File:Amitriptyline2DACS.svg · Wikimedia Commons · See Wikimedia Commons
amitriptyline
Sign in to saveAlso known as amitryptiline, 5-(gamma-dimethylaminopropylidene)-5H-dibenzo[a,d][1,4]cycloheptadiene, 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethylpropan-1-amine, 5-(3-dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene, 5-(3-dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptatriene, 10,11-dihydro-N,N-dimethyl-5H-dibenzo(a,d)heptalene-delta(5),gamma-propylamine, 10,11-dihydro-5-(gamma-dimethylaminopropylidene)-5H-dibenzo[a,d]cycloheptene, 10,11-dihydro-N,N-dimethyl-5H-dibenzo[a,d]heptalene-delta(5),gamma-propylamine
Amitriptyline, formerly sold under the brand name Elavil among others, is a tricyclic antidepressant primarily used to treat major depressive disorder, and 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.
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 477169407
- Drug.image
- Amitriptyline2DACS.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200
- Drug.image2
- Amitriptyline-from-picrate-xtal-3D-balls.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 250
- Drug.tradename
- Elavil, others
- Drug.MedlinePlus
- a682388
- Drug.DailyMedID
- Amitriptyline
- Drug.pregnancy_AU
- C
- Drug.routes_of_administration
- Oral, intramuscular injection
- Drug.class
- Tricyclic antidepressant (TCA)
- Drug.ATC_prefix
- N06
- Drug.ATC_suffix
- AA09
- Drug.legal_AU
- S4
- Drug.legal_BR
- C1
via Wikipedia infobox
Chemical data
- Formula
- C20H23N
- Molecular weight
- 277.4 g/mol
- IUPAC name
- N,N-dimethyl-3-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylidene)propan-1-amine
- SMILES
- CN(C)CCC=C1C2=CC=CC=C2CCC3=CC=CC=C31
- InChIKey
- KRMDCWKBEZIMAB-UHFFFAOYSA-N
- XLogP
- 5
- Polar surface area
- 3.2 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Research
10,509 papers- Amitriptyline's anticholinergic adverse drug reactions-A systematic multiple-indication review and meta-analysis.PloS one · 2023
- Classics in Chemical Neuroscience: Amitriptyline.ACS chemical neuroscience · 2021
- [Amitriptyline].Therapeutique (La Semaine des hopitaux) · 1969
- Amitriptyline for the treatment of fibromyalgia: a comprehensive review.Expert review of neurotherapeutics · 2015
- Amitriptyline intoxication in bullfrogs causes widening of QRS complexes in electrocardiogram.The Journal of veterinary medical science · 2023
via PubMed
Wikidata facts
- Mass
- 277.183
Show 5 more facts
- chemical formula
- C₂₀H₂₃N
- Commons category
- Amitriptyline
- World Health Organisation international non-proprietary name
- amitriptyline
- canonical SMILES
- CN(C)CCC=C1C2=CC=CC=C2CCC3=CC=CC=C31
- defined daily dose
- 75
Sources (7)
via Wikidata · CC0
~27 min read
Article
24 sectionsContents
- Medical uses
- Depression
- Pain
- Central post-stroke pain
- Headache
- Other indications
- Contraindications and precautions
- Side effects
- Overdose
- Interactions
- Pharmacology
- Pharmacodynamics
- Mechanism of action
- Pharmacokinetics
- Pharmacogenetics
- Chemistry
- History
- Society and culture
- Names
- Prescription trends
- Research
- See also
- References
- Further reading
Amitriptyline, formerly sold under the brand name Elavil among others, is a tricyclic antidepressant primarily used to treat major depressive disorder, and 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.
The most common side effects are dry mouth, drowsiness, dizziness, constipation, and weight gain. 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.