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Journal Article•DOI•

Chemical analysis of a benzofuran derivative, 2-(2-ethylaminopropyl)benzofuran (2-EAPB), eight synthetic cannabinoids, five cathinone derivatives, and five other designer drugs newly detected in illegal products

Nahoko Uchiyama, Yoshihiko Shimokawa, Maiko Kawamura, Ruri Kikura-Hanajiri, Takashi Hakamatsuka 
30 Jul 2014-Forensic Toxicology (Springer Japan)-Vol. 32, Iss: 2, pp 266-281
TL;DR: In this article, 19 newly distributed designer drugs were identified in 104 products in an ongoing survey of illegal products in Japan from November 2013 to May 2014, and a total of 33 designer drugs including compounds 1-19 were detected in the 104 illegal products, in 60 different combination patterns.
Abstract: From November 2013 to May 2014, 19 newly distributed designer drugs were identified in 104 products in our ongoing survey of illegal products in Japan. The identified compounds included 8 synthetic cannabinoids, FUB-PB-22 (1), 5-fluoro-NNEI indazole analog (5-fluoro-MN-18, 2), AM-2201 indazole analog (THJ-2201, 3), XLR-12 (4), 5-fluoro-AB-PINACA (5), 5-chloro-AB-PINACA (6), AB-CHMINACA (7), and 5-fluoro-AMB (8); 5 cathinone derivatives, DL-4662 (9), α-PHP (10), 4-methoxy-α-POP (11), 4-methoxy-α-PHPP (12), and 4-fluoro-α-PHPP (13); and 6 other substances, namely, the benzofuran derivative 2-(2-ethylaminopropyl)benzofuran (2-EAPB, 14), nitracaine (15), diclofensine (16), diphenidine (17), 1-benzylpiperidine (18), and acetylfentanyl (19). To our knowledge, this is the first report on the chemical properties of compounds 9–11 and 14. A total of 33 designer drugs, including compounds 1–19, were detected in the 104 illegal products, in 60 different combination patterns. The numbers of detected compounds per product ranged from 1 to 7. In addition, several products contained three different types of compounds, such as synthetic cannabinoids, cathinone derivatives, and phenethylamine derivatives per product. It is apparent that the types of compounds emerging as illegal products are becoming more diverse, as are their combinations.
Citations
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Journal Article•DOI•
Pharmacology of Indole and Indazole Synthetic Cannabinoid Designer Drugs AB-FUBINACA, ADB-FUBINACA, AB-PINACA, ADB-PINACA, 5F-AB-PINACA, 5F-ADB-PINACA, ADBICA, and 5F-ADBICA

[...]

Samuel D. Banister1, Samuel D. Banister2, Michael Moir1, Jordyn Stuart3, Richard C. Kevin1, Katie Wood1, Mitchell Longworth1, Shane M. Wilkinson1, Corinne Beinat2, Corinne Beinat1, Alexandra S. Buchanan, Michelle Glass4, Mark Connor3, Iain S. McGregor1, Michael Kassiou1 •
University of Sydney1, Stanford University2, Macquarie University3, University of Auckland4
17 Jul 2015-ACS Chemical Neuroscience
TL;DR: Synthetic cannabinoid designer drugs based on indole and indazole scaffolds and featuring l-valinamide or l-tert-leucinamide side chains and several analogues are synthesized and characterized, indicating that these SCs are cannabimimetic in vivo, consistent with anecdotal reports of psychoactivity in humans.
Abstract: Synthetic cannabinoid (SC) designer drugs based on indole and indazole scaffolds and featuring l-valinamide or l-tert-leucinamide side chains are encountered with increasing frequency by forensic researchers and law enforcement agencies and are associated with serious adverse health effects. However, many of these novel SCs are unprecedented in the scientific literature at the time of their discovery, and little is known of their pharmacology. Here, we report the synthesis and pharmacological characterization of AB-FUBINACA, ADB-FUBINACA, AB-PINACA, ADB-PINACA, 5F-AB-PINACA, 5F-ADB-PINACA, ADBICA, 5F-ADBICA, and several analogues. All synthesized SCs acted as high potency agonists of CB1 (EC50 = 0.24–21 nM) and CB2 (EC50 = 0.88–15 nM) receptors in a fluorometric assay of membrane potential, with 5F-ADB-PINACA showing the greatest potency at CB1 receptors. The cannabimimetic activities of AB-FUBINACA and AB-PINACA in vivo were evaluated in rats using biotelemetry. AB-FUBINACA and AB-PINACA dose-dependently...

