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Memantine HCl

Basic information Description References Safety Related Supplier
Memantine HCl Basic information
Memantine HCl Chemical Properties
Safety Information
  • Safety Statements 24/25
  • WGK Germany 3
  • HazardClass IRRITANT
  • HS Code 29213000
MSDS
Memantine HCl Usage And Synthesis
  • DescriptionMemantine 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.
  • ReferencesReisberg, Barry, et al. New England Journal of Medicine 348.14 (2003): 1333-1341.
    Lipton, Stuart A. Nature reviews Drug discovery 5.2 (2006): 160-170.
  • DescriptionMemantine, 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.
  • Chemical PropertiesCrystalline Solid
  • UsesUsed as an antiparkinsonian and antispasmodic
  • UsesAntiparkinsonian;Dopaminergic agonist
  • UsesAnti Alzheimer's
  • DefinitionChEBI: A hydrochloride obtained by reaction of memantine with one equivalent of hydrochloric acid. A low to moderate affinity uncompetitive (open-channel); NMDA receptor antagonist which binds preferentially to the NMDA receptor-operated cation channels.
  • brand nameNamenda(Forest).
  • Chemical SynthesisMemantine (XV) or 1-amino- 3,5-dimethyladamantane hydrochloride was first synthesized by Lilly as an anti-diabetic agent but was ineffective in lowering blood sugar. Several syntheses have been detailed in the literature. However the simplest synthesis of the drug was done in one step from the commercially available 3,5-dimethyl adamantine (122). Treatment of 122 with nitrogen trichloride (CAUTION: very explosive gas!) in the presence of aluminum trichloride (ratio of 1.5:1.2) gave the desired amino adamantine in 86% yield. However, a much safer alternative has been reported by Lilly scientists. Heating the commercially available 3,5-dimethyladamantane 122 in bromine gave the bromo derivative 123 (86%) which was then reacted with sulfuric acid in acetonitrile to provide quantitatively acetyl amino derivative 124 after aqueous workup. Hydrolysis of the acetyl group was done by heating 124 with sodium hydroxide in diethylene glycol to give 1-amino -3,5- adamantane (96%), which was then made into the hydrochloride salt in ether and recrystallized from ether and alcohol mixture to provide the final product memantine hydrochoride XV.

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