), 274-276. http://dx.doi.org/10.1080/02791072.2012.704592
24. Available from: https://www.gov.uk/government/uploads/system/ uploads/attachment_data/file/318693/ [Last access on 5th August, 2014]
25. Available from: http://www.sgul.ac.uk/research/projects/icdp/ourwork- programmes/pdfs/drd_ar_2013.pdf [Last access on 11th August, 2014]
26. Huang, X.M.; Johnson, M.P.; Nichols, D.E. Reduction in brain serotonin markers by alpha-ethyltryptamine (Monase). Eur. J. Pharmacol., 1991, 200(1), 187-90. http://dx.doi.org/10.1016/0014- 2999(91)90686-k
27. Greig, M.E.; Walk, R.A.; Gibbons, A.J. The effect of three tryptamine derivatives on serotonin metabolism in vitro and in vivo. J. Pharmacol. Exp. Ther., 1959, 127(2), 110-115. PubMed ID: 13851725
28. Ott, J. Ayahuasca Analogues: Pangæan Entheogens; Kennewick, WA, USA: Natural Products. 1994 pp. 81-83.
29. Strassman, R.J. Human psychopharmacology of N,Ndimethyltryptamine. Behav. Brain Res., 1996, 73(1-2), 121-124. http://dx.doi.org/10.1016/0166-4328(96)00081-2
30. Gable, R.S. Risk assessment of ritual use of oral dimethyltryptamine (DMT) and harmala alkaloids. Addiction, 2007, 102(1), 24-34. http://dx.doi.org/10.1111/j.1360-0443.2006. 01652.x
31. Szara, S.; Rockland, L.H.; Rosenthal, D.; Handlon, J.H. Psychological Effects and Metabolism of N,N-diethyltryptamine in Man. Arch. Gen. Psychiatry, 1966, 15(3), 320-329. PubMed ID: 5330062
32. Winter, J.C. Behavioral effects of n,n-diethyltryptamine: absence of antagonism by xylamidine tosylate. J. Pharmacol. Exp. Ther., 1969, 169(1), 7-16. PubMed ID: 5306645
33. Available from: https://www.erowid.org/library/books_online/ tihkal/tihkal03.shtml [Last access on 21th August, 2014].
34. Thiagaraj, H.V.; Russo, E.B.; Burnett, A.; Goldstein, E.; Thompson, C.M.; Parker, K.K. Binding properties of dipropyltryptamine at the human 5-HT1a receptor. Pharmacology, 2005, 74(4), 193-199. http://dx.doi.org/10.1159/000085649
35. Grof, S.; Soskin, R.A.; Richards, W.A.; Kurland A.A. DPT as an adjunct in psychotherapy of alcoholics, Int. Pharmacopsychiatry. 1973, 8(1), 104-115. PubMed ID: 4150711
36. Carbonaro, T.M.; Forster, M.J.; Gatch, M.B. Discriminative stimulus effects of N,N-diisopropyltryptamine, Psychopharmacology. 2013, 226(2), 241-246. http://dx.doi.org/10.1007/s00213-012-2891-x
37. Gatch, M.B.; Forster, M.J.; Janowsky, A., Eshleman, A.J. Abuse Liability Profile of Three Substituted Tryptamines. J. Pharmacol. Exp. Ther., 2011, 338(1), 280-289. http://dx.doi.org/10.1124/jpet. 111.179705
38. Nichols, D.E. Hallucinogens. Pharmacol. Ther., 2004, 101(2), 131-181. http://dx.doi.org/10.1016/j.pharmthera.2003.11.002
39. Shulgin, A.T.; Carter, M.F. N, N-Diisopropyltryptamine (DiPT) and 5-methoxy-N,N-diisopropyltryptamine (5-MeO-DiPT). Two orally active tryptamine analogs with CNS activity. Commun. Psychopharmacol., 1980, 4(5), 363-369. PubMed ID: 6949674
