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Alprazolam chemical structure
Systematic (IUPAC) name
CAS number 28981-97-7
ATC code N05BA12
PubChem 2118
DrugBank APRD00280
Chemical data
Formula C17H13ClN4
Mol. weight 308.8
Pharmacokinetic data
Bioavailability 80-90%
Metabolism Hepatic
Half life 6-12 hours
Excretion Renal
Therapeutic considerations
Pregnancy cat. D (USA)
Legal status Schedule IV(US)
Routes Oral

Alprazolam is a short-acting drug in the benzodiazepine class used to treat anxiety disorders and as an adjunctive treatment for depression.

Alprazolam was invented by Pfizer and is marketed under the trade name Xanax. Its patent expired in September 1993.



Alprazolam was originally marketed as an atypical benzodiazepine, but only classified as anxiety neurosis. Researchers later speculated, however, that alprazolam could be studied for serotonergic effects. On October 20, 1976, Dr. Guy Chouinard was the first to conduct a clinical trial of alprazolam in panic disorder. Patients diagnosed with panic disorder were included among participants in the study. 50 patients were given either the alprazolam or a placebo during an 8-week double-blind controlled study. Results proved that both somatic and psychic anxiety was decreased significantly in those who took the alprazolam, compared to the placebo.


Alprazolam is a triazolobenzodiazepine, that is, a benzodiazepine with a triazolo-ring attached to its structure. Alprazolam binds to the GABAA subtype of the GABA receptor, increasing inhibitory effects of GABA within the central nervous system. The binding site for benzodiazepines is distinct from the binding site for barbiturates and GABA on the GABA receptor.

Unlike other benzodiazepines, alprazolam may also have some antidepressant activity, although clinical evidence of this is lacking.


The mechanism of action is not fully understood. Alprazolam is readily absorbed from the gastrointestinal tract. The peak plasma concentration is achieved in 1-2 hours. Most of the drug is bound to plasma protein, mainly albumin. Alprazolam is hydroxylated in the liver to α-hydroxyalprazolam, which is also pharmacologically active. This and other metabolites are later excreted in urine as glucuronides. Some of the drug is also excreted in unchanged form.


alprazolam 2mg tablet bottle
alprazolam 2mg tablet bottle

The main medical uses for alprazolam include:

  • Treatment of panic disorder, with or without agoraphobia.
    Alprazolam is very effective in preventing panic attacks. However, despite its efficacy, many psychiatrists are reluctant to use alprazolam for this condition because of the possibility of dependence and interdose ("breakthrough") anxiety due to its short-acting nature. An extended-release formulation of alprazolam known as Xanax XR was introduced in 2001 and is often preferred.
  • Treatment of panic attacks.
    Alprazolam is taken as needed (PRN); 4 to 6 doses per day are the acceptable limit. If dependence seems to develop and/or the limit is exceeded, therapy may be reconsidered and/or discontinued.
  • Long-term treatment of severe anxiety disorders.
    Alprazolam may be used for long-term treatment of anxiety if other therapies either do not work or are contraindicated. Duration of therapy in this case is often four months or longer. The decision to use alprazolam for this purpose must be carefully made by a specialized psychiatrist, taking into account the individual's suffering, quality of life, loss of social performance and risk of dependence.
  • Adjunctive treatment of depression.
    SSRIs (e.g. sertraline or fluoxetine) are often co-administered with alprazolam at the outset of long-term SSRI anxiety treatment in order to counteract the initial anxiogenic (anxiety-producing) effects of SSRI treatment. Tricyclic antidepressants and buspirone are also used with alprazolam in refractory (resistant) cases of generalized anxiety disorder.
  • Other uses.
    Alprazolam may be used by specialists to treat severe cases of Borderline Personality Disorder. Some studies have shown positive results.


