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'''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]].<ref>{{cite web | url=https://www.caymanchem.com/product/20194 | title=4-cyano CUMYL-BUTINACA | publisher=Cayman Chemical}}</ref><ref>{{cite journal | vauthors = Yeter O | title = 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 = Journal of Analytical Toxicology | volume = 41 | issue = 9 | pages = 720–728 | date = November 2017 | pmid = 28977413 | doi = 10.1002/dta.2248 }}</ref><ref>{{cite journal | vauthors = Staeheli SN, Poetzsch M, Veloso VP, Bovens M, Bissig C, Steuer AE, Kraemer T | title = In vitro metabolism of the synthetic cannabinoids CUMYL-PINACA, 5F-CUMYL-PINACA, CUMYL-4CN-BINACA, 5F-CUMYL-P7AICA and CUMYL-4CN-B7AICA | journal = Drug Testing and Analysis | volume = 10 | issue = 1 | pages = 148–157 | date = January 2018 | pmid = 28885775 | doi = 10.1002/dta.2298 }}</ref><ref>{{cite journal | vauthors = Bovens M, Bissig C, Staeheli SN, Poetzsch M, Pfeiffer B, Kraemer T | title = Structural characterization of the new synthetic cannabinoids CUMYL-PINACA, 5F-CUMYL-PINACA, CUMYL-4CN-BINACA, 5F-CUMYL-P7AICA and CUMYL-4CN-B7AICA | journal = Forensic Science International | volume = 281 | pages = 98–105 | date = December 2017 | pmid = 29125990 | doi = 10.1016/j.forsciint.2017.10.020 | url = https://www.sciencedirect.com/science/article/pii/S0379073817304218 }}</ref><ref>{{cite journal|first1=Nevin Arıkan|last1=Ölmez|first2=Hicran|last2=Kapucu|first3=Neslihan Çallı|last3=Altun|first4=Bülent|last4=Eren|title=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|journal=Forensic Toxicology|date=January 2018|issn=1860-8965|pages=192–199|volume=36|issue=1|doi=10.1007/s11419-017-0372-y}}</ref><ref name=Åstrand>{{cite journal|first1=Anna|last1=Åstrand|first2=Svante|last2=Vikingsson|first3=Daniel|last3=Lindstedt|first4=Gunilla|last4=Thelander|title=Metabolism study for CUMYL-4CN-BINACA in human hepatocytes and authentic urine specimens: Free cyanide is formed during the main metabolic pathway|journal=Drug Testing and Analysis|volume=10|issue=8|pages=1270–1279|issn=1942-7611|doi=10.1002/dta.2373|pmid=29577658|date=2018|first5=Henrik|last5=Gréen|first6=Robert|last6=Kronstrand|first7=Ariane|last7=Wohlfarth}}</ref> It is a potent [[agonist]] for [[Cannabinoid receptor|cannabinoid receptors]] [[Cannabinoid receptor type 1|CB<sub>1</sub>]] and [[Cannabinoid receptor type 2|CB<sub>2</sub>]], with ''in vitro'' EC<sub>50</sub> values of 0.58 nM and 6.12 nM, respectively.<ref name=":0">{{Cite journal|last=Kevin|first=Richard|last2=Anderson|first2=Lyndsey|last3=McGregor|first3=Iain|last4=Boyd|first4=Rochelle|last5=Manning|first5=Jamie|last6=Glass|first6=Michelle|last7=Connor|first7=Mark|last8=Banister|first8=Samuel|date=|title=CUMYL-4CN-BINACA is an efficacious and potent pro-convulsant synthetic cannabinoid receptor agonist|url=https://www.frontiersin.org/articles/10.3389/fphar.2019.00595/|journal=Frontiers in Pharmacology|volume=|pages=|via=}}</ref> In mice, CUMYL-4CN-BINACA produces hypothermic and [[Convulsant|pro-convulsant]] effects via the CB<sub>1</sub> receptor,<ref name=":0" /> and anecdotal reports suggest it has an active dose of around 0.1 mg in humans.<ref>{{cite web|title=EMCDDA–Europol Joint Report on a new psychoactive substance: 1-(4-cyanobutyl)-N-(2-phenylpropan-2-yl)indazole-3-carboxamide (CUMYL-4CN-BINACA)|url=http://www.emcdda.europa.eu/publications/joint-reports/cumyl-4cn-binaca_en|website=www.emcdda.europa.eu}}</ref>
'''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]].<ref>{{cite web | url=https://www.caymanchem.com/product/20194 | title=4-cyano CUMYL-BUTINACA | publisher=Cayman Chemical}}</ref><ref>{{cite journal | vauthors = Yeter O | title = 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 = Journal of Analytical Toxicology | volume = 41 | issue = 9 | pages = 720–728 | date = November 2017 | pmid = 28977413 | doi = 10.1002/dta.2248 }}</ref><ref>{{cite journal | vauthors = Staeheli SN, Poetzsch M, Veloso VP, Bovens M, Bissig C, Steuer AE, Kraemer T | title = In vitro metabolism of the synthetic cannabinoids CUMYL-PINACA, 5F-CUMYL-PINACA, CUMYL-4CN-BINACA, 5F-CUMYL-P7AICA and CUMYL-4CN-B7AICA | journal = Drug Testing and Analysis | volume = 10 | issue = 1 | pages = 148–157 | date = January 2018 | pmid = 28885775 | doi = 10.1002/dta.2298 }}</ref><ref>{{cite journal | vauthors = Bovens M, Bissig C, Staeheli SN, Poetzsch M, Pfeiffer B, Kraemer T | title = Structural characterization of the new synthetic cannabinoids CUMYL-PINACA, 5F-CUMYL-PINACA, CUMYL-4CN-BINACA, 5F-CUMYL-P7AICA and CUMYL-4CN-B7AICA | journal = Forensic Science International | volume = 281 | pages = 98–105 | date = December 2017 | pmid = 29125990 | doi = 10.1016/j.forsciint.2017.10.020 }}</ref><ref>{{cite journal|first1=Nevin Arıkan|last1=Ölmez|first2=Hicran|last2=Kapucu|first3=Neslihan Çallı|last3=Altun|first4=Bülent|last4=Eren|title=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|journal=Forensic Toxicology|date=January 2018|issn=1860-8965|pages=192–199|volume=36|issue=1|doi=10.1007/s11419-017-0372-y}}</ref><ref name=Åstrand>{{cite journal|first1=Anna|last1=Åstrand|first2=Svante|last2=Vikingsson|first3=Daniel|last3=Lindstedt|first4=Gunilla|last4=Thelander|title=Metabolism study for CUMYL-4CN-BINACA in human hepatocytes and authentic urine specimens: Free cyanide is formed during the main metabolic pathway|journal=Drug Testing and Analysis|volume=10|issue=8|pages=1270–1279|issn=1942-7611|doi=10.1002/dta.2373|pmid=29577658|date=2018|first5=Henrik|last5=Gréen|first6=Robert|last6=Kronstrand|first7=Ariane|last7=Wohlfarth}}</ref> It is a potent [[agonist]] for [[Cannabinoid receptor|cannabinoid receptors]] [[Cannabinoid receptor type 1|CB<sub>1</sub>]] and [[Cannabinoid receptor type 2|CB<sub>2</sub>]], with ''in vitro'' EC<sub>50</sub> values of 0.58 nM and 6.12 nM, respectively.<ref name=":0">{{Cite journal|last=Kevin|first=Richard|last2=Anderson|first2=Lyndsey|last3=McGregor|first3=Iain|last4=Boyd|first4=Rochelle|last5=Manning|first5=Jamie|last6=Glass|first6=Michelle|last7=Connor|first7=Mark|last8=Banister|first8=Samuel|title=CUMYL-4CN-BINACA is an efficacious and potent pro-convulsant synthetic cannabinoid receptor agonist|journal=Frontiers in Pharmacology|volume=10|pages=595|doi=10.3389/fphar.2019.00595|pmid=31191320|pmc=6549035|year=2019}}</ref> In mice, CUMYL-4CN-BINACA produces hypothermic and [[Convulsant|pro-convulsant]] effects via the CB<sub>1</sub> receptor,<ref name=":0" /> and anecdotal reports suggest it has an active dose of around 0.1 mg in humans.<ref>{{cite web|title=EMCDDA–Europol Joint Report on a new psychoactive substance: 1-(4-cyanobutyl)-N-(2-phenylpropan-2-yl)indazole-3-carboxamide (CUMYL-4CN-BINACA)|url=http://www.emcdda.europa.eu/publications/joint-reports/cumyl-4cn-binaca_en|website=www.emcdda.europa.eu}}</ref>


