Chemistry:Isotonitazene

From HandWiki
Short description: Chemical compound
Isotonitazene
Isotonitazene.svg
Clinical data
Routes of
administration		By mouth, nasal spray, e-vape
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
Chemical and physical data
FormulaC23H30N4O3
Molar mass410.518 g·mol−1
3D model (JSmol)

Isotonitazene is a benzimidazole derived opioid analgesic drug related to etonitazene,[2][3][4] which has been sold as a designer drug.[5][6][7] It has only around half the potency of etonitazene in animal studies,[2][8][9][10][11][12][13] but it is likely even less potent in humans as was seen with etonitazene (1000 times as potent as morphine in animal models yet only 60 times as potent in humans).[2] Isotonitazene (obtained from an online vendor) was fully characterized in November 2019 in a paper where the authors performed a full analytical structure elucidation in addition to determination of the potency at the μ-opioid receptor using a biological functional assay in vitro. While isotonitazene was not compared directly to morphine in this assay, it was found to be around 2.5 times more potent than hydromorphone and slightly more potent than fentanyl.[2][14]

Side effects

Side effects of benzimidazole derived opioids are likely to be similar to those of fentanyl, which include itching, nausea and potentially serious respiratory depression, which can be life-threatening. [citation needed]

Isotonitazene has been detected in multiple fatalities in Europe since March 2019[15] and in the U.S. since August 2019, as reported by NPS Discovery, the Center for Forensic Science Research and Education, and NMS Labs.[16][17]

Legal status

The US Drug Enforcement Administration issued a notice of intent to publish a temporary order to schedule isotonitazene in Schedule I of the Controlled Substances Act,[18] which came into effect on 20 August 2020.[19]

