Skip to main content
Erschienen in: Rechtsmedizin 4/2012

01.08.2012 | CME Zertifizierte Fortbildung

Synthetische Cannabinoide

Forensische Relevanz und Interpretation analytischer Befunde

verfasst von: PD Dr. rer. nat. V. Auwärter, S. Kneisel, M. Hutter, A. Thierauf

Erschienen in: Rechtsmedizin | Ausgabe 4/2012

Einloggen, um Zugang zu erhalten

Zusammenfassung

In den vergangenen Jahren erreichte weltweit eine wahre Flut von neuen, auch als „legal highs“ bezeichneten Drogenprodukten den Markt. Während in einigen Teilen der Welt eher die amphetaminartigen Stimulanzien dominieren, stellen in Deutschland bisher die synthetischen Cannabinoide das größere Problem dar. Die hohe Dynamik, die durch rasche Aufnahme neuer Substanzen in die Anlagen des Betäubungsmittelgesetzes und den Ersatz auf Herstellerseite durch chemisch-strukturell leicht veränderte, neue Substanzen zustande kommt, stellt sowohl die Kriminaltechnik als auch die Toxikologie vor immense Herausforderungen.
Literatur
1.
Zurück zum Zitat Mechoulam R, Gaoni Y (1965) A total synthesis of dl-delta-1-tetrahydrocannabinol, the active constituent of hashish. J Am Chem Soc 87:3273–3275PubMedCrossRef Mechoulam R, Gaoni Y (1965) A total synthesis of dl-delta-1-tetrahydrocannabinol, the active constituent of hashish. J Am Chem Soc 87:3273–3275PubMedCrossRef
2.
Zurück zum Zitat Matsuda LA, Lolait SJ, Brownstein MJ et al (1990) Structure of a cannabinoid receptor and functional expression of the cloned cDNA. Nature 346:561–564PubMedCrossRef Matsuda LA, Lolait SJ, Brownstein MJ et al (1990) Structure of a cannabinoid receptor and functional expression of the cloned cDNA. Nature 346:561–564PubMedCrossRef
3.
Zurück zum Zitat Munro S, Thomas KL, Abu-Shaar M (1993) Molecular characterization of a peripheral receptor for cannabinoids. Nature 365:61–65PubMedCrossRef Munro S, Thomas KL, Abu-Shaar M (1993) Molecular characterization of a peripheral receptor for cannabinoids. Nature 365:61–65PubMedCrossRef
4.
Zurück zum Zitat Croxford JL (2003) Therapeutic potential of cannabinoids in CNS disease. CNS Drugs 17:179–202PubMedCrossRef Croxford JL (2003) Therapeutic potential of cannabinoids in CNS disease. CNS Drugs 17:179–202PubMedCrossRef
5.
Zurück zum Zitat Porter AC, Felder CC (2001) The endocannabinoid nervous system: unique opportunities for therapeutic intervention. Pharmacol Ther 90:45–60PubMedCrossRef Porter AC, Felder CC (2001) The endocannabinoid nervous system: unique opportunities for therapeutic intervention. Pharmacol Ther 90:45–60PubMedCrossRef
6.
Zurück zum Zitat Thakur GA, Tichkule R, Bajaj S, Makriyannis A (2009) Latest advances in cannabinoid receptor agonists. Expert Opin Ther Pat 19:1647–1673PubMedCrossRef Thakur GA, Tichkule R, Bajaj S, Makriyannis A (2009) Latest advances in cannabinoid receptor agonists. Expert Opin Ther Pat 19:1647–1673PubMedCrossRef
7.
Zurück zum Zitat Christensen R, Kristensen PK, Bartels EM et al (2007) Efficacy and safety of the weight-loss drug rimonabant: a meta-analysis of randomised trials. Lancet 370:1706–1713PubMedCrossRef Christensen R, Kristensen PK, Bartels EM et al (2007) Efficacy and safety of the weight-loss drug rimonabant: a meta-analysis of randomised trials. Lancet 370:1706–1713PubMedCrossRef
8.
Zurück zum Zitat Auwärter V, Dresen S, Weinmann W et al (2009) „Spice“ and other herbal blends: harmless incense or cannabinoid designer drugs? J Mass Spectrom 44:832–837PubMedCrossRef Auwärter V, Dresen S, Weinmann W et al (2009) „Spice“ and other herbal blends: harmless incense or cannabinoid designer drugs? J Mass Spectrom 44:832–837PubMedCrossRef
9.
