Alprazolam triazolobenzophenone

Alprazolam prodrug

Alprazolam triazolobenzophenone
Identifiers

IUPAC name {2-[3-(Aminomethyl)-5-methyl-4H-1,2,4-triazol-4-yl]-5-chlorophenyl}(phenyl)methanone
CAS Number	69505-70-0^Y
PubChem CID	15567865
ChemSpider	48057672
UNII	SC7MXP4H26
CompTox Dashboard (EPA)	DTXSID60574454
Chemical and physical data
Formula	C₁₇H₁₅ClN₄O
Molar mass	326.78 g·mol⁻¹
3D model (JSmol)	Interactive image
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

Alprazolam triazolobenzophenone is a chemical compound that is 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 ketone. 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]

References

^ 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.
^ "Novel Benzodiazepines. A review of the evidence of use and harms of Novel Benzodiazepines" (PDF). Advisory Council on the Misuse of Drugs. April 2020.