Pyrazolam

Pyrazolam

Systematic (IUPAC) name
8-Bromo-1-methyl-6-(pyridin-2-yl)-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
Clinical data
Routes of administration	Oral, Sublingual, rectal
Legal status	CA: Schedule IV
Pharmacokinetic data
Biological half-life	17 hours
Identifiers
CAS Number	39243-02-2
PubChem	CID 12562545
ChemSpider	15417688
UNII	8LH16383PK
Chemical data
Formula	C16H12BrN5
Molar mass	354.204 g/mol
SMILES CC1=NN=C2CN=C(C3=NC=CC=C3)C3=CC(Br)=CC=C3N12
InChI InChI=1S/C16H12BrN5/c1-10-20-21-15-9-19-16(13-4-2-3-7-18-13)12-8-11(17)5-6-14(12)22(10)15/h2-8H,9H2,1H3 Key:BGRWSFIQQPVEML-UHFFFAOYSA-N

Pyrazolam is a benzodiazepine derivative originally developed by a team led by Leo Sternbach at Hoffman-La Roche in the 1970s,^[1] and subsequently "rediscovered" and sold as a designer drug and research chemical starting in 2012.^[2]

Pyrazolam has structural similarities to alprazolam^[3] and bromazepam. Unlike other benzodiazepines, pyrazolam does not appear to undergo metabolism, instead being excreted unchanged in the urine.^[2][4] It is most selective for the α₂ and α₃ subtypes of the GABA_A receptor.^[5]

References

1. US 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.
3. Hester Jr, J. B.; Rudzik, A. D.; Kamdar, B. V. (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.
4. 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
5. Hester, J. B.; von Voigtlander, P. (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. doi:10.1021/jm00197a021.