Pyrazolam

{{Short description|Benzodiazepine}}

{{Drugbox

| drug_name =

| IUPAC_name = 8-Bromo-1-methyl-6-(pyridin-2-yl)-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine

| image = Pyrazolam-skeletal.svg

| image_class = skin-invert-image

| width = 150

| tradename =

| pregnancy_category=

| legal_AU = S4(customs (prohibited imports) regulations 1956 - schedule 4, 1956)

| legal_CA = Schedule IV

| legal_DE = NpSG

| legal_UK = Class C

| legal_US = Unscheduled

| legal_status =

| routes_of_administration = Oral, Sublingual, rectal

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life = 17 hours

| excretion =

| CAS_number = 39243-02-2

| ATCvet =

| ATC_prefix =

| ATC_suffix =

| PubChem = 12562545

| ChemSpiderID = 15417688

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 8LH16383PK

| ChEMBL = 3246831

| C=16 | H=12 | Br=1 | N=5

| smiles = CC1=NN=C2CN=C(C3=NC=CC=C3)C3=CC(Br)=CC=C3N12

| StdInChI = 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

| StdInChIKey = BGRWSFIQQPVEML-UHFFFAOYSA-N

}}

Pyrazolam (SH-I-04){{cite journal | vauthors = Clayton T, Poe MM, Rallapalli S, Biawat P, Savić MM, Rowlett JK, Gallos G, Emala CW, Kaczorowski CC, Stafford DC, Arnold LA, Cook JM | display-authors = 6 | title = A Review of the Updated Pharmacophore for the Alpha 5 GABA(A) Benzodiazepine Receptor Model | journal = International Journal of Medicinal Chemistry | volume = 2015 | pages = 430248 | year = 2015 | pmid = 26682068 | pmc = 4657098 | doi = 10.1155/2015/430248 | doi-access = free }} is a benzodiazepine derivative originally developed by a team led by Leo Sternbach at Hoffman-La Roche in the 1970s.{{Cite patent | country=US |number= 3954728 | title =Preparation of triazolo benzodiazepines and novel compounds | inventor = Sternbach LH, Walser A | assign1 = Hoffmann La Roche Inc | gdate = 4 May 1976 | postscript = . }} It has since been "rediscovered" and sold as a designer drug since 2012.{{cite journal | date=July 2013 | vauthors = Moosmann B, Hutter M, Huppertz LM, Ferlaino S, Redlingshöfer L, Auwärter V | title=Characterization of the designer benzodiazepine pyrazolam and its detectability in human serum and urine | journal=Forensic Toxicology | volume=31 | issue=2 | pages=263–271 | doi=10.1007/s11419-013-0187-4| s2cid = 23273522 }}{{cite journal | vauthors = Moosmann B, King LA, Auwärter V | title = Designer benzodiazepines: A new challenge | journal = World Psychiatry | volume = 14 | issue = 2 | pages = 248 | date = June 2015 | pmid = 26043347 | pmc = 4471986 | doi = 10.1002/wps.20236 }}{{cite journal | vauthors = Pettersson Bergstrand M, Helander A, Hansson T, Beck O | title = Detectability of designer benzodiazepines in CEDIA, EMIT II Plus, HEIA, and KIMS II immunochemical screening assays | journal = Drug Testing and Analysis | volume = 9 | issue = 4 | pages = 640–645 | date = April 2017 | pmid = 27366870 | doi = 10.1002/dta.2003 }}{{cite journal | vauthors = Høiseth G, Tuv SS, Karinen R | title = Blood concentrations of new designer benzodiazepines in forensic cases | journal = Forensic Science International | volume = 268 | pages = 35–38 | date = November 2016 | pmid = 27685473 | doi = 10.1016/j.forsciint.2016.09.006 }}{{cite journal | vauthors = Manchester KR, Maskell PD, Waters L | title = Experimental versus theoretical log D_7.4 , pK_a and plasma protein binding values for benzodiazepines appearing as new psychoactive substances | journal = Drug Testing and Analysis | volume = 10 | issue = 8 | pages = 1258–1269 | date = March 2018 | pmid = 29582576 | doi = 10.1002/dta.2387 | url = https://rke.abertay.ac.uk/en/publications/527a634d-decc-4d3a-bdca-08659bb13ed6 }}{{cite journal | vauthors = Manchester KR, Waters L, Haider S, Maskell PD | title = The blood-to-plasma ratio and predicted GABA_A-binding affinity of designer benzodiazepines | journal = Forensic Toxicology | volume = 40 | issue = 2 | pages = 349–356 | date = July 2022 | pmid = 36454409 | pmc = 9715504 | doi = 10.1007/s11419-022-00616-y | s2cid = 247455284 }}{{Excessive citations inline|date=November 2021}}

Pyrazolam has structural similarities to alprazolam{{cite journal | vauthors = Hester JB, Rudzik AD, Kamdar BV | title = 6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines which have central nervous system depressant activity | journal = Journal of Medicinal Chemistry | volume = 14 | issue = 11 | pages = 1078–1081 | date = November 1971 | pmid = 5165540 | doi = 10.1021/jm00293a015 }} and bromazolam. Unlike other benzodiazepines, pyrazolam does not appear to undergo metabolism, instead being excreted unchanged in the urine.