1-Adamantanamine hydrochloride Chemical Properties

Melting point:

>300 °C(lit.)

Boiling point:

308.63°C (rough estimate)

Density 

1.0276 (rough estimate)

refractive index 

1.6100 (estimate)

storage temp. 

Store below +30°C.

solubility 

H₂O: 50 mg/mL

form 

Fine Crystalline Powder

color 

White

Water Solubility 

soluble

Sensitive 

Hygroscopic

Merck 

14,374

BRN 

4198854

InChIKey

WOLHOYHSEKDWQH-UHFFFAOYSA-N

LogP

-1.64 at 23℃ and pH6.3

CAS DataBase Reference

665-66-7(CAS DataBase Reference)

EPA Substance Registry System

Amantadine hydrochloride (665-66-7)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-40-20/21/22

Safety Statements 

22-36/37-36-35-20/21

RIDADR 

UN 1759 8 / PGII

WGK Germany 

3

RTECS 

AU4375000

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29213000

Toxicity

LD50 orally in mice, rats: 700, 1275 mg/kg (Vernier)

MSDS

• Language:English Provider:1-Adamantanamine hydrochloride
• Language:English Provider:SigmaAldrich
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1-Adamantanamine hydrochloride Usage And Synthesis

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.

storage

Room temperature

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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