AMT (3-(2-aminopropyl)indole) and 5-IT (5-(2-aminopropyl)indole): An analytical challenge and implications for forensic analysis

Drug Testing and Analysis

Volumn 5, Issue 3, 2013, Pages 196-202

  Elliott, Simon P ^a   Brandt, Simon D ^b   Freeman, Sally ^c   Archer, Roland P ^d  

^a Inverness Medical Innovations   (United States)

^b LIVERPOOL JOHN MOORES UNIVERSITY   (United Kingdom)

^c UNIVERSITY OF MANCHESTER   (United Kingdom)

^d Longue Rue   (France)

Author keywords

3 IT; 5 IT; AMT; Clinical; Forensic; Internet; Isomers; Legal highs; Tryptamines

Indexed keywords

FORENSIC SCIENCE; POLYCYCLIC AROMATIC HYDROCARBONS;

3-IT; 5-IT; AMINOPROPYL; AMT; ANALYTICAL CHALLENGE; CLINICAL; FORENSIC; FORENSIC ANALYSIS; LEGAL HIGH; TRYPTAMINES;

ISOMERS;

3 (2 AMINOPROPYL)INDOLE; 5 (2 AMINOPROPYL)INDOLE; PSYCHOTROPIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG INTOXICATION; ELECTROSPRAY MASS SPECTROMETRY; FORENSIC IDENTIFICATION; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ION TRAP MASS SPECTROMETRY; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; ULTRAVIOLET SPECTROSCOPY;

EID: 84874692085     PISSN: 19427603     EISSN: 19427611     Source Type: Journal    
DOI: 10.1002/dta.1420     Document Type: Article

References (21)

1. A.T. Shulgin, A. Shulgin TIHKAL: The Continuation, Transform Press, Berkeley, CA, 1997.
2. A. Hofmann, F. Troxler Nouveaux dérivés de l'indole et leur préparation French Patent No. 1344579, 1963.
3. F. Troxler, A. Harnisch, G. Bormann, F. Seemann, L. Szabo Synthesen von Indolen mit (2-Aminoäthyl)-, (2-Aminopropyl)-oder Alkanolamin-Seitenketten am Sechsring. 5. Mitt. über synthetische Indol-Verbindungen. Helv. Chim. Acta 1968, 51, 1616.
4. EMCDDA/Europol. EMCDDA-Europol 2011 Annual Report on the Implementation of Council Decision 2005/387/JHA. Available at: http://www.emcdda.europa.eu/publications/implementation-reports/2011 [August 2012].
5. H.R. Snyder, L. Katz Alkylation of aliphatic nitro compounds with gramine. New synthesis of derivatives of tryptamine. J. Am. Chem. Soc. 1947, 69, 3140.
6. M.E. Greig, R.A. Walk, A.J. Gibbons Effect of three tryptamine derivatives on serotonin metabolism in vitro and in vivo. J. Pharmacol. Exp. Ther. 1959, 127, 110.
7. C.L. Zirkle, C. Kaiser, Monoamine oxidase inhibitors (nonhydrazine), in Psychopharmacological Agents Vol. 1, (Ed: M. Gordon ), Academic Press, New York, 1964, pp. 445.
8. A. Cerletti, M. Taeschler, H. Weidmann Pharmacologic studies on the structure-activity relationship of hydroxyindole alkylamines. Adv. Pharmacol. 1968, 6, 233.
9. A.T. Shulgin, Basic pharmacology and effects, in Hallucinogens. A Forensic Drug Handbook, Chapter 3, (Ed: R.R. Laing ), Elsevier Science Ltd, London, UK, 2003, pp. 67.
10. H.B. Murphree, E.H. Jenney, R.H. Dippy, C.C. Pfeiffer Effects in normal man of α-methyltryptamine and α-ethyltryptamine. Clin. Pharmacol. Ther. 1961, 2, 722.
11. L.E. Hollister, J.J. Prusmack, J.A. Paulsen, N. Rosenquist Comparison of three psychotropic drugs (psilocybin, JB-329, and IT-290) in volunteer subjects. J. Nerv. Ment. Dis. 1960, 131, 428.
12. H.B. Murphree Jr, E.H. Jenney, C.C. Pfeiffer Comparison of the effects of congeners of lysergic acid diethylamide and tryptophane in normal volunteers. Pharmacologist 1960, 2, 64.
13. A.T. Shulgin, D.E. Nichols, Characterization of three new psychotomimetics, in The Psychopharmacology of Hallucinogens, (Eds: R.C. Stillman, R.E. Willette ), Pergamon, New York, 1978, pp. 74.
14. H. Long, L.S. Nelson, R.S. Hoffman Alpha-methyltryptamine revisited via easy Internet access. Vet. Hum. Toxicol. 2003, 45, 149.
15. C.P. Holstege, A.B. Baer, M.A. Kirk Prolonged hallucinations following ingestion of alpha-methyl-tryptamine. J. Toxicol-Clin. Toxic. 2003, 41, 746.
16. J. Wilcox Psychoactive properties of alpha-methyltryptamine: Analysis from self reports of users. J. Psychoactive Drugs 2012, 44, 274.
17. D.M. Boland, W. Andollo, G.W. Hime, W.L. Hearn Fatality due to acute α-methyltryptamine intoxication. J. Anal. Toxicol. 2005, 29, 394.
18. S. Elliott, C. Smith Investigation of the first deaths in the United Kingdom involving the detection and quantitation of the piperazines BZP and 3-TFMPP. J. Anal. Toxicol. 2008, 32, 172.
19. Metabolomics toolbox. Available at: http://www.hmdb.ca/metabolites/HMDB00466 [10 August 2012].
20. C.P.B. Martins, S. Freeman, J.F. Alder, T. Passie, S.D. Brandt The profiling of psychoactive tryptamine drug synthesis focusing on mass spectrometry. Trends Anal. Chem. 2010, 29, 285.
21. M. Katagi, H. Tsutsumi, A. Miki, K. Nakajima, H. Tsuchihashi Analyses of clandestine tablets of amphetamines and their related designer drugs encountered in recent Japan. Jpn. J. Forensic Toxicol. 2002, 20, 303.