| Identification | More | [Name]
1-Adamantanamine hydrochloride | [CAS]
665-66-7 | [Synonyms]
1-ADAMANTANAMINE HCL
1-ADAMANTANAMINE HYDROCHLORIDE
1-ADAMANTANEAMMONIUM CHLORIDE
1-ADAMANTYLAMINE HYDROCHLORIDE
1-AMINOADAMANTANE HYDROCHLORIDE
ADAMANTAN-1-AMINE HYDROCHLORIDE
ADAMANTANAMINE HYDROCHLORIDE
AMANTADINE HCL
AMANTADINE HYDROCHLORIDE
TIMTEC-BB SBB003680
TRICYCLODECANE HYDROCHLORIDE
1-aminoadamantenehydrochloride
adamantinehydrochloride
adamantylaminehydrochloride
aminoadamantanehydrochloride
exp105-1
midantane
mydantane
nsc83653
symmetrel | [EINECS(EC#)]
211-560-2 | [Molecular Formula]
C10H18ClN | [MDL Number]
MFCD00074723 | [Molecular Weight]
187.71 | [MOL File]
665-66-7.mol |
| Chemical Properties | Back Directory | [Appearance]
Crystalline Solid | [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 | [Usage]
NMDA-receptor antagonist. Antiviral; antiparkinsonian | [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]
665-66-7(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R40:Limited evidence of a carcinogenic effect.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S22:Do not breathe dust .
S36/37:Wear suitable protective clothing and gloves .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 1759 8 / PGII | [WGK Germany ]
3
| [RTECS ]
AU4375000
| [TSCA ]
Yes | [HazardClass ]
IRRITANT | [HS Code ]
29213000 | [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. | [Toxicity]
LD50 orally in mice, rats: 700, 1275 mg/kg (Vernier) |
| Hazard Information | Back Directory | [Chemical Properties]
Crystalline Solid | [Originator]
Symmetrel,DuPont (Endo),US,1966 | [Uses]
antiviral, antiparkinsonian; treatment of drug-induced extrapyrimidal reactions | [Uses]
NMDA-receptor antagonist. Antiviral; antiparkinsonian | [Uses]
selective FP prostanoid receptor agonist, F-series prostaglandin analog. 200 times as potent as Latanoprost -20oC | [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 | [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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