Compound: memantine
SMILES: NC12CC3(CC(C1)(CC(C2)C3)C)C
InChIKey: BUGYDGFZZOZRHP-UHFFFAOYSA-N
Synonyms: memantine, 19982-08-2, 3,5-dimethyladamantan-1-amine, 1-Amino-3,5-dimethyladamantane, Memantina, 3,5-Dimethyl-1-adamantanamine, Memantinum, 3,5-Dimethyl-1-aminoadamantane, 1,3-Dimethyl-5-adamantanamine, nemdatine, Tricyclo[3.3.1.13,7]decan-1-amine, 3,5-dimethyl-, DRG-0267, 3,5-Dimethyltricyclo(3.3.1.1(3,7))decan-1-amine, W8O17SJF3T, DTXSID5045174, D-145, NSC-757843, 1,3-Dimethyl-5-aminoadamantane, DTXCID3025174, CHEBI:64312, D 145, Tricyclo(3.3.1.13,7)decan-1-amine, 3,5-dimethyl-, Memantin, N06DX01, RefChem:5992, D145, 690-724-9, Axura, Memantine [INN], Memantinum [INN-Latin], Memantina [INN-Spanish], 3,5-Dimethyl-1-adamantylamine, CHEMBL807, 3,5-dimethyladamantanylamine, Memantine (INN), alzantin, NCGC00015705-04, Memantine [INN:BAN], CAS-19982-08-2, HSDB 7327, 3,5-dimethyltricyclo[3.3.1.1~3,7~]decan-1-amine, UNII-W8O17SJF3T, DMAA [Antiparkinson Agent], MFCD02114015, DRG 0267, Exiba (TN), Spectrum_000607, MEMANTINE [MI], MEMANTINE [HSDB], Prestwick0_000978, Prestwick1_000978, Prestwick2_000978, Prestwick3_000978, Spectrum2_001408, Spectrum3_000923, Spectrum4_001022, Spectrum5_001355, MEMANTINE [VANDF], CBMicro_020348, Biomol-NT_000209, MEMANTINE [WHO-DD], SCHEMBL2688, Lopac0_000861, Oprea1_480562, BSPBio_001015, KBioGR_001543, KBioSS_001087, DivK1c_000068, SPBio_001456, SPBio_002926, 1-amino-3,5-dimethyladamantan, BPBio1_001117, BPBio1_001270, GTPL4253, orb1306483, SCHEMBL1938718, SCHEMBL7032803, HMS500D10, KBio1_000068, KBio2_001087, KBio2_003655, KBio2_006223, KBio3_001926, 1-amino-3,5-dimethyl adamantane, 1-amino-3,5-dimethyl-adamantane, Tricyclo(3.3.1.1(3,7))decan-1-amine, 3,5-dimethyl-, NINDS_000068, 3,5-Dimethyl-adamantan-1-ylamine, ALBB-013872, Tox21_110199, 3,5-Dimethyl-1-aminoadamantane HCl, BBL000737, BDBM50062599, EBC-26142, SBB002574, STK520682, AKOS000113995, AKOS015953276, AKOS016340748, Tox21_110199_1, CCG-204092, DB01043, DS-3152, NSC 757843, SDCCGSBI-0020417.P005, IDI1_000068, NCGC00015705-03, NCGC00015705-05, NCGC00015705-07, NCGC00015705-09, NCGC00015705-16, NCGC00024782-02, NCGC00024782-03, FM153268, ST057652, SBI-0020417.P004, AB00053600, EU-0053634, NS00000622, D08174, D94592, EN300-103626, AB00053600-13, AB00053600_14, AB00053600_15, Q412189, 3,5-dimethyl-Tricyclo[3.3.1.13,7]decan-1-amine, BRD-A79803969-003-16-1, BRD-A79803969-003-17-9, BRD-A79803969-003-18-7, 3,5-DIMETHYLTRICYCLO(3.3.1.1(SUP 3,7))DECAN-1-AMINE, TRICYCLO(3.3.1.1(SUP 3,7))DECAN-1-AMINE, 3,5-DIMETHYL-
Theoretical properties:
molecular_formula: C12H21N
molecular_weight: 179.30 g/mol
exact_mass: 179.167399674 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 1
rotatable_bond_count: 0
heavy_atom_count: 13
topological_polar_surface_area: 26 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Oil
color: Oil
solubility: soluble in water
Descriptions:
pubchem: Memantine is a primary aliphatic amine that is the 3,5-dimethyl derivative of 1-aminoadamantane. A low to moderate affinity uncompetitive (open-channel); NMDA receptor antagonist which binds preferentially to the NMDA receptor-operated cation channels. It has a role as an antidepressant, an antiparkinson drug, a dopaminergic agent, a NMDA receptor antagonist and a neuroprotective agent. It is a primary aliphatic amine and a member of adamantanes. It is a conjugate base of a memantinium(1+). It derives from a hydride of an adamantane.
chebi: A primary aliphatic amine that is the 3,5-dimethyl derivative of 1-aminoadamantane. A low to moderate affinity uncompetitive (open-channel); NMDA receptor antagonist which binds preferentially to the NMDA receptor-operated cation channels.
chembl: MEMANTINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: 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 2023, it was the 145th most commonly prescribed medication in the United States, with more than 3 million prescriptions.