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Xanax Chemical Structure

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Decoding Xanax: A Deep Dive into its Chemical Structure



Alprazolam, commonly known as Xanax, is a widely prescribed benzodiazepine used to treat anxiety disorders, panic attacks, and insomnia. Understanding its chemical structure is crucial to grasping its pharmacological properties, potential side effects, and interactions with other medications. This article will delve into the intricacies of alprazolam's chemical structure, explaining its key features and how they contribute to its therapeutic and potentially harmful effects.

I. The Molecular Blueprint: A Detailed Look at Alprazolam's Structure



Alprazolam's chemical formula is C<sub>17</sub>H<sub>13</sub>ClN<sub>4</sub>. This formula indicates that a single molecule of alprazolam contains 17 carbon atoms, 13 hydrogen atoms, one chlorine atom, and four nitrogen atoms. These atoms are arranged in a specific three-dimensional configuration, crucial to its functionality. The core structure comprises a tricyclic ring system, a characteristic feature of benzodiazepines. This system consists of two benzene rings fused to a seven-membered diazepine ring.

A crucial aspect of the structure is the presence of a chlorine atom attached to one of the benzene rings. This chlorine atom is not merely a structural component; it significantly influences the drug's pharmacodynamic properties, affecting its binding affinity to the GABA<sub>A</sub> receptor, a key player in the central nervous system.

The other substituents, including the nitrogen atoms and various carbon-hydrogen groups, further contribute to the overall shape and charge distribution of the molecule, influencing its interactions with receptor sites and metabolic pathways. The specific arrangement of these atoms leads to a molecule that is relatively lipophilic (fat-soluble), enabling it to readily cross the blood-brain barrier and exert its effects on the brain.

II. The Significance of the Tricyclic Ring System and Substituents



The tricyclic ring system, particularly the diazepine ring, is the key functional group responsible for alprazolam's interaction with the GABA<sub>A</sub> receptor. This receptor is a chloride ion channel that, when activated, increases chloride influx into nerve cells, hyperpolarizing them and inhibiting neuronal firing. Benzodiazepines, like alprazolam, act as allosteric modulators, meaning they bind to a site on the receptor distinct from the GABA binding site, enhancing the effects of GABA.

The specific substituents on the tricyclic ring system further fine-tune the interaction with the GABA<sub>A</sub> receptor. The chlorine atom, for instance, contributes to the high potency of alprazolam. Changes in these substituents can significantly alter the drug's affinity for the receptor, its duration of action, and its overall potency. This is why subtle changes in the chemical structure can lead to vastly different pharmacological profiles.

For example, the related benzodiazepine diazepam (Valium) differs from alprazolam in its substituents and exhibits a longer half-life and slightly different pharmacological effects.

III. Metabolic Considerations and Chemical Degradation



Alprazolam undergoes significant metabolism in the liver, primarily through the cytochrome P450 enzyme system. This metabolic process transforms alprazolam into various metabolites, some of which may retain pharmacological activity. Understanding these metabolic pathways is crucial for predicting drug interactions and potential toxicity. Certain medications or substances can inhibit or induce these enzymes, leading to altered alprazolam levels in the body and potentially increased or decreased effects. This emphasizes the importance of disclosing all medications to a physician before starting alprazolam treatment.

IV. Implications for Therapeutic Use and Side Effects



The precise chemical structure of alprazolam dictates its therapeutic actions as well as its potential side effects. Its ability to enhance GABAergic neurotransmission effectively reduces anxiety and promotes relaxation. However, the same mechanism can lead to side effects such as drowsiness, dizziness, impaired coordination, and cognitive impairment. The lipophilicity also contributes to the potential for dependence and withdrawal symptoms upon cessation of use.

Conclusion



Understanding the chemical structure of alprazolam provides a fundamental understanding of its mechanism of action, therapeutic uses, and potential side effects. The unique arrangement of atoms and the specific functional groups within its tricyclic ring system are crucial determinants of its pharmacological properties. This knowledge highlights the importance of responsible prescribing and use of this potent medication, emphasizing the need for careful monitoring and adherence to prescribed dosage regimens.


FAQs:



1. Is Xanax addictive? Yes, alprazolam is a potentially addictive substance, and long-term use can lead to dependence and withdrawal symptoms.

2. How does Xanax interact with alcohol? Combining Xanax with alcohol significantly increases the risk of respiratory depression and other serious adverse effects.

3. What are the common side effects of Xanax? Common side effects include drowsiness, dizziness, confusion, impaired coordination, and memory problems.

4. How long does Xanax stay in your system? The half-life of alprazolam is relatively short, but it can vary depending on factors like metabolism and dosage. Detection in urine tests can vary considerably.

5. Can I stop taking Xanax suddenly? No, abruptly stopping Xanax can lead to severe withdrawal symptoms. Discontinuation should always be done under the supervision of a healthcare professional.

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Molecular Structure, Spectroscopy and Photochemistry of Alprazolam 1 Aug 2021 · In this article, a comprehensive study of the molecular structure, spectroscopy, and photochemistry of alprazolam (Xanax®; 8-chloro-1-methyl-6-phenyl-4H- [1,2,4] triazolo [4,3-a]...

