Tacrine

Tacrine
Clinical data
Trade namesCognex
AHFS/Drugs.comMonograph
MedlinePlusa693039
Pregnancy
category
  • AU: C
Routes of
administration
Oral, rectal
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability2.4–36% (oral)
Protein binding55%
MetabolismHepatic (CYP1A2)
Elimination half-life2–4 hours
ExcretionRenal
Identifiers
  • 1,2,3,4-Tetrahydroacridin-9-amine
CAS Number
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.005.721 Edit this at Wikidata
Chemical and physical data
FormulaC13H14N2
Molar mass198.269 g·mol−1
3D model (JSmol)
Melting point183 °C (361 °F)
Boiling point358 °C (676 °F)
  • n1c3c(c(c2c1cccc2)N)CCCC3
  • InChI=1S/C13H14N2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1,3,5,7H,2,4,6,8H2,(H2,14,15) checkY
  • Key:YLJREFDVOIBQDA-UHFFFAOYSA-N checkY
  (verify)

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.[2]

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ Taraschenko OD, Barnes WG, Herrick-Davis K, Yokoyama Y, Boyd DL, Hough LB (April 2005). "Actions of tacrine and galanthamine on histamine-N-methyltransferase". Methods and Findings in Experimental and Clinical Pharmacology. 27 (3): 161–165. doi:10.1358/mf.2005.27.3.890872. PMID 15834447.