|CAS Registry Number||50-48-6|
|Synonyms||AMITRIPTYLINE;AMITRYPTYLLINE NA;3-(10,11-dihydro-5h-dibenzo[a,d]cyclohepten-5-ylidene)-n,n-dimethyl-1-propanamine;[3-(10,11-DIHYDRO-DIBENZO[A,D]CYCLOHEPTEN-5-YLIDENE)-PROPYL]-DIMETHYL-AMINE;10,11-Dihydro-5-(gamma-dimethylaminopropylidene)-5H-dibenzo(a,d)cycloheptene;10,11-dihydro-n,n-dimethyl-5h-dibenzo(a,d)heptalene-delta(sup5),gamma-propyl;10,11-Dihydro-N,N-dimethyl-5H-dibenzo(a,d)heptalene-delta5,gamma-propylamine;1-Propanamine, 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-|
|Trade names||Elavil, others|
|By mouth, intramuscular injection|
|Bioavailability||30–60% due to first pass metabolism|
|Biological half-life||10 to 50 hours|
|Chemical and physical data|
|Molar mass||277.403 g/mol|
|3D model (JSmol)||
Amitriptyline, sold under the brand name Elavil among others, is a medicine used to treat a number of mental illnesses. These include major depressive disorder and anxiety disorder, and less commonly attention deficit hyperactivity disorder and bipolar disorder. Other uses include prevention of migraines, treatment of neuropathic pain such as fibromyalgia and postherpetic neuralgia, and less commonly insomnia. It is in the tricyclic antidepressant (TCA) class and its exact mechanism of action is unclear. Amitriptyline is taken by mouth.
Common side effects include a dry mouth, trouble seeing, low blood pressure on standing, sleepiness, and constipation. Serious side effects may include seizures, an increased risk of suicide in those less than 25 years of age, urinary retention, glaucoma, and a number of heart issues. It should not be taken with MAO inhibitors or the medication cisapride. Amitriptyline may cause problems if taken during pregnancy. Use during breastfeeding appears to be relatively safe.
Amitriptyline was discovered in 1960 and approved by the US Food and Drug Administration (FDA) in 1961. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is available as a generic medication. The wholesale cost in the developing world as of 2014 is between 0.01 and 0.04 USD per dose. In the United States it costs about 0.20 USD per dose.
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