Bromazolam

Bromazolam
Legal status
Legal status
Identifiers
  • 8-bromo-6-phenyl-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC17H13BrN4
Molar mass353.223 g·mol−1
3D model (JSmol)
  • Brc1cc2C(=NCc3nnc(C)n3c2cc1)c4ccccc4
  • InChI=1S/C17H13BrN4/c1-11-20-21-16-10-19-17(12-5-3-2-4-6-12)14-9-13(18)7-8-15(14)22(11)16/h2-9H,10H2,1H3
  • Key:KCEIOBKDDQAYCM-UHFFFAOYSA-N

Bromazolam (XLI-268) is a triazolobenzodiazepine (TBZD) which was first synthesised in 1976, but was never marketed.[2] It has subsequently been sold as a designer drug, first being definitively identified by the EMCDDA in Sweden in 2016.[3] It is the bromo instead of chloro analogue of alprazolam and has similar sedative and anxiolytic effects to it and other benzodiazepines.[4][5] Bromazolam is a non subtype selective agonist at the benzodiazepine site of GABAA receptors, with a binding affinity of 2.81 nM at the α1 subtype, 0.69 nM at α2 and 0.62 nM at α5.[6] The "common" dosage range for users of bromazolam was reported to be 1–2 mg, suggesting its potency is similar to alprazolam.[7]

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ Manchester KR, Lomas EC, Waters L, Dempsey FC, Maskell PD (January 2018). "The emergence of new psychoactive substance (NPS) benzodiazepines: A review". Drug Testing and Analysis. 10 (1): 37–53. doi:10.1002/dta.2211. PMID 28471096.
  3. ^ "Europol 2016 Annual Report on the implementation of Council Decision 2005/387/JHA. EMCDDA" (PDF). European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) and European Union Agency for Law Enforcement Cooperation (Europol). 2017.
  4. ^ 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". Science & Justice. 58 (3): 219–225. doi:10.1016/j.scijus.2017.12.004. PMID 29685303.
  5. ^ 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.
  6. ^ Clayton T, Poe MM, Rallapalli S, Biawat P, Savić MM, Rowlett JK, et al. (2015). "A Review of the Updated Pharmacophore for the Alpha 5 GABA(A) Benzodiazepine Receptor Model". International Journal of Medicinal Chemistry. 2015: 430248. doi:10.1155/2015/430248. PMC 4657098. PMID 26682068.
  7. ^ "Critical review report: Bromazolam" (PDF). 20 October 2023.