Amantadine

Base Information

• Chemical Name: Amantadine
• CAS No.: 768-94-5
• Deprecated CAS: 744952-70-3
• Molecular Formula: C10H17N
• Molecular Weight: 151.252
• Hs Code.: 29213000
• European Community (EC) Number: 212-201-2
• NSC Number: 341865
• UNII: BF4C9Z1J53
• DSSTox Substance ID: DTXSID8022117
• Nikkaji Number: J6.971J
• Wikipedia: Amantadine
• Wikidata: Q409761,Q27453436
• NCI Thesaurus Code: C61632
• RXCUI: 620
• Pharos Ligand ID: CB68GN711F4T
• Metabolomics Workbench ID: 43183
• ChEMBL ID: CHEMBL660
• Mol file: 768-94-5.mol

Synonyms:1 Aminoadamantane;1-Aminoadamantane;Adamantylamine;Adekin;AL, Amantadin;Aman;Amanta;Amanta HCI AZU;Amanta Sulfate AZU;Amanta-HCI-AZU;Amanta-Sulfate-AZU;Amantadin AL;Amantadin AZU;Amantadin neuraxpharm;Amantadin ratiopharm;Amantadin Stada;Amantadin-neuraxpharm;Amantadin-ratiopharm;Amantadina Juventus;Amantadina Llorente;Amantadine;Amantadine Hydrochloride;Amantadine Sulfate;Amantadinneuraxpharm;Amantadinratiopharm;AmantaHCIAZU;AmantaSulfateAZU;Amixx;AZU, Amantadin;Cerebramed;Endantadine;Gen Amantadine;Gen-Amantadine;GenAmantadine;Hydrochloride, Amantadine;Infecto Flu;Infecto-Flu;InfectoFlu;Infex;Juventus, Amantadina;Llorente, Amantadina;Mantadix;Midantan;PMS Amantadine;PMS-Amantadine;PMSAmantadine;Stada, Amantadin;Sulfate, Amantadine;Symadine;Symmetrel;tregor;Viregyt;Wiregyt

Chemical Property of Amantadine

Chemical Property:

• Appearance/Colour: White to cream powder
• Vapor Pressure: 0.0852mmHg at 25°C
• Melting Point: 206-208 °C(lit.)
• Refractive Index: 1.557
• Boiling Point: 225.692 °C at 760 mmHg
• PKA: 10.1(at 25℃)
• Flash Point: 95.974 °C
• PSA: 26.02000
• Density: 1.067 g/cm³
• LogP: 2.61420
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: 1 M HCl: soluble5%, clear to hazy, colorless to faint yellow or
• Water Solubility.: Soluble in organic solvents. Insoluble in water.
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 151.136099547
• Heavy Atom Count: 11
• Complexity: 144

Purity/Quality:

>99% ^*data from raw suppliers

Amantadine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiviral Agents; Antiparkinson Agents
• Canonical SMILES: C1C2CC3CC1CC(C2)(C3)N
• Recent ClinicalTrials: Influenza Vaccination, ACEI and ARB in the Evolution of SARS-CoV2 Infection
• Recent EU Clinical Trials: AMANTADINE AND TRANSCRANIAL MAGNETIC STIMULATION FOR TREATING FATIGUE IN MULTIPLE SCLEROSIS: PHASE III STUDY, CONTROLLED, RANDOMIZED, CROSSED OVER AND DOUBLE BLIND
• Recent NIPH Clinical Trials: Randomized crossover trial comparing memantine or amantadine for Parkinson's disease with motor fluctuations in Juntendo
• Description: Amantadine is an agent that raises the concentration of dopamine in the synaptic cleft by releasing it from neurons and suppressing the process of reuptake.
• Uses: Building block for an L-piperidinamide catalyst used in an enantioselective Strecker reaction of phosphinoyl imines.1 Amantadine is a primary amine derivative of adamantane. It has an effect on mycoviruses, which are RNA-containing viruses. It has a very narrow spectrum of action and is used only for treating and preventing influenza A. It is also used for treating Parkinsonism. The exact mechanism of antiviral action of amantadine is not completely understood. It is believed that it is an ion channel blocker. It has also been suggested that amantadine inhibits absorption of viral particles into the host cell, which is expressed in the breakdown of diffusion of the virus into the cell, or inhibition of the “stripping process” of the virus. The main use is for the prevention of type A2 influenza. Synonyms of this drug are simmetrel, viregit, mantadan, and others. Amantadine is an antiviral drug. The properties in amantadine, which relieve symptoms of Parkinsonism were discovered by accident. Treatment of Parkinsonism with a combination of levodopa, anticholinergic drugs, and amantadine gives better results than using any of these drugs individually.
• Biological Functions: Amantadine was originally introduced as an antiviral compound, but it is modestly effective in treating symptoms of parkinsonism. It is useful in the early stages of parkinsonism or as an adjunct to levodopa therapy. Its mechanism of action in parkinsonism is not clear, but amantadine may affect dopamine release and reuptake. Additional sites of action may include antagonism at muscarinic and N-methyl-Daspartate (NMDA) receptors. Adverse effects include nausea, dizziness, insomnia, confusion, hallucinations, ankle edema, and livedo reticularis. Amantadine and the anticholinergics may exert additive effects on mental functioning
• Clinical Use: Prevention and treatment of influenza A H1N1 infections Amantadine is used for the treatment of diseases caused by influenza A strains.

