Pyrazolam

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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
Legal status	Unlicensed
Routes	Oral, Sublingual, rectal, Intravenous
Pharmacokinetic data
Half-life	17 hours ?
Identifiers
CAS number	39243-02-2
ATC code	?
PubChem	CID 12562545
Chemical data
Formula	C₁₆H₁₂Br N₅
Mol. mass	354.204 g/mol
SMILES CC1=NN=C2CN=C(C3=NC=CC=C3)C3=CC(Br)=CC=C3N12

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 designer drug starting in 2012.^[2] It is mainly an anxiolytic, but it has also shown anticonvulsant and hypnotic effects and has structural similarity to alprazolam.^[3] Pyrazolam has no active metabolites^[4] and has activity 12x stronger than diazepam while causing little ataxia and sedation. It is most selective for the α2 and α3 receptor subtypes^[5] which means it causes less ataxia and sedation when taken at therapeutic doses.

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

↑ US Patent 3954728 Preparation of triazolo benzodiazepines and novel compounds
↑ 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.
↑ 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
↑ 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-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

v t e Benzodiazepine derivatives

1,4-Benzodiazepines	Bromazepam Camazepam Carburazepam Chlordiazepoxide Cinazepam Cinolazepam Clonazepam Clorazepate Cyprazepam Delorazepam Demoxepam Devazepide * Diazepam Diclazepam Doxefazepam Elfazepam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Flubromazepam Fletazepam Fludiazepam Flunitrazepam Flurazepam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Iclazepam Ketazolam Lorazepam Lormetazepam Lufuradom * Meclonazepam Medazepam Menitrazepam Metaclazepam Motrazepam Nimetazepam Nitrazepam Nitrazepate Nordazepam Nortetrazepam Oxazepam Phenazepam Pinazepam Pivoxazepam Prazepam Proflazepam Quazepam QH-II-66 Reclazepam RO4491533 * Ro5-2904 Ro5-4864 * Sulazepam Temazepam Tetrazepam Tifluadom * Tolufazepam Tuclazepam Uldazepam

1,5-Benzodiazepines	Arfendazam Clobazam CP-1414S Lofendazam Triflubazam

2,3-Benzodiazepines *	Girisopam GYKI-52466 GYKI-52895 Nerisopam Talampanel Tofisopam

Triazolobenzodiazepines	Adinazolam Alprazolam Estazolam Flubromazolam Pyrazolam Triazolam

Imidazobenzodiazepines	Bretazenil Climazolam FG-8205 Flumazenil Imidazenil Iomazenil (¹²³I) L-655,708 Loprazolam Midazolam PWZ-029 Remimazolam Ro15-4513 Ro48-6791 Ro48-8684 Ro4938581 Sarmazenil SH-053-R-CH3-2′F

Oxazolobenzodiazepines	Cloxazolam Flutazolam Haloxazolam Mexazolam Oxazolam

Thienodiazepines	Bentazepam Brotizolam Ciclotizolam Clotiazepam Etizolam JQ1 * Olanzapine *

Pyridodiazepines	Lopirazepam Zapizolam

Pyrazolodiazepines	Razobazam * Ripazepam Zolazepam Zomebazam Zometapine *

Pyrrolodiazepines	Premazepam

Tetrahydroisoquinobenzodiazepines	Clazolam

Benzodiazepine prodrugs	Avizafone Rilmazafone

* atypical activity profile (not GABA_A receptor ligands)

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