Alprazolam, chemical structure, molecular formula, Reference … Procedure— Separately apply 10µLeach of the Test solution and each Standard solution to a thin-layer chromatographic plate (see Chromatography á621ñ)coated with a 0.50-mm layer of chromatographic silica gel mixture,and allow the spots to dry.Develop the chromatogram in a solvent system consisting of a mixture of chloroform,acetone,ethyl acetate,and methanol …

Molecular structure, spectroscopy and photochemistry of alprazolam 5 Jan 2022 · In this article, a comprehensive study of the molecular structure, spectroscopy, and photochemistry of alprazolam (Xanax®; 8-chloro-1-methyl-6-phenyl-4 H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine) is reported.

How are Xanax made? - ScienceOxygen 23 Nov 2023 · Xanax works by increasing the effects of a brain chemical called gamma-aminobutyric acid (GABA), which promotes calmness and produces a relaxed feeling. The drug decreases the level of excitement in the brain to treat anxiety and panic disorders .

The Solvation Structure of Alprazolam - ResearchGate 28 Jul 2016 · In this article, a comprehensive study of the molecular structure, spectroscopy, and photochemistry of alprazolam (Xanax®; 8-chloro-1-methyl-6-phenyl-4H-[1,2,4] triazolo[4,3-a][1,4]benzodiazepine...

Alprazolam | C17H13ClN4 | CID 2118 - PubChem Alprazolam | C17H13ClN4 | CID 2118 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more.

The solvation structure of alprazolam - Physical Chemistry Chemical ... Here, we use neutron diffraction in conjunction with molecular dynamics simulations to provide a detailed analysis of how water molecules interact with alprazolam in methanol/water mixtures. The agreement between the neutron diffraction and the molecular dynamics is extremely good. We discuss the results in the context of drug design.

Molecular Structure, Spectroscopy and Photochemistry of … In this article, a comprehensive study of the molecular structure, spectroscopy, and photochemistry of alprazolam (Xanax (R); 8-chloro-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine) is reported.

Alprazolam, What is Alprazolam? About its Science, Chemistry and Structure Find out about the science and chemistry of Alprazolam (Xanax), see colourful images of Alprazolam and explore interactive 3D molecules of Alprazolam

Chemical structure of alprazolam | Download Scientific Diagram In this paper, the detection of alprazolam by fullerene (C20) was studied by infra-red (IR), frontier molecular orbital (FMO) and natural bond orbital (NBO) computations.

Alprazolam Overview - Active Ingredient - RxReasoner Chemical formula: C₁₇H₁₃ClN₄ Molecular mass: 308.765 g/mol PubChem compound: 2118. Alprazolam, like other benzodiazepines, has a high affinity for the benzodiazepine binding site in the brain.

Molecular structure, spectroscopy and photochemistry of alprazolam 5 Jan 2022 · In this article, a comprehensive study of the molecular structure, spectroscopy, and photochemistry of alprazolam (Xanax®; 8-chloro-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine) is reported.

Alprazolam | C17H13ClN4 - ChemSpider ChemSpider record containing structure, synonyms, properties, vendors and database links for Alprazolam, 28981-97-7, Xanax, VREFGVBLTWBCJP-UHFFFAOYSA-N

Alprazolam - NIST Chemistry WebBook 6 Apr 2012 · Chemical structure: This structure is also available as a 2d Mol file or as a computed 3d SD file The 3d structure may be viewed using Java or Javascript.

Alprazolam | 28981-97-7 - ChemicalBook 27 Jan 2025 · Alprazolam (CAS 28981-97-7) information, including chemical properties, structure, melting point, boiling point, density, formula, molecular weight, uses, prices, suppliers, SDS and more, available at Chemicalbook.

Polymorphism of Alprazolam (Xanax): a review of its ... - PubMed A new polymorphic form of Alprazolam (Xanax), 8-chloro-1-methyl-6-phenyl-4H- [1,2,4]triazolo- [4,3-alpha] [1,4]benzodiazepine, C (17)H (13)ClN (4), has been investigated by means of X-ray powder diffraction (XRPD), single crystal X-ray diffraction, …

Alprazolam Xanax | 28981-97-7 - ChemicalBook 18 Dec 2024 · Alprazolam Xanax (CAS 28981-97-7) information, including chemical properties, structure, melting point, boiling point, density, formula, molecular weight, uses, prices, suppliers, SDS and more, available at Chemicalbook.

Alprazolam - an overview | ScienceDirect Topics Alprazolam is a chemical compound that is a short-lasting tranquilizer used to treat anxiety, panic disorders, and depressive syndrome. It is commonly known by its synonym, Xanax. AI generated definition based on: Synthesis of Essential Drugs , 2006

What are the metabolites of Xanax? - ScienceOxygen 23 Nov 2023 · It consists of a white crystalline powder, which can be soluble in both methanol and ethanol. See also Is it hard to get a 50 on CLEP exam? Where is alprazolam derived from? Xanax, otherwise known as alprazolam, is an antidepressant and anti-anxiety medication developed by Upjohn Laboratories of Kalamazoo, Michigan in the late 1960s.

Alprazolam Structure - C17H13ClN4 - Over 100 million chemical … The 3D chemical structure image of alprazolam is based on the ball-and-stick model which displays both the three-dimensional position of the atoms and the bonds between them. The radius of the spheres is therefore smaller than the rod lengths in order to provide a clearer view of the atoms and bonds throughout the chemical structure model of ...