374. Amantadine

Nomenclature

CAS number: 768-94-5
Tricyclo[3.3.1.13,7]decan-1-amine; 1-adamantanamine; 1-aminoadamantane; 1-aminodiamantane (obsolete); 1-aminotricyclo[3.3.1.13,7]decane.
C10H17N; mol wt 151.25.
C 79.41%, H 11.33%, N 9.26%.

Description and references

NMDA-receptor antagonist. Antiviral agent active vs influenza A and other RNA viruses; interacts with the M2 viral membrane matrix protein, blocking the release of viral RNA into the cytoplasm of infected cells. Prepn: H. Stetter et al., Ber. 93, 226 (1960) DOI; W. Haaf, ibid. 97, 3234 (1964) DOI; P. Kovacic, P. D. Roskos, Tetrahedron Lett. 1968, 5833. LC-MS/MS determn in serum: T. Arndt et al., Clin. Chim. Acta 359, 125 (2005) DOI PubMed. Antiviral activity: W. L. Davies et al., Science 144, 862 (1964) DOI PubMed. Pharmacology and toxicology: V. G. Vernier et al., Toxicol. Appl. Pharmacol. 15, 642 (1969) DOI PubMed. Comprehensive description: J. Kirschbaum, Anal. Profiles Drug Subs. 12, 1-36 (1983). Review of use vs influenza A: R. L. Tominack, F. G. Hayden, Infect. Dis. Clin. North Am. 1, 459-478 (1987) PubMed; of pharmacokinetics: F. Y. Aoki, D. S. Sitar, Clin. Pharmacokinet. 14, 35-51 (1988) DOI PubMed. Review of NMDA receptor binding and neuroprotective properties: J. Kornhuber et al., J. Neural Transm. 43, Suppl., 91-104 (1994). Series of articles on clinical experience in Parkinson's disease: ibid. 46, Suppl., 399-421 (1995). Review of therapeutic potential in hepatitis C infection: J. K. Lim et al., J. Viral Hepat. 12, 445-455 (2005) DOI PubMed.

Chemical structure

Properties

Crystals by sublimation, mp 160-190° (closed tube) (Stetter). Also reported as mp 180-192° (Haaf). pKa: 10.1. Sparingly sol in water.

Derivative

Hydrochloride.

Nomenclature

CAS number: 665-66-7
EXP-105-1; NSC-83653; Adekin (Desitin); Lysovir (Alliance); Mantadan (Boehringer, Ing.); Mantadine (Endo); Mantadix (BMS); Symmetrel (Endo); Virofral (Novo).
C10H17N.HCl; mol wt 187.71.
C 63.99%, H 9.67%, N 7.46%, Cl 18.89%.

Properties

Crystals from abs ethanol + anhydr ether, mp >360° (dec). Freely sol in water (at least 1:20); sol in alcohol, chloroform. Practically insol in ether. LD50 orally in mice, rats: 700, 1275 mg/kg (Vernier).

Derivative

Sulfate.

Nomenclature

CAS number: 31377-23-8
PK-Merz (Merz).
C10H17N.H2SO4.

Therapeutic Category

Antiviral; antiparkinsonian.

Therapeutic Category (Veterinary)

Antiviral; adjunct for chronic pain.

Keywords

Antidyskinetic; Antiparkinsonian; Antiviral; Adamantanes