File:Amitriptyline2DACS.svg · Wikimedia Commons · See Wikimedia Commons
Amitriptilin
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
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OverviewAI-generated
Amitriptyline is a chemical compound with the formula C₂₀H₂₃N. Its IUPAC name is N,N-dimethyl-3-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylidene)propan-1-amine. The compound has a mass of 277.183 and a defined daily dose of 75.
Chemical properties include an xlogp of 5, a topological polar surface area of 3.2, and a charge of 0. It has zero hydrogen bond donors and one hydrogen bond acceptor. The canonical SMILES notation for the molecule is CN(C)CCC=C1C2=CC=CC=C2CCC3=CC=CC=C31.
Amitriptyline is referenced by 4,158 other encyclopedia articles. A search for the term in PubMed yields a count of 10,509 entries.
Synthesized by Vinony from 19 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
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
- Has part
- carbon
- Mass
- 277.183
- Has use
- medication
Show 11 more facts
- chemical formula
- C₂₀H₂₃N
- significant drug interaction
- fluvoxamine
- Commons category
- Amitriptyline
- World Health Organisation international non-proprietary name
- amitriptyline
- medical condition treated
- migraine
- canonical SMILES
- CN(C)CCC=C1C2=CC=CC=C2CCC3=CC=CC=C31
- subject has role
- essential medicine
- physically interacts with
- solute carrier family 6 member 4
- legal status (medicine)
- boxed warning
- route of administration
- intravenous infusion and defusion
- defined daily dose
- 75
Sources (7)
via Wikidata · CC0