| Chemical Properties | Crystalline Solid |
| Originator | Symmetrel,DuPont (Endo),US,1966 |
| Uses | 1-Adamantanamine hydrochloride is used in the prophylactic or symptomatic treatment of influenza A. It is also used as an antiparkinsonian agent, to treat extra pyramidal reactions, and for postherpetic neuralgia. It is also used an NMDA-receptor antagoinst. |
| Uses | antiviral, antiparkinsonian; treatment of drug-induced extrapyrimidal reactions |
| Uses | selective FP prostanoid receptor agonist, F-series prostaglandin analog. 200 times as potent as Latanoprost -20oC |
| Uses | NMDA-receptor antagonist. Antiviral; antiparkinsonian |
| Definition | ChEBI: A hydrochloride obtained by combining amantadine and hydrochloric acid in equimolar amounts. |
| Manufacturing Process | 360 ml of 96% sulfuric acid and a solution of 13.6 grams (0.1 mol) of
adamantane in 100 ml of n-hexane were emulsified in the apparatus
described and provided with an inclined centrifugal stirrer. Then a mixture of
46 grams (1.7 mols) of liquid hydrocyanic acid and 29.6 grams (0.4 mol) of
tertiary butanol was added dropwise within 1.5 hours at about 25°C.
After 30 minutes of postreaction, the product was poured on ice. The granular
mass which precipitated [N-(adamantyl-1)formamide] was sucked off and
washed with water. The raw product (37 grams) was then refluxed for 10
hours with a solution of 60 grams of NaOH in 600 ml of diethylene glycol.
After cooling, the solution was diluted with 1.5 liters of water and subjected to
three extractions with ether. The amine was extracted from the ethereal
solution with 2 N HCl and liberated therefrom by the addition of solid NaOH
(while cooling). The alkaline solution was extracted with ether and the
ethereal solution was dried with solid NaOH. Distillation resulted in 10.6 grams
(70% of the theory) of 1-aminoadamantane which, after sublimation, melted
at 180°C to 192°C (seal capillary). It is converted to the hydrochloride. |
| Brand name | Symadine (Solvay Pharmaceuticals); Symmetrel
(Endo). |
| Therapeutic Function | Antiviral, Antiparkinsonian |
| General Description | Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards |
| Biological Activity | amantadine hydrochloride is an antiviral and an antiparkinsonian drug. |
| Biochem/physiol Actions | Amantadine hydrochloride is effective against influenza viruses both in vivo and in vitro. It is considered as an antagonist of the N-methyl-D-aspartate (NMDA) type glutamate receptor. Amantadine plays an important role in the release of dopamine, preventing dopamine reuptake and blocking microglial activation and neuroinflammation. |
| Clinical Use | Parkinson’s disease (but not drug-induced
extrapyramidal symptoms)
Post-herpetic neuralgia
Prophylaxis and treatment of influenza A |
| Safety Profile | Human poison by ingestion. Poison by ingestion, intraperitoneal, and intravenous routes. A human teratogen with developmental abnormalities of the circulatory system. Experimental reproductive effects. Human systemic effects by ingestion: distorted perceptions, euphoria, excitement, hallucinations. When heated to decomposition it emits very toxic fumes of NO, and HCl. |
| Drug interactions | Potentially hazardous interactions with other drugs
Memantine: increased risk of CNS toxicity - avoid;
effects of amantadine possibly enhanced. |
| Metabolism | Amantadine is metabolised in the liver to a minor extent,
mainly by N-acetylation. The renal amantadine clearance
is much higher than the creatinine clearance, suggesting
renal tubular secretion in addition to glomerular
filtration. After 4-5 days, 90% of the dose appears
unchanged in urine. The rate is considerably influenced by
urinary pH: a rise in pH brings about a fall in excretion. |
| Purification Methods | Dissolve the salt in dry EtOH, add a few drops of dry EtOH saturated with HCl gas, followed by dry Et2O to crystallise the hydrochloride. Dry the salt in a vacuum. [Stetter et al. Chem Ber 93 226 1960.] |
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