40. Bertol, E.; Mari, F.; Lodi, F.; Marozzi, E. Trattato di Tossicologia Forense; CEDAM, 2000, p. 471.
41. Lindenblatt, H.; Kraemer, E.; Holzmann-Erens, P.; Gouzoulis- Mayfrank, E.; Kovar, K.A. Quantitation of psilocin in human plasma by high-performance liquid chromatography and electrochemical detection: comparison of liquid-liquid extraction with automated on-line solid-phase extraction. J. Chromatogr. B. Biomed Sci. Appl., 1998, 709(2), 255-263. http://dx.doi.org/ 10.1016/s0378-4347(98)00067-x
42. Halpern, J.H. Hallucinogens and dissociative agents naturally growing in the United States. Pharmacol. Ther., 2004, 102(2), 131- 138.
43. Grieshaber, A.F.; Moore, K.A.; Levine, B. The detection of psilocin in human urine. J. Forensic Sci., 2001, 46(3), 627-630. PubMed ID: 11373000
44. Peden, N.R.; Macaulay, K.E.C.; Bisset, A.F.; Crooks, J.; Pelosi, A.J. Clinical toxicology of 'magic mushroom' ingestion. Postgrad. Med. J., 1981, 57(671), 543-545. http://dx.doi.org/10.1136/pgmj. 57.671.543
45. Hasler, F.; Grimberg, U.; Benz, M.A.; Huber, T.; Vollenweider F.X. Acute psychological and physiological effects of psilocybin in healthy humans: a double-blind, placebo-controlled dose-effect study. Psychopharmacology, 2004, 172(2), 145-156. http://dx.doi. org/10.1007/s00213-003-1640-6
46. Available from: http://www.erowid.org/experiences/exp.php? ID=50758. [Last access on 25th August, 2014].
47. Ujváry, I. Psychoactive natural products: overview of recent developments. Ann. Ist. Super. Sanita, 2014, 50(1), 12-27. DOI: 10.4415/ANN_14_01_04. [Last access on 25th August, 2014].
48. Moffat, A.C.; Osselton, M.D.; Widdop, B.; Watts J. Clarke's Analysis of Drugs and Poisons 4th Edition; Pharmaceutical Press, 2011, pp. 1004-1005.
49. Fuller, R.W.; Snoddy, H.D.; Perry, K.W. Tissue distribution, metabolism and effects of bufotenine administered to rats. Neuropharmacology, 1995, 34(7), 799-804. http://dx.doi.org/ 10.1016/0028-3908(95)00049-c
50. Ott, J. Pharmacology of Bufotenine. J. Psychoactive Drugs, 2001, 33(3), 273-81. http://dx.doi.org/10.1080/02791072.2001.10400574
51. Available from: http://www.erowid.org/chemicals/5meo_amt/ 5meo_amt_info2.shtml [Last access on 25th August, 2014].
52. Glennon, R.A.; Chaurasia, C.; Titeler, M. Binding of indolylalkylamines at 5-HT2 serotonin receptors: examination of a hydrophobic binding region. J. Med. Chem., 1990, 33(10), 2777- 2784.12 http://dx.doi.org/10.1021/jm00172a016
53. Tomaszewski, Z.; Johnson, M.P.; Huang, X.; Nichols, D.E. Benzofuran bioisosteres of hallucinogenic tryptamines. J. Med. Chem., 1992, 35(11), 2061-2064. http://dx.doi.org/10.1021/jm00089a017
