{"ATC Code":["N - Nervous system","N06 - Psychoanaleptics","N06D - Anti-dementia drugs","N06DX - Other anti-dementia drugs","N06DX01","N06DX01 - Memantine","QN - Nervous system","QN06 - Psychoanaleptics","QN06D - Anti-dementia drugs","QN06DX - Other anti-dementia drugs","QN06DX01 - Memantine"],"Absorption, Distribution and Excretion":"After an oral dose, memantine is well absorbed. Its peak drug concentrations are attained in about 3-7 hours. Memantine shows linear pharmacokinetics when given at normal therapeutic doses. This drug can be taken without regard to food, as there is no effect of food on memantine absorption.","Adverse Effects":"The most common adverse effects of memantine in clinical trials include dizziness, headache, confusion, diarrhea, and constipation. Additional adverse effects include fatigue, pain, hypertension, weight gain, hallucination, confusion, aggressive behavior, vomiting, abdominal pain, and urinary incontinence.","Aliases":["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","Dtxsid5045174","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","D145","690-724-9","Axura","3,5-Dimethyl-1-adamantylamine","CHEMBL807","3,5-dimethyladamantanylamine","alzantin","Ncgc00015705-04","(3,5-Dimethyl-1-adamantyl)amine hydrochloride","Cas-19982-08-2","HSDB 7327","3,5-dimethyltricyclo[3.3.1.1~3,7~]decan-1-amine","Unii-w8o17sjf3t","DMAA","Mfcd02114015","DRG 0267","Exiba","Spectrum_000607","Prestwick0_000978","Prestwick1_000978","Prestwick2_000978","Prestwick3_000978","Spectrum2_001408","Spectrum3_000923","Spectrum4_001022","Spectrum5_001355","CBMicro_020348","Biomol-NT_000209","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","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","T20993","Ab00053600-13","Ab00053600_14","Ab00053600_15","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-"],"Biological Half-Life":"The terminal elimination half-life of memantine ranges from 60 to 80 hours in humans.  Following administration of a single oral dose of 10 mg/kg memantine in rats, the elimination half-life was 2.36 ± 0.20 hours. Following a single intravenous dose of 2 mg/kg in rats, the elimination half-life was 2.28 ± 0.48 hours.","CAS":"19982-08-2","Chemical Classes":"Adamantanes","ChemicalClasses":["aniline"],"Chirality":"achiral","Color/Form":"Oil","Drug Classes":"Alzheimer Disease Agents","Drug Indication":"Memantine is used to manage moderate to severe Alzheimer's dementia.   A more recent systemic review and meta-analysis indicates that memantine is beneficial as a first line drug for the treatment of Alzheimer's dementia.  Cholinesterase inhibitors may be added to memantine for further beneficial effects on behavioral symptoms and other symptoms of dementia.","Drug Warnings":"FDA Pregnancy Risk Category: B /NO EVIDENCE OF RISK IN HUMANS. Adequate, well controlled studies in pregnant women have not shown increased risk of fetal abnormalities despite adverse findings in animals, or, in the absence of adequate human studies, animal studies show no fetal risk. The chance of fetal harm is remote but remains a possibility./","EliminationHalfLife":"60 – 80 hours","Erowid Experience Reports":[{"Author":"rararagi","Id":108837,"Title":"Useful But Not Recreational"},{"Author":"lps","Id":85730,"Title":"For Amphetamine Tolerance, Smoking Cessation"},{"Author":"Sonic","Id":111396,"Title":"Not Too Stimulated but Energetic Enough"},{"Author":"GlaciatedNorth","Id":114253,"Title":"Quarantrip"},{"Author":"Mastronaut","Id":107903,"Title":"Mem-oires"},{"Author":"AMA_Dragon","Id":104847,"Title":"Really Clean Disassociation"},{"Author":"pharmnerd","Id":103402,"Title":"For Opioid Dependence, Maybe"},{"Author":"GlaciatedNorth","Id":114624,"Title":"Quarantrip, the Summer Sequel"},{"Author":"CaptainOubliz","Id":100894,"Title":"Almost Mushroomesque"},{"Author":"name","Id":98107,"Title":"This One Is My Favourite"},{"Author":"EvDigital","Id":70393,"Title":"As Luck Would Have It"},{"Author":"viscosity","Id":86496,"Title":"Adventures in NMDA Receptor Antagonism"},{"Author":"stab","Id":93405,"Title":"Alzheimer Medicine High"},{"Author":"MadMastery","Id":114268,"Title":"Down the Mem-Hole"},{"Author":"feelwheel","Id":114916,"Title":"Feeling Normal At Last"},{"Author":"BitBitt","Id":115035,"Title":"Free From Humanity"},{"Author":"180OnTheDVP","Id":114110,"Title":"Just the Kick in the Teeth I Was Looking For"},{"Author":"180OnTheDVP","Id":114109,"Title":"Follow-Up to '24-Hour HellTrip'"},{"Author":"180OnTheDVP","Id":112468,"Title":"24-Hour HellTrip"},{"Author":"Lazyvegan","Id":32398,"Title":"A Few Words of Caution"},{"Author":"itstingsandithurts","Id":109789,"Title":"Being Disconnected From Reality"},{"Author":"Andex","Id":92047,"Title":"Good Day Later with a Double M-Hole"},{"Author":"itstingsandithurts","Id":109929,"Title":"A Dark Void I Call Home"},{"Author":"nervewing","Id":109838,"Title":"Wintry Void"},{"Author":"Goddess Mode","Id":105696,"Title":"Relentless