Skip to main content
SpringerLink
Log in

Symptoms, toxicities, and analytical results for a patient after smoking herbs containing the novel synthetic cannabinoid MAM-2201

  • Case report
  • Published:
Forensic Toxicology Aims and scope Submit manuscript

Abstract

We report a case of intoxication by the synthetic cannabinoid MAM-2201 ([1-(5-fluoropentyl)-1H-indol-3-yl](4-methyl-1-naphthalenyl)-methanone). A 31-year-old man smoked about 300 mg of a herbal blend. He experienced an acute transient psychotic state with agitation, aggression, anxiety, and vomiting associated with a sympathomimetic syndrome. MAM-2201 was detected and quantified in a plasma sample using liquid chromatography-tandem mass spectrometry (LC–MS–MS). The level was 49 ng/ml 1 h after smoking. The use of other drugs was analytically excluded. The presence of MAM-2201 was confirmed in the herbal blend using gas chromatography–mass spectrometry (GC–MS) and LC–high resolution MS. This is the first description of an analytically confirmed intoxication and of the determination of MAM-2201 in human blood plasma.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. United Nations Office on Drugs and Crime (UNODC) (2011) World drug report 2011

  2. Mechoulam R, Parker LA (2012) The endocannabinoid system and the brain. Annu Rev Psychol. doi:10.1146/annurev-psych-113011-143739

    PubMed  Google Scholar 

  3. Fattore L, Fratta W (2011) Beyond THC: the new generation of cannabinoid designer drugs. Front Behav Neurosci 5:60

    Article  PubMed  CAS  Google Scholar 

  4. Vardakou I, Pistos C, Spiliopoulou C (2010) Spice drugs as a new trend: mode of action, identification and legislation. Toxicol Lett 197:157–162

    Article  PubMed  CAS  Google Scholar 

  5. Ginsburg BC, McMahon LR, Sanchez JJ, Javors MA (2012) Purity of synthetic cannabinoids sold online for recreational use. J Anal Toxicol 36:66–68

    Article  PubMed  CAS  Google Scholar 

  6. Auwärter V, Dresen S, Weinmann W, Müller M, Pütz M, Ferreirós N (2009) ‘Spice’ and other herbal blends: harmless incense or cannabinoid designer drugs? J Mass Spectrom 44:832–837

    Article  PubMed  Google Scholar 

  7. 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 (Tokyo) 57:439–441

    Article  CAS  Google Scholar 

  8. 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 27:61–66

    Article  CAS  Google Scholar 

  9. Zuba D, Byrska B, Maciow M (2011) Comparison of “herbal highs” composition. Anal Bioanal Chem 400:119–126

    Article  PubMed  CAS  Google Scholar 

  10. Uchiyama N, Kikura-Hanajiri R, Goda Y (2011) Identification of a novel cannabimimetic phenylacetylindole, cannabipiperidiethanone, as a designer drug in a herbal product and its affinity for cannabinoid CB1 and CB2 receptors. Chem Pharm Bull (Tokyo) 59:1203–1205

    Article  CAS  Google Scholar 

  11. Uchiyama N, Kawamura M, Kikura-Hanajiri R, Goda Y (2011) Identification and quantitation of two cannabimimetic phenylacetylindoles JWH-251 and JWH-250, and four cannabimimetic naphthoylindoles JWH-081, JWH-015, JWH-200, and JWH-073 as designer drugs in illegal products. Forensic Toxicol 29:25–37

    Article  CAS  Google Scholar 

  12. Nakajima J, Takahashi M, Seto T, Suzuki J (2011) Identification and quantitation of cannabimimetic compound JWH-250 as an adulterant in products obtained via the Internet. Forensic Toxicol 29:51–55

    Article  CAS  Google Scholar 

  13. Nakajima J, Takahashi M, Seto T, Kanai C, Suzuki J, Yoshida M, Hamano T (2011) Identification and quantitation of two benzoylindoles AM-694 and (4-methoxyphenyl)(1-pentyl-1H-indol-3-yl)methanone, and three cannabimimetic naphthoylindoles JWH-210, JWH-122, and JWH-019 as adulterants in illegal products obtained via the Internet. Forensic Toxicol 29:95–110

    Article  CAS  Google Scholar 

  14. Nakajima J, Takahashi M, Nonaka R, Seto T, Suzuki J, Yoshida M, Kanai C, Hamano T (2011) Identification and quantitation of a benzoylindole (2-methoxyphenyl)(1-pentyl-1H-indol-3-yl)methanone and a naphthoylindole 1-(5-fluoropentyl-1H-indol-3-yl)-(naphthalene-1-yl)methanone (AM-2201) found in illegal products obtained via the Internet and their cannabinomimetic effects evaluated by in vitro [35S]GTPγS binding assays. Forensic Toxicol 29:132–141