54. Available from: http://www.erowid.org/chemicals/5meo_amt/ 5meo_amt_info1.shtml [Last access on 25th August, 2014].
55. Available from: http://www.erowid.org/chemicals/lsd/lsd_media2. shtml [Last access on 25th August, 2014].
56. Pachter, I.J.; Zacharias, D.E.; Ribeiro, O. Indole alkaloids of acer saccharinum (the Silver Maple), Dictyoloma incanescens, Piptadenia colubrina, and Mimosa hostilis; 1959, pp. 1285-1287. http://dx.doi.org/10.1021/jo01091a032
57. Shen, H.W.; Jiang, X.L.; Winter, J.C.; Yu, A.M. Psychedelic 5- Methoxy-N,N-dimethyltryptamine: metabolism, pharmacokinetics, drug interactions, and pharmacological actions, Curr. Drug Metab., 2010, 11(8), 659-666. http://dx.doi.org/10.2174/ 138920010794233495
58. Ott, J. Pharmepena-Psychonautics: Human intranasal, sublingual and oral pharmacology of 5-methoxy-N,N-dimethyl-tryptamine. J. Psychoactive Drugs, 2001, 33(4), 403-407. http://dx.doi.org/ 10.1080/02791072.2001.10399925
59. Sogawa, C.; Sogawa, N.; Tagawa, J.; Fujino, A.; Ohyama, K.; Asanuma, M.; Funada, M.; Kitayama S. 5-Methoxy-N,Ndiisopropyltryptamine (Foxy), a selective and high affinity inhibitor of serotonin transporter. Toxicol. Lett., 2007, 170(1), 75-82. http://dx.doi.org/10.1016/j.toxlet.2007.02.007
60. Muller, A.A. New drugs of abuse update: Foxy Methoxy. J. Emerg. Nurs., 2004, 30(5), 507-508. http://dx.doi.org/10.1016/j.jen. 2004.07.037
61. Fantegrossi, W.E.; Harrington, A.W.; Kiessel, C.L.; Eckler, J.R.; Rabin, R.A.; Winter, J.C.; Coop, A.; Rice, K.C.; Woods, J.H. Hallucinogen-like actions of 5-methoxy-N,N diisopropyltryptamine in mice and rats. Pharmacol. Biochem. Behav., 2006, 83(1), 122- 129. http://dx.doi.org/10.1016/j.pbb.2005.12.015
62. Tanaka, E.; Kamata, T.; Katagi, M.; Tsuchihashi, H.; Honda, K. A fatal poisoning with 5-methoxy-N,N-diisopropyltryptamine, Foxy. Forensic Sci. Int., 2006, 163(1-2), 152-154. http://dx.doi.org/ 10.1016/j.forsciint.2005.11.026
63. Nonaka, R.; Nagal, F.; Ogata, A.; Satoh, K. In vitro screening of psycgoactive drugs by [35S] GTPγS binding in rat brain membranes. Biol. Pharm. Bull., 2007, 30(12), 2328-2333. http://dx. doi.org/10.1248/bpb.30.2328
64. Available from: http://www.erowid.org/chemicals/5meo_mipt/ 5meo_mipt_effects.shtml [Last access on 25th August, 2014].
65. Al-Assmar, S.E. The seeds of the Hawaiian baby woodrose are a powerful hallucinogen. Arch. Intern. Med., 1999, 159(17), 2090. http://dx.doi.org/10.1001/archinte.159.17.2090
66. Available from: https://www.erowid.org/plants/hbw/hbw_effects. shtml [Last access on 25th August, 2014].
67. Available from: https://www.erowid.org/plants/morning_glory/ morning_glory.shtml [Last access on 25th August, 2014].
68. Available from: http://www.ehow.com/about_5073540_psychedeliceffects- morning-glory-seeds.html [Last access on 25th August, 2014].
69. Available from: http://www.erowid.org/library/books_online/tihkal/ tihkal48.shtml [Last access on 26th August, 2014].
70. Available from: http://www.erowid.org/library/books_online/ tihkal/tihkal11.shtml [Last access on 26th August, 2014].
71. Available from: http://www.erowid.org/library/books_online/ tihkal/tihkal06.shtml [Last access on 26th August, 2014].