Technology Process of Amantadine

There total 61 articles about Amantadine 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: 98.0%

(3r,5r,7r)-N-hydroxyadamantane-1-carboxamide (28309-44-6) → 1-Adamantanamine (768-94-5)

Guidance literature:

With potassium carbonate; In dimethyl sulfoxide; at 90 ℃; for 3h;

DOI:10.1039/c6ob01178k

Reference yield: 98.0%

1-nitroadamantane (7575-82-8) → 1-Adamantanamine (768-94-5)

Guidance literature:

With sodium dithionite; potassium carbonate; 1,1′-dioctyl-4,4′-bipyridinium; In water; acetonitrile; at 35 ℃; for 24h;

DOI:10.1021/jo00124a043

Reference yield: 96.0%

Adamantan-1-yl-[2,2,2-trifluoro-1-phenyl-eth-(Z)-ylidene]-amine (141903-89-1) → 2,2,2-Trifluoroacetophenone (434-45-7) + 1-Adamantanamine (768-94-5)

Guidance literature:

With water; boric acid; In ethanol; at 80 ℃; for 8h;

DOI:10.1021/ja00071a017

upstream raw materials:

1-Adamantyl bromide

diphenylphosphide ion

1-Azidoadamantane

adamantane-1-carboxamide

Downstream raw materials:

N-(adamantan-1-yl)ethane-1,2-diamine

N-(1-Adamantyl)-N'-(β-chlorethyl)-harnstoff

Methyl-N-(1-adamantyl)oxamat

2-Aminobenzoesaeure-amid

Refernces

• 1、 Yang,Xu,Han,Liu,Jin,Wang,Liu,Hu. "Synthesis, characterization, and antibacterial activity of two zinc(II) complexes with Schiff bases from halogenated salicylaldehyde and amantadine". . p. 634 - 642. Retrieved 2014.
• 2、 Battistini, Elisa,Gianolio, Eliana,Gref, Ruxandra,Couvreur, Patrick,Fuzerova, Silvia,Othman, Mohammad,Aime, Silvio,Badet, Bernard,Durand, Philippe. "High-relaxivity magnetic resonance imaging (MRI) contrast agent based on supramolecular assembly between a gadolinium chelate, a modified dextran, and poly-β-cyclodextrin". . p. 4551 - 4561. Retrieved 2008.
• 3、 Kawai, Risa,Yada, Shiho,Yoshimura, Tomokazu. "Characterization and solution properties of adamantane-containing quaternary-ammonium-salt-type amphiphilic ionic liquids". . . Retrieved 2019.
• 4、 Moiseev et al.. "". . . Retrieved 1976.
• 5、 -. "Method for synthesizing and preparing amantadine dry product". Paragraph 0070-0071; 0078-0091; 0098-0115. . Retrieved 2021/03/13.
• 6、 -. "The benzyl can be selectively removed by visible light or near visible light. Method for protecting allyl and propargyl group". Paragraph 0022. . Retrieved 2021/10/16.