Tacrine

Tacrine
Clinical data
Trade names	Cognex
AHFS/Drugs.com	Monograph
MedlinePlus	a693039
Pregnancy; category	AU: C;
Routes of; administration	Oral, rectal
ATC code	N06DA01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	2.4–36% (oral)
Protein binding	55%
Metabolism	Hepatic (CYP1A2)
Elimination half-life	2–4 hours
Excretion	Renal
Identifiers
	IUPAC name 1,2,3,4-Tetrahydroacridin-9-amine;
CAS Number	321-64-2 ;
IUPHAR/BPS	6687;
DrugBank	DB00382 ;
ChemSpider	1859 ;
UNII	4VX7YNB537;
ChEBI	CHEBI:45980 ;
ChEMBL	ChEMBL95 ;
PDB ligand	THA (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID1037272 ;
ECHA InfoCard	100.005.721
Chemical and physical data
Formula	C13H14N2
Molar mass	198.269 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	183 °C (361 °F)
Boiling point	358 °C (676 °F)
	SMILES n1c3c(c(c2c1cccc2)N)CCCC3;
	InChI 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) ; Key:YLJREFDVOIBQDA-UHFFFAOYSA-N ;
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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]

^ 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.
^ 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.