1.3- Dimethyladamantane Memantine

Ifenprodil (= l-Methyl-2-hydroxy-2-(4-hydroxyphenyl) ethyl-1 -(4-benzyl-piperidine)] -(aryl piperidine) [at(/o-3-(Indol-2-yl)-8-methyl-8-azabicyclo-[3.2.1] octane] (indolotropane) [Kynurenic acid (= 4-Hydroxy-2-quinolinecarboxylic acid)] (quinoline carboxylic acid) [Memantine (= 1-Amino-3,5 dimethyladamantane)] (amino adamantane, amino cyclic aliphatic) [Methadone (= 6-Dimethylamino-4,4-diphenyl-3-heptanone)] (aryl tertiary amine) [em/o-3-(l -Methylindol-2-yl)-8-methyl-8-azabicyclo-[3.2.1] octane(indolotropane) exo- 3-( 1 -Methylindol-2-yl)-8-methyl-8-... 

Memantine. 3,S-Dimethyltricyclo[3.3.I.I3 ]decan-1-amine 3,S-dimethyl-l-adamantanamine 1 -amino-3,5-dimethyladamantane DMAA D 145. C.jH N mol wt 179.31. C 80.38%, H 11.81%, N 7.81%. Deriv of adaman-tine, q.v.. with anti-parkinson activity. Prepn of the hydrochloride K. Gerzon et al. J. Med. Chem. 6, 760 (1963) of the free base and hydrochloride J. Mills, E. Krumkalns, UJS. pat. 3,391,142 (1968 to Lilly). GC and mass spec studies of memantine metabolites W. Wesemann et al, Arznei-mittel-Forsch. 27, 1471 (1977), Effects in parkinsonian patients P. -A. Fischer er at., Ibid, 1487. Series of articles on distribution, effects on neurobiological processes, clinical studies in control of micturition and limb muscle mobility ibid. 32, 1236-1276 (1982). Clinical studies as antispasmod-ic agent H. Rohde, Fortschr. Med. 100, 2023 (1982). Pharmacodynamics and pharmacokinetics W. Wesemann et al, Arzneimittel-Forsch. 33, 1122 (1983). 

Fig. 9.8 Chemical structures of memantine and its derivatives. Amantadine (1-aminoadamantane) (a) memantine (l-amino-3,5-dimethyladamantane) (b) NitroMemantine (c) and 1-amino-3,...

Substitution with the bulky aminoadamantane results in incomplete reaction with only four of the six positions substituted, Scheme 21. Most interestingly is the fact that geminal substitution was observed in relatively high yield (63%). This conclusion was supported by NMR and X-ray crystallography. Memantine (l-amino-3,5-dimethyladamantane) gave similar results with a yield of 69%, suggesting that the steric bulk... 

In pharmacology, two adamantane derivatives. Amantadine (1-adaman-taneamine hydrochloride) and Rimantadine (a-methyl-1-adamantane methy-lamine hydrochloride) have been well known because of their antiviral activity (Figure 3.5). The main indication of these drugs is prophylaxis and treatment of influenza A viral infections. They are also used in the treatment of Parkinsonism and inhibition of hepatitis C virus (HCV) [27]. Memantine (l-amino-3,5-dimethyladamantane) has been reported effective in slowing the progression of Alzheimer s disease [27]. 

---