Dissociative Aphrodisiac"},{"Author":"Ex-day tripper","Id":52958,"Title":"Nearly Neverending Trip"}],"Esters":[],"European Community (EC) Number":"690-724-9","FDA Pharmacological Classification":[{"Name":"FDA UNII","ReferenceNumber":25,"Value":{"StringWithMarkup":[{"String":"W8O17SJF3T"}]}},{"Name":"Active Moiety","ReferenceNumber":25,"Value":{"StringWithMarkup":[{"String":"MEMANTINE"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":25,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-22880","Length":4,"Start":29,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/NMDA"}],"String":"Mechanisms of Action [MoA] - NMDA Receptor Antagonists"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":25,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-22880","Length":20,"Start":40,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/N-methyl-D-aspartate"}],"String":"Established Pharmacologic Class [EPC] - N-methyl-D-aspartate Receptor Antagonist"}]}},{"Name":"FDA Pharmacology Summary","ReferenceNumber":25,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-4054","Length":9,"Start":0,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Memantine"},{"Extra":"CID-22880","Length":20,"Start":15,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/N-methyl-D-aspartate"},{"Extra":"CID-4054","Length":9,"Start":84,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/memantine"},{"Extra":"CID-22880","Length":4,"Start":102,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/NMDA"}],"String":"Memantine is a N-methyl-D-aspartate Receptor Antagonist. The mechanism of action of memantine is as a NMDA Receptor Antagonist."}]}},{"Name":"Non-Proprietary Name","ReferenceNumber":78,"Value":{"StringWithMarkup":[{"String":"MEMANTINE"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":78,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-22880","Length":20,"Start":0,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/N-methyl-D-aspartate"},{"Extra":"CID-22880","Length":4,"Start":48,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/NMDA"}],"String":"N-methyl-D-aspartate Receptor Antagonist [EPC]; NMDA Receptor Antagonists [MoA]"}]}}],"Formating":[],"HMDB ID":"HMDB0015177","HeavyAtomCount":13,"Human Drugs":"EMA approved medicines: Human medicine","IUPACName":"3,5-dimethyladamantan-1-amine","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","InChIKey":"BUGYDGFZZOZRHP-UHFFFAOYSA-N","Interactions":"Protein-bound Drugs: Because plasma protein binding of memantine is low (45%), a pharmacokinetic interaction with drugs that are highly protein bound (e.g., digoxin, warfarin) is unlikely.","KEGG Entries":[{"Id":"D04905","Interactions":[],"Synonyms":["Memantine hydrochloride","Namenda","Memary"]},{"Id":"D08174","Interactions":[],"Synonyms":["Memantine","Exiba"]}],"MeSH Headers":[{"Id":"M0013333","Link":"https://id.nlm.nih.gov/mesh/M0013333.html","Name":"Memantine","Ref":108},{"Id":"M0351817","Link":"https://id.nlm.nih.gov/mesh/M0351817.html","Name":"D-145","Ref":110},{"Id":"M0474758","Link":"https://id.nlm.nih.gov/mesh/M0474758.html","Name":"Axura","Ref":111},{"Id":"DescTree","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":"MeSH Tree","Ref":112},{"Id":"PubMed from MeSH","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":null,"Ref":134},{"Id":"M0001494","Link":"https://id.nlm.nih.gov/mesh/M0001494.html","Name":"Antiparkinson Agents","Ref":135},{"Id":"M0023499","Link":"https://id.nlm.nih.gov/mesh/M0023499.html","Name":"Dopamine Agents","Ref":136},{"Id":"M0028006","Link":"https://id.nlm.nih.gov/mesh/M0028006.html","Name":"Excitatory Amino Acid Antagonists","Ref":137}],"MeSH Pharmacological Classification":[{"Id":"M0001494","Link":"https://id.nlm.nih.gov/mesh/M0001494.html","Name":"Antiparkinson Agent","Ref":135},{"Id":"M0023499","Link":"https://id.nlm.nih.gov/mesh/M0023499.html","Name":"Dopamine Agent","Ref":136},{"Id":"M0028006","Link":"https://id.nlm.nih.gov/mesh/M0028006.html","Name":"Excitatory Amino Acid Antagonist","Ref":137}],"Mechanism of Action":"Continuous activation of the N-methyl-D-aspartate (NMDA) receptors in the central nervous system caused by _glutamate_ is thought to cause some of the Alzheimer's disease symptoms. This overactivation is thought to contribute to neurotoxicity due to the excitatory properties of glutamate. The pharmacological effect of memantine likely occurs via the drug's behavior as an uncompetitive (open-channel) NMDA receptor antagonist, preventing glutamate action on this receptor.  