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1-Adamantanamine hydrochloride

Product Name
1-Adamantanamine hydrochloride
CAS No.
665-66-7
Chemical Name
1-Adamantanamine hydrochloride
Synonyms
AMANTADINE HCL;AMANTADINE HYDROCHLORIDE;1-AMINOADAMANTANE HYDROCHLORIDE;symmetrel;1-ADAMANTANAMINE HCL;Mantadan;ADAMANTANAMINE HYDROCHLORIDE;Amantadine hydrochloride,1-Adamantanamine hydrochloride, 1-Adamantylamine hydrochloride, 1-Aminoadamantane hydrochloride;Adekin;virasol
CBNumber
CB4734376
Molecular Formula
C10H18ClN
Formula Weight
187.71
MOL File
665-66-7.mol
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1-Adamantanamine hydrochloride Property

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)
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Safety

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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
A1260
Product name
Amantadine hydrochloride
Packaging
5g
Price
$65.9
Updated
2024/03/01
Sigma-Aldrich
Product number
BP530
Product name
Amantadine hydrochloride
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
200MG
Price
$257
Updated
2024/03/01
Sigma-Aldrich
Product number
8.20015
Product name
1-Adamantaneammonium chloride
Purity
for synthesis
Packaging
10g
Price
$66.1
Updated
2024/03/01
Sigma-Aldrich
Product number
8.20015
Product name
1-Adamantaneammonium chloride
Purity
for synthesis
Packaging
50g
Price
$241
Updated
2024/03/01
Sigma-Aldrich
Product number
1018505
Product name
Amantadine hydrochloride
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$436
Updated
2024/03/01
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1-Adamantanamine hydrochloride Chemical Properties,Usage,Production

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.]

1-Adamantanamine hydrochloride Preparation Products And Raw materials

Raw materials

Preparation Products

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1-Adamantanamine hydrochloride Suppliers

TCI Chemicals (India) Pvt. Ltd.
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Biopharmacule Speciality Chemicals P Ltd (India)
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View Lastest Price from 1-Adamantanamine hydrochloride manufacturers

HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
1-Adamantanamine hydrochloride 665-66-7
Price
US $50.00-30.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000
Release date
2024-08-23
WUHAN FORTUNA CHEMICAL CO., LTD
Product
1-Adamantanamine hydrochloride 665-66-7
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
98.5%min
Supply Ability
500kg
Release date
2021-10-19
Hebei Weibang Biotechnology Co., Ltd
Product
1-Adamantanamine hydrochloride 665-66-7
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-11-06

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