Itameline

Itameline (INNTooltip International Nonproprietary Name; developmental code name RU-47213) is a non-selective muscarinic acetylcholine receptor agonist which was under development for the treatment of Alzheimer's disease and memory disorders but was never marketed.^[1][2][3] It has been referred to as a "nootropic" (cognitive enhancer).^[4][5]

Itameline

Clinical data
Other names	RU-47213; RU47213
Drug class	Non-selective muscarinic acetylcholine receptor agonist
Identifiers
IUPAC name (4-chlorophenyl) 5-[(E)-methoxyiminomethyl]-3,6-dihydro-2H-pyridine-1-carboxylate
CAS Number	145071-44-9 145071-44-9
PubChem CID	9571042
ChemSpider	7845508
UNII	5VO597V509
ChEMBL	ChEMBL2105092
Chemical and physical data
Formula	C14H15ClN2O3
Molar mass	294.74 g·mol−1
3D model (JSmol)	Interactive image
SMILES CO/N=C/C1=CCCN(C1)C(=O)OC2=CC=C(C=C2)Cl
InChI InChI=1S/C14H15ClN2O3/c1-19-16-9-11-3-2-8-17(10-11)14(18)20-13-6-4-12(15)5-7-13/h3-7,9H,2,8,10H2,1H3/b16-9+ Key:CTVQNEVLCGSTKL-CXUHLZMHSA-N

Itameline is a prodrug of RU-35963, an arecoline derivative.^[6][7][2] It is an agonist of the muscarinic acetylcholine M₁ receptor as well as of other muscarinic acetylcholine receptors.^{[8][6][9][7][2]} Itameline is described as being superior to arecoline in terms of potency, central selectivity, and duration of action.^[6][7] The drug shows antiamnesic effects in animals, for instance reversing scopolamine-induced memory deficits.^{[10][6][2][3]} Structurally, it is a tetrahydropyridine similarly to xanomeline and milameline.^[11]

Itameline was first described in the scientific literature by 1992.^[3] It was under development by Hoechst Marion Roussel and reached phase 2 clinical trials by 1998 prior to the discontinuation of its development.^[12][7][4]