    Article  CAS  Google Scholar 

  15. Simolka K, Lindigkeit R, Schiebel HM, Papke U, Ernst L, Beuerle T (2012) Analysis of synthetic cannabinoids in “spice-like” herbal highs: snapshot of the German market in summer 2011. Anal Bioanal Chem 404:157–171

    Article  PubMed  CAS  Google Scholar 

  16. Nakajima J, Takahashi M, Seto T, Yoshida M, Kanai C, Suzuki J, Hamano T (2012) Identification and quantitation of two new naphthoylindole drugs-of-abuse (1-(5-hydroxypentyl)-1H-indol-3-yl)(naphthalen-1-yl)methanone (AM-2202) and (1-(4-pentyl)-1H-indol-3-yl)(naphthalen-1-yl)methanone, with other synthetic cannabinoids in unregulated “herbal” products circulated in the Tokyo area. Forensic Toxicol 30:33–44

    Article  CAS  Google Scholar 

  17. Uchiyama N, Kawamura M, Kikura-Hanajiri R, Goda Y (2012) Identification of two new-type synthetic cannabinoids, N-(1-adamantyl)-1-pentyl-1H-indole-3-carboxamide (APICA) and N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide (APINACA), and detection of five synthetic cannabinoids, AM-1220, AM-2233, AM-1241, CB-13 (CRA-13), and AM-1248, as designer drugs in illegal products. Forensic Toxicol 30:114–125

    Article  CAS  Google Scholar 

  18. Kneisel S, Bisel P, Brecht V, Broecker S, Müller M, Auwärter V (2012) Identification of the cannabimimetic AM-1220 and its azepane isomer (N-methylazepan-3-yl)-3-(1-naphthoyl)indole in a research chemical and several herbal mixtures. Forensic Toxicol 30:126–134

    Article  CAS  Google Scholar 

  19. Vandrey R, Dunn KE, Fry JA, Girling ER (2012) A survey study to characterize use of Spice products (synthetic cannabinoids). Drug Alcohol Depend 120:238–241

    Article  PubMed  CAS  Google Scholar 

  20. Seely KA, Lapoint J, Moran JH, Fattore L (2012) Spice drugs are more than harmless herbal blends: a review of the pharmacology and toxicology of synthetic cannabinoids. Prog Neuropsychopharmacol Biol Psychiatry 39:234–243

    Article  PubMed  CAS  Google Scholar 

  21. Kikura-Hanajiri R, Uchiyama N, Goda Y (2011) Survey of current trends in the abuse of psychotropic substances and plants in Japan. Legal Med (Tokyo) 13:109–115

    Article  Google Scholar 

  22. Moosmann B, Kneisel S, Girreser U, Brecht V, Westphal F, Auwärter V (2012) Separation and structural characterization of the synthetic cannabinoids JWH-412 and 1-[(5-fluoropentyl)-1H-indol-3yl]-(4-methylnaphthalen-1-yl)methanone using GC–MS, NMR analysis and a flash chromatography system. Forensic Sci Int 220:e17–e22

    Article  PubMed  CAS  Google Scholar 

  23. Maurer HH, Pfleger K, Weber AA (2011) Mass spectral and GC data of drugs, poisons, pesticides, pollutants and their metabolites, 4th edn. Wiley-VCH, Weinheim

    Google Scholar 

  24. Peters FT, Drummer OH, Musshoff F (2007) Validation of new methods. Forensic Sci Int 165:216–224

    Article  PubMed  CAS  Google Scholar 

  25. Matuszewski BK, Constanzer ML, Chavez-Eng CM (2003) Strategies for the assessment of matrix effect in quantitative bioanalytical methods based on HPLC–MS/MS. Anal Chem 75:3019–3030

    Article  PubMed  CAS  Google Scholar 

  26. Muller H, Huttner HB, Kohrmann M, Wielopolski JE, Kornhuber J, Sperling W (2010) Panic attack after spice abuse in a patient with ADHD. Pharmacopsychiatry 43:152–153

    Article  PubMed  CAS  Google Scholar 

  27. Muller H, Sperling W, Kohrmann M, Huttner HB, Kornhuber J, Maler JM (2010) The synthetic cannabinoid Spice as a trigger for an acute exacerbation of cannabis induced recurrent psychotic episodes. Schizophr Res 118:309–310