Zurück zum Zitat Werse B, Morgenstern C (2011) Abschlussbericht – Online-Befragung zum Thema „Legal Highs“. Centre for Drug Research, Goethe-Universität, Frankfurt a. M. Werse B, Morgenstern C (2011) Abschlussbericht – Online-Befragung zum Thema „Legal Highs“. Centre for Drug Research, Goethe-Universität, Frankfurt a. M.
10.
Zurück zum Zitat Pabst A, Piontek D, Kraus L, Müller S (2010) Substanzkonsum und substanzbezogene Störungen. Ergebnisse des Epidemiologischen Suchtsurveys 2009. Sucht 56:327–336 Pabst A, Piontek D, Kraus L, Müller S (2010) Substanzkonsum und substanzbezogene Störungen. Ergebnisse des Epidemiologischen Suchtsurveys 2009. Sucht 56:327–336
11.
Zurück zum Zitat Werse B, Müller O, Schell C, Morgenstern C (2011) Jahresbericht MoSyD. Drogentrends in Frankfurt am Main 2010. Centre for Drug Research, Goethe-Universität, Frankfurt a. M. Werse B, Müller O, Schell C, Morgenstern C (2011) Jahresbericht MoSyD. Drogentrends in Frankfurt am Main 2010. Centre for Drug Research, Goethe-Universität, Frankfurt a. M.
12.
Zurück zum Zitat Howlett AC (1984) Inhibition of neuroblastoma adenylate cyclase by cannabinoid and nantradol compounds. Life Sci 35:1803–1810PubMedCrossRef Howlett AC (1984) Inhibition of neuroblastoma adenylate cyclase by cannabinoid and nantradol compounds. Life Sci 35:1803–1810PubMedCrossRef
13.
Zurück zum Zitat Howlett AC, Fleming RM (1984) Cannabinoid inhibition of adenylate cyclase. Pharmacology of the response in neuroblastoma cell membranes. Mol Pharmacol 26:532–538PubMed Howlett AC, Fleming RM (1984) Cannabinoid inhibition of adenylate cyclase. Pharmacology of the response in neuroblastoma cell membranes. Mol Pharmacol 26:532–538PubMed
14.
Zurück zum Zitat Caulfield MP, Brown DA (1992) Cannabinoid receptor agonists inhibit Ca current in NG108–15 neuroblastoma cells via a pertussis toxin-sensitive mechanism. Br J Pharmacol 106:231–232PubMedCrossRef Caulfield MP, Brown DA (1992) Cannabinoid receptor agonists inhibit Ca current in NG108–15 neuroblastoma cells via a pertussis toxin-sensitive mechanism. Br J Pharmacol 106:231–232PubMedCrossRef
15.
Zurück zum Zitat Mackie K, Hille B (1992) Cannabinoids inhibit N-type calcium channels in neuroblastoma-glioma cells. Proc Natl Acad Sci U S A 89:3825–3829PubMedCrossRef Mackie K, Hille B (1992) Cannabinoids inhibit N-type calcium channels in neuroblastoma-glioma cells. Proc Natl Acad Sci U S A 89:3825–3829PubMedCrossRef
16.
Zurück zum Zitat Devane WA, Hanus L, Breuer A et al (1992) Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258:1946–1949PubMedCrossRef Devane WA, Hanus L, Breuer A et al (1992) Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258:1946–1949PubMedCrossRef
17.
Zurück zum Zitat Johnson DE, Heald SL, Dally RD et al (1993) Isolation, identification and synthesis of an endogenous arachidonic amide that inhibits calcium channel antagonist 1,4-dihydropyridine binding. Prostaglandins Leukot Essent Fatty Acids 48:429–437PubMedCrossRef Johnson DE, Heald SL, Dally RD et al (1993) Isolation, identification and synthesis of an endogenous arachidonic amide that inhibits calcium channel antagonist 1,4-dihydropyridine binding. Prostaglandins Leukot Essent Fatty Acids 48:429–437PubMedCrossRef
18.
Zurück zum Zitat Mechoulam R, Ben-Shabat S, Hanus L et al (1995) Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors. Biochem Pharmacol 50:83–90PubMedCrossRef Mechoulam R, Ben-Shabat S, Hanus L et al (1995) Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors. Biochem Pharmacol 50:83–90PubMedCrossRef
19.
Zurück zum Zitat Mascia MS, Obinu MC, Ledent C et al (1999) Lack of morphine-induced dopamine release in the nucleus accumbens of cannabinoid CB(1) receptor knockout mice. Eur J Pharmacol 383:R1–2PubMedCrossRef Mascia MS, Obinu MC, Ledent C et al (1999) Lack of morphine-induced dopamine release in the nucleus accumbens of cannabinoid CB(1) receptor knockout mice. Eur J Pharmacol 383:R1–2PubMedCrossRef
