Memantine (CED0002049)

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:14 UTC

Update Date

2026-05-14 16:56:35 UTC

SynCED ID

CED0002049

Secondary Accession Numbers

CHEM002330
T3D2967

Identification

Common Name

Memantine

Class

Small Molecule

Description

Memantine (C12H21N) is an exogenous organic compound with an average molecular weight of 179.30 g/mol. At room temperature, it exists as a solid. Memantine belongs to the amines, a subclass of organonitrogen compounds within the organic compounds. This compound acts as an NMDA receptor antagonist and a dopaminergic agent. Its biological roles and applications include use as an antiparkinson drug, a neuroprotective agent, and an antidepressant. Memantine exerts its action through uncompetitive NMDA receptor antagonism, binding preferentially to the NMDA receptor-operated cation channels. It targets several proteins, including the D(2) dopamine receptor (DRD2), the Alpha-7 nicotinic cholinergic receptor subunit (CHRNA7), the antagonist/binder of 5-hydroxytryptamine receptor 3A (HTR3A), and glutamate receptor ionotropic NMDA 1 (GRIN1), 2A (GRIN2A), 2B (GRIN2B), and 3A (GRIN3A). Studies suggest that memantine binds more effectively than Mg2+ ions at the NMDA receptor. In the brain of demented patients, prolonged increased levels of glutamate can counter the voltage-dependent block of NMDA receptors by Mg2+ ions, allowing continuous influx of Ca2+ ions into cells and leading to neuronal degeneration. Memantine is recorded in 11 sources, including anti-dementia drugs within healthcare, pharmaceuticals, and veterinary products. Other sources include food preservation in food processing and cookware, floors in building and construction, soap detergents and smoking requisites in household cleaning and consumer products, and electrical and electronic equipment such as magnets, radio transmission systems, and electrically stimulated smoking devices. The recorded exposure route for this compound is oral.

Contaminant Type

Amine
Antidyskinetic
Antiparkinson Agent
Central Nervous System Agent
Dopamine Agent
Drug
Excitatory Amino Acid Antagonist
Human Neurotoxin
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,3-Dimethyl-5-adamantanamine	ChEBI
1-Amino-3,5-dimethyladamantane	ChEBI
3,5-Dimethyl-1-adamantanamine	ChEBI
3,5-Dimethyl-1-aminoadamantane	ChEBI
3,5-Dimethyltricyclo(3.3.1.1(3,7))decan-1-amine	ChEBI
Memantina	ChEBI
Memantinum	ChEBI
Exiba	Kegg
Axura	HMDB
Lundbeck brand OF memantine hydrochloride	HMDB
Merz brand OF memantine hydrochloride	HMDB
Ebixa	HMDB
Memantin	HMDB
Memantine hydrochloride	HMDB
Namenda	HMDB
1,3-Dimethyl-5-aminoadamantane	HMDB

Chemical Formula

C₁₂H₂₁N

Average Molecular Mass

179.302 g/mol

Monoisotopic Mass

179.167 g/mol

CAS Registry Number

19982-08-2

IUPAC Name

3,5-dimethyladamantan-1-amine

Traditional Name

memantine

SMILES

CC12CC3CC(C)(C1)CC(N)(C3)C2

InChI Identifier

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

InChI Key

BUGYDGFZZOZRHP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Monoalkylamines

Alternative Parents

Substituents

Organopnictogen compound
Hydrocarbon derivative
Primary aliphatic amine
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

adamantanes (CHEBI:64312 )
primary aliphatic amine (CHEBI:64312 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Biological Roles

dopaminergic agent ?
EC 3.1.1.7 (acetylcholinesterase) inhibitor (PMC11510615 )?An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.
antimicrobial agent (PMC11047579 )?
NMDA receptor antagonist (PMC2669703 , PMC13205055 )?
EC 3.1.1.8 (cholinesterase) inhibitor (PMC2773021 )?An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).
antagonist (PMC9221885 , PMC9501146 )?Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.
drug (PMC7762150 )?
pharmaceutical (PMC9696219 , PMC9696219 )?
psychotropic drug (PMC13390425 , PMC13390425 )?