Alprazolam is generally sold in generic form in Italy and the United States. It is also sold under many other brand names, depending on the country:

  • Aceprax - Uruguay
  • Alplax - Argentina
  • Alpralid - Israel
  • Alprax - India
  • Alviz - Indonesia
  • Alzolam - India, Malaysia
  • Apo-Alpraz - Canada (also made by other companies under different names)
  • Apraz - Brazil
  • Calmax - Ireland
  • Constan - Japan
  • Frontal XR - (an extended release formulation) Brazil
  • Frontal - Brazil
  • Frontin - Hungary, Slovak Republic, Czech Republic
  • Helex - Croatia, Slovenia
  • Kalma - Australia
  • Kinax (景安寧) - Taiwan
  • Ksalol - Serbia
  • Manorest - Sri Lanka
  • Misar - Croatia
  • Neurol - Czech Republic, Slovak Republic
  • Niravam - (formulation that dissolves on the tongue) United States
  • Paxal - Iceland
  • Prazolex - Romania
  • Ralozam - Australia
  • Restyl - Bahrain, Cyprus, Egypt, India, Iran, Iraq, Jordan, Kuwait, Lebanon, Libya, Oman, Qatar, Republic of Yemen, Saudi Arabia, Syria, United Arab Emirates
  • Sedipral - Paraguay
  • Solanax - Japan
  • Tafil AP - (an extended release formulation) Mexico
  • Tafil - Costa Rica, Denmark, El Salvador, Germany, Guatemala, Honduras, Mexico, Nicaragua, Panama, Venezuela
  • Trankimazin - Spain
  • Tranquinal - Ecuador, Peru
  • Xanax XR - (an extended release formulation) Israel [1], United States, Portugal
  • Xanax - Australia, Belgium, Croatia, Germany, Greece, Hungary, Ireland, Italy, Netherlands, New Zealand, Pakistan, Portugal, Switzerland, Turkey, United Kingdom, United States
  • Xanor - Austria, Finland, Norway, Philippines, South Africa, Sweden
  • Zamhexal - Australia
  • Zolarem - Bahrain, Benin, Burkina-Faso, Cyprus, Egypt, Ethiopia, Gambia, Ghana, Guinea, Iran, Iraq, Israel, Ivory Coast, Jordan, Kenya, Kuwait, Lebanon, Liberia, Libya, Malawi, Mali, Mauritania, Mauritius, Morocco, Niger, Nigeria, Oman, Qatar, Republic of Yemen, Saudi Arabia, Senegal, Seychelles, Sierra-Leone, South Africa, Sudan, Syria, Tanzania, Tunia, Uganda, United Arab Emirates, Zambia, Zimbabwe
  • Zoldac - Benin, Burkina-Faso, Ethiopia, Gambia, Ghana, Guinea, India, Ivory Coast, Kenya, Liberia, Malawi, Mali, Mauritania, Mauritius, Morocco, Niger, Nigeria, Senegal, Seychelles, Sierra-Leone, South Africa, Sudan, Tanzania, Tunia, Uganda, Zambia, Zimbabwe


Appearance is generally as follows in the United States.


Inscriptions on tablet vary depending on manufacturer.
.25 mg White oval tablet scored
.5 mg Peach oval tablet scored (.5 mg and .25 mg Alprazolam may also be found in White round tablet scored)
1 mg Blue oval scored tablet. May also be called a "football."
2 mg White rectangle multi-scored tablet. May also be called a "bar" or "stick."

Xanax XR

.5 mg White pentagonal tablet Imprinted "X /0.5"
1 mg Yellow square tablet Imprinted "X / 1"
2 mg Blue round tablet Imprinted "X / 2"
3 mg Green triangular tablet Imprinted "X / 3"

Source: [2]

Side effects

Common side effects of alprazolam can include:

  • Somnolence (drowsiness)
  • Euphoria
  • Confusion

Less common side effects can include:

  • Fatigue
  • Headache

Rare side effects can include:

  • Sleep apnea
    Hypoventilation (Respiratory depression)
    Blurred vision
    Difficulty in depth perception
    Slurred speech or dysarthria
    Changes in personality
    Amnesia (memory impairment)
    Vivid dreams and/or nightmares
    Changes in plasma cortisol and ACTH levels
    Blood dyscrasias
    Decreased salivation
    Increased salivation
    Elevated hepatic (liver) enzymes

Rare paradoxical side effects can include:

  • Nervousness
  • Anxiety
  • Agitation
  • Rage
  • Insomnia
  • Muscle spasms and rigidity

Paradoxical side effects are usually a result of too high a dose (sometimes deliberate) and/or combination with alcohol. Adjusting the dosage usually causes them to cease.

Concentrations of alprazolam in cigarette smokers may be reduced up to 50% when compared to non-smokers.[3].

