51052-62-1

Basic information

• Product Name: Memantine hydrochloride
• Synonyms: (s)-2-(2-oxopyrrolidin-1-yl)butanamide; (S)-1-pyrrolidineacetamid; (+-)-alpha-Ethyl-2-oxo-1-pyrrolidineacetamide; (S)-alpha-Ethyl-2-oxo-1-pyrrolidineacetamide; 1-Pyrrolidineacetamide; alpha-ethyl-2-oxo-; alpha-Ethyl-2-oxo-1-pyrrolidineacetamide; Etiracetamum [INN-Latin]; Keppra; Levetiracetam [INN]; Levetiracetamum [INN-Latin]; LEVITIRACETAM; UCB 6474; UCB-6474; UCB-L 059; Name:(S)-2-(2-Oxopyrrolidin-1-yl)butanamide (Levetiracetam); (2R)-2-(2-oxopyrrolidin-1-yl)butanamide; (2S)-2-(2-oxopyrrolidin-1-yl)butanamide; Levetiracetame
• CAS NO: 51052-62-1
• Molecular Formula: C12H21N
• Molecular Weight: 179.30184
• Mol File: 51052-62-1.mol

Chemical Properties

• Melting Point: 118-119℃
• Boiling Point: 395.9°C at 760 mmHg
• Flash Point: 193.2°C
• Appearance: /
• Density: 1.168g/cm³
• Vapor Pressure: 1.78E-06mmHg at 25°C
• Refractive Index: 1.518
• CAS DataBase Reference: Memantine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Memantine hydrochloride(51052-62-1)
• EPA Substance Registry System: Memantine hydrochloride(51052-62-1)

Safety Data

• Hazardous Substances Data: 51052-62-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Memantine hydrochloride is used as a therapeutic agent for the treatment of Alzheimer's disease. It functions by blocking excessive stimulation of NMDA receptors, which helps to prevent the neuronal damage caused by excitotoxicity and supports cognitive function in patients with Alzheimer's.
Used in Neuroprotection:
Memantine hydrochloride is used as a neuroprotective agent to safeguard neurons from excitotoxicity, which is a significant factor in the progression of neurodegenerative diseases like Alzheimer's. By modulating the activity of NMDA receptors, it helps to maintain a balance between neuronal excitation and inhibition, thus promoting overall brain health.
Used in Clinical Trials for Other Neurological Disorders:
Memantine hydrochloride is also being investigated for its potential use in treating other neurological disorders, such as Parkinson's disease, Huntington's disease, and multiple sclerosis. Its NMDA receptor antagonistic properties make it a promising candidate for managing the symptoms and progression of these conditions.

in vitro

Memantine（3，5-dimethyl-Tricyclo[3.3.1.13,7]decan-1-amine） 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

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.

InChI:InChI=1/C8H14N2O2/c1-2-6(8(9)12)10-5-3-4-7(10)11/h6H,2-5H2,1H3,(H2,9,12)/t6-/m0/s1

Upstream product

• 41100-52-1 memantine hydrochloride 
• 947238-46-2 2-chloro-N-(3,5-dimethyl-adamantan-1-yl)-acetamide 
• 17356-08-0 thiourea 
• 941-37-7 3,5-dimethyl-1-bromoadamantane 
• 19982-07-1 1-acetamido-3,5-dimethyladamantane 
• 1204184-74-6 2-(3,5-dimethyladamantan-1-yl)isoindoline-1,3-dione 
• 351329-88-9 1-formamido-3,5-dimethyltricyclo[3.3.1.1^3,7]decane 
• 702-79-4 1,3-dimethyladamantane 
• 63534-29-2 1-azido-3,5-dimethyladamantane 
• 40430-57-7 3, 5-dimethyl-1-adamantyl methyl ketone 
• 707-37-9 3,5-dimethyladamantanol 
• 702-79-4 1,3-dimethyl-adamantane 
• 75-05-8 acetonitrile 

