Identification of Novel Third-Generation Synthetic Cannabinoids in Products by Ultra-Performance Liquid Chromatography and Time-of-Flight Mass Spectrometry

被引:26
作者
Shanks, Kevin G. [1 ]
Behonick, George S. [1 ]
Dahn, Tim [1 ]
Terrell, Andrea [1 ]
机构
[1] AIT Labs, Indianapolis, IN 46241 USA
关键词
ACID AMIDE HYDROLASE; INHIBITOR URB597; FAAH; PAIN; KETONES; UR-144; HIGHS; CB1;
D O I
10.1093/jat/bkt062
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
Synthetic cannabinoids are a group of compounds that are structurally diverse and are commonly found in various herbal incense and potpourri blends, which are sold in convenience stores, smoke shops and over the Internet. During the past few years, multiple state and federal legislations have been enacted controlling various subsets of these compounds that have been detected in compound categories generally considered the first and second product generations. As shown in previous studies, as compounds become controlled, new compounds emerge and become prevalent. We report on the emergence and prevalence of five different compounds (A796,260, MAM-2201, UR-144, URB597 and XLR-11) in the state of Indiana through their qualitative detection in solid-dosage herbal products via rapid solvent extraction and ultra-performance liquid chromatography with time-of-flight mass spectrometry (UPLC/ToF). We demonstrate the use of UPLC/ToF to be a suitable tool in the identification of these substances in a crime laboratory or forensic laboratory setting, which ultimately enables a laboratory to design assays for the detection of specific analytes in biological specimens in regard to regional trends and prevalence.
引用
收藏
页码:517 / 525
页数:9
相关论文
共 21 条
  • [1] Mechanism of carbamate inactivation of FAAH: Implications for the design of covalent inhibitors and in vivo functional probes for enzymes
    Alexander, JP
    Cravatt, BF
    [J]. CHEMISTRY & BIOLOGY, 2005, 12 (11): : 1179 - 1187
  • [2] The fatty-acid amide hydrolase inhibitor URB597 does not affect triacylglycerol hydrolysis in rat tissues
    Clapper, Jason R.
    Duranti, Andrea
    Tontini, Andrea
    Mor, Marco
    Tarzia, Giorgio
    Piomelli, Daniele
    [J]. PHARMACOLOGICAL RESEARCH, 2006, 54 (05) : 341 - 344
  • [3] Drug Enforcement Adminstration, 2013, FED REG, V78
  • [4] Indol-3-yl-tetramethylcyclopropyl ketones:: Effects of indole ring substitution on CB2 cannabinoid receptor activity
    Frost, Jennifer M.
    Dart, Michael J.
    Tietje, Karin R.
    Garrison, Tiffany R.
    Grayson, George K.
    Daza, Anthony V.
    El-Kouhen, Odile F.
    Miller, Loan N.
    Li, Lanlan
    Yao, Betty B.
    Hsieh, Gin C.
    Pai, Madhavi
    Zhu, Chang Z.
    Chandran, Prasant
    Meyer, Michael D.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (06) : 1904 - 1912
  • [5] Indol-3-ylcycloalkyl Ketones: Effects of N1 Substituted Indole Side Chain Variations on CB2 Cannabinoid Receptor Activity
    Frost, Jennifer M.
    Dart, Michael J.
    Tietje, Karin R.
    Garrison, Tiffany R.
    Grayson, George K.
    Daza, Anthony V.
    El-Kouhen, Odile F.
    Yao, Betty B.
    Hsieh, Gin C.
    Pai, Madhavi
    Zhu, Chang Z.
    Chandran, Prasant
    Meyer, Michael D.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (01) : 295 - 315
  • [6] Use of High-Resolution Accurate Mass Spectrometry to Detect Reported and Previously Unreported Cannabinomimetics in "Herbal High" Products
    Hudson, Simon
    Ramsey, John
    King, Les
    Timbers, Sarah
    Maynard, Steve
    Dorgan, Paul I.
    Wood, David M.
    [J]. JOURNAL OF ANALYTICAL TOXICOLOGY, 2010, 34 (05) : 252 - 260
  • [7] Structure-activity relationships for 1-alkyl-3-(l-naphthoyl)indoles at the cannabinoid CB1 and CB2 receptors:: steric and electronic effects of naphthoyl substituents.: New highly selective CB2 receptor agonists
    Huffman, JW
    Zengin, G
    Wu, MJ
    Lu, JZ
    Hynd, G
    Bushell, K
    Thompson, ALS
    Bushell, S
    Tartal, C
    Hurst, DP
    Reggio, PH
    Selley, DE
    Cassidy, MP
    Wiley, JL
    Martin, BR
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (01) : 89 - 112
  • [8] 3-indolyl-1-naphthylmethanes:: New cannabimimetic Indoles provide evidence for aromatic stacking interactions with the CB1 cannabinoid receptor
    Huffman, JW
    Mabon, R
    Wu, MJ
    Lu, JZ
    Hart, R
    Hurst, DP
    Reggio, PH
    Wiley, JL
    Martin, BR
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (04) : 539 - 549
  • [9] UR-144 in products sold via the Internet: Identification of related compounds and characterization of pyrolysis products
    Kavanagh, Pierce
    Grigoryev, Andrej
    Savchuk, Sergey
    Mikhura, Irina
    Formanovsky, Andrew
    [J]. DRUG TESTING AND ANALYSIS, 2013, 5 (08) : 683 - 692
  • [10] Identification of Synthetic Cannabinoids in Herbal Incense Blends in the United States
    Logan, Barry K.
    Reinhold, Lindsay E.
    Xu, Allan
    Diamond, Francis X.
    [J]. JOURNAL OF FORENSIC SCIENCES, 2012, 57 (05) : 1168 - 1180