Cannabis Ruderalis

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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| IUPAC_name = 1-(4-Cyanobutyl)-N-(2-phenylpropan-2-yl)-1H-indazole-3-carboxamide
| IUPAC_name = 1-(4-Cyanobutyl)-''N''-(2-phenylpropan-2-yl)-1''H''-indazole-3-carboxamide
| image = CUMYL-4CN-BINACA.svg
| image = CUMYL-4CN-BINACA.svg
| width = 140px

<!--Clinical data-->
<!--Clinical data-->
| tradename =
| tradename =
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| pregnancy_US =
| pregnancy_US =
| pregnancy_category =
| pregnancy_category =
| legal_AU =
| legal_AU = S9
| legal_BR = F2
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-07-25}}</ref>
| legal_CA = Schedule II
| legal_CA = Schedule II
| legal_UK =
| legal_DE = Anlage II
| legal_US =
| legal_UK = Class B
| legal_US = Schedule I
| legal_UN = P II
| legal_UN_comment = <ref>{{Cite web |title=Substance Details CUMYL-4CN-BINACA |url=https://www.unodc.org/LSS/Substance/Details/c9a6b008-085a-4c8c-960a-ae1c3200ae25 |access-date=2024-01-22}}</ref>
| legal_status =
| legal_status =
| routes_of_administration =
| routes_of_administration =
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| CAS_number_Ref =
| CAS_number_Ref =
| CAS_number = 1631074-54-8
| CAS_number = 1631074-54-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = V6DM582RV1
| ATC_prefix =
| ATC_prefix =
| ATC_suffix =
| ATC_suffix =
| PubChem =
| PubChem = 117650402
| KEGG = C22722
| ChemSpiderID = 58190345
| ChemSpiderID = 58190345
| smiles = O=C(NC(C)(C)C1=CC=CC=C1)C2=NN(CCCCC#N)C3=C2C=CC=C3
| smiles = O=C(NC(C)(C)C1=CC=CC=C1)C2=NN(CCCCC#N)C3=C2C=CC=C3
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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|first1=Yeter Erol|last1=Öztürk|first2=Oya|last2=Yeter|first3=Serkan|last3=Öztürk|first4=Goksun|last4=Karakus|title=Detection of metabolites of the new synthetic cannabinoid CUMYL-4CN-BINACA in authentic urine samples and human liver microsomes using high-resolution mass spectrometry|url=http://onlinelibrary.wiley.com/doi/10.1002/dta.2248/abstract|journal=Drug Testing and Analysis|issn=1942-7611|pages=|doi=10.1002/dta.2248|pmid=28977413|first5=Ismail|last5=Ates|first6=Yalçın|last6=Buyuk|first7=Turkan|last7=Yurdun}}</ref><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><ref>{{cite journal|first1=Sandra N.|last1=Staeheli|first2=Michael|last2=Poetzsch|first3=Veronica P.|last3=Veloso|first4=Michael|last4=Bovens|title=In vitro metabolism of the synthetic cannabinoids CUMYL-PINACA, 5F–CUMYL-PINACA, CUMYL-4CN-BINACA, 5F–CUMYL-P7AICA and CUMYL-4CN-B7AICA|url=http://onlinelibrary.wiley.com/doi/10.1002/dta.2298/abstract|journal=Drug Testing and Analysisissn=1942-7611|pages=148–157|volume=10|issue=1|doi=10.1002/dta.2298|pmid=28885775|first5=Christian|last5=Bissig|first6=Andrea E.|last6=Steuer|first7=Thomas|last7=Kraemer}}</ref><ref>{{cite journal||first1=Michael|last1=Bovens|first2=Christian|last2=Bissig|first3=Sandra N.|last3=Staeheli|first4=Michael|last4=Poetzsch|title=Structural characterization of the new synthetic cannabinoids CUMYL-PINACA, 5F-CUMYL-PINACA, CUMYL-4CN-BINACA, 5F-CUMYL-P7AICA and CUMYL-4CN-B7AICA|url=https://www.sciencedirect.com/science/article/pii/S0379073817304218|journal=Forensic Science International|date=December 2017|issn=0379-0738|pages=98–105|volume=281|doi=10.1016/j.forsciint.2017.10.020|pmid=29125990|first5=Bernhard|last5=Pfeiffer|first6=Thomas|last6=Kraemer}}</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|url=https://link.springer.com/article/10.1007/s11419-017-0372-y|journal=Forensic Toxicology|date=January 2018|issn=1860-8965|pages=192–199|volume=36|issue=1|doi=10.1007/s11419-017-0372-y}}</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| vauthors = Arıkan Ölmez N, Kapucu H, Çallı Altun N, Eren B |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|s2cid=28058750}}</ref><ref name=Åstrand>{{cite journal | vauthors = Åstrand A, Vikingsson S, Lindstedt D, Thelander G, Gréen H, Kronstrand R, Wohlfarth A | 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 | date = March 2018 | pmid = 29577658 | doi = 10.1002/dta.2373 }}</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 | vauthors = Kevin RC, Anderson L, McGregor IS, Boyd R, Manning JJ, Glass M, Connor M, Banister SD | display-authors = 6 | title = CUMYL-4CN-BINACA Is an Efficacious and Potent Pro-Convulsant Synthetic Cannabinoid Receptor Agonist | journal = Frontiers in Pharmacology | volume = 10 | pages = 595 | year = 2019 | pmid = 31191320 | pmc = 6549035 | doi = 10.3389/fphar.2019.00595 | doi-access = free }}</ref> In mice, CUMYL-4CN-BINACA produces [[Hypothermia|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]] associated with its use.<ref>{{cite journal | vauthors = El Zahran T, Gerona R, Morgan BW, Pomerleau AC | 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<sup></sup> | journal = Clinical Toxicology | volume = 57 | issue = 6 | pages = 421–422 | date = June 2019 | pmid = 30442067 | doi = 10.1080/15563650.2018.1534241 | s2cid = 53566116 }}</ref>


==See also==
== See also ==
* [[4CN-AMB-BUTINACA]]
* [[5F-CUMYL-PINACA]]
* [[5F-CUMYL-PINACA]]
* [[5F-SDB-006]]
* [[5F-SDB-006]]
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* [[NNE1]]
* [[NNE1]]


==References==
== References ==
{{Reflist}}
{{Reflist}}


Latest revision as of 15:01, 22 January 2024

CUMYL-4CN-BINACA
Legal status
Legal status
Identifiers
  • 1-(4-Cyanobutyl)-N-(2-phenylpropan-2-yl)-1H-indazole-3-carboxamide
CAS Number
PubChem CID
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 as CUMYL-CYBINACA or SGT-78) is an indazole-3-carboxamide based synthetic cannabinoid that has been sold online as a designer drug.[3][4][5][6][7][8] 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.[9] In mice, CUMYL-4CN-BINACA produces hypothermic and pro-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 produce cyanide, raising concerns about liver toxicity.[8] There is one reported case of hyperthermia, rhabdomyolysis, and kidney 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. Retrieved 2023-08-27.
  2. ^ "Substance Details CUMYL-4CN-BINACA". Retrieved 2024-01-22.
  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. ^ a b Åstrand 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. ^ a b Kevin 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.
source: https://en.wikipedia.org/w/index.php?title=CUMYL-4CN-BINACA&diff=1197947844&oldid=828060103

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