Amitriptyline

Amitriptyline, sold under the brand name Elavil among others, is a tricyclic antidepressant primarily used to treat major depressive disorder, a variety of pain syndromes such as neuropathic pain, fibromyalgia, migraine and tension headaches. Due to the frequency and prominence of side effects, amitriptyline is generally considered a second-line therapy for these indications.

Amitriptyline
Clinical data
Pronunciation/ˌæmɪˈtrɪptɪliːn/
Trade namesElavil, others
AHFS/Drugs.comMonograph
MedlinePlusa682388
License data
Pregnancy
category
  • AU: C
Routes of
administration		By mouth, intramuscular injection
Drug classTricyclic antidepressant (TCA)
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability45%-53%
Protein binding96%
MetabolismLiver (CYP2D6, CYP2C19, CYP3A4)
Metabolitesnortriptyline, (E)-10-hydroxynortriptyline
Elimination half-life21 hours
ExcretionUrine: 12–80% after 48 hours; feces: not studied
Identifiers
  • 3-(10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-ylidene)-N,N-dimethylpropan-1-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.038
Chemical and physical data
FormulaC20H23N
Molar mass277.411 g·mol−1
3D model (JSmol)
Melting point197.5 °C (387.5 °F)
  • c3cc2c(/C(c1c(cccc1)CC2)=C\CCN(C)C)cc3
  • InChI=1S/C20H23N/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-12H,7,13-15H2,1-2H3 Y
  • Key:KRMDCWKBEZIMAB-UHFFFAOYSA-N Y
  (verify)

The most common side effects are dry mouth, drowsiness, dizziness, constipation, and weight gain. Of note is sexual dysfunction, observed primarily in males. Glaucoma, liver toxicity and abnormal heart rhythms are rare but serious side effects. Blood levels of amitriptyline vary significantly from one person to another, and amitriptyline interacts with many other medications potentially aggravating its side effects.

Amitriptyline was discovered in the late 1950s by scientists at Merck and approved by the US Food and Drug Administration (FDA) in 1961. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2021, it was the 107th most commonly prescribed medication in the United States, with more than 5 million prescriptions.

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