Downstream Products

• 100063-87-4 N'--N-<3,5-dimethyl-adamantyl-(1)>-harnstoff 
• 710333-37-2 N-3,5-(dimethyladamantan-1-yl)-4-methylbenzenesulfonamide 

Relevant articles and documents

Green preparation method of memantine

The method comprises the following steps: (1) mixing 1 - chlorine -3 and 5 - dimethyl adamantane with acetamide to obtain 1 -acetylamino -3 and 5 -dimethyladamantane. (2) The 1 -acetylamino -3, 5 -dimethyladamantane was deacetylated in a hot-water system to obtain a memantine. The preparation method provided by the invention is simple to operate. The method is safe, environment-friendly, high in yield and purity, cost-saving, low in production cost and beneficial to industrial production.

Synthesis, characterization, X-ray crystallography analysis and cell viability study of (η6-p-cymene)Ru(NH2R)X2 (X = Cl, Br) derivatives

Studies over the past few decades demonstrate the potential for metallodrugs as bioactive therapeutics. Here, we describe six new ruthenium(II) complexes with the general motif of (η6-p-cymene)Ru(NH2R)X2, where NH2R is either the influenza A antiviral drugs rimantadine or amantadine or the N-methyl-D-aspartate [NMDA] receptor antagonist, memantine and X = Cl or Br. All complexes were synthesized in high yield and purity and characterized by NMR spectroscopy and X-ray crystallography. Both the chlorine and bromine ruthenium(II) p-cymene complexes demonstrated cellular toxicity profiles similar to their respective free ligand, indicating that complexation to ruthenium(II) centers does not significantly increase toxicity of the bioactive ligand.

Cerium-Catalyzed C-H Functionalizations of Alkanes Utilizing Alcohols as Hydrogen Atom Transfer Agents

Modern photoredox catalysis has traditionally relied upon metal-to-ligand charge-transfer (MLCT) excitation of metal polypyridyl complexes for the utilization of light energy for the activation of organic substrates. Here, we demonstrate the catalytic application of ligand-to-metal charge-transfer (LMCT) excitation of cerium alkoxide complexes for the facile activation of alkanes utilizing abundant and inexpensive cerium trichloride as the catalyst. As demonstrated by cerium-catalyzed C-H amination and the alkylation of hydrocarbons, this reaction manifold has enabled the facile use of abundant alcohols as practical and selective hydrogen atom transfer (HAT) agents via the direct access of energetically challenging alkoxy radicals. Furthermore, the LMCT excitation event has been investigated through a series of spectroscopic experiments, revealing a rapid bond homolysis process and an effective production of alkoxy radicals, collectively ruling out the LMCT/homolysis event as the rate-determining step of this C-H functionalization.

Memantine hydrochloride synthesis method

The invention provides a memantine hydrochloride synthesis method, and belongs to the technical field of medicine synthesis. The preparation method comprises the following steps: carrying out a substitution reaction on 1-bromo-3,5-dimethyladamantane and acetamide to obtain 1-acetamido-3,5-dimethyladamantane, mixing the 1-acetamido-3,5-dimethyladamantane, an alcohol and an alkali, carrying out an alcoholysis reaction to obtain 1-amino-3,5-dimethyladamantane, and finally carrying out an acidification reaction on the 1-amino-3,5-dimethyladamantane and hydrochloric acid to obtain memantine hydrochloride. According to the method of the invention, 1-bromo-3,5-dimethyl adamantane and acetamide are used as the starting raw materials, so the sources of the raw materials are wide, the use of acetonitrile is avoided, and no pollution is caused to the human body and the environment; the use of catalysts is avoided in the whole reaction process, the reaction product is easy to separate, and the yield of the obtained memantine hydrochloride is high; and the method is mild in reaction condition and suitable for industrial production.

Deacetylative Amination of Acetyl Arenes and Alkanes with C-C Bond Cleavage

The Br?nsted acid-catalyzed synthesis of primary amines from acetyl arenes and alkanes with C-C bond cleavage is described. Although the conversion from an acetyl group to amine has traditionally required multiple steps, the method described herein, which uses an oxime reagent as an amino group source, achieves the transformation directly via domino transoximation/Beckmann rearrangement/Pinner reaction. The method was also applied to the synthesis of γ-aminobutyric acids, such as baclophen and rolipram.