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	258°C
Boiling Point	Not Available
Solubility	35 mg/mL (HCl salt), 0.9 mg/mL for free base

Predicted Properties

Property	Value	Source
Water Solubility	0.046 g/L	ALOGPS
logP	3.31	ALOGPS
logP	2.07	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	10.7	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.02 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	54.49 m³·mol⁻¹	ChemAxon
Polarizability	21.82 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-03fr-0900000000-4db94b4b87705e834d5d	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03e9-0900000000-65172d14e0f6b9102d73	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0900000000-ce475f103d528ff4d342	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0900000000-1c9199c5cf1c902223ae	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-08fr-0900000000-1bac817f714e7eec7488	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-2900000000-eb58e236084a93a3d37b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-4900000000-5a87d54400c3e9720ad0	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-052f-9500000000-95eb2b63a2392449ec4a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-9100000000-608b372857aacd60eb61	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00kf-9000000000-f283a81168372575c2aa	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0900000000-bbf1127413d0f995a000	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-08fr-1900000000-af0d7a2139a4f0101029	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-052f-9500000000-7d8b0b05d4e422cf43ff	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-4900000000-c38a0c0bf1d221876255	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-052f-9400000000-b9b0845988ac96d13655	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-9100000000-c0a9196c8aea3bbc9ba5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-044i-0900000000-dbaa35eb2bd2e8a926ee	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0900000000-fe3a10c3c4ef737f6317	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-08fr-0900000000-31518410ee334d4b0e50	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03e9-0900000000-d6a33792b66ebc7fcaa5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0900000000-ac61d90ba68b567ddee8	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-08fr-0900000000-33f368095aebd8d97509	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-2900000000-99e3d4de18e5f4256349	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0900000000-3c50a8971f34bfb12a25	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0900000000-8781008cdaa8bca3cca6	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03e9-0900000000-3510853e6d55d4387284	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0900000000-91170b903e5af6a1a238	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0900000000-855e1e3f6edd15ce811a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0900000000-995105a6b909b000887f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03e9-0900000000-01b7cb0dbee9cea1243a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01q9-0900000000-d5fdfd99bc401e75f44d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01q9-0900000000-8e06cea62d1b5b2287fd	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0900000000-07e8313e47d270feab02	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0900000000-8a0b61ba65a9638329fb	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0900000000-242508d651dfd0b38ea8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01t9-0900000000-710a53b2a03cd1789d69	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03e9-0900000000-5a27036df13f9084e497	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0900000000-606ea2f371ba1bea935e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0900000000-976ecc3522849ea60274	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0900000000-c425ae0c08340f42d771	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0900000000-c425ae0c08340f42d771	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0900000000-c425ae0c08340f42d771	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
608.0 Log mg/kg [340:1100]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Memantine exerts its action through uncompetitive NMDA receptor antagonism, binding preferentially to the NMDA receptor-operated cation channels. Prolonged increased levels of glutamate in the brain of demented patients are sufficient to counter the voltage-dependent block of NMDA receptors by Mg²⁺ ions and allow continuous influx of Ca²⁺ ions into cells, ultimately resulting in neuronal degeneration. Studies suggest that memantine binds more effectively than Mg²⁺ ions at the NMDA receptor, and thereby effectively blocks this prolonged influx of Ca²⁺ ions through the NMDA channel whilst preserving the transient physiological activation of the channels by higher concentrations of synaptically released glutamate. Thus memantine protects against chronically elevated concentrations of glutamate. Memantine also has antagonistic activity at the type 3 serotonergic (5-HT₃) receptor with a potency that is similar to that at the NMDA receptor, and lower antagonistic activity at the nicotinic acetylcholine receptor. This drug has no affinity for gamma-aminobutyric acid (GABA), benzodiazepine, dopamine, adrenergic, histamine, or glycine receptors or for voltage-dependent calcium, sodium, or potassium channels.

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Minimum Risk Level

Not Available

Symptoms

Side effects include pain, abnormal crying, leg pain, fever, increased apetite. Adverse drug reactions include: dizziness, confusion, headache, hallucinations, tiredness. Less common side effects include: vomiting, anxiety, hypertonia, cystitis, and increased libido. Doses of up to 400 mg have been tolerated.

