Identification of new synthetic cannabinoid analogue APINAC (adamantan-1-yl 1-pentyl-1H-indazole-3-carboxylate) with other synthetic cannabinoid MDMB(N)-Bz-F in illegal products
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Two synthetic cannabinoid analogues were detected using high-performance liquid chromatography (HPLC)–diode array detector, and gas chromatography–time-of-flight-mass spectrometry during the inspection of illegal products in an airmail package. The analogues were separated by semi-preparative HPLC, and their structures were determined by performing liquid chromatography–high-resolution-mass spectrometry, infrared analysis, and nuclear magnetic resonance spectroscopy. Compound 1 was MDMB(N)-Bz-F, which has been reported previously. Compound 2 was elucidated as adamantan-1-yl 1-pentyl-1H-indazole-3-carboxylate (APINAC), in which the amide group of APINACA was replaced with an ester group. Because there has been no chemical or pharmacological data about this compound until now, this is the first report of its detection in illegal products.
KeywordsMethyl 2-[1-(4-fluorobenzyl)-1H-indazole-3-carboxamido]-3,3-dimethylbutanoate 1-(4-Fluorobenzyl)-N-(1-methoxycarbonyl-2,2-dimethylpropyl)-1H-indazole-3-carboxamide [MDMB(N)-Bz-F] Adamantan-1-yl 1-pentyl-1H-indazole-3-carboxylate (APINAC) Synthetic cannabinoids Illegal product APINACA analogues
This research was supported by Research Grants (15181MFDS521 and 15182MFDS523) from the Ministry of Food and Drug Safety (MFDS) in Korea. We thank the Central Laboratory of Kangwon National University for providing us with technical assistance on the spectroscopic experiments.
Compliance with ethical standards
Conflict of interest
The authors declare that they have no conflict of interest.
This article does not contain any studies with human participants or animals performed by any of the authors.
- 1.Huffman JW (2009) Cannabimimetic indoles, pyrroles, and indenes: structure-activity relationships and receptor interactions. In: Reggio PH (ed) The cannabinoid receptors. Humana Press, New York, pp 49–94Google Scholar
- 8.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 30:114–125CrossRefGoogle Scholar
- 15.UNODC (2012) World drug report 2012. United Nations Office on Drugs and Crime, ViennaGoogle Scholar
- 20.Seely KA, Patton AL, Moran CL, Womack ML, Prather PL, Fantegrossi WE, Radominska-Pandya A, Endres GW, Channell KB, Smith NH, McCain KR, James LP, Moran JH (2013) Forensic investigation of K2, spice, and ‘‘bath salt’’ commercial preparations: a 3-year study of new designer drug products containing synthetic cannabinoid, stimulant, and hallucinogenic compounds. Forensic Sci Int 233:416–422CrossRefPubMedGoogle Scholar
- 25.EMCDDA (2015) New psychoactive substances in Europe: an update from the EU early warning system. European Monitoring Centre for Drugs and Drug Addiction. http://www.emcdda.europa.eu/publications/2015/new-psychoactive-substances. Accessed 8 June 2016
- 27.Uchiyama N, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (2013) 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. Forensic Toxicol 31:223–240CrossRefGoogle Scholar