CUMYL-4CN-BINACA

CUMYL-4CN-BINACA
Legal status
Legal status	AU: S9 (Prohibited substance); CA: Schedule II; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class B; US: Schedule I;
Identifiers
	IUPAC name 1-(4-Cyanobutyl)-N-(2-phenylpropan-2-yl)-1H-indazole-3-carboxamide;
CAS Number	1631074-54-8;
ChemSpider	58190345;
UNII	V6DM582RV1;
CompTox Dashboard (EPA)	DTXSID401009982 ;
Chemical and physical data
Formula	C22H24N4O
Molar mass	360.461 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(NC(C)(C)C1=CC=CC=C1)C2=NN(CCCCC#N)C3=C2C=CC=C3;
	InChI 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 as CUMYL-CYBINACA or SGT-78) is an indazole-3-carboxamide based synthetic cannabinoid that has been sold online as a designer drug.^[1]^[2]^[3]^[4]^[5]^[6] It is a potent agonist for cannabinoid receptors CB₁ and CB₂, with in vitro EC₅₀ values of 0.58 nM and 6.12 nM, respectively.^[7] In mice, CUMYL-4CN-BINACA produces hypothermic and pro-convulsant effects via the CB₁ receptor,^[7] and anecdotal reports suggest it has an active dose of around 0.1 mg in humans.^[8]

CUMYL-4CN-BINACA is metabolized to produce cyanide, raising concerns about liver toxicity.^[6] There is one reported case of hyperthermia, rhabdomyolysis, and kidney failure associated with its use.^[9]

References

^ "4-cyano CUMYL-BUTINACA". Cayman Chemical.
^ 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.
^ 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.
^ 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.
^ Ölmez, Nevin Arıkan; Kapucu, Hicran; Altun, Neslihan Çallı; Eren, Bülent (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.
^ ^a ^b Åstrand, Anna; Vikingsson, Svante; Lindstedt, Daniel; Thelander, Gunilla; Gréen, Henrik; Kronstrand, Robert; Wohlfarth, Ariane (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. ISSN 1942-7611. PMID 29577658.
^ ^a ^b Kevin, Richard; Anderson, Lyndsey; McGregor, Iain; Boyd, Rochelle; Manning, Jamie; Glass, Michelle; Connor, Mark; Banister, Samuel (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.{{cite journal}}: CS1 maint: unflagged free DOI (link)
^ "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.
^ El Zahran, Tharwat (August 2018). "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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[1] "4-cyano CUMYL-BUTINACA". Cayman Chemical.

[2] 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.

[3] 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.

[4] 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.

[5] Ölmez, Nevin Arıkan; Kapucu, Hicran; Altun, Neslihan Çallı; Eren, Bülent (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.

[Åstrand-6] Åstrand, Anna; Vikingsson, Svante; Lindstedt, Daniel; Thelander, Gunilla; Gréen, Henrik; Kronstrand, Robert; Wohlfarth, Ariane (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. ISSN 1942-7611. PMID 29577658.

[:0-7] Kevin, Richard; Anderson, Lyndsey; McGregor, Iain; Boyd, Rochelle; Manning, Jamie; Glass, Michelle; Connor, Mark; Banister, Samuel (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.{{cite journal}}: CS1 maint: unflagged free DOI (link)

[8] "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.

[9] El Zahran, Tharwat (August 2018). "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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See also

References