Treatment

As in any cases of overdose, general supportive measures should be utilized, and treatment should be symptomatic. Elimination of memantine can be enhanced by acidification of urine. (7)

Health Effects

Health Effect	Relationship	Direction	Description	Reference
inflammation	Has Therapeutic Effect On	Not Available	Not Available	PMC5891396
Alzheimer's disease	Not Available	Not Available	A neurodegenerative disease which causes neural atrophy, leading to dementia and memory loss.	PMC9330545 , PMC5249025
Alzheimer's disease	Has Therapeutic Effect On	Not Available	A neurodegenerative disease which causes neural atrophy, leading to dementia and memory loss.	PMC11594972 , PMC9696219
nausea	Associated With?	Not Available	A disorder characterized by a queasy sensation and/or the urge to vomit. (NCI CTCAE)	PMC12475202
vertigo	Associated With?	Not Available	A type of dizziness characterized by a sensation as if the external world were revolving around the patient (objective vertigo) or as if he himself were revolving in space (subjective vertigo).	PMC12475202
confusion	Associated With?	Not Available	A disorder characterized by a lack of clear and orderly thought and behavior. (NCI CTCAE)	PMC12475202
Toxic encephalopathy	Has Therapeutic Effect On	Not Available	Not Available	PMC11202106
anxiety disorder	Associated With?	Not Available	Not Available	PMC13390425
Neuropathology	Has Therapeutic Effect On	Not Available	Not Available	PMC3756137
Hallucinations	Associated With?	Not Available	Not Available	PMC13390425
Neurodegeneration	Has Therapeutic Effect On	Not Available	Not Available	PMC11594972
Delusion	Associated With?	increase	Not Available	PMC13390425
Delusion	Associated With?	Not Available	Not Available	PMC13390425

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000013	Soil?Soil serves as a critical medium for plant growth and sustains various ecological functions; however, it can become a reservoir for synthetic chemical contamination.	Agriculture & land management	PMC9696219 , PMC9696219
CEDs000380	Anti-dementia drugs?Anti-dementia drugs, primarily used to manage symptoms of cognitive decline in conditions such as Alzheimer's disease, include cholinesterase inhibitors and NMDA receptor antagonists.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000497	Floors?Floors in built environments can be a significant source of synthetic chemical contamination due to the materials and finishes used in their construction.	Building & Construction	PubChem
CEDs000511	Conductors Or Conductive Bodies Characterised By The Conductive Materials?Conductors, or conductive bodies, are materials that allow the flow of electrical current, typically made from metals such as copper, aluminum, or silver.	Electrical & Electronic Equipment	PubChem
CEDs000518	Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.	Electrical & Electronic Equipment	PubChem
CEDs000527	Magnets?Magnets, commonly used in various electrical and electronic applications, can be a source of synthetic chemical contamination due to the materials used in their production.	Electrical & Electronic Equipment	PubChem
CEDs000530	Radio Transmission Systems?Radio transmission systems utilize a variety of synthetic chemicals in their manufacturing and maintenance processes.	Electrical & Electronic Equipment	PubChem
CEDs000545	Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.	Food, food processing & cookware	PubChem
CEDs000556	Cigar Cigarettes?Cigar cigarettes are a source of synthetic chemical contamination due to the combustion of various tobacco blends and additives.	Household cleaning & consumer products	PubChem
CEDs000559	Non Electric Simulated Smoking Devices?Non-electric simulated smoking devices, often designed to mimic the experience of smoking without combustion, can be sources of synthetic chemical contamination due to the materials and chemicals used in their construction and operation.	Household cleaning & consumer products	PubChem
CEDs000560	Other Smoking Requisites?Other smoking requisites, including items such as lighters, matches, and rolling papers, can introduce synthetic chemical contamination through various components and additives.	Household cleaning & consumer products	PubChem
CEDs000563	Soap Detergents?Soap detergents are synthetic surfactants designed to enhance the cleaning efficacy of water by reducing surface tension, allowing for better interaction with dirt and grease.	Household cleaning & consumer products	PubChem
CEDs000580	Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.	Industrial manufacturing & chemical processing	PubChem
CEDs000596	Acaricides?Acaricides are synthetic chemicals specifically designed to target and control mite populations that can damage crops and plants.	Agriculture & land management	PubChem
CEDs000600	Herbicides And Algicides?Herbicides and algicides are synthetic chemicals primarily used to control unwanted plants and algae in various environments.	Agriculture & land management	PubChem
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000614	Essential Oils Or Perfumes?Essential oils and perfumes are complex mixtures of volatile compounds derived from natural or synthetic sources, commonly used for their aromatic properties.	Personal care & cosmetics	PubChem
CEDs000615	Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.	Personal care & cosmetics	PubChem
CEDs000650	Purses Luggage Hand Bags?Purses, luggage, and handbags are often manufactured using synthetic materials such as polyvinyl chloride (PVC), polyurethane, and various types of nylon.	Textiles, leather & furnishings	PubChem
CEDs000671	Airplanes And Helicopters?Airplanes and helicopters are significant sources of synthetic chemical contamination primarily through the use of aviation fuels, lubricants, and de-icing agents.	Aviation & Aerospace	PubChem
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	PubChem
CEDs000686	Clay Wares?Clay wares are ceramic products made from natural clay, often utilized in various construction applications such as tiles, bricks, and sanitary ware.	Building & Construction	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000735	Explosives?Explosives are chemical compounds or mixtures designed to undergo rapid decomposition, releasing energy in the form of gas and heat.	Defense & military infrastructure	PubChem
CEDs000739	Inks?Inks are complex mixtures composed of pigments or dyes, solvents, resins, and additives used primarily for printing and writing applications.	Paper, pulp & fiber products	PubChem
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	PubChem
CEDs00751	Feed	Agriculture & land management	PMC11945237
CEDs01080	Capsule	Healthcare, pharmaceuticals & veterinary products	PMC7822176 , PMC7822176
CEDs01125	Pharmaceutical Formulation	Healthcare, pharmaceuticals & veterinary products	PMC12132094
CEDs02264	Sediment	Aquatic systems & sediments	PMC9696219 , PMC9696219
CEDs03053	Hospital Wastewater	Wastewater, sanitation & biosolids	PMC12214922

