MEMANTINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H21N
Molecular Weight	179.3018
Optical Activity	NONE
Defined Stereocenters	0 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=BUGYDGFZZOZRHP-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C12H21N
Molecular Weight	179.3018
Charge	0
Count

Stereochemistry	MIXED
Additional Stereochemistry	No
Defined Stereocenters	0 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021487s010s012s014,021627s008lbl.pdf
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/9120573

NAMENDA (marketed under the brands Namenda among others) is an N-methyl-D-aspartate (NMDA) receptor antagonist indicated for the treatment of moderate to severe dementia of the Alzheimer’s type. Persistent activation of central nervous system N-methyl-D-aspartate (NMDA) receptors by the excitatory amino acid glutamate has been hypothesized to contribute to the symptomatology of Alzheimer’s disease. Memantine is postulated to exert its therapeutic effect through its action as a low to moderate affinity uncompetitive (open-channel) NMDA receptor antagonist which binds preferentially to the NMDA receptor-operated cation channels. There is no evidence that memantine prevents or slows neurodegeneration in patients with Alzheimer’s disease. Memantine showed low to negligible affinity for GABA, benzodiazepine, dopamine, adrenergic, histamine and glycine receptors and for voltage-dependent Ca2+, Na+ or K+ channels. Memantine also showed antagonistic effects at the 5HT3 receptor with a potency similar to that for the NMDA receptor and blocked nicotinic acetylcholine receptors with one-sixth to one-tenth the potency. In vitro studies have shown that memantine does not affect the reversible inhibition of acetylcholinesterase by donepezil, galantamine, or tacrine.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glutamate [NMDA] receptor 125 Target ID: CHEMBL2094124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9120573	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Moderate to severe dementia of the Alzheimer’s type 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021487s010s012s014,021627s008lbl.pdf	Primary		Approved 8583	NAMENDA Approved Use Namenda (memantine hydrochloride) is indicated for the treatment of moderate to severe dementia of the Alzheimer's type. Launch Date 2003

C_max

Value	Dose	Analyte	Population
6.2 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18498913	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	MEMANTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
25.34 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18498913	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	MEMANTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
19.69 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18498913	5 mg 14 times / 2 weeks multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered:	MEMANTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
540 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18498913	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	MEMANTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1853 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18498913	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	MEMANTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
386.37 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18498913	5 mg 14 times / 2 weeks multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered:	MEMANTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
66.86 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18498913	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	MEMANTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
62 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18498913	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	MEMANTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
64.57 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18498913	5 mg 14 times / 2 weeks multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered:	MEMANTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193	substrate 1388	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP 110 OCT1 620 OCT2 779 OCT3 159	CYP1A2 1197 CYP2E1 729 CYP2B6 776 CYP2A6 626 CYP2C19 1119 P-gp 2052 OCT2 434

Drug as perpetrator

Target	Modality	Activity
CYP 150	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-487_Namenda_Bioeqr_P1.pdf#page=12 Page: 12.0	no
OCT3 161	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16581093/	yes [Ki 236 uM]
OCT1 656	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16581093/	yes [Ki 3.7 uM]
OCT2 782	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16581093/	yes [Ki 7.3 uM]

Drug as victim

Target	Modality	Activity
CYP1A2 1197	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-487_Namenda_Bioeqr_P1.pdf#page=37 Page: 37.0	no
CYP2A6 626	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-487_Namenda_Bioeqr_P1.pdf#page=37 Page: 37.0	no
CYP2B6 776	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-487_Namenda_Bioeqr_P1.pdf#page=37 Page: 37.0	no
CYP2C19 1119	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-487_Namenda_Bioeqr_P1.pdf#page=37 Page: 37.0	no
CYP2C9 1193	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-487_Namenda_Bioeqr_P1.pdf#page=37 Page: 37.0	no
CYP2D6 1388	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-487_Namenda_Bioeqr_P1.pdf#page=37 Page: 37.0	no
CYP2E1 729	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-487_Namenda_Bioeqr_P1.pdf#page=37 Page: 37.0	no
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-487_Namenda_Bioeqr_P1.pdf#page=37 Page: 37.0	no
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-487_Namenda_Bioeqr_P1.pdf#page=37 Page: 37.0	no
OCT2 434	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9687576/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-487_Namenda_Pharmr_P1.pdf#page=16 Page: 16.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:64312	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:64312
ChemicalBook	CB7436657	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7436657
eMolecules	902095	https://www.emolecules.com/cgi-bin/more?vid=902095
MolPort	MolPort-002-041-858	https://www.molport.com/shop/molecule-link/MolPort-002-041-858

