Alprazolam triazolobenzophenone

Alprazolam triazolobenzophenone is a chemical compound which can be both a synthetic precursor and a prodrug for the benzodiazepine derivative alprazolam. At neutral pH it readily cyclizes to alprazolam, while in acidic conditions alprazolam undergoes a ring-opening reaction back to the triazolobenzophenone. A series of related acyl derivatives was researched in the 1980s as injectable water-soluble prodrugs of alprazolam,[1] but were never developed for medical use. Subsequently, this compound has been detected as a designer drug, first being identified from a seizure in Spain in March 2014.[2]

Alprazolam triazolobenzophenone
Identifiers
IUPAC name
  • {2-[3-(Aminomethyl)-5-methyl-4H-1,2,4-triazol-4-yl]-5-chlorophenyl}(phenyl)methanone
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H15ClN4O
Molar mass326.8 g·mol−1
3D model (JSmol)
SMILES
  • CC1=NN=C(N1C2=C(C=C(C=C2)Cl)C(=O)C3=CC=CC=C3)CN
InChI
  • InChI=1S/C17H15ClN4O/c1-11-20-21-16(10-19)22(11)15-8-7-13(18)9-14(15)17(23)12-5-3-2-4-6-12/h2-9H,10,19H2,1H3
  • Key:WWADXOXMCNJJKR-UHFFFAOYSA-N

See also

References
  1. Cho MJ, Sethy VH, Haynes LC (August 1986). "Sequentially labile water-soluble prodrugs of alprazolam". Journal of Medicinal Chemistry. 29 (8): 1346–50. doi:10.1021/jm00158a004. PMID 3016261.
  2. "Novel Benzodiazepines. A review of the evidence of use and harms of Novel Benzodiazepines" (PDF). Advisory Council on the Misuse of Drugs. April 2020.
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