Metabolism and toxicological analyses of hallucinogenic tryptamine analogues being abused in Japan

Forensic Toxicology

Volumn 28, Issue 1, 2010, Pages 1-8

  Kamata, Tooru ^a   Katagi, Munehiro ^a   Tsuchihashi, Hitoshi ^a  

^a Chuo ward   (Japan)

Author keywords

5 Methoxy N,N diisopropyltryptamine; Designer drug; Hallucinogenic tryptamines; Indole derivatives; Psilocin; Psilocybin

Indexed keywords

INDOLE DERIVATIVE; N,N DIISOPROPYL 5 METHOXYTRYPTAMINE; PSILOCIN; PSILOCYBINE;

BLOOD LEVEL; CHEMICAL ANALYSIS; DRUG ABUSE; FORENSIC TOXICOLOGY; HUMAN; JAPAN; LIQUID CHROMATOGRAPHY; MASS FRAGMENTOGRAPHY; METABOLISM; PRIORITY JOURNAL; REVIEW; TANDEM MASS SPECTROMETRY; URINE LEVEL;

PSILOCYBE CUBENSIS;

EID: 73349106209     PISSN: 18608965     EISSN: 18608973     Source Type: Journal    
DOI: 10.1007/s11419-009-0087-9     Document Type: Review

References (26)