20.
Zurück zum Zitat Fernandez-Ruiz J, Berrendero F, Hernandez ML et al (2000) The endogenous cannabinoid system and brain development. Trends Neurosci 23:14–20PubMedCrossRef Fernandez-Ruiz J, Berrendero F, Hernandez ML et al (2000) The endogenous cannabinoid system and brain development. Trends Neurosci 23:14–20PubMedCrossRef
21.
Zurück zum Zitat Johnson MR, Rice KC, Howlett A et al (1992) The cannabinoid receptor – pharmacologic identification, anatomical localization and cloning. NIDA Res Monogr 119:86–90PubMed Johnson MR, Rice KC, Howlett A et al (1992) The cannabinoid receptor – pharmacologic identification, anatomical localization and cloning. NIDA Res Monogr 119:86–90PubMed
22.
Zurück zum Zitat Pavlopoulos S, Thakur GA, Nikas SP et al (2006) Cannabinoid receptors as therapeutic targets. Curr Pharm Des 12:1751–1769PubMedCrossRef Pavlopoulos S, Thakur GA, Nikas SP et al (2006) Cannabinoid receptors as therapeutic targets. Curr Pharm Des 12:1751–1769PubMedCrossRef
23.
Zurück zum Zitat Ishac EJ, Jiang L, Lake KD et al (1996) Inhibition of exocytotic noradrenaline release by presynaptic cannabinoid CB1 receptors on peripheral sympathetic nerves. Br J Pharmacol 118:2023–2028PubMedCrossRef Ishac EJ, Jiang L, Lake KD et al (1996) Inhibition of exocytotic noradrenaline release by presynaptic cannabinoid CB1 receptors on peripheral sympathetic nerves. Br J Pharmacol 118:2023–2028PubMedCrossRef
24.
Zurück zum Zitat Kathmann M, Bauer U, Schlicker E et al (1999) Cannabinoid CB1 receptor-mediated inhibition of NMDA- and kainate-stimulated noradrenaline and dopamine release in the brain. Naunyn Schmiedebergs Arch Pharmacol 359:466–470PubMedCrossRef Kathmann M, Bauer U, Schlicker E et al (1999) Cannabinoid CB1 receptor-mediated inhibition of NMDA- and kainate-stimulated noradrenaline and dopamine release in the brain. Naunyn Schmiedebergs Arch Pharmacol 359:466–470PubMedCrossRef
25.
Zurück zum Zitat Nakazi M, Bauer U, Nickel T et al (2000) Inhibition of serotonin release in the mouse brain via presynaptic cannabinoid CB1 receptors. Naunyn Schmiedebergs Arch Pharmacol 361:19–24PubMedCrossRef Nakazi M, Bauer U, Nickel T et al (2000) Inhibition of serotonin release in the mouse brain via presynaptic cannabinoid CB1 receptors. Naunyn Schmiedebergs Arch Pharmacol 361:19–24PubMedCrossRef
26.
Zurück zum Zitat Shen M, Piser TM, Seybold VS, Thayer SA (1996) Cannabinoid receptor agonists inhibit glutamatergic synaptic transmission in rat hippocampal cultures. J Neurosci 16:4322–4334PubMed Shen M, Piser TM, Seybold VS, Thayer SA (1996) Cannabinoid receptor agonists inhibit glutamatergic synaptic transmission in rat hippocampal cultures. J Neurosci 16:4322–4334PubMed
27.
Zurück zum Zitat Szabo B, Müller T, Koch H (1999) Effects of cannabinoids on dopamine release in the corpus striatum and the nucleus accumbens in vitro. J Neurochem 73:1084–1089PubMedCrossRef Szabo B, Müller T, Koch H (1999) Effects of cannabinoids on dopamine release in the corpus striatum and the nucleus accumbens in vitro. J Neurochem 73:1084–1089PubMedCrossRef
28.
Zurück zum Zitat Felder CC, Joyce KE, Briley EM et al (1995) Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors. Mol Pharmacol 48:443–450PubMed Felder CC, Joyce KE, Briley EM et al (1995) Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors. Mol Pharmacol 48:443–450PubMed
29.
Zurück zum Zitat Lambert DM, Di Marzo V (1999) The palmitoylethanolamide and oleamide enigmas: are these two fatty acid amides cannabimimetic? Curr Med Chem 6:757–773PubMed Lambert DM, Di Marzo V (1999) The palmitoylethanolamide and oleamide enigmas: are these two fatty acid amides cannabimimetic? Curr Med Chem 6:757–773PubMed
30.
