Structure elucidation of a new open chain isomer of the cannabimimetic cyclopropoylindole A-796,260

Forensic Science International

Volumn 234, Issue , 2014, Pages 139-148

  Westphal, Folker ^a   Girreser, Ulrich ^b   Knecht, Siegfried ^c  

^a State Bureau of Criminal Investigation Schleswig Holstein   (Germany)

^b UNIVERSITY OF KIEL   (Germany)

^c Laboratory Frankfurt   (Germany)

Author keywords

GC MS; IR; New ring opened isomer of A 796,260; NMR; Product ion spectrometry of cyclopropoylindoles; Structure elucidation

Indexed keywords

1 [1 [2 (MORPHOLIN 4 YL)ETHYL]INDOL 3 YL] 3,4,4 TRIMETHYLPENT 2 EN 1 ONE; A 796 260; CANNABINOID RECEPTOR AGONIST; CYCLOPROPOYLINDOLE DERIVATIVE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG; [1 (2 MORPHOLIN 4 YLETHYL) 1H INDOL 3 YL] (2,2,3,3 TETRAMETHYLCYCLOPROPYL)METHANONE;

ARTICLE; CONTROLLED STUDY; DRUG DETERMINATION; DRUG PURITY; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMERISM; MASS FRAGMENTOGRAPHY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; RING OPENING; SEPARATION TECHNIQUE; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; TANDEM MASS SPECTROMETRY; WAGNER MEERWEIN REARRANGEMENT;

EID: 84890191914     PISSN: 03790738     EISSN: 18726283     Source Type: Journal    
DOI: 10.1016/j.forsciint.2013.11.006     Document Type: Article

References (20)

1. Shevyrin V., Melkozerov V., Nevero A., Eltsov O., Morzherin Y., Shafran Y. Identification and analytical properties of new synthetic cannabimimetics bearing 2,2,3,3-tetramethylcyclopropanecarbonyl moiety. Forensic Sci. Int. 2013, 226:62-73.
2. Dawson P.H., Sun W.F. A round robin on the reproducibility of standard operating conditions for the acquisition of library MS/MS spectra using triple quadrupols. Int. J. Mass Spectrom. Ion Processes 1984, 55:155-170.
3. T. Junge, P. Rösner, F. Westphal, Product ion mass spectra of important organic ions, a free printed version can be ordered from the authors.
4. + immonium ions. J. Mass Spectrom. 1996, 31:1047-1053.
5. Rösner P., Junge T. N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine, a representative of a new class of street drugs. Microgram 1994, 27(12):411-418.
6. Westphal F., Junge T., Rösner P., Fritschi G., Klein B., Girreser U. Mass spectral and NMR spectral data of two new designer drugs with an α-aminophenone structure: 4'-methyl-α-pyrrolidinohexanophenone and 4'-methyl-α-pyrrolidinobutyrophenone. Forensic Sci. Int. 2007, 169:32-42.
7. Westphal F., Junge T., Rösner P., Sönnichsen F., Schuster F. Mass and NMR spectroscopic characterization of 3,4-methylenedioxypyrovalerone: a designer drug with α-pyrrolidionophenone structure. Forensic Sci. Int. 2009, 190:1-8.
8. Westphal F., Junge T., Klein B., Fritschi G., Girreser U. Spectroscopic characterization of 3 4-methylenedioxypyrrolidinobutyrophenone: a new designer drug with α-pyrrolidinophenone structure. Forensic Sci. Int. 2011, 209:126-132.
9. Kneisel S., Westphal F., Bisel P., Brecht V., Broecker S., Auwärter V. Identification and structural characterization of the synthetic cannabinoid 3-(1-adamantoyl)-1-pentylindole as an additive in 'herbal incence'. J. Mass Spectrom. 2012, 47:195-200.
10. Westphal F., Junge T., Girreser U., Greibl W., Doering C. Mass, NMR and IR spectroscopic characterization of pentedrone and pentylone and identification of their isocathinone by-products. Forensic Sci. Int. 2012, 217:157-167.
11. Borth S., Hänsel W., Rösner P. T. Junge, Synthesis of 2,3- and 3,4-methylenedioxyphenylalkylamines and their regioisomeric differentiation by mass spectral analysis using GC-MS-MS. Forensic Sci. Int. 2000, 114:139-153.
12. Borth S., Hänsel W., Rösner P. T. Junge, Regioisomeric differentiation of 2,3- and 3,4-methylenedioxy ring-substituted phenylalkylamines by gas chromatography/tandem mass spectrometry. J. Mass Spectrom. 2000, 35:705-710.
13. Westphal F., Rösner P., Junge T. Differentiation of regioisomeric ring-substituted fluorophenethylamines with product ion spectrometry. Forensic Sci. Int. 2010, 194:53-59.
14. Westphal F., Junge T. Ring positional differentiation of isomeric N-alkylated fluorocathinones by gas chromatography/tandem mass spectrometry. Forensic Sci. Int. 2012, 223:97-105.
15. Stadler D., Bach Th. Diastereoselective domino reactions of chiral 2-substituted 1-(2',2', 3',3'-tetramethylcyclopropyl)-alkan-1-ols under Friedel-Crafts conditions. J. Org. Chem. 2009, 74:4747-4752.
16. Bunton C.A., del Pesco T.W. The mass spectra of some methyl norbornyl chlorides. Org. Mass Spectrom. 1969, 2:81-103.
17. Shaler T.A., Morton T.H. Fluorine shifts in gaseous cations. Analogues of Wagner-Meerwein rearrangements. J. Am. Chem. Soc. 1994, 116:9222-9226.
18. + ions. Org. Mass Spectrom. 1983, 18(5):215-218.
19. Speranza M., Filippi A. Chiral ions in the gas phase. Part 7. Wagner-Meerwein rearrangements in the gas phase: deuterium isotope effects on acid-induced dissociation of optically active phenylpropanols. Chem. Eur. J. 1999, 5(3):845-853.
20. Morton T.H. Decomposition via ion-neutral complexes. The Encyclopedia of Mass Spectrometry 2003, vol. 1:467-479. Elsevier Science, Amsterdam.