PubMed

Title	Date	PubMed
Glial activation and post-synaptic neurotoxicity: the key events in Streptozotocin (ICV) induced memory impairment in rats.	2014-02	24333387
Memantine in patients with moderate to severe Alzheimer's disease: meta-analyses using realistic definitions of response.	2014	24107324
The role of memantine in the treatment of psychiatric disorders other than the dementias: a review of current preclinical and clinical evidence.	2012-08-01	22784018
Memantine prevents aluminum-induced cognitive deficit in rats.	2011-11-20	21741993
[Effects of electroacupuncture on expression of Abeta positive cells of the hippocampus and SOD activity in rats with streptozocin-Alzheimer's disease].	2010-12	21290839
Memantine is a useful drug to prevent the spatial and non-spatial memory deficits induced by methamphetamine in rats.	2010-11	20553881
Antinociceptive Effect of Memantine and Morphine on Vincristine-induced Peripheral Neuropathy in Rats.	2010-09	20830263
Sensitive and rapid HPLC method for determination of memantine in human plasma using OPA derivatization and fluorescence detection: application to pharmacokinetic studies.	2010-08-30	21179320
Protective effects of memantine and epicatechin on catechol-induced toxicity on Müller cells in vitro.	2010-05-27	20347921
Memantine ameliorates scopolamine-induced amnesia in chicks trained on taste-avoidance learning.	2010-05	20170739
Inhibition of apoptosis in human retinal pigment epithelial cells treated with benzo(e)pyrene, a toxic component of cigarette smoke.	2010-05	19959636
NMDA antagonist memantine improves levodopa-induced dyskinesias and "on-off" phenomena in Parkinson's disease.	2010-03-15	20014061
Protection of DFP-induced oxidative damage and neurodegeneration by antioxidants and NMDA receptor antagonist.	2009-10-15	19615394
Memanti-nium chloride 0.1-hydrate.	2009-08-19	21577595
Treatment of acquired periodic alternating nystagmus with memantine: a case report.	2009-06-11	19512963
Characteristic effects of anti-dementia drugs on rat sleep patterns.	2009-03	19305123
Memantine dosing in patients with dementia.	2009-02	19155749
Role of N-methyl-D-aspartate receptors in polychlorinated biphenyl mediated neurotoxicity.	2009-01-10	19022367
Effects of memantine on neuronal structure and conditioned fear in the Tg2576 mouse model of Alzheimer's disease.	2008-12	18418360
Profound pain reduction after induction of memantine treatment in two patients with severe phantom limb pain.	2008-10	18806054
Ca2+ inhibits the association of memantine with N-methyl-D-aspartate (NMDA) receptor-gated ion channels.	2008-09	18758084
Does memantine induce bradycardia? A study in the French PharmacoVigilance Database.	2008-09	18500725
Methylmercury increases N-methyl-D-aspartate receptors on human SH-SY 5Y neuroblastoma cells leading to neurotoxicity.	2008-07-30	18597911
Memantine prevents the cognitive impairment induced by 3,4-methylenedioxymethamphetamine in rats.	2008-07-28	18582864
Galantamine-induced pisa syndrome: memantine as an alternative.	2008-06	18506913
Memantine-induced hepatitis with cholestasis in a very elderly patient.	2008-04-15	18413635
Memantine-induced myoclonus and delirium exacerbated by trimethoprim.	2008-03	18303133
Memantine for agitation/aggression and psychosis in moderately severe to severe Alzheimer's disease: a pooled analysis of 3 studies.	2008-03	18294023
Memantine and NMDA antagonism for chronic migraine: a potentially novel therapeutic approach?	2008-02	18194287
[Therapy of Alzheimer's disease: current status and future development].	2008	18826870
The attenuating effect of memantine on staurosporine-, salsolinol- and doxorubicin-induced apoptosis in human neuroblastoma SH-SY5Y cells.	2007-08-21	17996985
Exacerbation of myoclonus by memantine in a patient with Alzheimer disease.	2007-08	17632233
Memantine as adjunctive therapy in children diagnosed with autistic spectrum disorders: an observation of initial clinical response and maintenance tolerability.	2007-05	17690064
Visual hallucinations and agitation in Alzheimer's disease due to memantine: report of three cases.	2007-05	17030587
Safety and tolerability of once-daily versus twice-daily memantine: a randomised, double-blind study in moderate to severe Alzheimer's disease.	2007-03	17243195
A retrospective study of memantine in children and adolescents with pervasive developmental disorders.	2007-03	17016714
Simultaneous liquid chromatographic assay of amantadine and its four related compounds in phosphate-buffered saline using 4-fluoro-7-nitro-2,1,3-benzoxadiazole as a fluorescent derivatization reagent.	2006-05	16161183
Effect of BD 1047, a sigma1 receptor antagonist, in the animal models predictive of antipsychotic activity.	2006-02-22	17085854
Memantine: a review of its use in Alzheimer's disease.	2006	16906789
Exacerbation of Lewy bodies dementia due to memantine.	2005-12	16340086
Delusions and hallucinations in dementia with Lewy bodies: worsening with memantine.	2005-08-09	16087923
Development of subtle psychotic symptoms with memantine: a case report.	2005-05	15889961
A comparison of the predictive therapeutic and undesired side-effects of the NMDA receptor antagonist, memantine, in mice.	2005-05	15864070
Effect of NMDA receptor antagonists on behavioral impairment induced by chronic treatment with dexamethasone.	2004-07-20	15849376
How to overcome resistance of influenza A viruses against adamantane derivatives.	1998-02	9588841
Inhibition by memantine of the development of persistent oral dyskinesias induced by long-term haloperidol treatment of rats.	1996-10	8904651
Pharmacotoxic psychosis after memantine in Parkinson's disease.	1991-10-19	1681331
Susceptibility of primary human glial fibrillary acidic protein-positive brain cells to human immunodeficiency virus infection in vitro: anti-HIV activity of memantine.	1991-01	1707644
Methyl parathion acute toxicity: prophylaxis and therapy with memantine and atropine.	1990-05-01	2241428
[Memantine and neurogenic bladder disorders within the bounds of spastic conditions].	1982	6891227

