Structure via PubChem · Public domain (PubChem)
tacrine
Sign in to saveAlso known as CI-970, Cognex®, tetrahydroaminoacridine, 1,2,3,4-tetrahydro-9-acridinamine, Tetrahydroaminoacridine, Tetrahydroaminacrine, 9-amino-1,2,3,4-tetrahydroacridine
Tacrine is a centrally acting acetylcholinesterase inhibitor and indirect cholinergic agonist (parasympathomimetic). It was the first centrally acting cholinesterase inhibitor approved for the treatment of Alzheimer's disease, and was marketed under the trade name Cognex. Tacrine was first synthesised by Adrien Albert at the University of Sydney in 1949. It also acts as a histamine N-methyltransferase inhibitor.
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 470476624
- Drug.IUPAC_name
- 1,2,3,4-Tetrahydroacridin-9-amine
- Drug.image
- Tacrine-2D.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 150
- Drug.image2
- Tacrine3Dan.gif
- Drug.width2
- 200
- Drug.tradename
- Cognex
- Drug.MedlinePlus
- a693039
- Drug.pregnancy_AU
- C
- Drug.pregnancy_US
- C
- Drug.legal_AU
- S4
- Drug.legal_BR
- C1
- Drug.legal_UK
- POM
- Drug.legal_US
- Rx-only
- Drug.routes_of_administration
- Oral, rectal
- Drug.bioavailability
- 2.4–36% (oral)
via Wikipedia infobox
Chemical data
- Formula
- C13H14N2
- Molecular weight
- 198.26 g/mol
- IUPAC name
- 1,2,3,4-tetrahydroacridin-9-amine
- SMILES
- C1CCC2=NC3=CC=CC=C3C(=C2C1)N
- InChIKey
- YLJREFDVOIBQDA-UHFFFAOYSA-N
- XLogP
- 2.7
- Polar surface area
- 38.9 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
2,762 papers- Tacrine.Lancet (London, England) · 1995
- Therapeutic Potential of Multifunctional Tacrine Analogues.Current neuropharmacology · 2019
- Tacrine: In vivo veritas.Pharmacological research · 2017
- [Tacrine].Revista de medicina de la Universidad de Navarra · 1997
- The pharmacology of tacrine at N-methyl-d-aspartate receptors.Progress in neuro-psychopharmacology & biological psychiatry · 2017
via PubMed
Wikidata facts
- Mass
- 198.116
Show 4 more facts
- chemical formula
- C₁₃H₁₄N₂
- canonical SMILES
- C1CCC2=NC3=CC=CC=C3C(=C2C1)N
- Commons category
- Tacrine
- defined daily dose
- 0.12
via Wikidata · CC0
~3 min read
Article
6 sectionsContents
- Clinical use
- Adverse effects
- Overdose
- Pharmacokinetics
- References
- External links
Tacrine is a centrally acting acetylcholinesterase inhibitor and indirect cholinergic agonist (parasympathomimetic). It was the first centrally acting cholinesterase inhibitor approved for the treatment of Alzheimer's disease, and was marketed under the trade name Cognex. Tacrine was first synthesised by Adrien Albert at the University of Sydney in 1949. It also acts as a histamine N-methyltransferase inhibitor.
==Clinical use== Tacrine was the prototypical cholinesterase inhibitor for the treatment of Alzheimer's disease. William K. Summers received a patent for this use in 1989. Studies found that it may have a small beneficial effect on cognition and other clinical measures, though study data was limited and the clinical relevance of these findings was unclear.