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Forensic Toxicology

, Volume 28, Issue 2, pp 77–83 | Cite as

Chemical constituents and DNA sequence analysis of a psychotropic herbal product

  • Hiroyuki Kikuchi
  • Nahoko Uchiyama
  • Jun Ogata
  • Ruri Kikura-Hanajiri
  • Yukihiro Goda
Original Article

Abstract

In recent years, the distribution of a variety of psychotropic products, especially “spice” and “herbal blends,” which are advertised to have narcotic-like effects, has become more widespread in the Japanese illegal drug market. We recently found two synthetic annabinoids, cannabicyclohexanol and JWH-018, that serve as adulterants in herbal products purchased via the Internet. In this study, we focused on a herbal product being sold as incense, which showed unknown components by liquid chromatography-mass spectrometry (LC-MS). The product did not show any peak corresponding to the above synthetic cannabinoids, but seven other peaks were identified by high-performance liquid chromatography and LC-MS. We identified them as N-methyltyramine (1), (R)-normacromerine (2), (R)-macromerine (3), (S)-vasicine (4), mescaline (5), harmaline (6), and harmine (7) by polarimetry, LC-MS, gas chromatography-mass spectrometry, high-resolution mass spectrometry, and nuclear magnetic resonance spectroscopy. We also used DNA sequence analyses to identify the plant species of the product. As a result of the sequencing of trnL-F, internal transcribed spacer (ITS), and rpl16 intron regions, three sequences derived from Coryphantha macromeris (Cactaceae), Peganum harmala (Zygophyllaceae), and Turnera diffusa (Turneraceae) were observed. Compounds 2 and 3, both phenethylamines, were reported to cause hallucinogenic effects and are frequently found in Coryphantha genus (Cactaceae). Therefore, the plant source of these compounds was considered to be C. macromeris. Compound 5 is known to be a psychoactive phenethylamine found in peyote (Lophophora williamsii) and San Pedro cactus (Trichocereus pachanoi). The β-carboline alkaloids 6 and 7 are known to be found in the seeds of P. harmala. Therefore, there seems to be no contradiction between the chemical constituents and the plant species estimated by DNA analyses, except for compound 5. This is the first report dealing with identification of the psychoactive cactus C. macromeris and its constituent compounds in a herbal product distributed in the illegal drug market.

Keywords

(R)-Normacromerine (R)-Macromerine Herbal product Coryphantha macromeris LC-MS DNA analysis 