185 citations

Journal Article•DOI•
Comprehensive review of the detection methods for synthetic cannabinoids and cathinones

[...]

Akira Namera1, Maho Kawamura, Akihiro Nakamoto, Takeshi Saito2, Masataka Nagao1 •
Hiroshima University1, Tokai University2
06 Mar 2015-Forensic Toxicology
TL;DR: This review presents the various colorimetric detections, immunochemical assays, gas chromatographic–mass spectrometric methods, and liquid chromatographs proposed for the analysis of synthetic cannabinoids and cathinones.
Abstract: A number of N-alkyl indole or indazole-3-carbonyl analogs, with modified chemical structures, are distributed throughout the world as synthetic cannabinoids. Like synthetic cannabinoids, cathinone analogs are also abused and cause serious problems worldwide. Acute deaths caused by overdoses of these drugs have been reported. Various analytical methods that can cope with the rapid changes in chemical structures are required for routine analysis and screening of these drugs in seized and biological materials for forensic and clinical purposes. Although many chromatographic methods to analyze each drug have been published, there are only a few articles summarizing these analytical methods. This review presents the various colorimetric detections, immunochemical assays, gas chromatographic–mass spectrometric methods, and liquid chromatographic–mass spectrometric methods proposed for the analysis of synthetic cannabinoids and cathinones.

154 citations

Cites background from "Chemical analysis of a benzofuran d..."

