Isotonitazene

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Isotonitazene
Legal status
Legal status
Identifiers
  • N,N-diethyl-2-[2-[(4-isopropoxyphenyl)methyl]-5-nitro-benzimidazol-1-yl]ethanamine
CAS Number
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H30N4O3
Molar mass410.518 g·mol−1
3D model (JSmol)
  • CCN(CCn1c(Cc2ccc(cc2)OC(C)C)nc2c1ccc(c2)N(=O)=O)CC
  • InChI=1S/C23H30N4O3/c1-5-25(6-2)13-14-26-22-12-9-19(27(28)29)16-21(22)24-23(26)15-18-7-10-20(11-8-18)30-17(3)4/h7-12,16-17H,5-6,13-15H2,1-4H3
  • Key:OIOQREYBGDAYGT-UHFFFAOYSA-N

Isotonitazene is a benzimidazole derived opioid analgesic drug related to etonitazene[1], which has been sold as a designer drug.[2] It has only around half the potency of etonitazene in animal studies,[3][4][5][6][7][8] but this still makes it a similar strength to fentanyl and its analogues, and consequently isotonitazene can be expected[by whom?] to pose a significant risk of producing life-threatening respiratory depression, as well as other typical opioid side effects such as sedation, itching, nausea and vomiting.

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 2.5x more potent than hydromorphone and slightly more potent than fentanyl.[9]

Side effects

Side effects of benzimidazole derived opioids are expected[by whom?] 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 the US since August 2019.[10]

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.[11]

See also

References

  1. ^ Casy, A. F.; Wright, J. (October 1966). "Ionisation constants and partition coefficients of some analgesically active 2-benzylbenzimidazole derivatives and related compounds". Journal of Pharmacy and Pharmacology. 18 (10): 677–683. doi:10.1111/j.2042-7158.1966.tb07782.x. ISSN 2042-7158. PMID 4382076.
  2. ^ Power M. 40 Americans Are Dying Every Month From Taking this New, Legal Opioid. 2020 Mar 13. Vice.com
  3. ^ Hunger A, Kebrle J, Rossi A, Hoffmann K (October 1957). "[Synthesis of analgesically active benzimidazole derivatives with basic substitutions]" [Synthesis of analgesically active benzimidazole derivatives with basic substitutions]. Experientia. 13 (10): 400–1. doi:10.1007/BF02161116. PMID 13473817.
  4. ^ Rossi A, Hunger A, Kebrle J, Hoffmann K (1960). "Benzimidazol-Derivate und verwandte Heterocyclen. IV. Die Kondensation von o-Phenylendiamin mit α-Aryl- und γ-Aryl-acetessigester" [Benzimidazole derivatives and related heterocycles IV. The condensation of o-phenylenediamine with α-aryl and γ-aryl-acetoacetate]. Helvetica Chimica Acta (in German). 43 (4): 1046–1056. doi:10.1002/hlca.19600430413.
  5. ^ Rossi A, Hunger A, Kebrle J, Hoffmann K (1960). "Benzimidazol-Derivate und verwandte Heterocyclen V. Die Kondensation von o-Phenylendiamin mit aliphatischen und alicyclischen β-Ketoestern" [Benzimidazole derivatives and related heterocycles V. The condensation of o-phenylenediamine with aliphatic and alicyclic β-keto esters]. Helvetica Chimica Acta (in German). 43 (5): 1298–1313. doi:10.1002/hlca.19600430515.
  6. ^ Rossi A, Hunger A, Kebrle J, Hoffmann K (1960). "Benzimidazol-Derivate und verwandte Heterocyclen VI. Synthese von Phenyl-[1-aminoalkyl-benzimidazolyl-(2)]-essigsäure-estern und -amiden" [Benzimidazole derivatives and related Heterocycles VI. Synthesis of phenyl-[1-aminoalkyl-benzimidazolyl-(2)]-acetic acid esters and amides]. Helvetica Chimica Acta (in German). 43 (6): 1727–1733. doi:10.1002/hlca.19600430634.
  7. ^ Rossi A, Hunger A, Kebrle J, Hoffmann K (1961). "Benzimidazol-Derivate und verwandte Heterocyclen VII. Synthese neuer 2-Amino-benzimidazole" [Benzimidazole Derivatives and related Heterocycles VII. Synthesis of new 2-amino-benzimidazole]. Helvetica Chimica Acta (in German). 44 (5): 1273–1282. doi:10.1002/hlca.19610440513.
  8. ^ Gross F, Turrian H (October 1957). "Über Benzimidazolderivate mit starker analgetischer Wirkung" [Benzimidazole derivatives with strong analgesic effects]. Experientia. 13 (10): 401–3. doi:10.1007/BF02161117. PMID 13473818.
  9. ^ Blanckaert, Peter; Cannaert, Annelies; Uytfanghe, Katleen Van; Hulpia, Fabian; Deconinck, Eric; Calenbergh, Serge Van; Stove, Christophe (2019). "Report on a novel emerging class of highly potent benzimidazole NPS opioids: chemical and in vitro functional characterization of isotonitazene". Drug Testing and Analysis. n/a (n/a). doi:10.1002/dta.2738. ISSN 1942-7611.
  10. ^ Krotulski, Alex J.; Papsun, Donna M.; Kacinko, Sherri L.; Logan, Barry K. (February 2020). "Isotonitazene Quantitation and Metabolite Discovery in Authentic Forensic Casework". Journal of Analytical Toxicology. doi:10.1093/jat/bkaa016. PMID 32091095.
  11. ^ "Schedules of Controlled Substances: Temporary Placement of Isotonitazene in Schedule I". Federal Register. 18 June 2020.
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