665-66-7 Usage
Chemical Properties
Crystalline Solid
Originator
Symmetrel,DuPont (Endo),US,1966
Uses
Different sources of media describe the Uses of 665-66-7 differently. You can refer to the following data:
1. 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.
2. antiviral, antiparkinsonian; treatment of drug-induced extrapyrimidal reactions
3. selective FP prostanoid receptor agonist, F-series prostaglandin analog. 200 times as potent as Latanoprost -20oC
4. 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.]
Check Digit Verification of cas no
The CAS Registry Mumber 665-66-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,6 and 5 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 665-66:
(5*6)+(4*6)+(3*5)+(2*6)+(1*6)=87
87 % 10 = 7
So 665-66-7 is a valid CAS Registry Number.
InChI:InChI=1/C10H17N/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6,11H2/t7-,8+,9-,10-
665-66-7Relevant articles and documents
Preparation method of amantadine
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, (2021/06/13)
The invention discloses a preparation method of amantadine, which belongs to the technical field of organic chemical synthesis, and is characterized by comprising the following steps: taking a compound adamantane as an initial raw material, generating an intermediate 1-acetamido adamantane in the presence of acetonitrile, a polyion liquid PIL catalyst and sulfuric acid, and then hydrolyzing the intermediate into amantadine in a system of alcohol and alkali. The preparation method is environment-friendly, post-treatment is convenient, the use amount of sulfuric acid and acetonitrile is greatly reduced through the catalyst polyion liquid, and post-treatment is simple. The ionic liquid catalyst can be recycled, so that the cost is greatly saved, and the method is suitable for large-scale industrial production.
Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications
Zhao, Lixing,Hu, Chenyang,Cong, Xuefeng,Deng, Gongda,Liu, Liu Leo,Luo, Meiming,Zeng, Xiaoming
supporting information, p. 1618 - 1629 (2021/01/25)
Transition metal catalysis that utilizes N-heterocyclic carbenes as noninnocent ligands in promoting transformations has not been well studied. We report here a cyclic (alkyl)(amino)carbene (CAAC) ligand-promoted nitro deoxygenative hydroboration with cost-effective chromium catalysis. Using 1 mol % of CAAC-Cr precatalyst, the addition of HBpin to nitro scaffolds leads to deoxygenation, allowing for the retention of various reducible functionalities and the compatibility of sensitive groups toward hydroboration, thereby providing a mild, chemoselective, and facile strategy to form anilines, as well as heteroaryl and aliphatic amine derivatives, with broad scope and particularly high turnover numbers (up to 1.8 × 106). Mechanistic studies, based on theoretical calculations, indicate that the CAAC ligand plays an important role in promoting polarity reversal of hydride of HBpin; it serves as an H-shuttle to facilitate deoxygenative hydroboration. The preparation of several commercially available pharmaceuticals by means of this strategy highlights its potential application in medicinal chemistry.
A Simple Process for the Synthesis of 1-Aminoadamantane Hydrochloride
Le, Huy Binh,Nguyen, Huu Tung,Pham, Van Hien,Phan, Dinh Chau,Tran, Thi Hang,Vu, Binh Duong
, p. 77 - 80 (2020/02/15)
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