Zurück zum Zitat Wiley JL, Martin BR (2002) Cannabinoid pharmacology: implications for additional cannabinoid receptor subtypes. Chem Phys Lipids 121:57–63PubMedCrossRef Wiley JL, Martin BR (2002) Cannabinoid pharmacology: implications for additional cannabinoid receptor subtypes. Chem Phys Lipids 121:57–63PubMedCrossRef
31.
Zurück zum Zitat Forrester MB, Kleinschmidt K, Schwarz E, Young A (2011) Synthetic cannabinoid exposures reported to Texas poison centers. J Addict Dis 30:351–358PubMedCrossRef Forrester MB, Kleinschmidt K, Schwarz E, Young A (2011) Synthetic cannabinoid exposures reported to Texas poison centers. J Addict Dis 30:351–358PubMedCrossRef
32.
Zurück zum Zitat Hoyte CO, Jacob J, Monte AA et al (2012) A characterization of synthetic cannabinoid exposures reported to the National Poison Data System in 2010. Ann Emerg Med, DOI 10.1016/j.annemergmed.2012.03.007 Hoyte CO, Jacob J, Monte AA et al (2012) A characterization of synthetic cannabinoid exposures reported to the National Poison Data System in 2010. Ann Emerg Med, DOI 10.1016/j.annemergmed.2012.03.007
33.
34.
Zurück zum Zitat Schneir AB, Baumbacher T (2012) Convulsions associated with the use of a synthetic cannabinoid product. J Med Toxicol 8:62–64PubMedCrossRef Schneir AB, Baumbacher T (2012) Convulsions associated with the use of a synthetic cannabinoid product. J Med Toxicol 8:62–64PubMedCrossRef
35.
Zurück zum Zitat Aung MM, Griffin G, Huffman JW et al (2000) Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB(1) and CB(2) receptor binding. Drug Alcohol Depend 60:133–140PubMedCrossRef Aung MM, Griffin G, Huffman JW et al (2000) Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB(1) and CB(2) receptor binding. Drug Alcohol Depend 60:133–140PubMedCrossRef
36.
Zurück zum Zitat Compton DR, Rice KC, De Costa BR et al (1993) Cannabinoid structure-activity relationships: correlation of receptor binding and in vivo activities. J Pharmacol Exp Ther 265:218–226PubMed Compton DR, Rice KC, De Costa BR et al (1993) Cannabinoid structure-activity relationships: correlation of receptor binding and in vivo activities. J Pharmacol Exp Ther 265:218–226PubMed
37.
Zurück zum Zitat D’Ambra TE, Estep KG, Bell MR et al (1992) Conformationally restrained analogues of pravadoline: nanomolar potent, enantioselective, (aminoalkyl)indole agonists of the cannabinoid receptor. J Med Chem 35:124–135CrossRef D’Ambra TE, Estep KG, Bell MR et al (1992) Conformationally restrained analogues of pravadoline: nanomolar potent, enantioselective, (aminoalkyl)indole agonists of the cannabinoid receptor. J Med Chem 35:124–135CrossRef
38.
Zurück zum Zitat Deng H, Gifford AN, Zvonok AM et al (2005) Potent cannabinergic indole analogues as radioiodinatable brain imaging agents for the CB1 cannabinoid receptor. J Med Chem 48:6386–6392PubMedCrossRef Deng H, Gifford AN, Zvonok AM et al (2005) Potent cannabinergic indole analogues as radioiodinatable brain imaging agents for the CB1 cannabinoid receptor. J Med Chem 48:6386–6392PubMedCrossRef
39.
Zurück zum Zitat Frost JM, Dart MJ, Tietje KR et al (2010) Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity. J Med Chem 53:295–315PubMedCrossRef Frost JM, Dart MJ, Tietje KR et al (2010) Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity. J Med Chem 53:295–315PubMedCrossRef
40.
Zurück zum Zitat Huffman JW, Mabon R, Wu MJ et al (2003) 3-Indolyl-1-naphthylmethanes: new cannabimimetic indoles provide evidence for aromatic stacking interactions with the CB(1) cannabinoid receptor. Bioorg Med Chem 11:539–549PubMedCrossRef Huffman JW, Mabon R, Wu MJ et al (2003) 3-Indolyl-1-naphthylmethanes: new cannabimimetic indoles provide evidence for aromatic stacking interactions with the CB(1) cannabinoid receptor. Bioorg Med Chem 11:539–549PubMedCrossRef
41.
