Pyrazolam

Pyrazolam
Pyrazolam-skeletal.svg
Clinical data
Routes of
administration
Oral, Sublingual, rectal
Legal status
Legal status
Pharmacokinetic data
Elimination half-life 17 hours
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
Formula C16H12BrN5
Molar mass 354.211 g·mol−1
3D model (JSmol)

Pyrazolam (SH-I-04)[1] is a benzodiazepine derivative originally developed by a team led by Leo Sternbach at Hoffman-La Roche in the 1970s,[2] and subsequently “rediscovered” and sold as a designer drug starting in 2012.[3][4][5][6][7]

Pyrazolam has structural similarities to alprazolam[8] and bromazepam. Unlike other benzodiazepines, pyrazolam does not appear to undergo metabolism, instead being excreted unchanged in the urine.[3][9] It is most selective for the α2 and α3 subtypes of the GABAA receptor.[10]

Legal Status[edit]

United Kingdom[edit]

In the UK, pyrazolam has been classified as a Class C drug by section 5 of the May 2017 amendment to The Misuse of Drugs Act 1971 along with several other designer benzodiazepine drugs.[11]

See also[edit]

References[edit]

  1. ^ Clayton T, et al. A Review of the Updated Pharmacophore for the Alpha 5 GABA(A) Benzodiazepine Receptor Model. Int J Med Chem. 2015; 2015: 430248. doi:10.1155/2015/430248 PMID 26682068
  2. ^ ‹See Tfd›US 3954728, ”Preparation of triazolo benzodiazepines and novel compounds” 
  3. ^ a b Moosmann, B.; Hutter, M.; Huppertz, L. M.; Ferlaino, S.; Redlingshöfer, L.; Auwärter, V. (July 2013). “Characterization of the designer benzodiazepine pyrazolam and its detectability in human serum and urine”. Forensic Toxicology. 31 (2): 263–271. doi:10.1007/s11419-013-0187-4.
  4. ^ Bjoern Moosmann; Leslie A King; Volker Auwärter (June 2015). “Designer benzodiazepines: A new challenge”. World Psychiatry. 14 (2): 248. doi:10.1002/wps.20236. PMC 4471986. PMID 26043347.
  5. ^ Madeleine Pettersson Bergstrand; Anders Helander; Therese Hansson; Olof Beck (2016). “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.
  6. ^ Høiseth, Gudrun; Tuv, Silja Skogstad; Karinen, Ritva (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.
  7. ^ Manchester, Kieran R.; Maskell, Peter D.; Waters, Laura (2018). “Experimental versus theoretical log D7.4, pKa and plasma protein binding values for benzodiazepines appearing as new psychoactive substances”. Drug Testing and Analysis. 10 (8): 1258–1269. doi:10.1002/dta.2387. ISSN 1942-7611. PMID 29582576.
  8. ^ Hester Jr, J. B.; Rudzik, A. D.; Kamdar, B. V. (November 1971). “6-Phenyl-4H-s-triazolo[4,3-a][l,4]benzodiazepines Which Have Central Nervous System Depressant Activity”. J. Med. Chem. 14 (11): 1078–1081. doi:10.1021/jm00293a015. PMID 5165540.
  9. ^ Characterization of the designer benzodiazepines pyrazolam and flubromazepam and study on their detectability in human serum and urine samples, B. Moosmann, M. Hutter, L. M. Huppertz and V. Auwärter
  10. ^ Hester, J. B.; von Voigtlander, P. (November 1979). “6-Aryl-4H-s-triazolo[4,3-a][1,4]benzodiazepines. Influence of 1-substitution on pharmacological activity”. Journal of Medicinal Chemistry. 22 (11): 1390–1398. doi:10.1021/jm00197a021. PMID 42799.
  11. ^ “The Misuse of Drugs Act 1971 (Amendment) Order 2017”.