1-Adamantanamine hydrochloride CAS 665-66-7
Introduction：Basic information about 1-Adamantanamine hydrochloride CAS 665-66-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
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 HydrochlorideAmantadine Hydrochloride |
| CAS: | 665-66-7 |
| MF: | C10H18ClN |
| MW: | 187.71 |
| EINECS: | 211-560-2 |
| Product Categories: | Influenza Viruses;API;SYMADINE;inhibitor;Dopamine receptor;Intermediates & Fine Chemicals;Pharmaceuticals;API's;Adamantane derivatives;chiral;Adamantanes;1;665-66-7 |
| Mol File: | 665-66-7.mol |
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 |
| Major Application | pharmaceutical (small molecule) |
| InChI | 1S/C10H17N.ClH/c11-10-4-7-1-8(5-10)3-9(2-7)6-10;/h7-9H,1-6,11H2;1H/t7-,8+,9-,10-; |
| InChIKey | WOLHOYHSEKDWQH-UHFFFAOYSA-N |
| SMILES | Cl[H].[H][C@@]12C[C@@]3([H])C[C@@]([H])(C1)CC(N)(C2)C3 |
| 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 | TSCA listed |
| HazardClass | IRRITANT |
| HS Code | 29213000 |
| Storage Class | 8A - Combustible corrosive hazardous materials |
| Hazard Classifications | Acute Tox. 4 Oral |
| Toxicity | LD50 orally in mice, rats: 700, 1275 mg/kg (Vernier) |
| 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) ofadamantane in 100 ml of n-hexane were emulsified in the apparatusdescribed and provided with an inclined centrifugal stirrer. Then a mixture of46 grams (1.7 mols) of liquid hydrocyanic acid and 29.6 grams (0.4 mol) oftertiary butanol was added dropwise within 1.5 hours at about 25°C. After 30 minutes of postreaction, the product was poured on ice. The granularmass which precipitated [N-(adamantyl-1)formamide] was sucked off andwashed with water. The raw product (37 grams) was then refluxed for 10hours 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 tothree extractions with ether. The amine was extracted from the etherealsolution with 2 N HCl and liberated therefrom by the addition of solid NaOH(while cooling). The alkaline solution was extracted with ether and theethereal solution was dried with solid NaOH. Distillation resulted in 10.6 grams(70% of the theory) of 1-aminoadamantane which, after sublimation, meltedat 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.] |
| References | [1] Synthetic Communications, 2015, vol. 45, # 22, p. 2601 - 2607 [2] Patent: WO2007/96124, 2007, A1. Location in patent: Page/Page column 15-16 [3] Russian Journal of Organic Chemistry, 2015, vol. 51, # 12, p. 1703 - 1709 [4] Zh. Org. Khim., 2015, vol. 51, # 12, p. 1737 - 1743,7 |
1-Adamantanamine hydrochloride Preparation Products And Raw materials
| Raw materials | Hydrochloric acid-->Bromine-->Aluminum chloride-->Urea-->Chlorine-->Hydrogen-->Sodium sulfite-->Aluminium-nickel-->Dicyclopentadiene-->Amantadine-->Sodium hydroxide-->HYDROGEN CYANIDE-->Adamantane-->2-Adamantanamine hydrochloride |