Patents

Sample Use Guides

In Vivo Use Guide

Initial dose is 5 mg once daily. Increase dose in 5 mg increments to a maintenance dose of 10 mg twice daily. A minimum of 1 week of treatment with the previous dose should be observed before increasing the dose.

Route of Administration: Oral

In Vitro Use Guide

Neuronal SK-N-SH cells were treated with 10 uM memantine and was measured levels of secreted total A beta precursor protein APP (sAPP), APP alpha isoform and A beta((1-40)) in a time dependent manner for up to 24h. Memantine significantly decreased the levels of the secreted form of sAPP, sAPP alpha and A beta((1-40)) compared to vehicle treated cells.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:15:41 GMT 2025` Edited by `admin` on `Mon Mar 31 18:15:41 GMT 2025`
Record UNII	W8O17SJF3T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MEMANTINE

Official Name

English

NEMDATINE

Preferred Name

English

3,5-DIMETHYL-1-ADAMANTANAMINE

Systematic Name

English

D-145

Code

English

MEMANTINE [VANDF]

Common Name

English

MEMANTINE [MI]

Common Name

English

TRICYCLO(3.3.1.1(SUP 3,7))DECAN-1-AMINE, 3,5-DIMETHYL-

Common Name

English

1-AMINO-3,5-DIMETHYLADAMANTANE

Systematic Name

English

Memantine [WHO-DD]

Common Name

English

NSC-757843

Code

English

memantine [INN]

Common Name

English

DRG-0267

Code

English

3,5-DIMETHYLTRICYCLO(3.3.1.1(SUP 3,7))DECAN-1-AMINE

Systematic Name

English

MEMANTINE [HSDB]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1509