Pyrazolam

Pyrazolam (SH-I-04)^[2] is a benzodiazepine derivative originally developed by a team led by Leo Sternbach at Hoffman-La Roche in the 1970s.^[3] It has since been "rediscovered" and sold as a designer drug since 2012.^{[4][5][6][7][8][9][excessive citations]}

Pyrazolam

Clinical data
Routes of administration	Oral, Sublingual, rectal
Legal status
Legal status	AU: S4[1] CA: Schedule IV DE: NpSG (Industrial and scientific use only) UK: Class C US: Unscheduled
Pharmacokinetic data
Elimination 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
CompTox Dashboard (EPA)	DTXSID101043303
Chemical and physical data
Formula	C16H12BrN5
Molar mass	354.211 g·mol−1
3D model (JSmol)	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 has structural similarities to alprazolam^[10] and bromazolam. Unlike other benzodiazepines, pyrazolam does not appear to undergo metabolism, instead being excreted unchanged in the urine.^[4]

Legal status

United Kingdom

In the UK, pyrazolam has been classified as a Class C drug by section 5 of the May 2017 amendment to The Misuse of Drugs Act 1971 along with several other designer benzodiazepine drugs.^[11]

United States

Unscheduled at the federal level.

Alabama made Pyrazolam a schedule I substance on March 18th, 2014.^[12]

Synthesis

The condensation of bromazepam (1) with methylamine and titanium tetrachloride gives the amidine (2). Treatment with nitrous acid gives the nitrosylation product (3). Further reaction with hydrazine gives (4), which is treated with triethyl orthoacetate to complete the synthesis of pyrazolam.^[13]

See also

• List of benzodiazepines
• Pyeazolam
• Pynazolam