  • ...A-796260 [1-[2-(4-Morpholinyl)ethyl]-1H- indol-3-yl](2,2,3,3- tetramethylcyclopropyl)methanone A-834735 [1-[(Tetrahydro-2H-pyran-4- yl)methyl]-1H-indol-3-yl](2,2,3,3- tetramethylcyclopropyl)- methanone AB-001 Adamantan-1-yl(1-pentyl-1H-indol- 3-yl)methanone AB-005 [1-[(1-Methyl-2-piperidinyl)methyl]- 1H-indol-3-yl](2,2,3,3- tetramethylcyclopropyl)methanone AB-CHMINACA N-[(1S)-1-(Aminocarbonyl)- 2-methylpropyl]-1- (cyclohexylmethyl)-1H-indazole-3- carboxamide AB-FUBINACA N-(1-Amino-3-methyl-1-oxobutan-2- yl)-1-(4-fluorobenzyl)-1H-indazole- 3-carboxamide AB-PINACA N-(1-Amino-3-methyl-1-oxobutan-2- yl)-1-pentyl-1H-indazole-3- carboxamide ADB-FUBINACA N-(1-Amino-3,3-dimethyl-1- oxobutan-2-yl)-1-(4-fluorobenzyl)- 1H-indazole-3-carboxamide ADBICA N-(1-Amino-3,3-dimethyl-1- oxobutan-2-yl)-1-pentyl-1H-indole- 3-carboxamine ADB-PINACA N-(1-Amino-3,3-dimethyl-1- oxobutan-2-yl)-1-pentyl-1H- indazole-3-carboxamide AM-1220 [1-[(1-Methylpiperidin-2-yl)methyl]- 1H-indol-3-yl]-(naphthalen-1- yl)methanone A. Namera (&) M. Nagao Department of Forensic Medicine, Institute of Biomedical and Health Sciences, Hiroshima University, 1-2-3 Kasumi, Minamiku, Hiroshima 734-8553, Japan e-mail: namera@hiroshima-u.ac.jp M. Kawamura A. Nakamoto Forensic Science Laboratory, Hiroshima Prefectural Police Headquarters, Hiroshima, Japan T. Saito Department of Emergency and Critical Care Medicine, Tokai University School of Medicine, Isehara, Japan AM-1248 Adamantan-1-yl[1-[(1-methyl-2- piperidinyl)methyl]-1H-indol-3- yl]methanone AM-1241 (2-Iodo-5-nitrophenyl)-[1-(1- methylpiperidin-2-ylmethyl)-1H- indol-3-yl]methanone AM-2201 [1-(5-Fluoropentyl)-1H-indol-3-yl]- 1-naphthalenylmethanone AM-2233 (2-Iodophenyl)[1-[(1-methyl-2- piperidinyl)methyl]-1H-indol-3-yl]- methanone AM-679 (2-Iodophenyl)(1-pentyl-1H-indol-3- yl)methanone AM-694 1-[(5-Fluoropentyl)-1H-indol-3-yl]- (2-iodophenyl)methanone AMB Methyl (1-pentyl-1H-indazole-3- carbonyl)-L-valinate APICA N-(1-Adamantyl)-1-pentyl-1H- indole-3-carboxamide APINACA N-(1-Adamantyl)-1-pentyl-1H- indazole-3-carboxamide Cathinone 2-Amino-1-phenylpropan-1-one CI Chemical ionization EI Electron ionization ELISA Enzyme-linked immunosorbent assay ESI Electrospray ionization FDU-PB-22 Naphthalen-1-yl 1-(4-fluorobenzyl)- 1H-indole-3-carboxylate 5F-PB-22 1-(5-Fluoropentyl)-8-quinolinyl ester-1H-indole-3-carboxylic acid FUB-PB-22 Quinolin-8-yl-1-(4-fluorobenzyl)-1H- indole-3-carboxylate GC Gas chromatography GC–MS Gas chromatography–mass spectrometry GC–MS-MS Gas chromatography–tandem mass spectrometry HU-210 3-(1,10-Dimethylheptyl)6aR,7,10,10aR-tetrahydro-1- hydroxy-6,6-dimethyl-6H- dibenzo[b,d]pyran-9-methanol JWH-015 1-Naphthalenyl(2-methyl-1-propyl- 1H-indol-3-yl)methanone JWH-018 1-Naphthalenyl(1-pentyl-1H-indol-3- yl)methanone JWH-019 1-Naphthalenyl(1-hexyl-1H-indol-3- yl)methanone JWH-030 1-Naphthalenyl(1-pentyl-1H-pyrrol- 3-yl)methanone JWH-073 1-Naphthalenyl(1-butyl-1H-indol-3- yl)methanone JWH-200 1-Naphthalenyl[1-[2-(4- morpholinyl)ethyl]-1H-indol-3- yl]methanone JWH-203 2-(2-Chlorophenyl)-1-(1-pentyl-1H- indol-3-yl)ethanone JWH-250 2-(2-Methoxyphenyl)-1-(1-pentyl- 1H-indol-3-yl)ethanone JWH-251 2-(2-Methylphenyl)-1-(1-pentyl-1H- indol-3-yl)ethanone JWH-307 [5-(2-Fluorophenyl)-1-pentyl-1H- pyrrol-3-yl](naphthalene-1- yl)methanone LC Liquid chromatography LC–MS Liquid chromatography–mass spectrometry LC–MS-MS Liquid chromatography–tandem mass spectrometry LLE Liquid–liquid extraction LOD Limit of detection LOQ Limit of quantification MAM-2201 [1-(5-Fluoropentyl)-1H-indol-3- yl](4-methyl-1- naphthalenyl)methanone MDPBP 30,40-Methylenedioxy-apyrrolidinobutiophenone MDPPP 30,40-Methylenedioxy-apyrrolidinopropiophenone MDPV 3,4-Methylenedioxypyrovalerone MN-18 N-1-Naphthalenyl-1-pentyl-1H- indazole-3-carboxamide MOPPP 40-Methoxy-apyrrolidinopropiophenone NM-2201 Naphthalen-1-yl 1-(5-fluoropentyl)- 1H-indole-3-carboxylate NMR Nuclear magnetic resonance NNEI N-1-Naphthalenyl-1-pentyl-1H- indole-3-carboxamide MPBP 40-Methyl-a-pyrrolidinobutiophenone MPHP 40-Methyl-a- pyrrolidinohexanophenone MPPP 40-Methyl-apyrrolidinopropiophenone MRM Multiple reaction monitoring MS Mass spectrometry MS-MS Tandem mass spectrometry NPB-22 8-Quinolinyl 1-pentyl-1H-indazole- 3-carboxylate a-PBP a-Pyrrolidinobutiophenone a-PHP a-Pyrrolidinohexanophenone PP Protein precipitation a-PPP a-Pyrrolidinopropiophenone PTFE Polytetrafluoroethylene PV8 1-Phenyl-2-(pyrrolidin-1-yl)heptan- 1-one PV9 1-Phenyl-2-(pyrrolidin-1-yl)octan-1- one a-PVP 1-Phenyl-2-(pyrrolidin-1-yl)pentan1-one, a-pyrrolidinovalerophenone PX1 (S)-N-(1-Amino-1-oxo-3- phenylpropan-2-yl)-1-(5- fluoropentyl)-1H-indole-3- carboxamide QUPIC Quinolin-8-yl 1-pentyl-1H-indole-3- carboxylate QUCHIC Quinolin-8-yl 1-(cyclohexylmethyl)- 1H-indole-3-carboxylate RCS-4 (4-Methoxyphenyl)(1-pentyl-1H- indol-3-yl)methanone SDB-005 Naphthalen-1-yl 1-pentyl-1H- indazole-3-carboxylate SIM Selected ion monitoring SPE Solid-phase extraction SPME Solid-phase microextraction SRM Selected reaction monitoring THJ-018 1-Naphthalenyl(1-pentyl-1H-indazol- 3-yl)methanone THJ-2201 [1-(5-Fluoropentyl)-1H-indazol-3- yl](naphthalen-1-yl)methanone TLC Thin-layer chromatography TOFMS Time-of-flight mass spectrometry UV Ultraviolet UR-144 (1-Pentyl-1H-indol-3-yl)(2,2,3,3- tetramethylcyclopropyl)methanone XLR-11 [1-(5-Fluoropentyl)-1H-indol-3- yl](2,2,3,3- tetramethylcyclopropyl)methanone XLR-12 (2,2,3,3-Tetramethylcyclopropyl)[1- (4,4,4-trifluorobutyl)-1H-indol-3- yl]methanone...