Memantine has a preference for the NMDA receptor-operated cation channels. Despite these antagonist effects, memantine has not been proven to prevent or retard the neurodegeneration seen in patients diagnosed with Alzheimer’s disease.","Melting Point":"White to off white fine powder. Crystals from alcohol/ether. MP: 290-295 °C, also reported as 290-295 °C. Soluble in water. /Memantine hydrochloride/","Metabolism/Metabolites":"This drug is partially metabolized in the liver. The hepatic CYP450 enzyme system does not majorly contribute to the metabolism of this drug.","MolecularFormula":"C\u003csub\u003e12\u003c/sub\u003eH\u003csub\u003e21\u003c/sub\u003eN","MolecularWeight":"179.30 g/mol","Pharmacodynamics":"**General effects**  This drug inhibits calcium influx into cells that is normally caused by chronic NMDA receptor activation by glutamate. This leads to the improvement of Alzheimer's dementia symptoms, demonstrated by increased cognition and other beneficial central nervous system effects.   **Effects on neuroplasticity**  Like other NMDA receptor antagonists, memantine at high doses can reduce neuronal synaptic plasticity that is involved in learning and memory processes. At lower concentrations, which are normally used in the clinical setting, memantine can enhance neuronal synaptic plasticity in the brain, improve memory, and act as a neuroprotectant against the destruction of neurons caused by excitatory neurotransmitters.   **Effect on various receptors**  Memantine has demonstrated minimal activity for GABA, benzodiazepine, dopamine, adrenergic, histamine, and glycine receptors, as well as voltage-dependent Ca2+, Na+ or K+ channels. This drug has shown antagonist activity at the 5HT3 receptors. Laboratory studies suggest that memantine does not affect the reversible inhibition of the acetylcholinesterase normally caused by donepezil, galantamine, or tacrine.","Physical Description":"Solid","PubChemId":4054,"Record Description":["LiverTox|CNS|Alzheimers agent|NMDA receptor antagonist"],"Records":{"UNII":{"Impurities":[]}},"RefChem":"5992","RefCount":4,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Memantine","Name":"Memantine","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q412189","Name":"Memantine","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/DB01043","Name":"Memantine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/4054","Name":"Memantine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=19982-08-2","Name":"Memantine","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0015177","Name":"Memantine","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/D08174","Name":"Memantine","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/W8O17SJF3T","Name":"Memantine","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID5045174","Name":"Memantine","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 4054, memantine. Accessed May 5, 2026. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/4054\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/4054\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Memantine. UNII: W8O17SJF3T. Global Substance Registration System. Accessed May 5, 2026. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/W8O17SJF3T\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/W8O17SJF3T\u003c/a\u003e","Anvisa. RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial. Diário Oficial da União. March 31, 2023. Accessed May 5, 2026. \u003ca href=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992\u003ehttps://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992\u003c/a\u003e"],"SMILES":"CC12CC3CC(C1)(CC(C3)(C2)N)C","SaltData":[{"AcidCount":1,"Amine":"Memantine","AmineCount":1,"Formula":"Cl","Name":"hydrochloride","RName":"hydrochloride","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 81.957 63.616\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#3050f8\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h82v64H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"m58.119 35.574-13.594-.782M44.525 34.792l-4.52 20.501M40.005 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class=\"atom\"\u003e\u003cpath d=\"M38.604 5.459h-.72l-2.619-4.066h-.03l.03.596q.023.357.023.732v2.738h-.565V.56h.714l2.608 4.054h.029l-.017-.327-.024-.477q-.006-.262-.006-.482V.56h.577zM42.91 5.459h-.619V3.173h-2.512v2.286h-.613V.56h.613v2.072h2.512V.56h.619zM45.415 6.949h-1.943v-.3l.772-.779q.221-.221.371-.393.154-.175.232-.339.079-.168.079-.364 0-.243-.147-.368-.142-.129-.371-.129-.214 0-.379.075-.16.075-.328.207l-.193-.243q.171-.146.393-.246.225-.1.507-.1.411 0 .65.207t.239.575q0 .229-.096.432-.093.2-.264.397-.168.196-.393.418l-.615.603v.018h1.486z\"/\u003e\u003c/g\u003e\u003cpath stroke=\"#3050f8\" d=\"m33.51 4.83-4.319 2.494\" class=\"hi\"/\u003e\u003c/g\u003e\u003cg class=\"mol\"\u003e\u003cg fill=\"#1ff01f\" stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M78.641 29.957q-.786 0-1.239.529-.452.524-.452 1.447 0 .911.417 1.447.422.529 1.268.529.321 0 .607-.053.292-.06.565-.143v.536q-.273.101-.565.149-.292.053-.697.053-.744 0-1.25-.309-.5-.31-.75-.876-.25-.571-.25-1.339 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Elimination of memantine can be enhanced by acidification of urine. (L1712)","UNII":"W8O17SJF3T","Wikidata":"Q412189","Wikipedia":"Memantine","XLogP":3.3}