Alprazolam
[CAS# 28981-97-7]

Identification

• Classification: API >> Nervous system medication >> Other nervous system medication
• Name: Alprazolam
• Synonyms: 8-Chloro-1-methyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine
• Molecular Formula: C₁₇H₁₃ClN₄
• Molecular Weight: 308.77
• CAS Registry Number: 28981-97-7
• EC Number: 249-349-2
• SMILES: CC1=NN=C2N1C3=C(C=C(C=C3)Cl)C(=NC2)C4=CC=CC=C4

Properties

• Melting point: 228-228.5 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Reproductive toxicity	Lact.	-	H362
Reproductive toxicity	Repr.	1B	H360
Reproductive toxicity	Repr.	2	H361
Reproductive toxicity	Repr.	1A	H360
Specific target organ toxicity - single exposure	STOT SE	3	H336
Flammable liquids	Flam. Liq.	2	H225

• Controlled Substance: DEA Drug Code Number: 2882

Discovery and Applications

Alprazolam, also known by the brand name Xanax, is a widely used prescription medication that belongs to the benzodiazepine class and is used to treat anxiety and panic disorders. Alprazolam was developed by Upjohn Laboratories (now part of Pfizer) in the 1960s and introduced to the market in 1981. Its discovery was the result of efforts to develop benzodiazepines with greater selectivity and fewer side effects than earlier drugs, such as diazepam (Valium). Alprazolam has a chemical structure of C17H13ClN4 and consists of a benzodiazepine core and a triazole ring fused to the diazepine ring, which enhances its anxiolytic potency.

Alprazolam is primarily used to treat anxiety disorders, particularly generalized anxiety disorder (GAD) and panic disorder. It works by enhancing the activity of GABA, a neurotransmitter that inhibits the excitation of neurons. By increasing the inhibitory effects of GABA, alprazolam helps reduce anxiety, induce calmness, and relax muscles. Its rapid onset of action makes it effective for acute anxiety attacks, providing relief within an hour of administration.

Alprazolam binds to the benzodiazepine receptor site on the GABA_A receptor, increasing the receptor's affinity for GABA. This results in an increased influx of chloride ions, which hyperpolarizes the neuronal membrane and decreases its excitability. This mechanism produces the sedative, anxiolytic, and muscle relaxant effects that are characteristic of benzodiazepines.

Despite its effectiveness, alprazolam also has a high potential for abuse and dependence. Its rapid onset and powerful sedative effects can lead to abuse, especially by those seeking immediate relief from anxiety or recreational excitement. Long-term use can produce physical and psychological dependence, so it is important to follow prescribed guidelines and taper the medication under medical supervision to avoid withdrawal symptoms.

Alprazolam is classified as a Schedule IV controlled substance in the United States, which has a lower potential for abuse than Schedule I through III drugs, but is also subject to regulation. Similar regulatory measures exist internationally to prevent abuse while ensuring its use for therapeutic purposes.

References

1990. Situational exposure treatment versus panic control treatment for agoraphobia. A case study. Journal of Behavior Therapy and Experimental Psychiatry.
DOI: 10.1016/0005-7916(90)90009-a

1990. Physical dependence Induced In DBA/2J mice by benzodiazepine receptor full agonists, but not by the partial agonist Ro 16-6028. European Journal of Pharmacology.
DOI: 10.1016/0014-2999(90)94138-n

1990. Risk factors for adverse drug reactions — epidemiological approaches. European Journal of Clinical Pharmacology.
DOI: 10.1007/bf00315403