CUMYL-4CN-BINACA is metabolized to produce [[cyanide]], raising concerns about liver toxicity.<ref name=Åstrand/> There is one reported case of [[hyperthermia]], [[rhabdomyolysis]], and [[Kidney failure|renal failure]] associated with its use.<ref>{{Cite journal|last=El Zahran|first=Tharwat|date=August 2018|title=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|journal=Clinical Toxicology|language=en|volume=|pages=1–2|doi=10.1080/15563650.2018.1534241|pmid=30442067}}</ref>
CUMYL-4CN-BINACA is metabolized to produce [[cyanide]], raising concerns about liver toxicity.<ref name=Åstrand/> There is one reported case of [[hyperthermia]], [[rhabdomyolysis]], and [[Kidney failure|renal failure]] associated with its use.<ref>{{Cite journal|last=El Zahran|first=Tharwat|date=August 2018|title=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|journal=Clinical Toxicology|language=en|volume=57|issue=6|pages=421–422|doi=10.1080/15563650.2018.1534241|pmid=30442067}}</ref>


== See also ==
== See also ==

Revision as of 17:54, 19 July 2019

CUMYL-4CN-BINACA
Legal status
Legal status
Identifiers
  • 1-(4-Cyanobutyl)-N-(2-phenylpropan-2-yl)-1H-indazole-3-carboxamide
CAS Number
ChemSpider
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 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 renal failure associated with its use.[9]

See also

References

  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.
  6. ^ 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.
  7. ^ 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)
  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.
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