Chemistry:5F-CUMYL-PINACA

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Short description: Chemical compound
5F-CUMYL-PINACA
5F-CUMYL-PINACA.svg
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC22H26FN3O
Molar mass367.468 g·mol−1
3D model (JSmol)

5F-CUMYL-PINACA (also known as SGT-25 and sometimes sold in e-cigarette form as C-Liquid)[1] is an indazole-3-carboxamide based synthetic cannabinoid.[2] 5F-CUMYL-PINACA acts as a potent agonist for the cannabinoid receptors, with the original patent claiming approximately 4x selectivity for CB1, having an EC50 of <0.1 nM for human CB1 receptors and 0.37 nM for human CB2 receptors.[3] In more recent assays using different techniques, 5F-CUMYL-PINACA was variously found to have an EC50 of 0.43 nM at CB1 and 11.3 nM at CB2, suggesting a somewhat higher CB1 selectivity of 26 times,[4] or alternatively 15.1 nM at CB1 and 34.8 nM at CB2 with only 2.3 times selectivity, however these figures cannot be directly compared due to the different assay techniques used in each case.[5]

Legal status

In the United States, 5F-CUMYL-PINACA was temporarily emergency scheduled by the DEA in 2019.[6] and made a permanent Schedule I Controlled Substance on April 7, 2022.[7] Sweden's public health agency suggested classifying 5F-CUMYL-PINACA as a hazardous substance on November 10, 2014.[8]

See also

References

  1. "5F-Cumyl-PINACA in 'e-liquids' for electronic cigarettes: comprehensive characterization of a new type of synthetic cannabinoid in a trendy product including investigations on the in vitro and in vivo phase I metabolism of 5F-Cumyl-PINACA and its non-fluorinated analog Cumyl-PINACA". Forensic Toxicology 37 (1): 186–196. 13 November 2018. doi:10.1007/s11419-018-0451-8. PMID 30636986. 
  2. "5-fluoro CUMYL-PINACA (CRM)". Cayman Chemical. https://www.caymanchem.com/product/17726. 
  3. Bowden (11 April 2013). "Patent WO 2014167530 - Cannabinoid compounds". New Zealand Patent application 623626. https://patents.google.com/patent/WO2014167530A1. 
  4. "Pharmacology of Cumyl-Carboxamide Synthetic Cannabinoid New Psychoactive Substances (NPS) CUMYL-BICA, CUMYL-PICA, CUMYL-5F-PICA, CUMYL-5F-PINACA, and Their Analogues". ACS Chemical Neuroscience 8 (10): 2159–2167. October 2017. doi:10.1021/acschemneuro.7b00267. PMID 28792725. 
  5. "Cannabimimetic activities of cumyl carboxamide-type synthetic cannabinoids". Forensic Toxicology 36 (1): 170–177. January 2018. doi:10.1007/s11419-017-0374-9. ISSN 1860-8965. 
  6. "Schedules of Controlled Substances: Temporary Placement of 5F-EDMB-PINACA, 5F-MDMB-PICA, FUB-AKB48, 5F-CUMYL-PINACA, and FUB-144 into Schedule I". Federal Register. 16 April 2019. https://www.federalregister.gov/documents/2019/04/16/2019-07460/schedules-of-controlled-substances-temporary-placement-of-5f-edmb-pinaca-5f-mdmb-pica-fub-akb48. 
  7. "Schedules of Controlled Substances: Placement of 5F-EDMB-PINACA, 5FMDMB-PICA, FUB-AKB48, 5F-CUMYLPINACA, and FUB-144 in Schedule I". Federal Register 87 (67). 7 April 2022. https://www.govinfo.gov/content/pkg/FR-2022-04-07/pdf/2022-07320.pdf. 
  8. "Cannabinoider föreslås bli klassade som hälsofarlig vara" (in sv). Public Health Agency of Sweden. 10 November 2014. https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2014/november/cannabinoider-foreslas-bli-klassade-som-halsofarlig-vara/.