Alprazolam triazolobenzophenone

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

[edit]

^ 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.

v t e Benzodiazepines
1,4-Benzodiazepines	2-Oxoquazepam 3-Hydroxyphenazepam Bromazepam BMS-906024* Camazepam Carburazepam Chlordiazepoxide Cinazepam Cinolazepam Clonazepam Cloniprazepam Clorazepate Cyprazepam Delorazepam Demoxepam Desmethylflunitrazepam Devazepide* Diazepam Diclazepam Difludiazepam Doxefazepam Elfazepam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Flubromazepam Fletazepam Fludiazepam Flunitrazepam Flurazepam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Iclazepam Irazepine* Kenazepine Ketazolam Lorazepam Lormetazepam Lufuradom* Meclonazepam Medazepam Menitrazepam Metaclazepam Motrazepam N-Desalkylflurazepam Nifoxipam Nimetazepam Nitemazepam Nitrazepam Nitrazepate Nordazepam Nortetrazepam Oxazepam Phenazepam Pinazepam Pivoxazepam Prazepam Proflazepam Quazepam QH-II-66 Reclazepam RO4491533* Ro05-4082 Ro5-4864* Ro07-5220 Ro07-9749 Ro20-8065 Ro20-8552 SH-I-048A Sulazepam Temazepam Tetrazepam Tifluadom* Timelotem* Tolufazepam Triflunordazepam Tuclazepam Uldazepam
1,5-Benzodiazepines	Arfendazam Clobazam CP-1414S Lofendazam Triflubazam
2,3-Benzodiazepines*	Girisopam GYKI-52466 GYKI-52895 Nerisopam Talampanel Tofisopam
Triazolobenzodiazepines	Adinazolam Alprazolam Balovaptan* Bromazolam Clonazolam Estazolam Fluadinazolam Flualprazolam Flubromazolam Flunitrazolam Nitrazolam Phenazolam Pyrazolam Rilmazolam (active metabolite of Rilmazafone) Triazolam
Imidazobenzodiazepines	Bretazenil Climazolam EVT-201 FG-8205 Flumazenil GL-II-73 Imidazenil ¹²³I-Iomazenil L-655,708 Loprazolam Midazolam PWZ-029 Remimazolam Ro15-4513 Ro48-6791 Ro48-8684 Ro4938581 Sarmazenil SH-053-R-CH3-2′F
Oxazolobenzodiazepines	Cloxazolam Flutazolam Haloxazolam Mexazolam Oxazolam
Thienodiazepines	Bentazepam Clotiazepam Ro09-9212
Thienotriazolodiazepines	α-Hydroxyetizolam Apafant* Brotizolam Ciclotizolam Clotizolam Deschloroclotizolam Deschloroetizolam Etizolam Flubrotizolam Fluclotizolam Fluetizolam Israpafant* JQ1* Metizolam
Thienobenzodiazepines*	Olanzapine Telenzepine
Pyridodiazepines	Lopirazepam
Pyridotriazolodiazepines	Zapizolam
Pyrazolodiazepines	Razobazam* Ripazepam Zolazepam Zomebazam Zometapine*
Pyrrolodiazepines	Premazepam
Tetrahydroisoquinobenzodiazepines	Clazolam
Pyrrolobenzodiazepines*	Anthramycin
Benzodiazepine prodrugs	Alprazolam triazolobenzophenone Avizafone Rilmazafone
* atypical activity profile (not GABA_A receptor ligands)

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See also

References