Memantine hydrochloride

Base Information

• Chemical Name: Memantine hydrochloride
• CAS No.: 41100-52-1
• Molecular Formula: C12H21N^.HCl
• Molecular Weight: 215.766
• Hs Code.: 2921300090
• European Community (EC) Number: 255-219-6
• NSC Number: 757843,102290
• UNII: JY0WD0UA60
• DSSTox Substance ID: DTXSID90961439
• Wikidata: Q27133218
• NCI Thesaurus Code: C47601
• RXCUI: 236685
• Pharos Ligand ID: FVF7QH1J64M4
• Metabolomics Workbench ID: 63323
• ChEMBL ID: CHEMBL1699
• Mol file: 41100-52-1.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 hydrochloride

Chemical Property:

• Appearance/Colour: Crystalline solid
• Vapor Pressure: 0.0393mmHg at 25°C
• Melting Point: 292 °C
• Boiling Point: 239.8 °C at 760 mmHg
• Flash Point: 92.3 °C
• PSA: 26.02000
• LogP: 4.19640
• Storage Temp.: -20°C Freezer
• Solubility.: Soluble in Water (up to 20 mg/ml)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 215.1440774
• Heavy Atom Count: 14
• Complexity: 240

Purity/Quality:

99% purity ^*data from raw suppliers

Memantine hydrochloride ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CC3CC(C1)(CC(C3)(C2)N)C.Cl
• Recent ClinicalTrials: Motor Neurone Disease - Systematic Multi-Arm Adaptive Randomised Trial
• Recent EU Clinical Trials: Motor Neurone Disease Systematic Multi-arm Adaptive Randomised Trial (MND-SMART)
• Recent NIPH Clinical Trials: A study to evaluate combination therapy of memantine hydrochloride with donepezil hydrochloride compared with dose escalation of donepezil hydrochloride in the patient with Alzheimer's disease who have treated with donepezil hydrochloride
• Description: Memantine HCl is the HCl form of Memantine. Memantine is a well- known neuroprotective drug used for the treatment of Alzheimer’s disease. It is believed to be the first neuroprotective drug that has achieve clinical approval by US FDA as well as European. The development of Alzheimer’s disease involves the misfolded mutant proteins such as β-amyloid peptide (Aβ, particularly Aβ1?42). These misfolded mutant protein can increase the NMDA response and further cause severe excitotoxicity. Memantine suppresses this process through acting as the antagonist of the N-methyl-d- aspartate-sensitive glutamate receptor (NMDARs). Memantine is also under investigation as a potential treatment for other kind of neurodegenerative disorders such as HIV-associated dementia, neuropathic pain, glaucoma, depression, Huntington’s disease, ALS and movement disorders, among other. Memantine, a NMDA receptor antagonist, was co-developed by Forest Laboratories with Merz Pharmaceuticals and marketed under the trade name Namenda for the treatment of Alzheimer’s disease in the US after its approval in October, 2003. This drug has been available in many European and Asian markets before getting approval in the US. Memantine is an NMDA receptor antagonist that blocks NMDA-induced currents in rat retinal ganglion cells by 90% when used at a concentration of 12 μM. It reverses inhibition of dephosphorylation of the synthetic tau phosphopeptide p17 (tau194-207) induced by the endogenous inhibitor of protein phosphatase 2A (PP2A) I1PP2A in vitro. In vivo, memantine (2 mg/kg) restores PP2A activity, decreases GSK-3β and amyloid-β (Aβ) levels in the hippocampus, cerebral cortex, and ventricular areas, and attenuates spatial learning and memory in the AAV1-I1PP2A rat model of Alzheimer''s disease. Memantine (20 mg/kg) reduces responding on the ethanol-associated lever in a cue-induced ethanol-seeking test in rats. It also decreases secretion of matrix metalloproteinase-9 (MMP-9), degradation of collagen IV, the size of cerebral ischemia-induced brain infarcts, and neuronal cell death in a mouse model of focal cerebral ischemia.
• Uses: Used as an antiparkinsonian and antispasmodic Antiparkinsonian;Dopaminergic agonist Anti Alzheimer's

Technology Process of Memantine hydrochloride

There total 20 articles about Memantine hydrochloride 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: 100.0%

2,2,2-trichloroethyl 3,5-dimethyladamantylcarbamate (1058345-42-8) → memantine hydrochloride (41100-52-1)

Guidance literature:

2,2,2-trichloroethyl 3,5-dimethyladamantylcarbamate; With acetic acid; zinc; at 20 ℃; for 2h;

With acetyl chloride; In methanol; at 40 ℃; for 16h; Heating;

DOI:10.1002/chem.200702027

Reference yield: 99.3%

1-acetamido-3,5-dimethyladamantane (19982-07-1) → memantine hydrochloride (41100-52-1)

Guidance literature:

1-acetamido-3,5-dimethyladamantane; With sodium hydroxide; In diethylene glycol; for 6h; Reflux;

With water; In dichloromethane; diethylene glycol; at 20 ℃; for 0.25h;

With hydrogenchloride; In ethyl acetate; at 0 - 30 ℃; for 6h;

Reference yield: 97.4%

1-nitro-3,5-dimethyl-adamantane (6588-68-7) → memantine hydrochloride (41100-52-1)

Guidance literature:

1-nitro-3,5-dimethyl-adamantane; With hydrogen; In ethanol; at 80 ℃; for 0.5h; under 750.075 - 18751.9 Torr; Autoclave;

With hydrogenchloride; for 0.5h;

upstream raw materials:

memantine*

1-acetamido-3,5-dimethyladamantane

1-chloro-3,5-dimethyl-adamantane

1-formamido-3,5-dimethyltricyclo[3.3.1.1^3,7]decane

Refernces

• 1、 -. "Preparation method of 3,5-dimethyladamantanamine hydrochloride". Paragraph 0032-0047. . Retrieved 2021/12/07.
• 2、 An, Qing,Chen, Yuegang,Liu, Weimin,Pan, Hui,Wang, Xin,Wang, Ziyu,Zhang, Kaining,Zuo, Zhiwei. "Cerium-Catalyzed C-H Functionalizations of Alkanes Utilizing Alcohols as Hydrogen Atom Transfer Agents". supporting information. p. 6216 - 6226. Retrieved 2020/04/27.