72. Fantegrossi, W.E.; Reissig, C.J.; Katz, E.B.; Yarosh, H.L.; Rice, K.C; Winter, J.C. Hallucinogen-like effects of N,Ndipropyltryptamine (DPT): possible mediation by serotonin 5- HT1A and 5-HT2A receptors in rodents. Pharmacol. Biochem. Behavior., 2008, 88(3), 358-365. http://dx.doi.org/10.1016/ j.pbb.2007.09.007
73. Sitaram, B.R.; Lockett, L.; Talomsin, R.; Blackman, G.L.; McLeod, W.R. In vivo metabolism of 5-methoxy-N, N-dimethyltryptamine and N,N-dimethyltryptamine in the rat. Biochem. Pharmacol., 1987, 36(9), 1509-1512. http://dx.doi.org/10.1016/0006-2952(87) 90118-3
74. Available from: www.erowid.org/experiences/exp_front.shtml [Last access on 26th August, 2014].
75. Available from: http://www.erowid.org/library/books_online/ tihkal/tihkal.shtml#index [Last access on 26th August, 2014].
76. Dargan,P.I.; Wood, D.M. Novel Psychoactive Substances: Classification, Pharmacology and Toxicology; Elsevier, 2013.
77. Available from: http://www.erowid.org/chemicals/5meo_dalt/ 5meo_dalt_info1.shtml [Last access on 26th August, 2014].
78. Available from: www.erowid.org/chemicals/ [Last access on 26th August, 2014].
79. Available from: http://www.erowid.org/chemicals/lsa/lsa_effects. shtml [Last access on 26th August, 2014].
80. Wood, D.M.; Conran, P.; Dargan, P.I. ICD-10 coding: poor identification of recreational drug presentations to a large emergency department. Emerg. Med. J., 2011, 28(5), 387-389. http://dx.doi.org/10.1136/emj.2009.088344
81. Holstege, C.P., Baer, A.B.; Kirk M.A. Prolonged hallucinations following ingestion of alpha-methyl-tryptamine. J. Toxicol. Clin. Toxicol., 2003, 41(5), 641-752. http://dx.doi.org/10.1081/clt- 120030949
82. Long, H.; Hoffman, R.S.; Nelson, L.S. Alpha-methyltryptamine revisited due to easy internet access, EAPCCT XXIII International Congress, 2003.
83. Dailey, R.M.; Nelson, L.D.; Scaglione, J.M. Tachycardia and rhabdomyolysis after intentional ingestion of N,N-Dipropyltryptamine. J. Toxicol. Clin. Toxicol., 2003, 41(5), 742-743.
84. Brush, D.E.; Bird, S.B.; Boyer, E.W. Monoamine oxidase inhibitor poisoning resulting from Internet misinformation on illicit substances. J. Toxicol. Clin. Toxicol., 2004, 42(2), 191-195. http://dx.doi.org/10.1081/clt-120030949
85. Wilson, J.M.; McGeorge, F.; Smolinske, S.; Meatherall, R. A "Foxy" intoxication. Forensic Sci. Int., 2005, 148(1), 31-36. http:// dx.doi.org/10.1016/j.forsciint.2004.04.017
86. Alatrash, G.; Majhail, N.S.; Pile, J.C. Rhabdomyolysis after ingestion of "Foxy", a hallucinogenic tryptamine derivative. Mayo Clin. Proc., 2006, 81(4), 550-551. http://dx.doi.org/10.4065/81. 4.550
87. Smolinske, S.C.; Rastogi, R.; Schenkel S. "Foxy" methoxy: a new drug of abuse. J. Med. Toxicol., 2005, 1(1), 22-25. http://dx. doi.org/10.1007/bf03160901
88. Meatherall, R.; Sharma, P. "Foxy", a designer tryptamine hallucinogen. J. Anal. Toxicol., 2003, 27(5), 313-317. http://dx.doi. org/10.1093/jat/27.5.313