    [...]

  • ...The substitution of the indole skeleton with the indazole moiety, such as in THJ-018 and THJ-2201 [21], has also been observed in these analogs....

    [...]

  • ...The substitution of the indole skeleton with the indazole moiety, such as in THJ-018 and THJ-2201 [21], has also been ob- served in these analogs....

    [...]

Journal Article•DOI•
The newest cathinone derivatives as designer drugs: an analytical and toxicological review.

[...]

Milena Majchrzak1, Rafał Celiński, Piotr Kuś1, Teresa Kowalska1, Mieczysław Sajewicz1 •
University of Silesia in Katowice1
01 Jan 2018-Forensic Toxicology
TL;DR: In this review, the new synthetic cathinones that have appeared on the illegal drug market during the period 2014–2017 are highlighted, and their characterization by gas chromatography–mass spectrometry and liquid chromatography-tandem mass spectromaetry is presented.
Abstract: Currently, among new psychoactive substances, cathinone derivatives constitute the biggest group, which are mainly classified into N-alkylated, 3,4-methylenedioxy-N-alkylated, N-pyrrolidinyl, and 3,4-methylenedioxy-N-pyrrolidinyl derivatives. These derivatives are actively being subjected to minor modifications at the alkyl chains or the aromatic ring to create new synthetic cathinones with the goal of circumventing laws. In this review, the new synthetic cathinones that have appeared on the illegal drug market during the period 2014–2017 are highlighted, and their characterization by gas chromatography–mass spectrometry and liquid chromatography–tandem mass spectrometry is presented. Various key words were used to conduct an extensive literature search across a number of databases, specifically for synthetic cathinones that emerged between 2014 and 2017. More than 30 new cathinone derivatives were discovered. The preexisting parental compounds for the new derivatives are also referenced, and their mass spectral data are compiled in a table to facilitate their identification by forensic toxicologists. To our knowledge, this is the most current review presenting new synthetic cathinones. Political authorities should take measures to implement and enforce generic scheduling (comprehensive system) laws to control the diversely modified synthetic cathinones. Supplementing the existing databases with new findings can greatly facilitate the efforts of forensic toxicologists.

121 citations

Additional excerpts

  • ...1-[2-(Pyrrolidin-1-yl)-heptan-1- onyl]4-fluorobenzene 4-F-a-PHPP, 4-fluoro-apyrrolidinoheptanophenone 2014 [57]...

    [...]

  • ...1-[2-(Pyrrolidin-1-yl)-heptan-1-onyl]-4methoxybenzene 4-Methoxy-a-PHPP, 4-methoxy-apyrrolidinoheptanophenone 2014 [57]...

    [...]

  • ...1-[2-(Pyrrolidin-1-yl)-octan-1- onyl]-4methoxybenzene 4-Methoxy-a-POP, 4-methoxy-apyrrolidinooctanophenone 2014 [57]...