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References

  1. 1.
    Higashikawa Y, Suzuki S (2008) Studies on 1-(2-phenethyl)-4-(N-propionylanilino)piperidine (fentanyl) and its related compounds. VI. Structure-analgesic activity relationship for fentanyl, methyl-substituted fentanyls and other analogues. Forensic Toxicol 26:1–5CrossRefGoogle Scholar
  2. 2.
    Kanai K, Takekawa K, Kumamoto T, Ishikawa T, Ohmori T (2008) Simultaneous analysis of six phenethylamine-type designer drugs by TLC, LC-MS, and GC-MS. Forensic Toxicol 26:6–12CrossRefGoogle Scholar
  3. 3.
    Zaitsu K, Katagi M, Kamata HT, Miki A, Tsuchihashi H (2008) Discrimination and identification of regioisomeric β-keto analogues of 3,4-methylenedioxyamphetamines by gas chromatography-mass spectrometry. Forensic Toxicol 26: 45–51CrossRefGoogle Scholar
  4. 4.
    Uchiyama N, Kikura-Hanajiri R, Ogata J, Goda Y (2010) Chemical analysis of synthetic cannabinoids as designer drugs in herbal products. Forensic Sci Int. doi:10.1016/j.forsciint. 2010.01.004Google Scholar
  5. 5.
    Kikura-Hanajiri R, Kawamura M, Maruyama T, Kitajima M, Takayama H, Goda Y (2009) Simultaneous analysis of mitragynine, 7-hydroxymitragynine, and other alkaloids in the psychotropic plant “kratom” (Mitragyna speciosa) by LC-ESI-MS. Forensic Toxicol 27:67–74CrossRefGoogle Scholar
  6. 6.
    Uchiyama N, Kikura-Hanajiri R, Kawahara N, Haishima Y, Goda Y (2009) Identification of a cannabinoid analog as a new type of designer drug in a herbal product. Chem Pharm Bull 57:439–441CrossRefPubMedGoogle Scholar
  7. 7.
    Uchiyama N, Kikura-Hanajiri R, Kawahara N, Goda Y (2009) Identification of a cannabimimetic indole as a designer drug in a herbal product. Forensic Toxicol 27:61–66CrossRefGoogle Scholar
  8. 8.
    Lindigkeit R, Boehme A, Eiserloh I, Luebbecke M, Wiggermann M, Ernst L, Beuerle T (2009) Spice: a never ending story? Forensic Sci Int 191:58–63CrossRefPubMedGoogle Scholar
  9. 9.
    Auwarter V, Dresen S, Weinmann W, Muller M, Putz M, Ferreiros N (2009) Spice and other herbal blends: harmless incense or cannabinoid designer drug? J Mass Spectrom 44:832–837CrossRefPubMedGoogle Scholar
  10. 10.
    Ono M, Shimamine M, Takahashi K (1976) Studies on hallucinogens. I. Synthesis of mescaline sulfate (in Japanese with English abstract). Bull Natl Inst Hyg Sci 91:33–35Google Scholar
  11. 11.
    Kikura-Hanajiri R, Kawamura M, Uchiyama N, Ogata J, Kamakura H, Saisho K, Goda Y (2008) Analytical data of designated substances (Shitei-Yakubutsu) controlled by the Pharmaceutical Affairs Law in Japan, part I: GC-MS and LC-MS (in Japanese with English abstract). Yakugaku Zasshi 128:971–979CrossRefPubMedGoogle Scholar
  12. 12.
    Sato H, Sakamura S, Obata Y (1970) The isolation and characterization of N-methyltyramine, tyramine and hordenine from sawa millet seeds. Agr Biol Chem 34:1254–1255Google Scholar
  13. 13.
    Keller W, McLaughlin J (1972) Cactus alkaloids XIII: isolation of (−)-normacromerine from Coryphantha macromeris var. runyonii. J Pharm Sci 61:147–148CrossRefPubMedGoogle Scholar
  14. 14.
    Hodgkins JE, Brown SD, Massingill JL (1967) Two new alkaloids in cacti. Tetrahedron Lett 14:1321–1324CrossRefPubMedGoogle Scholar
  15. 15.
    Joshi BS, Newton MG, Lee DW, Barber AD, Pelletier, SW (1996) Reversal of absolute stereochemistry of the pyrrolo [2, 1-b] quinazoline alkaloids vasicine, vasicinone, vasicinol and vasicinolone. Tetrahedron: Asymmetry 7:25–28CrossRefGoogle Scholar
  16. 16.
    Pummangura S, McLaughlin JL (1981) Cactus alkaloids. XLVII. β-Phenethylamines from the “Missouri Pincushion”, Coryphantha (Neobessya) missouriensis. J Nat Prod 44:614–616CrossRefGoogle Scholar
  17. 17.
    Pummangura S, Nichols DE, McLaughlin JL (1977) Cactus alkaloids XXXIII: β-phenethylamines from the Guatemalan cactus Pilosocereus maxonii. J Pharm Sci 66:1485–1487CrossRefPubMedGoogle Scholar
  18. 18.
    Vanderveen RL, West LG, McLaughlin JL (1974) N-Methyltyramine from Opuntia clavata. Phytochemistry 13: 866–867CrossRefGoogle Scholar
  19. 19.
    Bourn WM, Keller WJ, Bonfiglio JF (1978) Psychoactivity of normacromerine in animals. Life Sci 23:1175–1184CrossRefPubMedGoogle Scholar
  20. 20.
    Bruhn JG, Agurell S (1974) Two new alkaloids from Coryphantha calipensis H. Bravo. J Pharm Sci 63:574–576CrossRefPubMedGoogle Scholar
  21. 21.
    Hornemann KM, Neal JM, McLaughlin JL (1972) Cactus alkaloids XII: β-phenethylamins alkaloids of the genus Coryphantha. J Pharm Sci 61:41–45CrossRefPubMedGoogle Scholar
  22. 22.
    Keller WJ (1980) Catecholamine metabolism in a psychoactive cactus. Clin Toxicol 16:233–243CrossRefPubMedGoogle Scholar
  23. 23.
    Halpern JH (2004) Hallucinogens and dissociative agents naturally growing in the United States. Pharmacol Ther 102: 131–138CrossRefPubMedGoogle Scholar
  24. 24.
    Callaway JC, McKenna DJ, Grob CS, Brito GS, Raymon LP, Poland RE, Andrade EN, Andrade EO, Mash DC (1999) Pharmacokinetics of Hoasca alkaloids in healthy humans. J Ethnopharmacol 65:243–256CrossRefPubMedGoogle Scholar
  25. 25.
    Taberlet P, Gielly L, Pautou G, Bouvet J (1991) Universal primers for amplification of three non-coding regions of chloroplast DNA. Plant Mol Biol 17:1105–1109CrossRefPubMedGoogle Scholar
  26. 26.
    Suh Y, Thien LB, Reeve HE, Zimmer EA (1993) Molecular evolution and phylogenetic implications of internal transcribed spacer sequences of ribosomal DNA in Winteraceae. Am J Bot 80:1042–1055CrossRefGoogle Scholar
  27. 27.
    Butterworth CA, Wallace RS (2004) Phylogenetic studies of Mammillaria (Cactaceae)—insights from chloroplast sequence variation and hypothesis testing using the parametric bootstrap. Am J Bot 91:1086–1098CrossRefGoogle Scholar

Copyright information

© Japanese Association of Forensic Toxicology 2010

Authors and Affiliations

  • Hiroyuki Kikuchi
    • 1
  • Nahoko Uchiyama
    • 1
  • Jun Ogata
    • 1
  • Ruri Kikura-Hanajiri
    • 1
  • Yukihiro Goda
    • 1
  1. 1.National Institute of Health SciencesTokyoJapan

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