upChemical structure of alprazolam, a common triazolobenzodiazepine
Triazolobenzodiazepines (TBZD) are a class of
benzodiazepine
Benzodiazepines (BZD, BDZ, BZs), sometimes called "benzos", are a class of depressant drugs whose core chemical structure is the fusion of a benzene ring and a diazepine ring. They are prescribed to treat conditions such as anxiety disorders, ...
(BZD) derivative pharmaceutical drugs. Chemically, they differ from other benzodiazepines by having an additional fused
triazole
A triazole is a heterocyclic compound featuring a five-membered ring of two carbon atoms and three nitrogen atoms with molecular formula C2H3N3. Triazoles exhibit substantial isomerism, depending on the positioning of the nitrogen atoms within t ...
ring.
Examples include:
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Adinazolam
AdinazolamFR Patent 2248050 (marketed under the brand name Deracyn) is a tranquilizer of the triazolobenzodiazepine (TBZD) class, which are benzodiazepines (BZDs) fused with a triazole ring. It possesses anxiolytic, anticonvulsant, sedative, and ...
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Alprazolam
Alprazolam, sold under the brand name Xanax, among others, is a fast-acting, potent tranquilizer of medium duration in the triazolobenzodiazepine (TBZD) class, which are benzodiazepines (BZDs) fused with a triazole ring. It is most commonly u ...
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Bromazolam
Bromazolam (XLI-268) is a triazolobenzodiazepine (TBZD) which was first synthesised in 1976, but was never marketed. It has subsequently been sold as a designer drug, first being definitively identified by the EMCDDA in Sweden in 2016. It is the ...
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Clonazolam
Clonazolam (also known as clonitrazolam) is a drug of the triazolobenzodiazepine (TBZD) class, which are benzodiazepines (BZDs) fused with a triazole ring. It has had very little research done about its effects and metabolism, and has been so ...
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Estazolam
Estazolam, sold under the brand name Prosom among others, is a tranquilizer medication of the triazolobenzodiazepine (TBZD) class, which are benzodiazepines (BZDs) fused with a triazole ring . It possesses anxiolytic, anticonvulsant, hypnotic, s ...
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Flualprazolam
Flualprazolam is a tranquilizer of the triazolobenzodiazepine (TBZD) class, which are benzodiazepines (BZDs) fused with a triazole ring. It was first synthesised in 1976, but was never marketed. It can be seen as the triazolo version of fludia ...
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Flubromazolam
Flubromazolam (JYI-73) is a triazolobenzodiazepine (TBZD), which are benzodiazepine (BZD) derivatives. Flubromazolam is reputed to be highly potent, and concerns have been raised that clonazolam and flubromazolam in particular may pose compara ...
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Flunitrazolam
Flunitrazolam (FNTZ, Flunazolam) is a triazolobenzodiazepine (TBZD), which are benzodiazepine (BZD) derivatives, that has been sold online as a designer drug, and is a potent hypnotic and sedative drug similar to related compounds such as flun ...
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Nitrazolam
Nitrazolam is a triazolobenzodiazepine (TBZD)
, which are benzodiazepine (BZD) derivatives, that has been sold online as a designer drug.
It is closely related to Clonazolam or Flunitrazolam, only differing by the removal of a Chlorine or Fluo ...
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Pyrazolam
Pyrazolam (SH-I-04) is a benzodiazepine derivative originally developed by a team led by Leo Sternbach at Hoffman-La Roche in the 1970s. It has since been "rediscovered" and sold as a designer drug since 2012.
Pyrazolam has structural similar ...
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Triazolam
Triazolam, sold under the brand name Halcion among others, is a central nervous system (CNS) depressant tranquilizer of the triazolobenzodiazepine (TBZD) class, which are benzodiazepine (BZD) derivatives. It possesses pharmacological properties ...
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Zapizolam
Synthesis
Synthesis of 1-methyltriazolobenzodiazepines (alprazolam type) is possible by heating 1,4-benzodiazepin-2-
thiones with hydrazine and acetic acid in ''n''-butanol under reflux.
[Hester JB, Duchamp DJ, Chidester CG (1971): "A synthetic approach to new 1,4-benzodiazepine derivatives." Tetrahedron Letters, Vol. 12, pp. 1609-1612.]
References
External links
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