5F-CUMYL-PINACA

5F-CUMYL-PINACA
Legal status
Legal status
Identifiers
IUPAC name
  • 1-(5-Fluoropentyl)-N-(2-phenylpropan-2-yl)-1H-indazole-3-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC22H26FN3O
Molar mass367.468 g·mol−1
3D model (JSmol)
SMILES
  • O=C(NC(C)(C)C1=CC=CC=C1)C2=NN(CCCCCF)C3=C2C=CC=C3
InChI
  • InChI=1S/C22H26FN3O/c1-22(2,17-11-5-3-6-12-17)24-21(27)20-18-13-7-8-14-19(18)26(25-20)16-10-4-9-15-23/h3,5-8,11-14H,4,9-10,15-16H2,1-2H3,(H,24,27)
  • Key:XSHGVIPHMOTDCS-UHFFFAOYSA-N

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]

In the United States, 5F-CUMYL-PINACA became a Schedule I Controlled Substance in 2019.[6]

Sweden's public health agency suggested classifying 5F-CUMYL-PINACA as a hazardous substance on November 10, 2014.[7]

See also

References

  1. ↑ Angerer V, Franz F, Moosmann B, Bisel P, Auwärter V (13 November 2018). "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. doi:10.1007/s11419-018-0451-8. PMC 6315005. PMID 30636986.
  2. ↑ "5-fluoro CUMYL-PINACA (CRM)". Cayman Chemical. Retrieved 22 November 2018.
  3. ↑ Bowden; et al. (11 April 2013). "Patent WO 2014167530 - Cannabinoid compounds". New Zealand Patent application 623626. Retrieved 22 November 2018.
  4. ↑ Longworth M, Banister SD, Boyd R, Kevin RC, Connor M, McGregor IS, Kassiou M (October 2017). "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. doi:10.1021/acschemneuro.7b00267. PMID 28792725.
  5. ↑ Asada A, Doi T, Tagami T, Takeda A, Satsuki Y, Kawaguchi M, Nakamura A, Sawabe Y (January 2018). "Cannabimimetic activities of cumyl carboxamide-type synthetic cannabinoids". Forensic Toxicology. 36 (1): 170–177. doi:10.1007/s11419-017-0374-9. ISSN 1860-8965. S2CID 7996915.
  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.
  7. ↑ "Cannabinoider föreslås bli klassade som hälsofarlig vara" [Cannabinoids suggested classified as health endangering substance] (in Swedish). Public Health Agency of Sweden. 10 November 2014. Retrieved 11 July 2015.
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