Long-term treatment with alprazolam may lead to physical and/or psychological dependence. Users often develop a tolerance to the drug's sedative effects, though tolerance to its anxiolytic efficacy rarely develops when used at theraputic dosage levels.

There is now a general consensus among many psychiatrists that alprazolam (a so-called 'high-potency' benzodiazepine) poses a particularly high risk for misuse, abuse and dependence. Withdrawal after long-term treatment should be done slowly over a period of weeks (or even months) to avoid serious withdrawal symptoms such as agitation, panic attacks, rebound anxiety, muscle cramps and seizures. Some patients may benefit from a substitution with diazepam or clonazepam as these drugs remain in the bloodstream longer and have a somewhat lower risk of dependency.

Patients taking a dosing regimen larger than 4mg per day have an increased potential for emotional and physical dependence. Patients who have this dependence may find it difficult to discontinue use and should seek a healthcare professional immediately so they may put you on a proper regimen to discontinue use. In addition to dependence, this medication may cause withdrawal symptoms, and in some cases has been known to cause seizures. The use of this medication may also cause a reaction called rebound anxiety. When a patient discontinues use, they may experience the symptoms they had before taking medication, but this is usually short lived. Symptoms may also be accompanied other reactions including changes in mood, anxiety or sleep. Rebound anxiety is usually a result of abrupt discontinuation of this medication; patients who taper off are less likely to experience these symptoms.


Use of alprazolam should be avoided in individuals with the following conditions:

  • Myasthenia gravis
    Acute intoxication with alcohol, narcotics, or other psychoactive substances
    Severe hypoventilation
    Acute narrow-angle glaucoma
    Severe liver deficiencies (e.g. hepatitis and cirrhosis)
    Severe sleep apnea
    Hypersensitivity or allergy to any drug in the benzodiazepine class

Women who are pregnant should avoid alprazolam. Children of mothers who are taking alprazolam are considered at risk for withdrawal symptoms during the postnatal period. Some children born under these conditions have been reported to have neonatal flaccidity and respiratory problems. Likewise, nursing mothers should avoid alprazolam due to the fact that Benzodiazepines are known to be passed into breast milk. This can cause infants to become lethargic and loose weight. [4] [5]

Elderly individuals should be cautious in the use of alprazolam due to the possibility of increased sensitivity to side effects, especially loss of coordination and drowsiness. [6]

Eating grapefruits or drinking grapefruit juice should be avoided by those taking alprazolam.

Patients at a High Risk for Abuse and Dependence

At a particularly high risk for misuse, abuse, and dependence are:

  • Patients with a history of alcohol or drug abuse and/or dependence
  • Emotionally unstable patients
  • Patients with severe personality disorders
  • Patients with chronic pain or other physical disorders

Patients from the aforementioned group should be monitored very closely during therapy for signs of abuse and development of dependence. Discontinue therapy if any of these signs are noted. Long-term therapy in these patients is not recommended.

Recreational use

alprazolam 2mg tablets
alprazolam 2mg tablets

Alprazolam, like all benzodiazepines, has the potential for abuse, especially in individuals prone to addiction. Although it is not manufactured illegally, it is often diverted to the black market. The state of relaxation, anxiolysis, disinhibition and euphoria induced by benzodiazepines is the main reason for their illicit use.

Injecting alprazolam is highly dangerous. When crushed in water, it will not dissolve, potentially causing severe damage to arteries. While it is somewhat soluble in alcohol, the combination of the two, particularly when injected, can easily cause a serious (and potentially fatal) overdose. Alprazolam may also be insufflated.

Alprazolam is sometimes used with other recreational drugs to relieve the panic or distress of dysphoric reactions to psychedelics such as LSD and also to promote sleep in the "come-down" period following use of recreational drugs with stimulant or insomniac properties (such as LSD, cocaine, amphetamines, DXM, and MDMA). It is also often used in conjunction with marijuana or heroin to potentiate the relaxing effect. It is also sometimes used by heroin addicts to suppress withdrawal symptoms.

Legal status

In the United States, alprazolam is a prescription drug and is assigned to Schedule IV of the Controlled Substances Act by the Drug Enforcement Administration. Internationally, alprazolam is included under the United Nations Convention on Psychotropic Substances[7].


External links

  • Link page to external chemical sources.

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This guide is licensed under the GNU Free Documentation License. It uses material from the Wikipedia.

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