Benzodiazepines have been touted as safer alternatives to their barbiturate predecessor since their arrival on the market in 1960. Their proposed improved safety is based on their reported reduced drug interactions, lower abuse potential, and decreased respiratory depression. Benzodiazepines bind to the GABAA receptor and positively modulate GABAergic transmission and hyperpolarization of neuronal membranes. Individual agents are utilized differently depending on their varying degrees of hypnotic, anxiolytic, antiepileptic, muscle relaxant, and amnestic properties. Benzodiazepines are frequently classified by their half-life (t½), a key pharmacokinetic parameter that dictates the agents’ ability to precipitate dangerous withdrawals. The majority of benzodiazepines undergo phase I hepatic metabolism via cytochrome p450 that introduce the potential for drug interactions. Following hepatic metabolism, almost all agents within this drug class have active metabolites that have extended half-lives beyond that of the parent drug that prolong the duration of activity. Urine drug screens are an essential component of medication monitoring and require a foundational understanding of the parent drug, its metabolites, and what the available immunoassay is designed to detect. A similar drug class that is frequently grouped with benzodiazepines are Z-drugs. These agents were developed in attempt to create a sleep aid that lacked the undesirable qualities of benzos with an improved safety profile. Z-drugs share the common characteristic of being short-acting in nature and are proposed to cause less disruption in the normal sleep cycle than benzodiazepines.