The chemistry and pharmacology of synthetic cannabinoid SDB-006 and its regioisomeric fluorinated and methoxylated analogs

Samuel D. Banister*, Alexander Olson, Matthew Winchester, Jordyn Stuart, Amelia R. Edington, Richard C. Kevin, Mitchell Longworth, Marco Herrera, Mark Connor, Iain S. Mcgregor, Roy R. Gerona, Michael Kassiou

*Corresponding author for this work

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Synthetic cannabinoids are the largest and most structurally diverse class of new psychoactive substances, with manufacturers often using isomerism to evade detection and circumvent legal restriction. The regioisomeric methoxy- and fluorine-substituted analogs of SDB-006 (N-benzyl-1-pentyl-1H-indole-3-carboxamide) were synthesized and could not be differentiated by gas chromatography-mass spectrometry (GC-MS), but were distinguishable by liquid chromatography-quadrupole time-of-flight-MS (LC-QTOF-MS). In a fluorescence-based plate reader membrane potential assay, SDB-006 acted as a potent agonist at human cannabinoid receptors (CB1 EC50 = 19 nM). All methoxy- and fluorine-substituted analogs showed reduced potency compared to SDB-006, although the 2-fluorinated analog (EC50 = 166 nM) was comparable to known synthetic cannabinoid RCS-4 (EC50 = 146 nM). Using biotelemetry in rats, SDB-006 and RCS-4 evoked comparable reduction in body temperature (~0.7°C at a dose of 10 mg/kg), suggesting lower potency than the recent synthetic cannabinoid AB-CHMINACA (>2°C, 3 mg/kg).

Original languageEnglish
Pages (from-to)1099-1109
Number of pages11
JournalDrug Testing and Analysis
Volume10
Issue number7
Early online date23 Feb 2018
DOIs
Publication statusPublished - Jul 2018

Keywords

  • AB-CHMINACA
  • Cannabinoid
  • JWH-018
  • RCS-4
  • SDB-006

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    Banister, S. D., Olson, A., Winchester, M., Stuart, J., Edington, A. R., Kevin, R. C., ... Kassiou, M. (2018). The chemistry and pharmacology of synthetic cannabinoid SDB-006 and its regioisomeric fluorinated and methoxylated analogs. Drug Testing and Analysis, 10(7), 1099-1109. https://doi.org/10.1002/dta.2362