Zurück zum Zitat Huffman JW, Padgett LW (2005) Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes. Curr Med Chem 12:1395–1411PubMedCrossRef Huffman JW, Padgett LW (2005) Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes. Curr Med Chem 12:1395–1411PubMedCrossRef
42.
Zurück zum Zitat Huffman JW, Padgett LW, Isherwood ML et al (2006) 1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: new high affinity ligands for the cannabinoid CB1 and CB2 receptors. Bioorg Med Chem Lett 16:5432–5435PubMedCrossRef Huffman JW, Padgett LW, Isherwood ML et al (2006) 1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: new high affinity ligands for the cannabinoid CB1 and CB2 receptors. Bioorg Med Chem Lett 16:5432–5435PubMedCrossRef
43.
Zurück zum Zitat Huffman JW, Szklennik PV, Almond A et al (2005) 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg Med Chem Lett 15:4110–4113PubMedCrossRef Huffman JW, Szklennik PV, Almond A et al (2005) 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorg Med Chem Lett 15:4110–4113PubMedCrossRef
44.
Zurück zum Zitat Makriyannis A, Deng H (2001) Cannabimimetic indole derivatives, W.I.P. Organization (Patent) Makriyannis A, Deng H (2001) Cannabimimetic indole derivatives, W.I.P. Organization (Patent)
45.
Zurück zum Zitat Showalter VM, Compton DR, Martin BR, Abood ME (1996) Evaluation of binding in a transfected cell line expressing a peripheral cannabinoid receptor (CB2): identification of cannabinoid receptor subtype selective ligands. J Pharmacol Exp Ther 278:989–999PubMed Showalter VM, Compton DR, Martin BR, Abood ME (1996) Evaluation of binding in a transfected cell line expressing a peripheral cannabinoid receptor (CB2): identification of cannabinoid receptor subtype selective ligands. J Pharmacol Exp Ther 278:989–999PubMed
46.
Zurück zum Zitat Mir A, Obafemi A, Young A, Kane C(2011) Myocardial infarction associated with use of the synthetic cannabinoid K2. Pediatrics 128:e1622–e1627PubMedCrossRef Mir A, Obafemi A, Young A, Kane C(2011) Myocardial infarction associated with use of the synthetic cannabinoid K2. Pediatrics 128:e1622–e1627PubMedCrossRef
47.
Zurück zum Zitat Schmid K, Niederhoffer N, Szabo B (2003) Analysis of the respiratory effects of cannabinoids in rats. Naunyn Schmiedebergs Arch Pharmacol 368:301–308PubMedCrossRef Schmid K, Niederhoffer N, Szabo B (2003) Analysis of the respiratory effects of cannabinoids in rats. Naunyn Schmiedebergs Arch Pharmacol 368:301–308PubMedCrossRef
48.
Zurück zum Zitat Advisory Council on the Misuse of Drugs (ACMD) (2009) Consideration of the major cannabinoid agonists. Home Office, London Advisory Council on the Misuse of Drugs (ACMD) (2009) Consideration of the major cannabinoid agonists. Home Office, London
49.
Zurück zum Zitat Howlett AC, Barth F, Bonner TI et al (2002) International Union of Pharmacology. XXVII. Classification of cannabinoid receptors. Pharmacol Rev 54:161–202PubMedCrossRef Howlett AC, Barth F, Bonner TI et al (2002) International Union of Pharmacology. XXVII. Classification of cannabinoid receptors. Pharmacol Rev 54:161–202PubMedCrossRef
50.
Zurück zum Zitat Thakur GA, Nikas SP, Makriyannis A (2005) CB1 cannabinoid receptor ligands. Mini Rev Med Chem 5:631–640PubMedCrossRef Thakur GA, Nikas SP, Makriyannis A (2005) CB1 cannabinoid receptor ligands. Mini Rev Med Chem 5:631–640PubMedCrossRef
51.
Zurück zum Zitat Huffman J (2009) Cannabimimetic indoles, pyrroles, and indenes: structure-activity relationships and receptor interactions. In: Reggio PH (Hrsg) The cannabinoid receptors. Humana, New York Huffman J (2009) Cannabimimetic indoles, pyrroles, and indenes: structure-activity relationships and receptor interactions. In: Reggio PH (Hrsg) The cannabinoid receptors. Humana, New York
52.