    Article  PubMed  Google Scholar 

  28. Schneir AB, Cullen J, Ly BT (2011) “Spice” girls: synthetic cannabinoid intoxication. J Emerg Med 40:296–299

    Article  PubMed  Google Scholar 

  29. Gunderson EW, Haughey HM, Ait-Daoud N, Joshi AS, Hart CL (2012) “Spice” and “K2″ herbal highs: a case series and systematic review of the clinical effects and biopsychosocial implications of synthetic cannabinoid use in humans. Am J Addict 21:320–326

    Article  PubMed  Google Scholar 

  30. Cohen J, Morrison S, Greenberg J, Saidinejad M (2012) Clinical presentation of intoxication due to synthetic cannabinoids. Pediatrics 129:e1064–e1067

    Article  PubMed  Google Scholar 

  31. Castellanos D, Thornton G (2012) Synthetic cannabinoid use: recognition and management. J Psychiatr Pract 18:86–93

    Article  PubMed  Google Scholar 

  32. Vandrey R, Umbricht A, Strain EC (2011) Increased blood pressure after abrupt cessation of daily cannabis use. J Addict Med 5:16–20

    Article  PubMed  Google Scholar 

  33. Ashton JC (2012) Synthetic cannabinoids as drugs of abuse. Curr Drug Abuse Rev 5:158–168

    Article  PubMed  CAS  Google Scholar 

  34. Gash A, Karliner JS, Janowsky D, Lake CR (1978) Effects of smoking marihuana on left ventricular performance and plasma norepinephrine: studies in normal men. Ann Intern Med 89:448–452

    PubMed  CAS  Google Scholar 

  35. Weiss JL, Watanabe AM, Lemberger L, Tamarkin NR, Cardon PV (1972) Cardiovascular effects of delta-9-tetrahydrocannabinol in man. Clin Pharmacol Ther 13:671–684

    PubMed  CAS  Google Scholar 

  36. Lapoint J, James LP, Moran CL, Nelson LS, Hoffman RS, Moran JH (2011) Severe toxicity following synthetic cannabinoid ingestion. Clin Toxicol 49:760–764

    Article  CAS  Google Scholar 

  37. Mir A, Obafemi A, Young A, Kane C (2011) Myocardial infarction associated with use of the synthetic cannabinoid K2. Pediatrics 128:e1622–e1627

    Article  PubMed  Google Scholar 

  38. Korczyn AD, Eshel Y (1982) Mydriasis induced by tetrahydrocannabinol (THC) in rats. Invest Ophthalmol Vis Sci 22:408–410

    PubMed  CAS  Google Scholar 

  39. Niederhoffer N, Schmid K, Szabo B (2003) The peripheral sympathetic nervous system is the major target of cannabinoids in eliciting cardiovascular depression. Naunyn Schmiedebergs Arch Pharmacol 367:434–443

    Article  PubMed  CAS  Google Scholar 

  40. Derungs A, Schietzel S, Meyer MR, Maurer HH, Krahenbuhl S, Liechti ME (2011) Sympathomimetic toxicity in a case of analytically confirmed recreational use of naphyrone (naphthylpyrovalerone). Clin Toxicol 49:691–693

    Article  CAS  Google Scholar 

  41. Hudson S, Ramsey J (2011) The emergence and analysis of synthetic cannabinoids. Drug Test Anal 3:466–478

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Division of Clinical Pharmacology and Toxicology, Department of Biomedicine and Department of Internal Medicine, University Hospital and University of Basel, Basel, Switzerland

    Adrian Derungs & Matthias E. Liechti

  2. Department of Forensic Pharmacology and Toxicology, Institute of Forensic Medicine, University of Zurich, Zurich, Switzerland

    Andrea E. Schwaninger & Thomas Kraemer

  3. Department of Emergency Medicine, University Hospital Basel, Basel, Switzerland

    Gregory Mansella & Roland Bingisser

Authors
  1. Adrian Derungs
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Andrea E. Schwaninger
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Gregory Mansella
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Roland Bingisser
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Thomas Kraemer
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Matthias E. Liechti
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Matthias E. Liechti.

Additional information

A. Derungs and A. E. Schwaninger contributed equally to this work.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Derungs, A., Schwaninger, A.E., Mansella, G. et al. Symptoms, toxicities, and analytical results for a patient after smoking herbs containing the novel synthetic cannabinoid MAM-2201. Forensic Toxicol 31, 164–171 (2013). https://doi.org/10.1007/s11419-012-0166-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11419-012-0166-1

Keywords

Search

Navigation