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CUMYL-4CN-BINACA

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
CUMYL-4CN-BINACA
Legal status
Legal status
Identifiers
  • 1-(4-Cyanobutyl)-N-(2-phenylpropan-2-yl)-1H-indazole-3-carboxamide
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC22H24N4O
Molar mass360.461 g·mol−1
3D model (JSmol)
  • O=C(NC(C)(C)C1=CC=CC=C1)C2=NN(CCCCC#N)C3=C2C=CC=C3
  • InChI=1S/C22H24N4O/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,4,9-10,16H2,1-2H3,(H,24,27)
  • Key:JGTSOWOPISVAHG-UHFFFAOYSA-N

CUMYL-4CN-BINACA (also known asCUMYL-CYBINACA orSGT-78) is anindazole-3-carboxamide basedsynthetic cannabinoid that has been sold online as adesigner drug.[3][4][5][6][7][8] It is a potentagonist forcannabinoid receptorsCB1 andCB2, within vitro EC50 values of 0.58 nM and 6.12 nM, respectively.[9] In mice, CUMYL-4CN-BINACA produceshypothermic andpro-convulsant effects via the CB1 receptor,[9] and anecdotal reports suggest it has an active dose of around 0.1 mg in humans.[10]

CUMYL-4CN-BINACA is metabolized to producecyanide, raising concerns about liver toxicity.[8] There is one reported case ofhyperthermia,rhabdomyolysis, andkidney failure associated with its use.[11]

See also

[edit]

References

[edit]
  1. ^Anvisa (2023-07-24)."RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União (published 2023-07-25).Archived from the original on 2023-08-27. Retrieved2023-08-27.
  2. ^"Substance Details CUMYL-4CN-BINACA". Retrieved2024-01-22.
  3. ^"4-cyano CUMYL-BUTINACA". Cayman Chemical.
  4. ^Yeter O (November 2017). "Identification of the Synthetic Cannabinoid 1-(4-cyanobutyl)-N-(2-phenylpropan-2-yl)-1H-indazole-3-carboxamide (CUMYL-4CN-BINACA) in Plant Material and Quantification in Post-Mortem Blood Samples".Journal of Analytical Toxicology.41 (9):720–728.doi:10.1002/dta.2248.PMID 28977413.
  5. ^Staeheli SN, Poetzsch M, Veloso VP, Bovens M, Bissig C, Steuer AE, Kraemer T (January 2018). "In vitro metabolism of the synthetic cannabinoids CUMYL-PINACA, 5F-CUMYL-PINACA, CUMYL-4CN-BINACA, 5F-CUMYL-P7AICA and CUMYL-4CN-B7AICA".Drug Testing and Analysis.10 (1):148–157.doi:10.1002/dta.2298.PMID 28885775.
  6. ^Bovens M, Bissig C, Staeheli SN, Poetzsch M, Pfeiffer B, Kraemer T (December 2017). "Structural characterization of the new synthetic cannabinoids CUMYL-PINACA, 5F-CUMYL-PINACA, CUMYL-4CN-BINACA, 5F-CUMYL-P7AICA and CUMYL-4CN-B7AICA".Forensic Science International.281:98–105.doi:10.1016/j.forsciint.2017.10.020.PMID 29125990.
  7. ^Arıkan Ölmez N, Kapucu H, Çallı Altun N, Eren B (January 2018). "Identification of the synthetic cannabinoid N-(2-phenyl-propan-2-yl)-1-(4-cyanobutyl)-1H-indazole-3-carboxamide (CUMYL-4CN-BINACA) in a herbal mixture product".Forensic Toxicology.36 (1):192–199.doi:10.1007/s11419-017-0372-y.ISSN 1860-8965.S2CID 28058750.
  8. ^abÅstrand A, Vikingsson S, Lindstedt D, Thelander G, Gréen H, Kronstrand R, Wohlfarth A (March 2018). "Metabolism study for CUMYL-4CN-BINACA in human hepatocytes and authentic urine specimens: Free cyanide is formed during the main metabolic pathway".Drug Testing and Analysis.10 (8):1270–1279.doi:10.1002/dta.2373.PMID 29577658.
  9. ^abKevin RC, Anderson L, McGregor IS, Boyd R, Manning JJ, Glass M, et al. (2019)."CUMYL-4CN-BINACA Is an Efficacious and Potent Pro-Convulsant Synthetic Cannabinoid Receptor Agonist".Frontiers in Pharmacology.10 595.doi:10.3389/fphar.2019.00595.PMC 6549035.PMID 31191320.
  10. ^"EMCDDA–Europol Joint Report on a new psychoactive substance: 1-(4-cyanobutyl)-N-(2-phenylpropan-2-yl)indazole-3-carboxamide (CUMYL-4CN-BINACA)".www.emcdda.europa.eu.
  11. ^El Zahran T, Gerona R, Morgan BW, Pomerleau AC (June 2019). "A novel synthetic cannabinoid (Cumyl-4-cyano-BINACA) resulting in hyperthermia, rhabdomyolysis, and renal failure in a 29-year-old patient: it's not meningitis".Clinical Toxicology.57 (6):421–422.doi:10.1080/15563650.2018.1534241.PMID 30442067.S2CID 53566116.
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