Flubromazolam
Flubromazolam.svg
Legal status
Legal status
Identifiers
  • 8-bromo-6-(2-fluorophenyl)-1-methyl-4H-[1,2,4]triazolo[4,3-a] [1,4]benzodiazepine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H12BrFN4
Molar mass371.213 g·mol−1
3D model (JSmol)
  • BrC1=CC3=C(C=C1)[N]2C(=NN=C2C)CN=C3C4=C(C=CC=C4)F
  • InChI=1S/C17H12BrFN4/c1-10-21-22-16-9-20-17(12-4-2-3-5-14(12)19)13-8-11(18)6-7-15(13)23(10)16/h2-8H,9H2,1H3 ☒N
  • Key:VXGSZBZQCBNUIP-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)

Flubromazolam (JYI-73) [2][3][4] is a triazolobenzodiazepine (TBZD), which are benzodiazepine (BZD) derivatives.[5][6][7][8][9][10][11] Flubromazolam is reputed to be highly potent, and concerns have been raised that clonazolam and flubromazolam in particular may pose comparatively higher risks than other designer benzodiazepines, due to their ability to produce strong sedation and amnesia at oral doses of as little as 0.5 mg.[12][13] Life-threatening adverse reactions have been observed at doses of only 3 mg of flubromazolam.[14]

Legal status

Sweden

Flubromazolam has been classified as an illegal substance in Sweden after seizures by customs and police, as well as indications from the EMCDDA of wider use as a recreational drug.[15]

Switzerland

Flubromazolam is illegal in Switzerland as of December 2015.[16]

United Kingdom

In the UK, flubromazolam has been classified as a Class C drug by the May 2017 amendment to The Misuse of Drugs Act 1971 along with several other designer benzodiazepine drugs.[17]

Australia

In Australia, flubromazolam is Schedule 9 under federal law.[18]

United States

Flubromazolam is controlled in Virginia. In December 2022 the DEA announced it might be placing Flubromazolam under temporary Schedule I status for 2 years starting on January 23, 2023. Unless the DEA submits to extend or place into permanent Schedule I status this order will expire on January 23, 2025. Bromazolam itself and the de-fluoro, chloro substituted analog Phenazolam was not included in this emergency scheduling action.[19]

See also

References

  1. ^ "(Proposed Rule) Schedules of Controlled Substances: Temporary Placement of Etizolam, Flualprazolam, Clonazolam, Flubromazolam, and Diclazepam in Schedule I". Drug Enforcement Administration. December 23, 2022.
  2. ^ Cook JM, et al. Stereospecific anxiolytic and anticonvulsant agents with reduced muscle-relaxant, sedative-hypnotic and ataxic effects. US7618958
  3. ^ Borer R, Gerecke M, Kyburz E (22 October 1986). "Patent EP 0072029 B1 - Triazolobenzazepines, process and intermediates for their preparation and medicines containing them". Retrieved 6 August 2015.
  4. ^ Hester JB, Rudzik AD, Kamdar BV (November 1971). "6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines which have central nervous system depressant activity". Journal of Medicinal Chemistry. 14 (11): 1078–81. doi:10.1021/jm00293a015. PMID 5165540.
  5. ^ "Flubromazolam". Cayman Chemical. Retrieved 20 November 2015.
  6. ^ Huppertz LM, Bisel P, Westphal F, Franz F, Auwärter V, Moosmann B (July 2015). "Characterization of the four designer benzodiazepines clonazolam, deschloroetizolam, flubromazolam, and meclonazepam, and identification of their in vitro metabolites". Forensic Toxicology. 33 (2): 388–395. doi:10.1007/s11419-015-0277-6. S2CID 33278305.
  7. ^ Chaslot M, El Balkhi S, Robin T, Morichon J, Picard N, Saint-Marcoux F (June 2016). "Exploration des métabolites de 8 benzodiazépines de synthèse". Toxicologie Analytique et Clinique. 28 (2): S32. doi:10.1016/j.toxac.2016.03.053.
  8. ^ Pettersson Bergstrand M, Helander A, Hansson T, Beck O (April 2017). "Detectability of designer benzodiazepines in CEDIA, EMIT II Plus, HEIA, and KIMS II immunochemical screening assays". Drug Testing and Analysis. 9 (4): 640–645. doi:10.1002/dta.2003. PMID 27366870.
  9. ^ Høiseth G, Tuv SS, Karinen R (November 2016). "Blood concentrations of new designer benzodiazepines in forensic cases". Forensic Science International. 268: 35–38. doi:10.1016/j.forsciint.2016.09.006. PMID 27685473.
  10. ^ Manchester KR, Maskell PD, Waters L (March 2018). "Experimental versus theoretical log D7.4, pKa and plasma protein binding values for benzodiazepines appearing as new psychoactive substances" (PDF). Drug Testing and Analysis. 10 (8): 1258–1269. doi:10.1002/dta.2387. PMID 29582576.
  11. ^ Wohlfarth, Ariane; Vikingsson, Svante; Roman, Markus; Andersson, Mikael; Kugelberg, Fredrik C.; Green, Henrik; Kronstrand, Robert (May 2017). "Looking at flubromazolam metabolism from four different angles: Metabolite profiling in human liver microsomes, human hepatocytes, mice and authentic human urine samples with liquid chromatography high-resolution mass spectrometry". Forensic Science International. Special Issue on the 54th Annual Meeting of the International Association of Forensic Toxicologists (TIAFT) Brisbane from August 28 to September 1, 2016. 274: 55–63. doi:10.1016/j.forsciint.2016.10.021. ISSN 0379-0738. PMID 27863836.
  12. ^ Moosmann B, King LA, Auwärter V (June 2015). "Designer benzodiazepines: A new challenge". World Psychiatry. 14 (2): 248. doi:10.1002/wps.20236. PMC 4471986. PMID 26043347.
  13. ^ Huppertz, Laura M.; Moosmann, Bjoern; Auwärter, Volker (January 2018). "Flubromazolam – Basic pharmacokinetic evaluation of a highly potent designer benzodiazepine". Drug Testing and Analysis. 10 (1): 206–211. doi:10.1002/dta.2203. ISSN 1942-7611. PMID 28378533.
  14. ^ Łukasik-Głębocka M, Sommerfeld K, Teżyk A, Zielińska-Psuja B, Panieński P, Żaba C (2016). "Flubromazolam--A new life-threatening designer benzodiazepine". Clinical Toxicology. 54 (1): 66–8. doi:10.3109/15563650.2015.1112907. PMID 26585557. S2CID 4114360.
  15. ^ "Fler ämnen föreslås bli klassade som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten.
  16. ^ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Der Bundesrat.
  17. ^ "The Misuse of Drugs Act 1971 (Amendment) order 2017". Retrieved 4 April 2023.
  18. ^ Scheduling proposals referred to the November 2015 meeting of the Advisory Committee on Medicines Scheduling (ACMS#16) 2.6 Flubromazolam
  19. ^ "Schedules of Controlled Substances: Temporary Placement of Etizolam, Flualprazolam, Clonazolam, Flubromazolam, and Diclazepam in Schedule I". Federal Register. 23 December 2022. Retrieved 4 April 2023.
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