Memantine

Memantine
Clinical data
Trade names	Axura, Ebixa, Namenda, others
Other names	1-Amino-3,5-dimethyladamantane; 3,5-Dimethyladamantan-1-amine; Dimethyladamantanamine; DMAA; D145; D-145
AHFS/Drugs.com	Monograph
MedlinePlus	a604006
License data	US DailyMed: Memantine;
Pregnancy; category	AU: B2;
Routes of; administration	By mouth
Drug class	NMDA receptor antagonist
ATC code	N06DX01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	100%
Protein binding	45%
Metabolism	Minimal
Metabolites	• Memantine glucuronide; • 6-Hydroxymemantine; • 1-Nitrosomemantine
Elimination half-life	60–80 hours
Excretion	Urine (57–82% unchanged)
Identifiers
	IUPAC name 3,5-dimethyltricyclo[3.3.1.13,7]decan-1-amine;
CAS Number	19982-08-2 ; as HCl: 41100-52-1;
PubChem CID	4054; as HCl: 181458;
IUPHAR/BPS	4253;
DrugBank	DB01043 ; as HCl: DBSALT000456;
ChemSpider	3914 ; as HCl: 157849;
UNII	W8O17SJF3T; as HCl: JY0WD0UA60;
KEGG	D08174 ; as HCl: D04905;
ChEBI	CHEBI:64312; as HCl: CHEBI:64323;
ChEMBL	ChEMBL807 ; as HCl: ChEMBL1699;
PDB ligand	377 (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID5045174 ;
ECHA InfoCard	100.217.937
Chemical and physical data
Formula	C12H21N
Molar mass	179.307 g·mol−1
3D model (JSmol)	Interactive image; as HCl: Interactive image;
	SMILES NC12CC3CC(C)(C1)CC(C)(C3)C2; ; as HCl: Cl.NC12CC3CC(C)(C1)CC(C)(C3)C2;
	InChI InChI=1S/C12H21N/c1-10-3-9-4-11(2,6-10)8-12(13,5-9)7-10/h9H,3-8,13H2,1-2H3 ; Key:BUGYDGFZZOZRHP-UHFFFAOYSA-N ; ; as HCl: InChI=1S/C12H21N.ClH/c1-10-3-9-4-11(2,6-10)8-12(13,5-9)7-10;/h9H,3-8,13H2,1-2H3;1H; Key:LDDHMLJTFXJGPI-UHFFFAOYSA-N;
	(verify)

Memantine, sold under the brand name Namenda among others, is a medication used to slow the progression of moderate-to-severe Alzheimer's disease. It is taken by mouth.

Common side effects include headache, constipation, sleepiness, and dizziness. Severe side effects may include blood clots, psychosis, and heart failure. It is believed to work by acting on NMDA receptors, working as a pore blocker of these ion channels.

Memantine was first discovered in 1963. It was approved for medical use in Germany in 1989, in the European Union in 2002, and in the United States in 2003. It is available as a generic medication. In 2022, it was the 150th most commonly prescribed medication in the United States, with more than 3 million prescriptions.