Tacrine

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.

Tacrine
Clinical data
Trade namesCognex
AHFS/Drugs.comMonograph
MedlinePlusa693039
Pregnancy
category
  • AU: C
Routes of
administration
Oral, rectal
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)
  • UK: POM (Prescription only)
  • US: ℞-only
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
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) Y
  • Key:YLJREFDVOIBQDA-UHFFFAOYSA-N Y
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