5829. Memantine

Nomenclature

CAS number: 19982-08-2
3,5-Dimethyltricyclo[3.3.1.13,7]decan-1-amine; 3,5-dimethyl-1-adamantanamine; 1-amino-3,5-dimethyladamantane; DMAA; D-145.
C12H21N; mol wt 179.30.
C 80.38%, H 11.81%, N 7.81%.

Description and references

NMDA-receptor antagonist; deriv of adamantane, q.v. Prepn of the hydrochloride: K. Gerzon et al., J. Med. Chem. 6, 760 (1963); of the free base and hydrochloride: J. Mills, E. Krumkalns, US 3391142 (1968 to Lilly). Series of articles on pharmacology and metabolism: Arzneim.-Forsch. 27, 1471-1489 (1977); on neuropharmacology and clinical efficacy: ibid. 32, 1236-1276 (1982). Pharmacodynamics and pharmacokinetics: W. Wesemann et al., ibid. 33, 1122 (1983). NMDA-receptor binding study: J. Kornhuber et al., Eur. J. Pharmacol. 166, 589 (1989); and neuroprotective properties: idem et al., J. Neural Transm. 43, Suppl., 91 (1994). Clinical studies as antispasmodic: H. Rohde, Fortschr. Med. 100, 2023 (1982); in senile dementia: R. Grtelmeyer, H. Erbler, Arzneim.-Forsch. 42, 904 (1992). Review of clinical experience in neurodegenerative disorders: K. K. Jain, Expert Opin. Invest. Drugs 9, 1397-1406 (2000).

Chemical structure

Properties

Oil, nD25 1.4941.

Derivative

Hydrochloride.

Nomenclature

CAS number: 41100-52-1
Akatinol (Merz); Auxura (Merz); Ebixa (Lundbeck); Namenda (Forest).
C12H21N.HCl; mol wt 215.76.
C 66.80%, H 10.28%, N 6.49%, Cl 16.43%.

Properties

Fine white to off-white powder. Crystals from alcohol/ether, mp 258° (Mills, Krumkalns); also reported as mp 290-295° (Gerzon). Sol in water.

Therapeutic Category

Neuroprotective; antispasmodic; antiparkinsonian.

Keywords

Antiparkinsonian; Antispasmodic; NMDA Receptor Antagonist; Neuroprotective