AMantadine
amantadine
CAS: 768-94-5
Molecular Formula: C10H17N
AMantadine - Names and Identifiers
| Name | amantadine |
| Synonyms | Symadine amantadine Symmetrel 1-Amantadine 1-ADAMANTAMINE 1-Adamantanamin 1-Adamantanamine 1-ADAMANTYLAMINE 1-ADAMANTANAMINE 1-Aminoadamatane adamantan-1-amine 1-aminodiamantane 1-Aminoadamantane 1-AMINOADAMANTANE Tricyclo[3.3.1.13,7]decan-1-amine Tricyclo[3.3.1.1(3,7)]decane-1-amine |
| CAS | 768-94-5 |
| EINECS | 212-201-2 |
| 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- |
| InChIKey | DKNWSYNQZKUICI-UHFFFAOYSA-N |
AMantadine - Physico-chemical Properties
| Molecular Formula | C10H17N |
| Molar Mass | 151.25 |
| Density | 0.9510 (rough estimate) |
| Melting Point | 206-208°C(lit.) |
| Boling Point | 263.29°C (rough estimate) |
| Flash Point | 96°C |
| Water Solubility | Soluble in organic solvents. Insoluble in water. |
| Solubility | Slightly soluble in water, soluble in chloroform |
| Vapor Presure | 0.0852mmHg at 25°C |
| Appearance | White to light yellow powder |
| Color | White to cream |
| Merck | 14,374 |
| BRN | 2204333 |
| pKa | 10.1(at 25℃) |
| Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
| Refractive Index | 1.5220 (estimate) |
| MDL | MFCD00074732 |
| Physical and Chemical Properties | Melting point 180-192 ° C (sublimation), slightly soluble in water. |
| Use | For the production of synthetic adamantane derivatives amantadine hydrochloride and the like. |
AMantadine - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | YD1925000 |
| FLUKA BRAND F CODES | 10-34 |
| HS Code | 29213000 |
| Toxicity | LD50 oral in rat: 900mg/kg |
AMantadine - Reference
| Reference Show more | 1. [IF=7.963] Chenzhi Hou et al."Application of multi-parameter population model based on endogenous population biomarkers and flow volume in wastewater epidemiology."Sci Total Environ. 2021 Mar;759:143480 |
AMantadine - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Background | amantadine was approved by the U. S. Food and Drug Administration as a prophylactic against influenza in October 1966, it was subsequently approved for the treatment of influenza Virus in adults. The drug was found to relieve symptoms of Parkinson's disease, a drug-induced extrapyramidal syndrome, in 1969. The U. S. Food and Drug Administration approved controlled release formulations of amantadine in 2017 for the treatment of dyskinesia in patients with Parkinson's disease. |
| mechanism of action | amantadine is a weak antagonist of NMDA-type glutamate receptors, increases the release of dopamine and blocks the reuptake of dopamine, as well as the anticholinergic effect of Trihexyphenidyl. The drug may also promote the release of norepinephrine from nerve endings in the brain. Can treat Parkinson's disease movement disorders, but also can improve Parkinson's disease long-term use of dopaminergic drugs after the emergence of dyskinesia. |
| precautions | the effect of amantadine may be weak, and patients with severe symptoms need to be combined with other drugs; amantadine may cause hallucinations and other reactions, especially in patients with decreased intelligence, advanced age, rigidity, middle and advanced stage, etc. The anti-abnormal effect of amantadine may be maintained for less than 1 year; A small number of patients taking amantadine may be abnormal urination, limb edema reaction; Night taking amantadine may affect sleep, or cause involuntary movements during sleep, should avoid taking medicine in the afternoon; taking amantadine needs to be increased from a small dose titration. |
| side effect | reticulate bruising of the skin, characterized by the appearance of reticular, slightly purple markings on the skin, mainly in the legs. Another common side effect is ankle edema, which may be a redistribution of body fluids and does not suggest cardio-renal insufficiency. Others such as dizziness, Sleep Initiation and Maintenance Disorders and neuroticism, Nausea, Vomit, anorexia, dry mouth, constipation. Occasional depression, Anxiety, hallucinations, confusion, ataxia, Head Pain, rare convulsions. Leukopenia and neutropenia were rare. |
| Use | antiviral, also anti-paralysis. It is used for the production of a synthetic adamantane derivative, amantadine hydrochloride, etc. structural units of catalysts for the synthesis of adamantane derivatives such as amantadine hydrochloride, the catalyst can be used for the enantioselective Strecker reaction of phosphonoimine |
| production method | is obtained by bromination of adamantane followed by reaction with urea. The process is as follows: the adamantane is added into a dry glass-lined reaction tank, bromine is added dropwise, the temperature is slowly raised, the temperature is increased from 50 ℃ to 65-75 ℃ in 1H, and the reaction is refluxed for 6H, the final temperature reached 110 °c (the boiling point of the material gradually increased as the reactants changed). The reaction was allowed to stand overnight. Then, the solution of 7% sodium bisulfite was added dropwise to remove excess bromine, filtered, and the filter cake was washed with water to pH = 7 and dried naturally to give bromoadamantane. The bromoadamantane and urea were mixed well and heated to 180 °c. The reaction was started and the internal temperature was increased to 230-240 °c. After completion of the reaction, the temperature was naturally lowered, concentrated hydrochloric acid was added and dissolved, and the mixture was transferred to a distillation tank, and sodium hydroxide was added for alkalization, followed by steam distillation to obtain amantadine. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:01:54
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View History
AMantadine
(6S,2Z)-6,7-ISOPROPYLIDENEDIOXY-3,7-DIMETHYL-2-OCTEN-1-OL
N-乙基-N-(2-羟乙基)苯胺
1-乙氧羰基-1-环戊醇
DIMETHYL 5-(3-METHYLPHENYL)-2-OXO-2,3-DIHYDRO-1H-2LAMBDA4-PYRROLO[1,2-C][1,3]THIAZOLE-6,7-DICARBOXYLATE
Folic Acid Impurity 9
alpha,alpha-dimethyl-4-methylenecyclohexanemethanol
双(7-甲基辛基) 环己烷-1,2-二羧酸酯
Crispioside A
OXAMIC ACID HYDRAZIDE
(6S,2Z)-6,7-ISOPROPYLIDENEDIOXY-3,7-DIMETHYL-2-OCTEN-1-OL
N-乙基-N-(2-羟乙基)苯胺
1-乙氧羰基-1-环戊醇
DIMETHYL 5-(3-METHYLPHENYL)-2-OXO-2,3-DIHYDRO-1H-2LAMBDA4-PYRROLO[1,2-C][1,3]THIAZOLE-6,7-DICARBOXYLATE
Folic Acid Impurity 9
alpha,alpha-dimethyl-4-methylenecyclohexanemethanol
双(7-甲基辛基) 环己烷-1,2-二羧酸酯
Crispioside A
OXAMIC ACID HYDRAZIDE