89. Available from: http://www.aapcc.org/annual-reports/ [Last access on 26th August, 2014].
90. Shimizu, E.; Watanabe, H.; Kojima, T.; Hagiwara, H.; Fujisaki, M.; Miyatake, R.; Hashimoto, K.; Iyo, M. Combined intoxication with methylone and 5-MeO-MiPT. Prog. Neuropsychopharmacol. Biol. Psychiatry, 2007, 31(1), 288-291. http://dx.doi.org/10.1016/ j.pnpbp.2006.06.012
91. Jovel, A.; Felthous, A.; Bhattacharyya, A. Delirium Due to Intoxication from the Novel Synthetic Tryptamine 5-MeO-DALT. J. Forensic Sci., 2014, 59(3), 844-846. http://dx.doi.org/10.1111/ 1556-4029.12367
92. Boland, D.M.; Andollo, W.; Hime, G.W.; Hearn, W.L. Fatality due to acute α methyltryptamine intoxication. J. Anal. Toxicol., 2005, 29(5), 394-397. http://dx.doi.org/10.1093/jat/29.5.394
93. Butin, J.W. Agranulocytosis following Monase therapy. J Kans. Med. Soc., 1962, 63, 338-340. http://dx.doi.org/10.1016/0002- 9343(86)90274-3
94. Morano, R.A.; Spies, C.; Walker, F.B.; Plank, S.M. Fatal intoxication involving etryptamine. J. Forensic Sci., 1993, 38(3), 721-725. PubMed ID: 8099943
95. Daldrup, T.; Heller, C.; Matthiensen, U.; Honus, S.; Bresges, A.; Haarhoff, K. Etryptamine, a new designer drug with a fatal effect, Z. Rechtsmed., 1986, 97(1), 61-68. DOI: 10.1007/BF00200960
96. Sklerov, J.; Levine, B.; Moore, K.A.; King, T.; Fowler, D. A fatal intoxication following the ingestion of 5-methoxy-n,ndimethyltryptamine in an Ayahuasca preparation. J. Anal. Toxicol., 2005, 29(8), 838-841. http://dx.doi.org/10.1093/jat/29.8.838
97. Available from: http://www.erowid.org/chemicals/5meo_dipt/ 5meo_dipt_media1.shtml [Last access on 26th August, 2014].
98. Hylin, J.W.; Watson, D.P. Ergoline Alkaloids in Tropical Wood Roses, Science, 1965, 148(3669), 499-500. http://dx.doi.org/ 10.1126/science.148.3669.499
99. Available from: https://www.erowid.org/experiences/exp.php? ID=7110 [Last access on 26th August, 2014].
100. Göpel, C.; Maras, A.; Schmidt, M.H. Hawaiian baby rose wood: case report of an argyreia nervosa induced toxic psychosis. Psychiatr. Praxis., 2003, 30(4), 223-224. http://dx.doi.org/10.1055/ s-2003-39490
101. Montesano, C.; Sergi, M.; Moro, M.; Napoletano, S.; Romolo, F.S.; Del Carlo, M.; Compagnone, D.; Curini, R. Screening of methylenedioxyamphetamine- and piperazine-derived designer drugs in urine by LC-MS/MS using neutral loss and precursor ion scan. J. Mass Spectrom., 2013, 48(1), 49-59. http://dx.doi.org/ 10.1002/jms.3115
102. Strano-Rossi, S.; Anzillotti, L.; Castrignanò, E.; Romolo, F.S.; Chiarotti, M. Ultra high performance liquid chromatographyelectrospray ionization-tandem mass spectrometry screening method for direct analysis of designer drugs, "spice" and stimulants in oral fluid. J. Chromatogr. A, 2012, 1258, 37-42. http://dx.doi.org/10.1016/j.chroma.2012.07.098
103. Favretto, D.; Pascali, J.P.; Tagliaro, F. New challenges and innovation in forensic toxicology: Focus on the "New Psychoactive Substances", J. Chromatogr. A, 2013, 1287, 84-95. http://dx.doi. org/10.1016/j.chroma.2012.12.049
104. Vorce, S.P.; Sklerov, J.H. A general screening and confirmation approach to the analysis of designer tryptamines and phenethylamines in blood and urine using GC-EI-MS and HPLCelectrospray- MS. J. Anal. Toxicol., 2004, 28(6), 407-410. http://dx.doi.org/10.1093/jat/28.6.407