Zurück zum Zitat Atwood BK, Huffman J, Straiker A, Mackie K (2010) JWH018, a common constituent of „Spice“ herbal blends, is a potent and efficacious cannabinoid CB receptor agonist. Br J Pharmacol 160:585–593PubMedCrossRef Atwood BK, Huffman J, Straiker A, Mackie K (2010) JWH018, a common constituent of „Spice“ herbal blends, is a potent and efficacious cannabinoid CB receptor agonist. Br J Pharmacol 160:585–593PubMedCrossRef
53.
Zurück zum Zitat Teske J, Weller JP Fieguth A et al (2010) Sensitive and rapid quantification of the cannabinoid receptor agonist naphthalen-1-yl-(1-pentylindol-3-yl)methanone (JWH-018) in human serum by liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci 878:2659–2663PubMedCrossRef Teske J, Weller JP Fieguth A et al (2010) Sensitive and rapid quantification of the cannabinoid receptor agonist naphthalen-1-yl-(1-pentylindol-3-yl)methanone (JWH-018) in human serum by liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci 878:2659–2663PubMedCrossRef
54.
Zurück zum Zitat Dresen S, Kneisel S, Weinmann W et al (2011) Development and validation of a liquid chromatography-tandem mass spectrometry method for the quantitation of synthetic cannabinoids of the aminoalkylindole type and methanandamide in serum and its application to forensic samples. J Mass Spectrom 46:163–171PubMedCrossRef Dresen S, Kneisel S, Weinmann W et al (2011) Development and validation of a liquid chromatography-tandem mass spectrometry method for the quantitation of synthetic cannabinoids of the aminoalkylindole type and methanandamide in serum and its application to forensic samples. J Mass Spectrom 46:163–171PubMedCrossRef
55.
Zurück zum Zitat Kacinko SL, Xu A, Homan JW et al (2011) Development and validation of a liquid chromatography-tandem mass spectrometry method for the identification and quantification of JWH-018, JWH-073, JWH-019, and JWH-250 in human whole blood. J Anal Toxicol 35:386–393PubMedCrossRef Kacinko SL, Xu A, Homan JW et al (2011) Development and validation of a liquid chromatography-tandem mass spectrometry method for the identification and quantification of JWH-018, JWH-073, JWH-019, and JWH-250 in human whole blood. J Anal Toxicol 35:386–393PubMedCrossRef
56.
Zurück zum Zitat Ammann J, Mc Laren JM, Gerostamoulos D, Beyer J et al (2012) Detection and quantification of new designer drugs in human blood: part 1 – synthetic cannabinoids. J Anal Toxicol 36:372–380PubMedCrossRef Ammann J, Mc Laren JM, Gerostamoulos D, Beyer J et al (2012) Detection and quantification of new designer drugs in human blood: part 1 – synthetic cannabinoids. J Anal Toxicol 36:372–380PubMedCrossRef
57.
Zurück zum Zitat Poklis JL, Amira D, Wise LE et al (2012) Detection and disposition of JWH-018 and JWH-073 in mice after exposure to „Magic Gold“ smoke. Forensic Sci Int. DOI 10.1016/j.forsciint.2012.02.003 Poklis JL, Amira D, Wise LE et al (2012) Detection and disposition of JWH-018 and JWH-073 in mice after exposure to „Magic Gold“ smoke. Forensic Sci Int. DOI 10.1016/j.forsciint.2012.02.003
58.
Zurück zum Zitat Shanks KG, Dahn T, Terrell AR (2012) Detection of JWH-018 and JWH-073 by UPLC-MS-MS in postmortem whole blood casework. J Anal Toxicol 36:145–152PubMedCrossRef Shanks KG, Dahn T, Terrell AR (2012) Detection of JWH-018 and JWH-073 by UPLC-MS-MS in postmortem whole blood casework. J Anal Toxicol 36:145–152PubMedCrossRef
59.
Zurück zum Zitat Kneisel S, Auwärter V (2012) Analysis of 30 synthetic cannabinoids in serum by liquid chromatography-electrospray ionization tandem mass spectrometry after liquid-liquid extraction. J Mass Spectrom. DOI 10.1002/jms.3020 Kneisel S, Auwärter V (2012) Analysis of 30 synthetic cannabinoids in serum by liquid chromatography-electrospray ionization tandem mass spectrometry after liquid-liquid extraction. J Mass Spectrom. DOI 10.1002/jms.3020
