Amantadine Sulfate
Basic information
- CAS
31377-23-8- Standard SMILES
NC12CC3CC(CC(C3)C1)C2.NC12CC3CC(CC(C3)C1)C2.O=S(=O)(O)O- InChIKey
MYWTWSQFJLXGGQ-UHFFFAOYSA-N- Molecular formula
- C20H36N2O4S
- Average molar mass
- 400.6 g/mol
- Monoisotopic mass
- 400.23957881
Overview
Amantadine sulfate is an alkylammonium sulfate salt obtained by combining amantadine and sulfuric acid in a 2:1 ratio. Used as an antiviral and antiparkinson drug. It has a role as a non-narcotic analgesic, an antiviral drug, an antiparkinson drug, a dopaminergic agent and a NMDA receptor antagonist. It contains an adamantan-1-aminium.
Names & identifiers
- Preferred name
- Amantadine Sulfate
- IUPAC
- bis(adamantan-1-amine);sulfuric acid
- English name
- 1-Adamantanamine sulfate
- Molecular formula
- C10H19NO4S
- Molecular weight
- 249.33
Names & synonyms
Amantadine SulfateAmantadine sulphate9921T5P019CHEBI:78351RefChem:111823250-604-531377-23-8Adamantan-1-amine hemisulfateAmantadine (sulfate)MFCD000772511-Aminoadamantane sulphateTricyclo(3.3.1.1(3,7))decan-1-amine, sulfate (2:1)
Show more names
antadineADAMANTYLAMINE SULFATE1-ADAMANTAMINE SULFATE1-AMINOADAMANTANSULFATEAMANTADINE SULFATE 99+%1-Adamantylamine sulfate1-Adamantanamine sulfate1-ADAMANTANAMINE SULPHATE
31377-23-8 (sulfate)Amantadine Sulfate; Infex; PK-Merz; Tricyclo[3.3.1.13,7]decan-1-amine SulfateTricyclo[3.3.1.13,7]decan-1-amine, sulfate (2:1)1-Adamantylamine sulphateAmantadine sulphate [INN]1-Adamantanamine HemisulfateAMANTADINE HEMISULFATEorb1707739
Database identifiers
- CAS
31377-23-8
Properties
Computed structural properties
- Topological polar surface area
- 135 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 0
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 225
Physicochemical properties
- Melting point
- 300 °C · 300 °C
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- Aqueous Acid (Slightly), Aqueous Base (Slightly)
- form
- Fine Crystalline Powder
- color
- White
- PH
- 4.9 · 4.9 (100g/l, H2O, 20°C) (slurry)
- Stability
- Hygroscopic
- InChI
- InChI=1S/C10H17N.H2O4S/c11-10-4-7-1-8(5-10)3-9(2-7)6-10;1-5(2,3)4/h7-9H,1-6,11H2;(H2,1,2,3,4)
- InChIKey
- MYWTWSQFJLXGGQ-JUMAMQMDSA-N
- SMILES
- NC12CC3CC(CC(C3)C1)C2.S(O)(O)(=O)=O
- CAS DataBase Reference
- 31377 · 31377-23-8(CAS DataBase Reference)
- FDA UNII
- 9921 T5P019 · 9921T5P019
- UNSPSC Code
- 12352107 · 12352107
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (25%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 4 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationREACH registered substance: Amantadine sulphate (INNM) (EC: 250-604-5)
Hazard Classes and CategoriesAcute Tox. 4 (25%)
Safety data
- wgk
- WGK 3 highly water endangering
- hs_code
- 2921 30 99
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319
- REACH Registrations
- Active
- Precautionary statements
- P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Agents used in the treatment of Parkinson's disease. The most commonly used drugs act on the dopaminergic system in the striatum and basal ganglia or are centrally acting muscarinic antagonists.
Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.
Any drugs that are used for their effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons.
A subclass of analgesic agents that typically do not bind to OPIOID RECEPTORS and are not addictive. Many non-narcotic analgesics are offered as NONPRESCRIPTION DRUGS.
Applications
UsesAmantadine (1-Adamantanamine) sulfate is an orally avtive and potent antiviral agent with activity against influenza A viruses. Amantadine sulfate inhibits several ion channels such as NMDA and M2, and also inhibits Coronavirus ion channels. Amantadine sulfate also has anti-orthopoxvirus and anticancer activity. Amantadine sulfate can be used for Parkinson's disease, postoperative cognitive dysfunction (POCD) and COVID-19 research[1][2][3][4][5][6].
Preparation methods
PreparationAmantadine hydrochloride was dissolved in distilled water, and sodium sulfate solution (anhydrous sodium sulfate dissolved in distilled water) was added dropwise with stirring at room temperature. A large amount of white precipitate was formed. After the addition was complete, the solution was filtered, washed with water, and dried to obtain 1-ADAMANTANAMINE SULFATE.
Additional notes
DefinitionChEBI: An alkylammonium sulfate salt obtained by combining amantadine and sulfuric acid in a 2:1 ratio. Used as an antiviral and antiparkinson drug.
Related reactions
0 records
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Compound notes
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