Flualprazolam

Flualprazolam is a tranquilizer of the triazolobenzodiazepine (TBZD) class, which are benzodiazepines (BZDs) fused with a triazole ring. It was first synthesised in 1976,[2] but was never marketed. It has subsequently been sold as a designer drug,[3][4][5][6] first being definitively identified as such in Sweden in 2018.[7][8] It can be described as the 2'-fluoro derivative of alprazolam or the fluoro instead of chloro analogue of triazolam, and has similar sedative and anxiolytic effects.[9][10][11][12][13]

Flualprazolam
Legal status
Legal status
Identifiers
IUPAC name
  • 8-chloro-6-(2-fluorophenyl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC17H12ClFN4
Molar mass326.76 g·mol−1
3D model (JSmol)
SMILES
  • CC1=NN=C2N1C3=C(C=C(C=C3)Cl)C(=NC2)C4=CC=CC=C4F
InChI
  • InChI=1S/C17H12ClFN4/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
  • Key:MPZVLJCMGPYWQQ-UHFFFAOYSA-N

Flualprazolam is banned in Sweden, also is illegal in the UK.[14] In December 2019, the World Health Organization recommended flualprazolam for international scheduling as a Schedule IV medication under the Convention on Psychotropic Substances.[15]

See also

References
  1. https://www.oregon.gov/pharmacy/Documents/Permanently_Adopted_TrackedChanges_Div_041_Div_080_BP_8-2020.pdf
  2. US 3987052, Hester JB, et al., "6-Phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines."
  3. Wagmann L, Manier SK, Bambauer TP, Felske C, Eckstein N, Flockerzi V, Meyer MR (February 2020). "Toxicokinetics and analytical toxicology of flualprazolam: metabolic fate, isozyme mapping, human plasma concentration, and main urinary excretion products". Journal of Analytical Toxicology. 44 (6): 549–558. doi:10.1093/jat/bkaa019. PMID 32104896.
  4. Papsun, Donna M.; Krotulski, Alex J.; Homan, Joe; Temporal, Keith D. H.; Logan, Barry K. (June 2020). "Flualprazolam Blood Concentrations in 197 Forensic Investigation Cases". Journal of Analytical Toxicology. 45 (3): 226–232. doi:10.1093/jat/bkaa070. PMID 32542312.
  5. Rice, Kathleen; Hikin, Laura; Lawson, Alexander; Smith, Paul R.; Morley, Stephen (August 2020). "Quantification of Flualprazolam in Blood by LC–MS-MS: A Case Series of Nine Deaths". Journal of Analytical Toxicology. 45 (4): 410–416. doi:10.1093/jat/bkaa098. PMID 32780842.
  6. Ling, Jiang; Zhang, Wenqi; Yan, Xiaojun; Liu, Wenlong; Wang, Yanyan; Ding, Yanjun (August 2022). "Sensitive detection and primary metabolism analysis of flualprazolam in blood". Journal of Forensic and Legal Medicine. 90: 102388. doi:10.1016/j.jflm.2022.102388. ISSN 1752-928X. PMID 35691207.
  7. Svenska Narkotika Polisföreningens Tidskrift, June 1 2018
  8. Kriikku P, Rasanen I, Ojanperä I, Thelander G, Kronstrand R, Vikingsson S (February 2020). "Femoral blood concentrations of flualprazolam in 33 postmortem cases". Forensic Science International. 307: 110101. doi:10.1016/j.forsciint.2019.110101. hdl:10138/323513. PMID 31865266. S2CID 209448865.
  9. Waters L, Manchester KR, Maskell PD, Haegeman C, Haider S (May 2018). "The use of a quantitative structure-activity relationship (QSAR) model to predict GABA-A receptor binding of newly emerging benzodiazepines" (PDF). Science & Justice. 58 (3): 219–225. doi:10.1016/j.scijus.2017.12.004. PMID 29685303.
  10. Zawilska JB, Wojcieszak J (July 2019). "An expanding world of new psychoactive substances-designer benzodiazepines". Neurotoxicology. 73: 8–16. doi:10.1016/j.neuro.2019.02.015. PMID 30802466. S2CID 73461430.
  11. Moosmann B, Auwärter V (October 2018). "Designer Benzodiazepines: Another Class of New Psychoactive Substances". Handbook of Experimental Pharmacology. Springer International Publishing. 252: 383–410. doi:10.1007/164_2018_154. ISBN 978-3-030-10561-7. PMID 30367253.
  12. Chetraru E, Ameline A, Gheddar L, Raul JS, Kintz P (February 2018). "Les "designer benzodiazepines" : qu'en sait-on aujourd'hui ?". Toxicologie Analytique et Clinique. 30 (1): 5–18. doi:10.1016/j.toxac.2017.12.001. ISSN 2352-0078.
  13. Mei V, Concheiro M, Pardi J, Cooper G (October 2019). "Validation of an LC-MS/MS Method for the Quantification of 13 Designer Benzodiazepines in Blood". Journal of Analytical Toxicology. 43 (9): 688–695. doi:10.1093/jat/bkz063. PMID 31436813.
  14. Riksdagsförvaltningen. "Förordning (1992:1554) om kontroll av narkotika". riksdagen.se (in Swedish).
  15. "News: December 2019 – WHO: World Health Organization recommends 12 NPS for scheduling". www.unodc.org.
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