Memantine Chemical Properties
- Melting point:258 °C
- Boiling point:239.8±8.0 °C(Predicted)
- Density 1.046
- refractive index nD25 1.4941
- storage temp. Store at RT
- CAS DataBase Reference19982-08-2(CAS DataBase Reference)
Memantine Usage And Synthesis
- OriginatorAkatinol,Merz,W. Germany,1983
- DefinitionChEBI: A primary aliphatic amine that is the 3,5-dimethyl derivative of 1-aminoadamantane. A low to moderate affinity uncompetitive (open-channel); NMDA receptor antagonist which binds preferentially to the NMDA receptor-operated cation channels.
- Manufacturing ProcessA mixture of 24 g of 1,3-dimethyladamantane and 80 ml of bromine was refluxed for 6 hours. The reaction product mixture was cooled, taken up in about 200 ml of chloroform, and poured onto ice. The excess bromine was removed by adding sodium hydrosulfite. The chloroform layer was separated from the aqueous layer, dried, concentrated in vacuo, and distilled at reduced pressure to yield 30.5 g of product having a boiling point of about 118°C at 5- 6 mm; nD25 = 1.5169-1.5182. The product was identified by nuclear magnetic resonance (NMR) and elemental analyses as 1-bromo-3,5- dimethyladamantane.
A mixture of 20 g of 1-bromo-3,5-dimethyladamantane, 75 ml of acetonitrile, and 150 ml of concentrated sulfuric acid was allowed to react overnight at ambient room temperature. The red reaction product mixture was poured over crushed ice, and the white solid which precipitated was taken up in benzene and the benzene solution dried over sodium hydroxide pellets. The benzene solution was filtered from the drying agent and evaporated to dryness in vacuo to yield 18.2 g of product having a melting point of about 97°C and identified by infrared spectrum as 1-scetamido-3,5-dimethyladamantane.
A mixture of 18 g of 1-acetamido-3,5-dimethyladamantane, 38 g of sodium hydroxide, and 300 ml of diethylene glycol was refluxed for a period of 6 hours. The reaction product mixture was cooled and poured onto about 2,000 ml of crushed ice. The basic solution thus obtained was extracted five times with 250 ml portions of benzene and the aqueous layer was discarded. The combined benzene extracts were dried over sodium hydroxide and the dried benzene solution concentrated in vacuo to give a crude oil weighing 14 g and having nD25 = 1.4941, A 4 g sample of the crude oil was dissolved in ether and the solution saturated with anhydrous hydrogen chloride. The solid which precipitated was filtered off and recrystallized from a mixture of alcohol and ether to yield product weighing 3.5 g and melting at 258°C.
It was identified by analysis as 1-amino-3,5-dimethyladamantane hydrochloride.
- Therapeutic FunctionSpasmolytic
- Biological ActivityAn antagonist at the NMDA receptor, binding to the ion channel site. Used in the treatment of Parkinsonism.
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