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1-Adamantanamine hydrochloride

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1-Adamantanamine hydrochloride Basic information
Product Name:1-Adamantanamine hydrochloride
Synonyms:Amantadine hydrochloride,1-Adamantanamine hydrochloride, 1-Adamantylamine hydrochloride, 1-Aminoadamantane hydrochloride;Amantadine Hydrochloride (200 mg);1-AdaMantanaMine hydrochloride, 99+% 100GR;1-AdaMantanaMine hydrochloride, 99+% 25GR;1-AdaMantanaMine hydrochloride, 99+% 5GR;1-adamantane amine hydrochloride;1-Adamantanamine Hydrochleride;1-Aminoadamantane Hydrochloride Amantadine Hydrochloride
Product Categories:Influenza Viruses;API;Intermediates & Fine Chemicals;Dopamine receptor;SYMADINE;inhibitor;Adamantane derivatives;chiral;Adamantanes;Pharmaceuticals;API's;1
Mol File:665-66-7.mol
1-Adamantanamine hydrochloride Structure
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
CAS DataBase Reference665-66-7(CAS DataBase Reference)
EPA Substance Registry SystemAmantadine 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
WGK Germany 3
RTECS AU4375000
HazardClass IRRITANT
HS Code 29213000
ToxicityLD50 orally in mice, rats: 700, 1275 mg/kg (Vernier)
MSDS Information
1-Adamantanamine hydrochloride English
SigmaAldrich English
ACROS English
ALFA English
1-Adamantanamine hydrochloride Usage And Synthesis
Chemical PropertiesCrystalline Solid
OriginatorSymmetrel,DuPont (Endo),US,1966
Uses1-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.
Usesantiviral, antiparkinsonian; treatment of drug-induced extrapyrimidal reactions
Usesselective FP prostanoid receptor agonist, F-series prostaglandin analog. 200 times as potent as Latanoprost -20oC
UsesNMDA-receptor antagonist. Antiviral; antiparkinsonian
DefinitionChEBI: A hydrochloride obtained by combining amantadine and hydrochloric acid in equimolar amounts.
Manufacturing Process360 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 nameSymadine (Solvay Pharmaceuticals); Symmetrel (Endo).
Therapeutic FunctionAntiviral, Antiparkinsonian
Safety ProfileHuman 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.
Purification MethodsDissolve 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.]
Tag:1-Adamantanamine hydrochloride(665-66-7) Related Product Information
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