    [...]

  • ...36 246, 228, 175 140, 141, 105, 96, 77 [53, 57]...

    [...]

  • ...1-[2-(Pyrrolidin-1-yl)-hexan-1- onyl]benzene a-PHP, a-pyrrolidinohexanophenone 2014 [57]...

    [...]

Journal Article•DOI•
AH-7921: the list of new psychoactive opioids is expanded

[...]

Maria Katselou1, Ioannis Papoutsis1, Panagiota Nikolaou1, Chara Spiliopoulou1, Sotiris Athanaselis1 •
National and Kapodistrian University of Athens1
21 Feb 2015-Forensic Toxicology
TL;DR: AH-7921 is a current public health risk, and better international collaboration, effective legislation and continuous community alertness are needed to tackle this current growing problem.
Abstract: AH-7921 is a structurally unique synthetic opioid analgesic that has recently entered the drug arena in Europe, the USA, and Japan. Although it was synthesized and patented in the mid-1970s, it was first identified in a seized sample purchased via the Internet in July 2012 and formally brought to the attention of the European Union early warning system in August 2012 by the United Kingdom. Several in vitro experiments and animal model studies established the morphine-like analgesic action of AH-7921 as a μ-opioid receptor agonist that has been found to be several times more potent than codeine and at least as potent as morphine. This novel psychoactive substance has already led to eight non-fatal intoxications and 16 deaths in Sweden, the United Kingdom, Norway, and the USA. Thus, AH-7921 is a current public health risk, and better international collaboration, effective legislation and continuous community alertness are needed to tackle this current growing problem. The aim of this review is to summarize the current knowledge about this drug concerning its chemistry, pharmacology, and toxicology, as well as its international legal status. The limited existing analytical methodologies for the determination of AH-7921 in biological samples are also presented. Published or reported AH-7921-related cases, fatalities, or intoxications, and self reports from drug users are reviewed.

102 citations

Journal Article•DOI•
Death after use of the synthetic cannabinoid 5F-AMB.

[...]

Kevin G. Shanks, George S. Behonick
01 May 2016-Forensic Science International
TL;DR: The death of an individual that was associated with the synthetic cannabinoid 5F-AMB was reported and cause and manner of death was certified as accidental death due to synthetic cannabinoid toxicity.

89 citations

Cites background from "Chemical analysis of a benzofuran d..."

  • ...Introduction (S)-methyl-2-(1-(5-fluoropentyl)-1H-indazole-3-carboxamido)-3-methylbutanoate, otherwise known as 5F-AMB, 5F-AMB-PINACA, or 5F-AMP, is a newer synthetic cannabinoid that was first reported as a constituent in herbal incense and potpourri products on the Japanese drug market in 2014 (1)....

    [...]

References
More filters
Journal Article•DOI•
Neurochemical profiles of some novel psychoactive substances.

[...]

L. L. Iversen1, Simon Gibbons2, Ric Treble, Vincent Setola3, Xi Ping Huang3, Bryan L. Roth3 •
University of Oxford1, University College London2, University of North Carolina at Chapel Hill3
30 Jan 2013-European Journal of Pharmacology
TL;DR: There was a lack of correlation between results of functional uptake experiments and in vitro binding assays for the monoamine transporters, and there was also no correlation between the human behavioral effects of the substances and the results of bindingsAssays for a range of receptor targets.

157 citations

"Chemical analysis of a benzofuran d..." refers background in this paper

  • ...However, the benzofuran derivatives 5-APB [5-(2-aminopropyl)benzofuran] and 6-APB [6(2-aminopropyl)benzofuran] have been reported as potent triple monoamine reuptake inhibitors for dopamine, norepinephrine, and serotonin in vitro [15]....

    [...]

Journal Article•DOI•
Two new-type cannabimimetic quinolinyl carboxylates, QUPIC and QUCHIC, two new cannabimimetic carboxamide derivatives, ADB-FUBINACA and ADBICA, and five synthetic cannabinoids detected with a thiophene derivative α-PVT and an opioid receptor agonist AH-7921 identified in illegal products

[...]

