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Bromazolam (CAS 71368-80-4; Name: 8-bromo-1-methyl6-phenyl-4H-S-triazolo[4,3-a][1,4]benzodiazepine) is a triazolobenzodiazepine that was originally developed as a candidate medication but was never approved for use. Bromazolam phase I metabolism is mediated primarily by several isoforms of the CYP450 enzyme system (CYP2B6, CYP2C19, CYP3A4, CYP3A5 and CYP2C9), whereas phase II metabolism involves the isoenzymes UGT1A4 and UGT2810.

What is Bromazolam?

Bromazolam is also structurally related to flubromazepam, from which it differs by the lack of a fluorine at the 2-position of the phenyl ring. Bromazolam is also structurally similar to pyrazolam, whereby the pyridinyl group has been replaced by a phenyl group.

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Bromazolam was first synthesized in the 1970s by Hester et al. A convenient synthesis method has been reported in the patent literature. Introduction of a triazole ring into the 1,4-benzodiazepine precursor (8-bromo-1-methyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine) gave DE(chloro)-bromo-alprazolam. The 1,4 benzodiazepine precursor can be prepared by cyclization of 2-amino-5-bromobenzophenone with chloroacetylchloride.

Where to get Triazolobenzodiazepine

Bromazolam is soluble in dimethylformamide at a concentration of 30 mg/mL, in dimethylsulphoxide at 20 mg/mL, in ethanol at 10 mg/mL, in methanol at 1 mg/mL and in a 1:1 mixture of dimethylformamide and phosphate-buffered saline (pH 7.2) at 0.5 mg/mL.

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Synthetic Bromazolam has been characterized by proton and carbon nuclear magnetic resonance (1H NMR and 13C NMR), mass spectrometry (MS) and infra-red spectroscopy (IR). DE(chloro)-bromo-alprazolam is available as a reference material from various commercial suppliers and is used in routine analysis for forensic and clinical investigations.

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Benzodiazepines (BZDs) act as positive allosteric modulators on the gamma-aminobutyric acid (GABA)_A receptor [1]. GABA represents the main inhibitor neurotransmitter in the brain and plays an important role in modulating the activity of many neurons, including those in the amygdala and prefrontal cortex [1].

How to use Bromazolam?

The GABA_A receptor is a ligand-gated chloride-selective ion channel build-up of five subunits: two α, two ß (the binding site for endogenous neurotransmitter) and one γ. BZDs bind to the pocket created by α and γ subunits and induce a conformational change in the GABA_A receptors.