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
chemische verbinding
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
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1961
- Admin. routes
- oral, parenteral
- Indications
- diabetes mellitus, reproductive system disease, pain, neuropathy
via ChEMBL · EBI
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
Article · Nederlands
Amitriptyline, onder andere verkrijgbaar onder de merknamen Tryptizol, Sarotex en Redomex, is een tricyclisch antidepressivum. Het is een witte kristalachtige stof, meestal verkrijgbaar in tabletvorm. Amitriptyline wordt voornamelijk voorgeschreven bij klinische depressies. Daarnaast kan het - in lage doseringen - worden voorgeschreven bij slapeloosheid, migraine en chronische pijn. De stof is opgenomen in de lijst van essentiële geneesmiddelen van de WHO.
Abstract from DBpedia / Wikipedia · CC BY-SA