Pyrazolam

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Pyrazolam
Pyrazolam-skeletal.svg
Systematic (IUPAC) name
8-bromo-1-methyl-6-(pyridin-2-yl)-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
Clinical data
Legal status
  • Legal
Routes Oral, Sublingual, rectal
Pharmacokinetic data
Half-life 17 hours
Identifiers
CAS number 39243-02-2
ATC code ?
PubChem CID 12562545
ChemSpider 15417688
Chemical data
Formula C16H12BrN5 
Mol. mass 354.204 g/mol

Pyrazolam is a benzodiazepine derivative originally developed by a team lead by Leo Sternbach at Hoffman-La Roche in the 1970s,[1] and subsequently "rediscovered" and sold as a research chemical starting in 2012.[2] It is mainly an anxiolytic, but it has also shown anticonvulsant and hypnotic effects at high doses. Pyrazolam has structural similarities to alprazolam[3] Unlike other benzodiazepines pyrazolam does not appear to undergo metabolism, instead being excreted unchanged in the urine, no metabolites have been found in the urine of volunteers [4][5] and has anxiolytic activity 12x stronger than diazepam while causing little ataxia and sedation when used in its anxiolytic dose range. It is most selective for the α2 and α3 receptor subtypes[6]

Binding data (GABA):[citation needed]

α1 3.84±0.25
α2 1.31±0.19
α3 1.48±0.21
α5 3.72±0.32

References[edit]

  1. ^ US Patent 3954728 Preparation of triazolo benzodiazepines and novel compounds
  2. ^ Moosmann, B.; Hutter, M.; Huppertz, L. M.; Ferlaino, S.; Redlingshöfer, L.; Auwärter, V. (2013). "Characterization of the designer benzodiazepine pyrazolam and its detectability in human serum and urine". Forensic Toxicology 31 (2): 263. doi:10.1007/s11419-013-0187-4.  edit
  3. ^ 6-Phenyl-4H-s-triazolo[4,3-a][l,4]benzodiazepines Which Have Central Nervous System Depressant Activity J. Med. CHem Vol 14, No 11 Pages 1078-1081
  4. ^ http://www.uniklinik-freiburg.de/fileadmin/mediapool/08_institute/rechtsmedizin/pdf/Poster2013/Mossmann_DPHG2013.pdf>
  5. ^ Characterization of the designer benzodiazepine pyrazolam and its detectability in human serum and urine - Forensic Toxicology July 2013, Volume 31, Issue 2, pp 263-271
  6. ^ 6-Aryl-4H-s-triazolo[4,3-a][1,4]benzodiazepines. Influence of 1-substitution on pharmacological activity - J. Med. Chem., 1979, 22 (11), pp 1390–1398

Further reading[edit]

List of relevant reviews at Pubmed