60.
Zurück zum Zitat Coulter C, Garnier M, Moore C (2011) Synthetic cannabinoids in oral fluid. J Anal Toxicol 35:424–430PubMedCrossRef Coulter C, Garnier M, Moore C (2011) Synthetic cannabinoids in oral fluid. J Anal Toxicol 35:424–430PubMedCrossRef
61.
Zurück zum Zitat Salomone A, Gerace E, D’Urso F et al (2012) Simultaneous analysis of several synthetic cannabinoids, THC, CBD and CBN, in hair by ultra-high performance liquid chromatography tandem mass spectrometry. Method validation and application to real samples. J Mass Spectrom 47:604–610PubMedCrossRef Salomone A, Gerace E, D’Urso F et al (2012) Simultaneous analysis of several synthetic cannabinoids, THC, CBD and CBN, in hair by ultra-high performance liquid chromatography tandem mass spectrometry. Method validation and application to real samples. J Mass Spectrom 47:604–610PubMedCrossRef
62.
Zurück zum Zitat Hutter M, Kneisel S, Auwärter V, Neukamm MA (2012) Determination of 22 synthetic cannabinoids in human hair by liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci (in press) Hutter M, Kneisel S, Auwärter V, Neukamm MA (2012) Determination of 22 synthetic cannabinoids in human hair by liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci (in press)
63.
Zurück zum Zitat Möller I, Wintermeyer A, Bender K et al (2011) Screening for the synthetic cannabinoid JWH-018 and its major metabolites in human doping controls. Drug Test Anal 3:609–620PubMedCrossRef Möller I, Wintermeyer A, Bender K et al (2011) Screening for the synthetic cannabinoid JWH-018 and its major metabolites in human doping controls. Drug Test Anal 3:609–620PubMedCrossRef
64.
Zurück zum Zitat Hutter M, Broecker S, Kneisel S, Auwärter V (2012) Identification of the major urinary metabolites in man of seven synthetic cannabinoids of the aminoalkylindole type present as adulterants in ‚herbal mixtures‘ using LC-MS/MS techniques. J Mass Spectrom 47:54–65PubMedCrossRef Hutter M, Broecker S, Kneisel S, Auwärter V (2012) Identification of the major urinary metabolites in man of seven synthetic cannabinoids of the aminoalkylindole type present as adulterants in ‚herbal mixtures‘ using LC-MS/MS techniques. J Mass Spectrom 47:54–65PubMedCrossRef
65.
Zurück zum Zitat Moran CL, Le VH, Chimalakonda KC et al (2011) Quantitative measurement of JWH-018 and JWH-073 metabolites excreted in human urine. Anal Chem 83:4228–4236PubMedCrossRef Moran CL, Le VH, Chimalakonda KC et al (2011) Quantitative measurement of JWH-018 and JWH-073 metabolites excreted in human urine. Anal Chem 83:4228–4236PubMedCrossRef
66.
Zurück zum Zitat Johansson E, Halldin MM (1989) Urinary excretion half-life of delta 1-tetrahydrocannabinol-7-oic acid in heavy marijuana users after smoking. J Anal Toxicol 13:218–223PubMed Johansson E, Halldin MM (1989) Urinary excretion half-life of delta 1-tetrahydrocannabinol-7-oic acid in heavy marijuana users after smoking. J Anal Toxicol 13:218–223PubMed
67.
Zurück zum Zitat Fraser AD, Worth D (2003) Urinary excretion profiles of 11-nor-9-carboxy-Delta9-tetrahydrocannabinol: a Delta9-THC-COOH to creatinine ratio study #2. Forensic Sci Int 133:26–31PubMedCrossRef Fraser AD, Worth D (2003) Urinary excretion profiles of 11-nor-9-carboxy-Delta9-tetrahydrocannabinol: a Delta9-THC-COOH to creatinine ratio study #2. Forensic Sci Int 133:26–31PubMedCrossRef
Metadaten
Titel
Synthetische Cannabinoide
Forensische Relevanz und Interpretation analytischer Befunde
verfasst von
PD Dr. rer. nat. V. Auwärter
S. Kneisel
M. Hutter
A. Thierauf
Publikationsdatum
01.08.2012
Verlag
Springer-Verlag
Erschienen in
Rechtsmedizin / Ausgabe 4/2012
Print ISSN: 0937-9819
Elektronische ISSN: 1434-5196
DOI
https://doi.org/10.1007/s00194-012-0810-4

