Pyrazolam

Last updated
Pyrazolam
Pyrazolam-skeletal.svg
Clinical data
Routes of
administration 		Oral, Sublingual, rectal
Legal status
Legal status
Pharmacokinetic data
Elimination half-life 17 hours
Identifiers
  • 8-Bromo-1-methyl-6-(pyridin-2-yl)-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C16H12BrN5
Molar mass 354.211 g·mol−1
3D model (JSmol)
  • CC1=NN=C2CN=C(C3=NC=CC=C3)C3=CC(Br)=CC=C3N12
  • 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 (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 ]

Contents

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]

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

Pyrazolam synthesis.svg

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

References

  1. ↑ (customs (prohibited imports) regulations 1956 - schedule 4, 1956)
  2. ↑ Clayton T, Poe MM, Rallapalli S, Biawat P, Savić MM, Rowlett JK, et al. (2015). "A Review of the Updated Pharmacophore for the Alpha 5 GABA(A) Benzodiazepine Receptor Model". International Journal of Medicinal Chemistry. 2015: 430248. doi: 10.1155/2015/430248 . PMC   4657098 . PMID   26682068.
  3. ↑ US 3954728,Sternbach LH, Walser A,"Preparation of triazolo benzodiazepines and novel compounds",issued 4 May 1976, assigned to Hoffmann La Roche Inc.
  4. 1 2 Moosmann B, Hutter M, Huppertz LM, 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. S2CID   23273522.
  5. ↑ Moosmann B, King LA, Auwärter V (June 2015). "Designer benzodiazepines: A new challenge". World Psychiatry. 14 (2): 248. doi:10.1002/wps.20236. PMC   4471986 . PMID   26043347.
  6. ↑ Pettersson Bergstrand M, Helander A, Hansson T, Beck O (April 2017). "Detectability of designer benzodiazepines in CEDIA, EMIT II Plus, HEIA, and KIMS II immunochemical screening assays". Drug Testing and Analysis. 9 (4): 640–645. doi:10.1002/dta.2003. PMID   27366870.
  7. ↑ Høiseth G, Tuv SS, Karinen R (November 2016). "Blood concentrations of new designer benzodiazepines in forensic cases". Forensic Science International. 268: 35–38. doi:10.1016/j.forsciint.2016.09.006. PMID   27685473.
  8. ↑ Manchester KR, Maskell PD, Waters L (March 2018). "Experimental versus theoretical log D7.4 , pKa and plasma protein binding values for benzodiazepines appearing as new psychoactive substances". Drug Testing and Analysis. 10 (8): 1258–1269. doi:10.1002/dta.2387. PMID   29582576.
  9. ↑ Manchester KR, Waters L, Haider S, Maskell PD (July 2022). "The blood-to-plasma ratio and predicted GABAA-binding affinity of designer benzodiazepines". Forensic Toxicology. 40 (2): 349–356. doi:10.1007/s11419-022-00616-y. PMC   9715504 . PMID   36454409. S2CID   247455284.
  10. ↑ Hester JB, Rudzik AD, Kamdar BV (November 1971). "6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines which have central nervous system depressant activity". Journal of Medicinal Chemistry. 14 (11): 1078–1081. doi:10.1021/jm00293a015. PMID   5165540.
  11. ↑ "The Misuse of Drugs Act 1971 (Amendment) Order 2017". legislation.gov.uk.
  12. ↑ "Controlled Substances List" (PDF). Alabama Public Health. February 22, 2024.
  13. ↑ Leo Henryk Sternbach & Armin Walser, U.S. patent 3,954,728 (1976 to Hoffmann La Roche Inc).
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