Pyrazolam

Pyrazolam

Clinical data
Routes of administration	Oral, Sublingual, rectal
Legal status
Legal status	CA: Schedule IV
Pharmacokinetic data
Biological half-life	17 hours
Identifiers
IUPAC name 8-Bromo-1-methyl-6-(pyridin-2-yl)-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
CAS Number	39243-02-2
PubChem (CID)	12562545
ChemSpider	15417688
UNII	8LH16383PK
ChEMBL	CHEMBL3246831
Chemical and physical data
Formula	C16H12BrN5
Molar mass	354.204 g/mol
3D model (Jmol)	Interactive image
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 starting in 2012.^[2][3][4][5]

Pyrazolam has structural similarities to alprazolam^[6] and bromazepam. Unlike other benzodiazepines, pyrazolam does not appear to undergo metabolism, instead being excreted unchanged in the urine.^[2][7] It is most selective for the α₂ and α₃ subtypes of the GABA_A receptor.^[8]

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. (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.
3. 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.
4. 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. doi:10.1002/dta.2003. PMID 27366870.
5. Høiseth, Gudrun; Tuv, Silja Skogstad; Karinen, Ritva (2016). "Blood concentrations of new designer benzodiazepines in forensic cases". Forensic Science International. doi:10.1016/j.forsciint.2016.09.006.
6. 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.
7. 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
8. 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.