Synthesis, crystallographic studies, molecular modeling and in vitro biological studies of silver(I) complexes with aminoadamantane ligands

Silver(I) complexes with amantadine (atd) and memantine (mtn) were synthesized and characterized. Elemental, thermogravimetric and mass spectrometric analyses indicated a 1:2 metal/ligand ratio, with the molecular composition AgC20H34N2·NO3 for Ag–atd and AgC24H42N2·NO3·H2O for Ag–mtn. The crystal structures of the silver(I) complexes were determined by single crystal X-ray diffractometric studies and show the coordination of amantadine and memantine to the Ag(I) ion by the nitrogen atom of the NH2 group. The spectral analysis by infrared and 1H, 13C and {15N,1H} nuclear magnetic resonance (NMR) spectroscopies confirmed the coordination sites of the ligands to the silver ions. Computational studies revealed modes of vibration and bond lengths similar to those found experimentally. The in vitro antibacterial activity assays showed that amantadine is not active over the tested strains while memantine showed a low activity against Staphylococcus aureus and Pseudomonas aeruginosa. On the other hand, the complexes had a pronounced antibacterial activity over the same strains with minimum inhibitory concentration (MIC) values in the micromolar range. Biophysical assays based on fluorescence spectroscopy indicated that the silver(I) complexes interact weakly with bovine serum albumin, while agarose gel electrophoresis and competitive binding experiments revealed that the compounds interact with DNA by non-covalent interactions.

CRYSTAL OF 1-AMINO-3,5-DIMETHYL ADAMANTANE HYDROCHLORIDE

PROBLEM TO BE SOLVED: To provide a crystals of 1-amino-3,5-dimethyl adamantane hydrochloride that has excellent fluidity. SOLUTION: Provided is a crystal of 1-amino-3,5-dimethyl adamantane hydrochloride having a crystal aspect ratio of 1.0 to 1.5. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

Synthesis, molecular docking studies, and antimicrobial evaluation of new structurally diverse ureas

A series of new urea derivatives (3a-p) have been synthesized from readily available isocyanates and amines in good to high yields. All synthesized compounds were fully characterized using 1H NMR, 13C NMR, IR, and mass spectrometry. Additionally, the structure of the compound (3n) was confirmed by single-crystal X-ray diffraction. Furthermore, all compounds were evaluated for antimicrobial activity against five bacteria and two fungi. Last but not the least, molecular docking studies with Candida albicans dihydropteroate synthetase were performed and the results are presented herein.

A hydrochloric acid just preparation method

The invention discloses a method for preparing memantine hydrochloride. The method is characterized in that the method provided by the invention uses 1-bromo-3,5-dimethyladamantane (represented by a general formula IV in the description) as a starting material which is subjected to an amination reaction with acetamine to obtain a key intermediate 1-actamido-3,5-dimethyladmantane (represented by a general formula III in the description); the compound represented by the general formula III is subjected to alcoholysis in a mixture system of inorganic base and n-butyl alcohol for deacetylated to obtain memantine; memantine is treated using hydrochloric acid in a ketone solvent to obtain memantine hydrochloride. The method provided by the invention overcomes deficiencies in the prior art and has the advantages that the raw materials are simple and readily available, the reaction steps are simple and short, and the operations are convenient and fast, therefore, the method is suitable for industrial production.

Direct Primary Amination of Alkylmetals with NH-Oxaziridine

A method for the primary electrophilic amination of primary, secondary, and tertiary organometallic substrates from a bench-stable NH-oxaziridine reagent is described. This facile and highly chemoselective transformation occurs at ambient temperature and without transition metal catalysts or purification by column chromatography to provide alkylamine products in a single step. Density functional theory (DFT) calculations revealed that, despite the basicity of alkylmetals, the direct NH-transfer pathway is favored over proton and O-transfer.