1. W.E. Fantegrossi K.S. Murnane C.J. Reissig 2008 The behavioral pharmacology of hallucinogens Biochem Pharmacol 75 17 33 10.1016/j.bcp.2007.07. 018 1:CAS:528:DC%2BD2sXhsVCksLjO 17977517 (Pubitemid 350235393)
2. A. Hofmann R. Heim A. Brack H. Kobel 1958 Psilocybin, ein psychotroper Wirkstoff aus dem mexikanischen Rauschpilz Psilocybe mexicana Heim Experientia 14 107 109 10.1007/BF02159243 1:CAS:528:DyaF3cXhvVequw%3D%3D 13537892
3. A.T. Shulgin M.F. Carter 1980 N,N-Diisopropyltryptamine (DIPT) and 5-methoxy-N,N-diisopropyltryptamine (5-MeODIPT). Two orally active tryptamine analogs with CNS activity Commun Psychopharmacol 4 363 369 1:CAS:528: DyaL3MXlt1Khs7g%3D 6949674
4. N. Uchiyama R. Kikura-Hanajiri N. Kawahara Y. Goda 2009 Identification of a cannabimimetic indole as a designer drug in a herbal product Forensic Toxicol 27 61 66 10.1007/s11419-009-0069-y 1:CAS:528:DC%2BD1MXos1Cgsrs%3D
5. R. Kikura-Hanajiri M. Kawamura T. Maruyama M. Kitajima H. Takayama Y. Goda 2009 Simultaneous analysis of mitragynine, 7-hydroxymitragynine, and other alkaloids in the psychotropic plant "kratom" (Mitragyna speciosa) by LC-ESI-MS Forensic Toxicol 27 67 74 10.1007/s11419-009-0070-5 1:CAS:528:DC%2BD1MXos1Cgsrk%3D
6. T. Kamata M. Nishikawa M. Katagi H. Tsuchihashi 2003 Optimized glucuronide hydrolysis for the detection of psilocin in human urine samples J Chromatogr B 796 421 427 10.1016/j.jchromb.2003.08.030 1:CAS:528: DC%2BD3sXosVyitrc%3D (Pubitemid 37329685)
7. T. Kamata M. Nishikawa M. Katagi H. Tsuchihashi 2006 Direct detection of serum psilocin glucuronide by LC/MS and LC/MS/MS: time-courses of total and free (unconjugated) psilocin concentrations in serum specimens of a "magic mushroom" user Forensic Toxicol 24 36 40 10.1007/s11419-006-0006-2 1:CAS:528:DC%2BD28XpvFOiu7k%3D (Pubitemid 44257287)
8. T. Kamata M. Katagi H.T. Kamata A. Miki N. Shima K. Zaitsu M. Nishikawa E. Tanaka K. Honda H. Tsuchihashi 2006 Metabolism of the psychotomimetic tryptamine derivative 5-methoxy-N,N-diisopropyltryptamine in humans: identification and quantification of its urinary metabolites Drug Metab Dispos 34 281 287 10.1124/dmd.105.005835 1:CAS:528:DC%2BD28XhtVCntbY%3D 16280455 (Pubitemid 43145029)
9. T. Kamata M. Katagi H. Kamata A. Miki N. Shima K. Zaitsu M. Nishikawa H. Tsuchihashi 2007 Urinary excretion profiles of 5-methoxy-N,N- diisopropyltryptamine and its relevant metabolites in humans J Health Sci 53 585 590 10.1248/jhs.53.585 1:CAS:528:DC%2BD2sXhtlelt7%2FI (Pubitemid 47535666)
10. A. Horita L.J. Weber 1961 The enzymic dephosphorylation and oxidation of psilocybin and psilocin by mammalian tissue homogenates Biochem Pharmacol 7 47 54 10.1016/0006-2952(61)90124-1 1:CAS:528:DyaF3MXhtFemu78%3D 13715852
11. A. Horita L.J. Weber 1962 Dephosphorylation of psilocybin in the intact mouse Toxicol Appl Pharmacol 4 730 737 10.1016/0041-008X(62)90102-3 1:CAS:528:DyaF3sXlsFKgug%3D%3D 13954905
12. G. Sticht H. Käferstein 2000 Detection of psilocin in body fluids Forensic Sci Int 113 403 407 10.1016/S0379-0738(00)00213-9 1:CAS:528: DC%2BD3cXmtF2rt7Y%3D 10978655 (Pubitemid 30649765)
13. A.F. Grieshaber K.A. Moore B. Levine 2001 The detection of psilocin in human urine J Forensic Sci 46 627 630 1:CAS:528:DC%2BD3MXktFKisLk%3D 11373000
14. F. Hasler D. Bourquin R. Brenneisen T. Bär F.X. Vollenweider 1997 Determination of psilocin and 4-hydroxyindole-3-acetic acid in plasma by HPLC-ECD and pharmacokinetic profiles of oral and intravenous psilocybin in man Pharm Acta Helv 72 175 184 10.1016/S0031-6865(97)00014-9 1:CAS:528: DyaK2sXjsVKmtLc%3D 9204776 (Pubitemid 27246716)
15. F. Hasler D. Bourquin R. Brenneisen F.X. Vollenweider 2002 Renal excretion profiles of psilocin following oral administration of psilocybin: a controlled study in man J Pharm Biomed Anal 30 331 339 10.1016/S0731-7085(02) 00278-9 1:CAS:528:DC%2BD38XmtlGqtL4%3D 12191719 (Pubitemid 35013499)
16. H. Lindenblatt E. Kramer P. Holzmann-Erens E. Gouzoulis-Mayfrank K.A. Kovar 1998 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 709 255 263 10.1016/S0378-4347(98)00067-X 1:CAS:528:DyaK1cXjtVKls7o%3D (Pubitemid 28255358)
17. R. Meatherall P. Sharma 2003 Foxy, a designer tryptamine hallucinogen J Anal Toxicol 27 313 317 1:CAS:528:DC%2BD3sXlsVSkt78%3D 12908946
18. J.M. Wilson F. McGeorge S. Smolinske R. Meatherall 2005 A foxy intoxication Forensic Sci Int 148 31 36 10.1016/j.forsciint.2004.04.017 1:CAS:528:DC%2BD2cXhtVyrtb%2FE 15607587 (Pubitemid 40029393)
19. S. Narimatsu R. Yonemoto K. Saito K. Takaya T. Kumamoto T. Ishikawa M. Asanuma M. Funada K. Kiryu S. Naito Y. Yoshida S. Yamamoto N. Hanioka 2006 Oxidative metabolism of 5-methoxy-N,N-diisopropyltryptamine (Foxy) by human liver microsomes and recombinant cytochrome P450 enzymes Biochem Pharmacol 71 1377 1385 10.1016/j.bcp.2006.01.015 1:CAS:528:DC%2BD28XivVOjtrg%3D 16510126
20. Shima N, Kamata T, Kamata H, Zaitsu K, Katagi M, Tsuchihashi H (2007) Determination of 5-MeO-MIPT and its metabolites in blood and urine. Abstracts of the 127th Annual Meeting of The Pharmaceutical Society of Japan, 28P1-pm231 (CD-ROM)
21. Katagi M, Kamata T, Tsuchihashi H (2009) Identification of major urinary metabolites of tryptamine-derived hallucinogens. Abstracts of the 57th Annual Conference on Mass Spectrometry, Osaka, Japan, pp. 266-267
22. R.P. Chamakura 1994 Tryptamines Microgram 27 316 329
23. T. Keller A. Schneider P. Regenscheit R. Dirnhofer T. Rücker J. Jaspers W. Kisser 1999 Analysis of psilocybin and psilocin in Psilocybe subcubensis GUZMÄN by ion mobility spectrometry and gas chromatography-mass spectrometry Forensic Sci Int 99 93 105 10.1016/S0379-0738(98)00168-6 1:CAS:528:DyaK1MXhs1Cns78%3D 10077856 (Pubitemid 29017670)
24. S.P. Vorce J.H. Sklerov 2004 A general screening and confirmation approach to the analysis of designer tryptamines and phenethylamines in blood and urine using GC-EIMS and HPLC-electrospray-MS J Anal Toxicol 28 407 410 1:CAS:528:DC%2BD2cXnsVehtLY%3D 15516287
25. T. Kamata M. Nishikawa M. Katagi H. Tsuchihashi 2005 Liquid chromatography-mass spectrometric and liquid chromatography-tandem mass spectrometric determination of hallucinogenic indoles psilocin and psilocybin in "magic mushroom" samples J Forensic Sci 50 336 340 10.1520/JFS2004276 1:CAS:528:DC%2BD2MXivFKmsL8%3D 15813544
26. E. Tanaka T. Kamata M. Katagi H. Tsuchihashi K. Honda 2006 A fatal poisoning with 5-methoxy-N,N-diisopropyltryptamine, Foxy Forensic Sci Int 163 152 154 10.1016/j.forsciint.2005.11.026 1:CAS:528:DC%2BD28XhtVWqtLjJ 16406422 (Pubitemid 44442804)