105. Wohlfarth, A.; Weinmann, W.; Dresen, S. LC-MS/MS screening method for designer amphetamines, tryptamines, and piperazines in serum. Anal. Bioanal. Chem., 2010, 396(7), 2403-2414. http://dx. doi.org/10.1007/s00216-009-3394-4
106. Meyer, M.R.; Caspar, A.; Brandt, S.D.; Maurer, H.H. A qualitative/ quantitative approach for the detection of 37 tryptamine-derived designer drugs, 5 β-carbolines, ibogaine, and yohimbine in human urine and plasma using standard urine screening and multi-analyte approaches. Anal. Bioanal. Chem., 2014, 406(1), 225-237. http://dx.doi.org/10.1007/s00216-013-7425-9
107. Chen, B.H.; Liu, J.T.; Chen, W.X.; Chen, H.M.; Lin, C.H. A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. Talanta, 2008, 74(4), 512-517. http://dx.doi.org/10.1016/j.talanta.2007.06.012
108. Ishida, T.; Kudo, K.; Kiyoshima, A.; Inoue, H.; Tsuji, A., Ikeda, N. Sensitive determination of alpha-methyltryptamine (AMT) and 5- methoxy-N,N-diisopropyltryptamine (5MeO-DiPT) in whole blood and urine using gas chromatography-mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 2005, 823(1), 47-52. http://dx.doi.org/10.1016/j.jchromb.2004.10.067
109. Pichini, S.; Pujadas, M.; Marchei, E.; Pellegrini, M.; Fiz, J.; Pacifici, R.; Zuccaro, P.; Farré, M.; de la Torre, R. Liquid chromatographyatmospheric pressure ionization electrospray mass spectrometry determination of "hallucinogenic designer drugs" in urine of consumers. J. Pharm. Biomed. Anal., 2008, 47(2), 335-342. http://dx.doi.org/10.1016/j.jpba.2007.12.039
110. Helander, A.; Bäckberg, M.; Hultén, P., Al-Saffar, Y., Beck, O. Detection of new psychoactive substance use among emergency room patients: Results from the Swedish STRIDA project. Forensic Sci. Int., 2014, 243C, 23-29. http://dx.doi.org/10.1016/ j.forsciint.2014.02.022
111. Al-Saffar, Y.; Stephanson, N.N.; Beck, O. Multicomponent LCMS/ MS screening method for detection of new psychoactive drugs, legal highs, in urine-experience from the Swedish population. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 2013, 930, 112- 120. http://dx.doi.org/10.1016/j.jchromb.2013.04.043
112. Katagi, M.; Kamata, T.; Zaitsu, K.; Shima, N.; Kamata, H.; Nakanishi, K.; Nishioka, H.; Miki, A.; Tsuchihashi, H. Metabolism and toxicologic analysis of tryptamine-derived drugs of abuse. Ther. Drug Monit., 2010, 32(3), 328-331. http://dx.doi.org/ 10.1097/ftd.0b013e3181dcb40c
113. Wang, M.J.; Liu, J.T.; Chen, H.M.; Lin, J.J.; Lin, C.H. Comparison of the separation of nine tryptamine standards based on gas chromatography, high performance liquid chromatography and capillary electrophoresis methods. J. Chromatogr. A., 2008, 1181(1-2), 131-136. http://dx.doi.org/10.1016/j.chroma.2007.12.031
114. Strano Rossi, S.; Odoardi, S.; Gregori, A.; Peluso, G.; Ripani L.; Ortar, G.; Serpelloni, G.; Romolo, F.S. An analytical approach to the forensic identification of different classes of new psychoactive substances (NPSs) in seized materials. Rapid Commun. Mass Spectrom., 2014, 28(17), 1904-1916. http://dx.doi.org/10.1002/ rcm.6969
115. Hugel, J.; Meyers, F.A.; Lankin, D.C. Analysis of the hallucinogens, in Handbook of forensic drug analysis, Editor: Frederick P. Smith, 2005, 153-234.