Weitere Artikel der Ausgabe 4/2012

Rechtsmedizin 4/2012 Zur Ausgabe

Neu im Fachgebiet Rechtsmedizin

Molekularpathologische Untersuchungen im Wandel der Zeit

Open Access Biomarker Leitthema

Um auch an kleinen Gewebeproben zuverlässige und reproduzierbare Ergebnisse zu gewährleisten ist eine strenge Qualitätskontrolle in jedem Schritt des Arbeitsablaufs erforderlich. Eine nicht ordnungsgemäße Prüfung oder Behandlung des …

Vergleichende Pathologie in der onkologischen Forschung

Pathologie Leitthema

Die vergleichende experimentelle Pathologie („comparative experimental pathology“) ist ein Fachbereich an der Schnittstelle von Human- und Veterinärmedizin. Sie widmet sich der vergleichenden Erforschung von Gemeinsamkeiten und Unterschieden von …

Gastrointestinale Stromatumoren

Open Access GIST CME-Artikel

Gastrointestinale Stromatumoren (GIST) stellen seit über 20 Jahren ein Paradigma für die zielgerichtete Therapie mit Tyrosinkinaseinhibitoren dar. Eine elementare Voraussetzung für eine mögliche neoadjuvante oder adjuvante Behandlung bei …

Personalisierte Medizin in der Onkologie

Aufgrund des erheblichen technologischen Fortschritts in der molekularen und genetischen Diagnostik sowie zunehmender Erkenntnisse über die molekulare Pathogenese von Krankheiten hat in den letzten zwei Jahrzehnten ein grundlegender …