See also

References

  1. ↑ Riksdagsförvaltningen. "Förordning (1992:1554) om kontroll av narkotika Svensk författningssamling 1992:1992:1554 t.o.m. SFS 2021:301 - Riksdagen". https://www.riksdagen.se/sv/dokument-lagar/dokument/svensk-forfattningssamling/forordning-19921554-om-kontroll-av-narkotika_sfs-1992-1554. 
  2. ↑ 2.0 2.1 2.2 2.3 "Report on a novel emerging class of highly potent benzimidazole NPS opioids: Chemical and in vitro functional characterization of isotonitazene". Drug Testing and Analysis 12 (4): 422–430. April 2020. doi:10.1002/dta.2738. PMID 31743619. 
  3. ↑ "Ionisation constants and partition coefficients of some analgesically active 2-benzylbenzimidazole derivatives and related compounds". The Journal of Pharmacy and Pharmacology 18 (10): 677–683. October 1966. doi:10.1111/j.2042-7158.1966.tb07782.x. PMID 4382076. 
  4. ↑ "DARK Classics in Chemical Neuroscience: Etonitazene and Related Benzimidazoles". ACS Chemical Neuroscience 12 (7): 1072–1092. April 2021. doi:10.1021/acschemneuro.1c00037. PMID 33760580. 
  5. ↑ "40 Americans Are Dying Every Month from Taking This New, Legal Opioid". Vice. 13 March 2020. https://www.vice.com/en_us/article/wxebjb/40-americans-are-dying-every-month-from-taking-this-new-legal-opioid. 
  6. ↑ "Isotonitazene as a contaminant of concern in the illegal opioid supply: A practical synthesis and cost perspective". The International Journal on Drug Policy 86: 102939. September 2020. doi:10.1016/j.drugpo.2020.102939. PMID 32977186. 
  7. ↑ "Critical Review Report: Isotonitazene". Expert Committee on Drug Dependence, Forty-third Meeting. Geneva: World Health Organization. 12–20 October 2020. p. 7. https://www.who.int/docs/default-source/controlled-substances/43rd-ecdd/isonitazene-43rd-final-complete-a.pdf. Retrieved 20 May 2022. "Street names: Iso; Nitazene; Toni" .
  8. ↑ "[Synthesis of analgesically active benzimidazole derivatives with basic substitutions]". Experientia 13 (10): 400–401. October 1957. doi:10.1007/BF02161116. PMID 13473817. 
  9. ↑ "Benzimidazol-Derivate und verwandte Heterocyclen. IV. Die Kondensation von o-Phenylendiamin mit α-Aryl- und γ-Aryl-acetessigester" (in German). Helvetica Chimica Acta 43 (4): 1046–1056. 1960. doi:10.1002/hlca.19600430413. https://www.scribd.com/doc/78122927/Benzimidazole-Derivatives-and-Related-Hetero-Cycles-IV-the-Condensation-of-O-phenylenediamine-With-a-And-Gamma-Aryl-Acetoacetate-Helv-Chim-Acta-19. 
  10. ↑ "Benzimidazol-Derivate und verwandte Heterocyclen V. Die Kondensation von o-Phenylendiamin mit aliphatischen und alicyclischen β-Ketoestern" (in German). Helvetica Chimica Acta 43 (5): 1298–1313. 1960. doi:10.1002/hlca.19600430515. https://www.scribd.com/doc/78122989/Benzimidazole-derivatives-and-related-heterocycles-V-The-condensation-of-o-phenylenediamine-with-aliphatic-and-alicyclic-%C3%9F-keto-esters-Helv-Chim-Ac. 
  11. ↑ "Benzimidazol-Derivate und verwandte Heterocyclen VI. Synthese von Phenyl-[1-aminoalkyl-benzimidazolyl-(2)-essigsäure-estern und -amiden"] (in German). Helvetica Chimica Acta 43 (6): 1727–1733. 1960. doi:10.1002/hlca.19600430634. https://www.scribd.com/doc/78122995/Benzimidazole-Derivatives-and-Related-Hetero-Cycles-VI-Synthesis-of-Phenyl-1-Aminoalkyl-benzimidazolyl-2-Acetic-Acid-Esters-and-Amides-Helv-Ch. 
  12. ↑ "Benzimidazol-Derivate und verwandte Heterocyclen VII. Synthese neuer 2-Amino-benzimidazole" (in German). Helvetica Chimica Acta 44 (5): 1273–1282. 1961. doi:10.1002/hlca.19610440513. https://www.scribd.com/doc/78123010/Benzimidazole-Derivatives-and-Related-Hetero-Cycles-VII-Synthesis-of-New-2-Amino-benzimidazole-Helv-Chim-Acta-1961-44-5-1273-1282. 
  13. ↑ "[Benzimidazole derivatives with strong analgesic effects]". Experientia 13 (10): 401–403. October 1957. doi:10.1007/BF02161117. PMID 13473818. 
  14. ↑ "In vitro functional characterization of a panel of non-fentanyl opioid new psychoactive substances". Archives of Toxicology 94 (11): 3819–3830. November 2020. doi:10.1007/s00204-020-02855-7. PMID 32734307. https://biblio.ugent.be/publication/8687070. 
  15. ↑ "Acute Intoxications and Fatalities Associated With Benzimidazole Opioid (Nitazene Analog) Use: A Systematic Review". Therapeutic Drug Monitoring 44 (4): 494–510. August 2022. doi:10.1097/FTD.0000000000000970. PMID 35149665. 
  16. ↑ "Isotonitazene Quantitation and Metabolite Discovery in Authentic Forensic Casework". Journal of Analytical Toxicology 44 (6): 521–530. July 2020. doi:10.1093/jat/bkaa016. PMID 32091095. 
  17. ↑ "Emerging Characteristics of Isotonitazene-Involved Overdose Deaths: A Case-Control Study". Journal of Addiction Medicine 15 (5): 429–431. November 2020. doi:10.1097/ADM.0000000000000775. PMID 33234804. 
  18. ↑ "Schedules of Controlled Substances: Temporary Placement of Isotonitazene in Schedule I". 18 June 2020. https://www.federalregister.gov/documents/2020/06/18/2020-12304/schedules-of-controlled-substances-temporary-placement-of-isotonitazene-in-schedule-i. 
  19. ↑ "Schedules of Controlled Substances: Temporary Placement of Isotonitazene in Schedule I". 20 August 2020. https://www.federalregister.gov/documents/2020/08/20/2020-17951/schedules-of-controlled-substances-temporary-placement-of-isotonitazene-in-schedule-i. 



Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Isotonitazene&oldid=3329793"