Nahoko Uchiyama, Satoru Matsuda, Maiko Kawamura, Ruri Kikura-Hanajiri, Yukihiro Goda 
15 Mar 2013-Forensic Toxicology
TL;DR: In this paper, two new types of quinolinyl carboxylates, quinolin-8-yl 1-pentyl-(1H-indole)-3-carboxylate (QUCHIC) and quinoline-8 -yl 1-(cyclohexylmethyl)-1Hindole-3 -carboxylate (QUChIC, 2), were identified as designer drugs in illegal products.
Abstract: We identified two new-type cannabimimetic quinolinyl carboxylates, quinolin-8-yl 1-pentyl-(1H-indole)-3-carboxylate (QUPIC, 1) and quinolin-8-yl 1-(cyclohexylmethyl)-1H-indole-3-carboxylate (QUCHIC, 2); and two new cannabimimetic carboxamide derivatives, N-(1-amino-3,3-dimethyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1H-indazole-3-carboxamide (ADB-FUBINACA, 3) and N-(1-amino-3,3-dimethyl-1-oxobutan-2-yl)-1-pentyl-1H-indole-3-carboxamide (ADBICA, 4), as designer drugs in illegal products. Compound 3 was reported to have a potent affinity for cannabinoid CB1 receptor by Pfizer in 2009, but this is the first report of its detection in illegal products. No chemical or pharmacological data for compounds 1, 2, and 4 have appeared until now, making this the first report on these compounds. We also detected synthetic cannabinoids, APICA N-(5-fluoropentyl) analog (5), APINACA N-(5-fluoropentyl) analog (6), UR-144 N-(5-chloropentyl) analog (7), JWH-122 N-(5-chloropentyl) analog (8), and AM-2201 4-methoxynaphthyl analog (4-MeO-AM-2201, 9) herein as newly distributed designer drugs in Japan. It is of interest that compounds 1 and 2 were detected with their synthetic component, 8-quinolinol (10). A stimulant thiophene analog, α-pyrrolidinovalerothiophenone (α-PVT, 11), and an opioid receptor agonist, 3,4-dichloro-N-([1-(dimethylamino)cyclohexyl]methyl)benzamide (AH-7921, 12), were also detected as new types of designer drugs coexisting with several synthetic cannabinoids and cathinone derivatives in illegal products.

156 citations

"Chemical analysis of a benzofuran d..." refers background or methods in this paper

  • ...These compounds are analogs of known cannabimimetic substances, QUPIC (PB22) [6], AM-2201, and AB-PINACA [4], respectively, the pharmacological effects for which have not been reported....

    [...]

  • ...We measured the accurate mass numbers of the target compounds by liquid chromatography–quadrupole time-offlight mass spectrometry (LC–QTOF-MS) in the ESI mode according to our previous report [6]....

    [...]

Journal Article•DOI•
Identification of a cannabimimetic indole as a designer drug in a herbal product

[...]

Nahoko Uchiyama, Ruri Kikura-Hanajiri, Nobuo Kawahara, Yukihiro Goda
19 Mar 2009-Forensic Toxicology
TL;DR: A cannabimimetic indole has been identified as a new adulterant in a herbal product being sold illegally in Japan for its expected narcotic effect as mentioned in this paper, which was reported as a potent cannabinoid receptor agonist possessing a pharmacological cannabolimetic activity.
Abstract: A cannabimimetic indole has been identified as a new adulterant in a herbal product being sold illegally in Japan for its expected narcotic effect. Liquid chromatography-mass spectrometry and gas chromatography-mass spectrometry analyses indicated that the product contained two major compounds. One was identified as a cannabinoid analog (1RS,3SR)-3-[4-(1,1-dimethyloctyl)-2-hydroxyphenyl]cyclohexan-1-ol (1) by direct comparison with the authentic compound, which we reported previously. The other compound (2) showed a molecular weight of 341 daltons, and accurate mass spectral measurements showed its elemental composition to be C24H23NO. Both mass and nuclear magnetic resonance spectrometric data revealed that 2 was 1-pentyl-3-(1-naphthoyl)indole [or naphthalen-1-yl-(1-pentylindol-3-yl)methanone] being identical to JWH-018, which was synthesized by Wiley and coworkers in 1998. This compound was reported as a potent cannabinoid receptor agonist possessing a pharmacological cannabimimetic activity.

140 citations

Journal Article•DOI•
URB-754: A new class of designer drug and 12 synthetic cannabinoids detected in illegal products

[...]