Pathways

2 pathwaysPathway Source: PathBank

Memantine Action Pathway

Memantine Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Acetylcholinesterase	P22303	Humans	Predicted (SEA)	Prediction Confidence Score 0.293 Applicability Domain 1.0 Statistical Significance 0.0495 Supporting Reference Compounds 406 E-value 385.743
Click to view 3D structure	Acetylcholinesterase	O42275	Electrophorus electricus	Predicted (SEA)	Prediction Confidence Score 0.282 Applicability Domain 1.0 Statistical Significance 0.0383 Supporting Reference Compounds 206 E-value 297.851
Click to view 3D structure	Glutamate receptor ionotropic, NMDA 2C	Q00961	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.275 Applicability Domain 1.0 Statistical Significance 0.0071 Supporting Reference Compounds 35 E-value 54.9616
Click to view 3D structure	Cholinesterase	P81908	Equus caballus	Predicted (SEA)	Prediction Confidence Score 0.27 Applicability Domain 1.0 Statistical Significance 0.0529 Supporting Reference Compounds 201 E-value 411.745
Click to view 3D structure	Glutamate receptor ionotropic, NMDA 1	P35439	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.263 Applicability Domain 1.0 Statistical Significance 5.00e-04 Supporting Reference Compounds 22 E-value 3.89246
Click to view 3D structure	Matrix protein 2	P06821	Influenza A virus	Predicted (SEA)	Prediction Confidence Score 0.213 Applicability Domain 0.455 Statistical Significance 3.00e-05 Supporting Reference Compounds 4 E-value 0.233548
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	Prediction Confidence Score 0.196 Applicability Domain 0.455 Statistical Significance 0.7773 Supporting Reference Compounds 562 E-value 6050.91
Click to view 3D structure	Metabotropic glutamate receptor 2	Q14416	Humans	Predicted (SEA)	Prediction Confidence Score 0.184 Applicability Domain 0.216 Low confidence Statistical Significance 0.4499 Supporting Reference Compounds 85 E-value 3502.83
Click to view 3D structure	Metabotropic glutamate receptor 6	O15303	Humans	Predicted (SEA)	Prediction Confidence Score 0.181 Applicability Domain 0.216 Low confidence Statistical Significance 0.2598 Supporting Reference Compounds 39 E-value 2022.83
Click to view 3D structure	Matrix protein 2	P0DOF8	Influenza A virus (A/Udorn/307/1972(H3N2))	Predicted (SEA)	Prediction Confidence Score 0.181 Applicability Domain 0.455 Statistical Significance 4.00e-05 Supporting Reference Compounds 4 E-value 0.311397
Click to view 3D structure	Bifunctional epoxide hydrolase 2	P34914	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.173 Applicability Domain 0.217 Low confidence Statistical Significance 0.3738 Supporting Reference Compounds 29 E-value 2909.77
Click to view 3D structure	Bifunctional epoxide hydrolase 2	P34913	Humans	Predicted (SEA)	Prediction Confidence Score 0.173 Applicability Domain 0.217 Low confidence Statistical Significance 0.6965 Supporting Reference Compounds 93 E-value 5422.28
Click to view 3D structure	Metabotropic glutamate receptor 3	Q14832	Humans	Predicted (SEA)	Prediction Confidence Score 0.173 Applicability Domain 0.216 Low confidence Statistical Significance 0.3723 Supporting Reference Compounds 40 E-value 2898.09
Click to view 3D structure	Protein deacetylase HDAC6	Q9UBN7	Humans	Predicted (SEA)	Prediction Confidence Score 0.169 Applicability Domain 0.217 Low confidence Statistical Significance 0.9603 Supporting Reference Compounds 553 E-value 7475.78
Click to view 3D structure	Dipeptidase 1	P22412	Sus scrofa	Predicted (SEA)	Prediction Confidence Score 0.159 Applicability Domain 0.159 Low confidence Statistical Significance 0.0046 Supporting Reference Compounds 1 E-value 36.0442
Click to view 3D structure	Metabotropic glutamate receptor 2	P31421	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.155 Applicability Domain 0.194 Low confidence Statistical Significance 0.7516 Supporting Reference Compounds 53 E-value 5851.38
Click to view 3D structure	Metabotropic glutamate receptor 3	P31422	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.155 Applicability Domain 0.194 Low confidence Statistical Significance 0.5895 Supporting Reference Compounds 39 E-value 4588.98
Click to view 3D structure	Histone deacetylase 3	O15379	Humans	Predicted (SEA)	Prediction Confidence Score 0.151 Applicability Domain 0.217 Low confidence Statistical Significance 0.971 Supporting Reference Compounds 257 E-value 7559.55
Click to view 3D structure	Histone deacetylase 2	Q92769	Humans	Predicted (SEA)	Prediction Confidence Score 0.15 Applicability Domain 0.217 Low confidence Statistical Significance 0.9762 Supporting Reference Compounds 307 E-value 7599.87
