M9292
Memantine hydrochloride
≥98% (GC), powder, NMDA glutamate receptor antagonist
Synonym(s):
3,5-Dimethyl-1-adamantanamine hydrochloride, 3,5-Dimethylamantadine hydrochloride, 3,5-Dimethyltricyclo[3.3.1.13,7]decan-1-amine hydrochloride
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About This Item
Empirical Formula (Hill Notation):
C12H21N · HCl
CAS Number:
Molecular Weight:
215.76
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
255-219-6
MDL number:
Product Name
Memantine hydrochloride, ≥98% (GC)
Quality Level
assay
≥98% (GC)
form
powder
originator
Forest Labs
SMILES string
Cl.C[C@]12CC3C[C@](C)(C1)CC(N)(C3)C2
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/t9-,10+,11-,12-;
InChI key
LDDHMLJTFXJGPI-VXMZOEJHSA-N
Gene Information
human ... DRD1(1812), DRD2(1813), DRD3(1814), DRD4(1815), DRD5(1816)
Application
Memantine hydrochloride has been used:
- as a media supplement to serve as a control to study the neuroprotective effects of erythropoietin in N-methyl-D-aspartate receptor-induced toxicity
- to intraperitoneally inject experimental animal to study its effect on traumatic injury
- as a test compound to determine the dynamic range and selectivity of retinal pigment epithelium tissue penetration
Biochem/physiol Actions
Low-affinity NMDA glutamate receptor antagonist; stimulates dopamine release.
Memantine is effective against Alzheimer′s disease and Parkinson′s disease. It is also useful in treating epilepsy, motor neurone disease and trauma.
Features and Benefits
This compound is a featured product for ADME Tox and Neuroscience research. Discover more featured ADME Tox and Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Glutamate Receptors (Ion Channel Family) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Forest Labs. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.
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Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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M Weller et al.
Brain research, 613(1), 143-148 (1993-06-04)
Effects of amantadine and memantine on NMDA receptor-mediated glutamate toxicity were studied in cultured cerebellar, cortical and mesencephalic neurons. Both drugs protected cerebellar and cortical neurons against glutamate toxicity, memantine being consistently more effective than amantadine but less effective than
Anton N Shuvaev et al.
International journal of molecular sciences, 22(15) (2021-08-08)
Spinocerebellar ataxias are a family of fatal inherited diseases affecting the brain. Although specific mutated proteins are different, they may have a common pathogenetic mechanism, such as insufficient glutamate clearance. This function fails in reactive glia, leading to excitotoxicity and
C G Parsons et al.
Neuropharmacology, 32(12), 1337-1350 (1993-12-01)
Memantine (1-amino-3,5-dimethyladamantan) was tested as an antagonist of N-methyl-D-aspartate (NMDA) receptors on cultured superior collicular and hippocampal neurones using the patch clamp technique and its actions were compared to those of Mg2+ ions, ketamine, dextrorphan, dextromethorphan, phencyclidine and dizocilpine (MK-801).