Nahoko Uchiyama, Maiko Kawamura, Ruri Kikura-Hanajiri, Yukihiro Goda
10 Apr 2013-Forensic Science International
TL;DR: It is of interest that the product of a reaction between two different types of designer drugs, namely, a cannabinoid-related designer drug and a cathinone-type designer drug, was found in one illegal product.

139 citations

"Chemical analysis of a benzofuran d..." refers methods in this paper

  • ...Analytical conditions Each sample solution was analyzed by ultra-performance liquid chromatography–electrospray ionization mass spectrometry (UPLC–ESI-MS) and by gas chromatography– mass spectrometry (GC–MS) in the electron ionization (EI) mode according to our previous report [12]....

    [...]

Journal Article•DOI•
Indol-3-ylcycloalkyl Ketones: Effects of N1 Substituted Indole Side Chain Variations on CB2 Cannabinoid Receptor Activity

[...]

Jennifer M. Frost, Michael J. Dart, Karin R. Tietje, Tiffany Runyan Garrison, George K. Grayson, Anthony V. Daza, Odile F. El-Kouhen, B B Yao, Gin C. Hsieh, Madhavi Pai, Chang Z. Zhu, Prasant Chandran, Michael Meyer 
14 Jan 2010-Journal of Medicinal Chemistry
TL;DR: N1 aromatic side chains also afforded several high affinity CB(2) receptor agonists but were generally less potent in an in vitro CB( 2) functional assay than were nonaromatic side chain analogues.
Abstract: Several 3-acylindoles with high affinity for the CB(2) cannabinoid receptor and selectivity over the CB(1) receptor have been prepared. A variety of 3-acyl substituents were investigated, and the tetramethylcyclopropyl group was found to lead to high affinity CB(2) agonists (5, 16). Substitution at the N1-indole position was then examined. A series of aminoalkylindoles was prepared and several substituted aminoethyl derivatives were active (23-27, 5) at the CB(2) receptor. A study of N1 nonaromatic side chain variants provided potent agonists at the CB(2) receptor (16, 35-41, 44-47, 49-54, and 57-58). Several polar side chains (alcohols, oxazolidinone) were well-tolerated for CB(2) receptor activity (41, 50), while others (amide, acid) led to weaker or inactive compounds (55 and 56). N1 aromatic side chains also afforded several high affinity CB(2) receptor agonists (61, 63, 65, and 69) but were generally less potent in an in vitro CB(2) functional assay than were nonaromatic side chain analogues.

134 citations

Related Papers (5)
Two new-type cannabimimetic quinolinyl carboxylates, QUPIC and QUCHIC, two new cannabimimetic carboxamide derivatives, ADB-FUBINACA and ADBICA, and five synthetic cannabinoids detected with a thiophene derivative α-PVT and an opioid receptor agonist AH-7921 identified in illegal products

[...]

15 Mar 2013-Forensic Toxicology
Nahoko Uchiyama, Satoru Matsuda, Maiko Kawamura, Ruri Kikura-Hanajiri, Yukihiro Goda 
New cannabimimetic indazole derivatives, N-(1-amino-3-methyl- 1-oxobutan-2-yl)-1-pentyl-1H-indazole-3-carboxamide (AB-PINACA) and N-(1-amino-3-methyl-1-oxobutan-2-yl)-1- (4-fluorobenzyl)-1H-indazole-3-carboxamide (AB-FUBINACA) identified as designer drugs in illegal products

[...]

01 Jan 2013-Forensic Toxicology
Nahoko Uchiyama, Satoru Matsuda, Daigo Wakana, Ruri Kikura-Hanajiri, Yukihiro Goda 
'Spice' and other herbal blends: harmless incense or cannabinoid designer drugs?

[...]

01 May 2009-Journal of Mass Spectrometry
Volker Auwärter, Sebastian Dresen, Wolfgang Weinmann, Michael Müller, Michael Pütz, Nerea Ferreirós 
Changes in the prevalence of synthetic cannabinoids and cathinone derivatives in Japan until early 2012

[...]

01 Jan 2013-Forensic Toxicology
Ruri Kikura-Hanajiri, Nahoko Uchiyama, Maiko Kawamura, Yukihiro Goda 
Changes in the prevalence of new psychoactive substances before and after the introduction of the generic scheduling of synthetic cannabinoids in Japan

[...]

01 Jul 2014-Drug Testing and Analysis
Ruri Kikura-Hanajiri, Nahoko Uchiyama Maiko Kawamura, Yukihiro Goda