Click to view 3D structure	Metabotropic glutamate receptor 1	Q13255	Humans	Predicted (SEA)	Prediction Confidence Score 0.149 Applicability Domain 0.189 Low confidence Statistical Significance 0.8762 Supporting Reference Compounds 68 E-value 6820.92
Click to view 3D structure	Metabotropic glutamate receptor 8	O00222	Humans	Predicted (SEA)	Prediction Confidence Score 0.145 Applicability Domain 0.188 Low confidence Statistical Significance 0.7989 Supporting Reference Compounds 48 E-value 6219.14
Click to view 3D structure	Spermidine synthase	Q6QA75	Sus scrofa	Predicted (SEA)	Prediction Confidence Score 0.143 Applicability Domain 0.143 Low confidence Statistical Significance 0.0018 Supporting Reference Compounds 1 E-value 13.7793
Click to view 3D structure	Spermidine synthase	Q4CXJ6	Trypanosoma cruzi (strain CL Brener)	Predicted (SEA)	Prediction Confidence Score 0.143 Applicability Domain 0.143 Low confidence Statistical Significance 0.0018 Supporting Reference Compounds 1 E-value 13.7793
Click to view 3D structure	Spermidine synthase	Q9NFS5	Plasmodium falciparum	Predicted (SEA)	Prediction Confidence Score 0.143 Applicability Domain 0.143 Low confidence Statistical Significance 0.0018 Supporting Reference Compounds 1 E-value 13.7793
Click to view 3D structure	Serine/threonine-protein phosphatase 2A 65 kDa regulatory subunit A alpha isoform	Q76MZ3	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.143 Applicability Domain 0.143 Low confidence Statistical Significance 0.0061 Supporting Reference Compounds 1 E-value 47.4102
Click to view 3D structure	Acetylcholinesterase	P22303	Humans	Known	Not Available
Click to view 3D structure	Glutamate receptor ionotropic, NMDA 2A	Q12879	Humans	Known	Memantine exerts its action through uncompetitive NMDA receptor antagonism, binding preferentially to the NMDA receptor-operated cation channels. Prolonged increased levels of glutamate in the brain of demented patients are sufficient to counter the voltage-dependent block of NMDA receptors by Mg²⁺ ions and allow continuous influx of Ca²⁺ ions into cells and ultimately neuronal degeneration. Studies suggest that memantine binds more effectively than Mg²⁺ ions at the NMDA receptor, and thereby effectively blocks this prolonged influx of Ca²⁺ ions through the NMDA channel whilst preserving the transient physiological activation of the channels by higher concentrations of synaptically released glutamate. Thus memantine protects against chronically elevated concentrations of glutamate.
Click to view 3D structure	Glutamate receptor ionotropic, NMDA 2B	Q13224	Humans	Known	Memantine exerts its action through uncompetitive NMDA receptor antagonism, binding preferentially to the NMDA receptor-operated cation channels. Prolonged increased levels of glutamate in the brain of demented patients are sufficient to counter the voltage-dependent block of NMDA receptors by Mg²⁺ ions and allow continuous influx of Ca²⁺ ions into cells and ultimately neuronal degeneration. Studies suggest that memantine binds more effectively than Mg²⁺ ions at the NMDA receptor, and thereby effectively blocks this prolonged influx of Ca²⁺ ions through the NMDA channel whilst preserving the transient physiological activation of the channels by higher concentrations of synaptically released glutamate. Thus memantine protects against chronically elevated concentrations of glutamate.
Click to view 3D structure	Glutamate receptor ionotropic, NMDA 3A	Q8TCU5	Humans	Known	Memantine exerts its action through uncompetitive NMDA receptor antagonism, binding preferentially to the NMDA receptor-operated cation channels. Prolonged increased levels of glutamate in the brain of demented patients are sufficient to counter the voltage-dependent block of NMDA receptors by Mg²⁺ ions and allow continuous influx of Ca²⁺ ions into cells and ultimately neuronal degeneration. Studies suggest that memantine binds more effectively than Mg²⁺ ions at the NMDA receptor, and thereby effectively blocks this prolonged influx of Ca²⁺ ions through the NMDA channel whilst preserving the transient physiological activation of the channels by higher concentrations of synaptically released glutamate. Thus memantine protects against chronically elevated concentrations of glutamate.
Click to view 3D structure	Glutamate receptor ionotropic, NMDA 1	Q05586	Humans	Known	Not Available
Click to view 3D structure	5-hydroxytryptamine receptor 3A	P46098	Humans	Known	Not Available
Click to view 3D structure	Alpha-7 nicotinic cholinergic receptor subunit	Q693P7	Humans	Known	Not Available
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Known	Not Available
Click to view 3D structure	Solute carrier family 22 member 1	O15245	Humans	Known	Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB01043

