Memantine

Base Information

• Chemical Name: Memantine
• CAS No.: 19982-08-2
• Deprecated CAS: 51052-62-1
• Molecular Formula: C12H21N
• Molecular Weight: 179.305
• Hs Code.: 2921300090
• European Community (EC) Number: 690-724-9
• UNII: W8O17SJF3T
• DSSTox Substance ID: DTXSID5045174
• Wikipedia: Memantine
• Wikidata: Q412189
• NCI Thesaurus Code: C73269
• RXCUI: 6719
• Pharos Ligand ID: FVF7QH1J64M4
• Metabolomics Workbench ID: 43285
• ChEMBL ID: CHEMBL807
• Mol file: 19982-08-2.mol

Synonyms:1,3-Dimethyl-5-aminoadamantane;1-Amino-3,5-dimethyladamantane;Axura;D 145;D-145;D145;Ebixa;Memantin;Memantine;Memantine Hydrochloride;Namenda

Chemical Property of Memantine

Chemical Property:

• Appearance/Colour: White powder.
• Vapor Pressure: 0.00667mmHg at 25°C
• Melting Point: 153oC
• Refractive Index: nD25 1.4941
• Boiling Point: 239.8 °C at 760 mmHg
• PKA: 10.79±0.60(Predicted)
• Flash Point: 92.3 °C
• PSA: 26.02000
• Density: 1.046 g/cm³
• LogP: 4.19640
• Storage Temp.: Store at RT
• Solubility.: Chloroform (Slightly), DMSO (Slightly)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 179.167399674
• Heavy Atom Count: 13
• Complexity: 240

Purity/Quality:

99.9% ^*data from raw suppliers

Memantine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Alzheimer Disease Agents
• Canonical SMILES: CC12CC3CC(C1)(CC(C3)(C2)N)C
• Recent ClinicalTrials: Memantine for the Treatment of Cognitive Impairment in Systemic Lupus Erythematosus
• Recent EU Clinical Trials: Efficacy and safety of memantine as antimanic and mood-stabilizing medication for adolescents with Bipolar Disorder: a multi-center, randomized, double-blind, placebo-controlled clinical trial
• Recent NIPH Clinical Trials: Memantine RCT
• Description: Memantine is a potent antagonist of the N-methyl-D-aspartate (NMDA) receptor. Experimentally, memantine inhibits and reverses the abnor-mal activity of a protein phosphatase (PP-2A) that leads to tauhyperphosphorylation and to neurofibrillary degeneration inAD. Memantine is effective and well toler-ated in patients with severe AD and wasapproved by the FDA for the treatment of moderate-to-severe AD.
• Uses: antiulcer Recent phase 3 clinical trials have shown that Memantine is an effective way of treatment of both mild and moderate-to-severe Alzheimer''s disease and possibly vascular dementia (multi-infarct dementia). Memantine’s method of action involves an uncompetitive, low-affinity, open-channel blocker; it enters the receptor-associated ion channel preferentially when it is excessively open, and, most importantly, its off-rate is relatively fast so that it does not substantially accumulate in the channel to interfere with normal synaptic transmission.
• Therapeutic Function: Spasmolytic
• Clinical Use: NMDA-receptor antagonist: Treatment of moderate to severe dementia in Alzheimer’s disease

Technology Process of Memantine

There total 25 articles about Memantine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.2%

1-acetamido-3,5-dimethyladamantane (19982-07-1) → memantine* (19982-08-2,51052-62-1)

Guidance literature:

With sodium hydroxide; In hexan-1-ol; at 130 ℃; for 18h; Temperature; Solvent;

Reference yield: 96.0%

1-azido-3,5-dimethyladamantane (63534-29-2) → memantine* (19982-08-2,51052-62-1)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 24h; under 760.051 Torr; Schlenk technique;

DOI:10.1021/acs.orglett.5b02155

Reference yield: 90.0%

3,5-dimethyl-1-bromoadamantane (941-37-7) → memantine* (19982-08-2,51052-62-1)

Guidance literature:

3,5-dimethyl-1-bromoadamantane; With ammonium acetate; In N,N-dimethyl-formamide; at 150 ℃; for 5.5h;

With hydrogenchloride; In water; N,N-dimethyl-formamide; at 5 ℃; for 0.5h;

upstream raw materials:

1-acetamido-3,5-dimethyladamantane

memantine hydrochloride

2-chloro-N-(3,5-dimethyl-adamantan-1-yl)-acetamide

thiourea

Downstream raw materials:

memantine hydrochloride

Refernces

• 1、 McDarmont, Sarah L.,Jones, Meredith H.,McMillen, Colin D.,Smith, Everett Clinton,Pienkos, Jared A.,Joslin, Evan E.. "Synthesis, characterization, X-ray crystallography analysis and cell viability study of (η6-p-cymene)Ru(NH2R)X2 (X = Cl, Br) derivatives". . . Retrieved 2021.
• 2、 dos Santos Pereira, Anna Karla,Nakahata, Douglas Hideki,Manzano, Carlos Marrote,de Alencar Simoni, Déborah,Pereira, Douglas Henrique,Lustri, Wilton Rogério,Formiga, André Luiz Barboza,Corbi, Pedro Paulo. "Synthesis, crystallographic studies, molecular modeling and in vitro biological studies of silver(I) complexes with aminoadamantane ligands". . . Retrieved 2019.
• 3、 -. "Memantine hydrochloride synthesis method". Paragraph 0061; 0067-0070; 0074; 0080-0084' 0088; 0094-0098. . Retrieved 2020/03/09.