GC-MS and GC-IR analysis of regioisomeric cannabinoids related to 1-(5-fluoropentyl)-3-(1-naphthoyl)-indole

作者: Jack DeRuiter , Forrest Smith , Younis Abiedalla , Logan Neel , C. Randall Clark

DOI: 10.1016/J.FORC.2018.07.005

关键词:

摘要: Abstract The compounds in this study are the regioisomeric 2-, 3-, 4-, 5-, 6- and 7-(1-naphthoyl) substituted 1-(5-fluoropentyl)-indoles 3-(1-naphthoyl) isomer series is also known as AM-2201. These structurally similar to JWH-018 except for additional fluorine at terminal end of n-pentyl side-chain. six have identical elemental composition (C24H22FNO) differ position attachment 1-napthoyl group on indole ring. electron ionization mass spectra showed major fragment ions with a molecular radical cation significant abundance m/z 359. 127 155 naphthyl naphthoyl cations. There prominent ion 342 [M−17]+ EI-MS 1-(5-fluoropentyl)-3-, 5- 6-(1-naphthoyl)-indoles due loss hydroxyl most (AM-2201). were separated using gas chromatography capillary column containing trifluoropropylmethyl polysiloxane (Rtx-200) stationary phase. elution order appears be related steric crowding ring substituents. 7- 2-(1-naphthoyl) isomers eluted first possibility maximum interactions between naphthyol alkyl side-chains. vapor phase infrared differentiate among these based 1-naphthoyl compared non-fluorinated analogues, its equivalents.

参考文章(23)
Yuichi Kanaoka, Yoshio Ban, Takeshi Oishi, Osamu Yonemitsu, Masanao Terashima, Tetsuo Kimura, Masako Nakagawa, Infrared Spectra of Some Indole and Pyrrole Compounds Chemical & Pharmaceutical Bulletin. ,vol. 8, pp. 294- 301 ,(1960) , 10.1248/CPB.8.294
Brady K Atwood, John Huffman, Alex Straiker, Ken Mackie, JWH018, a common constituent of ‘Spice’ herbal blends, is a potent and efficacious cannabinoid CB1 receptor agonist British Journal of Pharmacology. ,vol. 160, pp. 585- 593 ,(2010) , 10.1111/J.1476-5381.2009.00582.X
Amber Thaxton, Tarek S. Belal, Forrest Smith, Jack DeRuiter, Karim M. Abdel-Hay, C. Randall Clark, Mass spectral studies on 1‐n‐pentyl‐3‐(1‐naphthoyl)indole (JWH‐018), three deuterium‐labeled analogues and the inverse isomer 1‐naphthoyl‐3‐n‐pentylindole Rapid Communications in Mass Spectrometry. ,vol. 29, pp. 871- 877 ,(2015) , 10.1002/RCM.7171
Samuel D. Banister, Jordyn Stuart, Trent Conroy, Mitchell Longworth, Madhura Manohar, Corinne Beinat, Shane M. Wilkinson, Richard C. Kevin, David E. Hibbs, Michelle Glass, Mark Connor, Iain S. McGregor, Michael Kassiou, Structure–activity relationships of synthetic cannabinoid designer drug RCS-4 and its regioisomers and C4 homologues Forensic Toxicology. ,vol. 33, pp. 355- 366 ,(2015) , 10.1007/S11419-015-0282-9
Vadim Shevyrin, Vladimir Melkozerov, Alexander Nevero, Oleg Eltsov, Yuri Morzherin, Yuri Shafran, Identification and analytical properties of new synthetic cannabimimetics bearing 2,2,3,3-tetramethylcyclopropanecarbonyl moiety. Forensic Science International. ,vol. 226, pp. 62- 73 ,(2013) , 10.1016/J.FORSCIINT.2012.12.009
Forrest T. Smith, Jack DeRuiter, Karim Abdel-Hay, C. Randall Clark, GC–MS and FTIR evaluation of the six benzoyl-substituted-1-pentylindoles: Isomeric synthetic cannabinoids Talanta. ,vol. 129, pp. 171- 182 ,(2014) , 10.1016/J.TALANTA.2014.05.023
Roger G. Pertwee, PHARMACOLOGY OF CANNABINOID CB1 AND CB2 RECEPTORS Pharmacology & Therapeutics. ,vol. 74, pp. 129- 180 ,(1997) , 10.1016/S0163-7258(97)82001-3
Jussara Amato, Nunzia Iaccarino, Bruno Pagano, Vincenzo Compagnone, Fabiana Di Rosa, Giuseppe Peluso, Ettore Novellino, Antonio Randazzo, NMR Assignment of N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide Seized as Herbal Incense for the First Time in Italy JOURNAL OF FORENSIC SCIENCE & CRIMINOLOGY. ,vol. 2, pp. 1- ,(2014) , 10.15744/2348-9804.1.403
Susanna Every-Palmer, Synthetic cannabinoid JWH-018 and psychosis: An explorative study Drug and Alcohol Dependence. ,vol. 117, pp. 152- 157 ,(2011) , 10.1016/J.DRUGALCDEP.2011.01.012