HMDB ID

HMDB0015177

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

DrugSyn.org

MSDS

Link

General References

Cacabelos R, Takeda M, Winblad B: The glutamatergic system and neurodegeneration in dementia: preventive strategies in Alzheimer's disease. Int J Geriatr Psychiatry. 1999 Jan;14(1):3-47. [PubMed: 10029935]
Rogawski MA, Wenk GL: The neuropharmacological basis for the use of memantine in the treatment of Alzheimer's disease. CNS Drug Rev. 2003 Fall;9(3):275-308. [PubMed: 14530799]
Robinson DM, Keating GM: Memantine: a review of its use in Alzheimer's disease. Drugs. 2006;66(11):1515-34. [PubMed: 16906789]
Rogawski MA: Low affinity channel blocking (uncompetitive) NMDA receptor antagonists as therapeutic agents--toward an understanding of their favorable tolerability. Amino Acids. 2000;19(1):133-49. [PubMed: 11026482]
Rammes G, Rupprecht R, Ferrari U, Zieglgansberger W, Parsons CG: The N-methyl-D-aspartate receptor channel blockers memantine, MRZ 2/579 and other amino-alkyl-cyclohexanes antagonise 5-HT(3) receptor currents in cultured HEK-293 and N1E-115 cell systems in a non-competitive manner. Neurosci Lett. 2001 Jun 22;306(1-2):81-4. [PubMed: 11403963]
Drugs.com - http://www.drugs.com/cons/Memantine.html
RxList: The Internet Drug Index (2009). - http://www.rxlist.com/

Memantine (CED0002049)

Structure for CHEM002330: Memantine

Structure